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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:52:54 UTC

Update Date

2021-10-01 18:39:45 UTC

HMDB ID

HMDB0244744

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phorbol 12-myristate 13-acetate

Description

13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. Based on a literature review very few articles have been published on 13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phorbol 12-myristate 13-acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phorbol 12-myristate 13-acetate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004241508282D          

 44 47  0  0  0  0            999 V2000
   -7.1434   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4289   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7145   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0000   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2855   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1447   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1447   -7.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592   -9.1505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -9.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -9.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0026   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9409   -9.5607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0026   -7.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6476   -7.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4519   -7.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9663   -6.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7821   -7.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8099   -8.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4519   -9.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2761   -9.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6476   -9.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5737  -10.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323  -10.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5158  -11.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8751   -9.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6967   -9.8510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881   -7.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737   -7.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7612   -6.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8558   -6.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737   -7.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7487   -7.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -7.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5112   -7.1985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7487   -6.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 28 34  1  0  0  0  0
 34 35  2  0  0  0  0
 22 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 17 40  1  0  0  0  0
 36 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END

HMDB0244744
     RDKit          3D
Phorbol 12-myristate 13-acetate
100103  0  0  0  0  0  0  0  0999 V2000
   13.1328    0.7006   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7563    1.3049   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7421    0.1985   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3604    0.8135   -0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3635   -0.2947   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342    0.1225   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6039    1.1513    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944    1.6201    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    0.4910    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.1871    1.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -1.3321    2.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344   -1.2551    2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -0.9726    0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -1.0077    1.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.2398    2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813   -0.7688    0.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760   -0.7742    0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    0.6439    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173    0.8818   -1.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474    0.8094    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5607    1.4471    1.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554   -0.5236    0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5185   -0.5589    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4918    0.0199    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8898   -0.1788    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9834   -0.9802    1.7143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2711    0.8776   -1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3720    1.9981   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5060    2.9414   -1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6714    2.7531    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5752    2.7084    1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5099    3.6757    0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4663    5.0470    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957    3.1093   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345    1.7621   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082   -1.5794   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9273   -2.8606    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1554   -4.1628   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1977   -2.9987    1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864   -1.7537   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956   -1.9312   -1.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4741   -2.5275   -2.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274   -2.5206   -3.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128   -3.0945   -3.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0945   -0.3416   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6831    1.3255    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6157    0.6747   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6119    1.7609   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5487    2.0754    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9218   -0.5526   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7693   -0.2853    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2290    1.2764   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2151    1.5377    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5526   -1.1032   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4765   -0.7513    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7173    0.5366   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3039   -0.7640   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2465    2.0450    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275    0.7402    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9641    2.0723   -0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9672    2.3381    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951    1.0913    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436   -0.1588   -0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    0.6556    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4081   -0.5240    1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4693   -1.7265    0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
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 27 84  1  0
 29 85  1  0
 33 86  1  0
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 38 93  1  0
 38 94  1  0
 39 95  1  0
 39 96  1  0
 39 97  1  0
 43 98  1  0
 43 99  1  0
 43100  1  0
M  END


  Mrv1533004241508282D          

 44 47  0  0  0  0            999 V2000
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    0.7158   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1447   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1447   -7.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0026   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 23 24  2  0  0  0  0
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 25 26  1  0  0  0  0
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 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
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 31 32  2  0  0  0  0
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 17 40  1  0  0  0  0
 36 40  1  0  0  0  0
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 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244744

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3

> <INCHI_KEY>
PHEDXBVPIONUQT-UHFFFAOYSA-N

> <FORMULA>
C36H56O8

> <MOLECULAR_WEIGHT>
616.836

> <EXACT_MASS>
616.397518763

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
72.55738271169525

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
5.692159238333332

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.933225775162544

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.570370247698069

> <JCHEM_PKA_STRONGEST_BASIC>
-2.731613546488827

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
169.31830000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetradecanoylphorbol acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244744
     RDKit          3D
Phorbol 12-myristate 13-acetate
100103  0  0  0  0  0  0  0  0999 V2000
   13.1328    0.7006   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7563    1.3049   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7421    0.1985   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3635   -0.2947   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342    0.1225   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 22 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 37 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 42 44  2  0
 40 17  1  0
 35 20  1  0
 40 36  1  0
 35 28  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  0
 11 67  1  0
 12 68  1  0
 12 69  1  0
 13 70  1  0
 13 71  1  0
 17 72  1  0
 18 73  1  0
 19 74  1  0
 19 75  1  0
 19 76  1  0
 21 77  1  0
 22 78  1  0
 23 79  1  0
 25 80  1  0
 25 81  1  0
 26 82  1  0
 27 83  1  0
 27 84  1  0
 29 85  1  0
 33 86  1  0
 33 87  1  0
 33 88  1  0
 34 89  1  0
 35 90  1  0
 36 91  1  0
 38 92  1  0
 38 93  1  0
 38 94  1  0
 39 95  1  0
 39 96  1  0
 39 97  1  0
 43 98  1  0
 43 99  1  0
 43100  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0     -13.334 -17.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.001 -16.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.667 -17.081   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.333 -16.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.000 -17.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.666 -16.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.332 -17.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.999 -16.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.665 -17.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.331 -16.311   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.002 -17.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.336 -16.311   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.670 -17.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.003 -16.311   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.003 -14.771   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.337 -17.081   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.671 -16.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.005 -17.081   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.005 -18.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.338 -16.311   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.223 -17.847   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.338 -14.771   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.542 -13.811   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.044 -14.153   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.004 -12.949   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.527 -13.179   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.712 -15.541   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.044 -16.928   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.582 -16.859   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.542 -17.271   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.404 -18.805   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.820 -19.410   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.163 -20.912   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.833 -18.250   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.367 -18.388   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.005 -14.001   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.671 -13.231   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.154 -12.964   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.198 -11.784   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.671 -14.771   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.131 -14.771   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.361 -13.437   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.821 -13.437   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.131 -12.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   40                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   30                                             
CONECT   21   20                                                            
CONECT   22   20   23   36                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   30   34                                             
CONECT   29   28                                                            
CONECT   30   28   20   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   28   35                                                  
CONECT   35   34                                                            
CONECT   36   22   37   40                                                  
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   17   36   41                                             
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

COMPND    HMDB0244744
HETATM    1  C1  UNL     1      13.133   0.701  -0.569  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.756   1.305  -0.737  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.742   0.199  -0.588  1.00  0.00           C  
HETATM    4  C4  UNL     1       9.360   0.814  -0.758  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.363  -0.295  -0.608  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.934   0.122  -0.746  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.604   1.151   0.313  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.194   1.620   0.250  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.162   0.491   0.421  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.309  -0.187   1.730  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.483  -1.332   2.082  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.034  -1.255   2.168  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.298  -0.973   0.923  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.182  -1.008   1.313  1.00  0.00           C  
HETATM   15  O1  UNL     1      -0.552  -1.240   2.473  1.00  0.00           O  
HETATM   16  O2  UNL     1      -1.081  -0.769   0.314  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.476  -0.774   0.551  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.955   0.644   0.244  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.517   0.882  -1.187  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.447   0.809   0.452  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.561   1.447   1.718  1.00  0.00           O  
HETATM   22  C19 UNL     1      -5.055  -0.524   0.618  1.00  0.00           C  
HETATM   23  C20 UNL     1      -6.519  -0.559   0.841  1.00  0.00           C  
HETATM   24  C21 UNL     1      -7.492   0.020   0.156  1.00  0.00           C  
HETATM   25  C22 UNL     1      -8.890  -0.179   0.595  1.00  0.00           C  
HETATM   26  O4  UNL     1      -8.983  -0.980   1.714  1.00  0.00           O  
HETATM   27  C23 UNL     1      -7.271   0.878  -1.040  1.00  0.00           C  
HETATM   28  C24 UNL     1      -6.372   1.998  -0.734  1.00  0.00           C  
HETATM   29  O5  UNL     1      -6.506   2.941  -1.785  1.00  0.00           O  
HETATM   30  C25 UNL     1      -6.671   2.753   0.511  1.00  0.00           C  
HETATM   31  O6  UNL     1      -7.575   2.708   1.343  1.00  0.00           O  
HETATM   32  C26 UNL     1      -5.510   3.676   0.532  1.00  0.00           C  
HETATM   33  C27 UNL     1      -5.466   5.047   1.160  1.00  0.00           C  
HETATM   34  C28 UNL     1      -4.496   3.109  -0.086  1.00  0.00           C  
HETATM   35  C29 UNL     1      -4.935   1.762  -0.554  1.00  0.00           C  
HETATM   36  C30 UNL     1      -4.608  -1.579  -0.363  1.00  0.00           C  
HETATM   37  C31 UNL     1      -3.927  -2.861   0.179  1.00  0.00           C  
HETATM   38  C32 UNL     1      -4.155  -4.163  -0.541  1.00  0.00           C  
HETATM   39  C33 UNL     1      -4.198  -2.999   1.665  1.00  0.00           C  
HETATM   40  C34 UNL     1      -3.186  -1.754  -0.426  1.00  0.00           C  
HETATM   41  O7  UNL     1      -2.396  -1.931  -1.523  1.00  0.00           O  
HETATM   42  C35 UNL     1      -2.474  -2.528  -2.707  1.00  0.00           C  
HETATM   43  C36 UNL     1      -1.327  -2.521  -3.652  1.00  0.00           C  
HETATM   44  O8  UNL     1      -3.513  -3.094  -3.025  1.00  0.00           O  
HETATM   45  H1  UNL     1      13.094  -0.342  -0.177  1.00  0.00           H  
HETATM   46  H2  UNL     1      13.683   1.326   0.167  1.00  0.00           H  
HETATM   47  H3  UNL     1      13.616   0.675  -1.546  1.00  0.00           H  
HETATM   48  H4  UNL     1      11.612   1.761  -1.727  1.00  0.00           H  
HETATM   49  H5  UNL     1      11.549   2.075   0.039  1.00  0.00           H  
HETATM   50  H6  UNL     1      10.922  -0.553  -1.360  1.00  0.00           H  
HETATM   51  H7  UNL     1      10.769  -0.285   0.402  1.00  0.00           H  
HETATM   52  H8  UNL     1       9.229   1.276  -1.739  1.00  0.00           H  
HETATM   53  H9  UNL     1       9.215   1.538   0.071  1.00  0.00           H  
HETATM   54  H10 UNL     1       8.553  -1.103  -1.339  1.00  0.00           H  
HETATM   55  H11 UNL     1       8.476  -0.751   0.411  1.00  0.00           H  
HETATM   56  H12 UNL     1       6.717   0.537  -1.752  1.00  0.00           H  
HETATM   57  H13 UNL     1       6.304  -0.764  -0.622  1.00  0.00           H  
HETATM   58  H14 UNL     1       7.246   2.045   0.101  1.00  0.00           H  
HETATM   59  H15 UNL     1       6.828   0.740   1.302  1.00  0.00           H  
HETATM   60  H16 UNL     1       4.964   2.072  -0.737  1.00  0.00           H  
HETATM   61  H17 UNL     1       4.967   2.338   1.058  1.00  0.00           H  
HETATM   62  H18 UNL     1       3.195   1.091   0.382  1.00  0.00           H  
HETATM   63  H19 UNL     1       4.144  -0.159  -0.466  1.00  0.00           H  
HETATM   64  H20 UNL     1       4.243   0.656   2.507  1.00  0.00           H  
HETATM   65  H21 UNL     1       5.408  -0.524   1.822  1.00  0.00           H  
HETATM   66  H22 UNL     1       3.892  -1.832   3.040  1.00  0.00           H  
HETATM   67  H23 UNL     1       3.710  -2.149   1.287  1.00  0.00           H  
HETATM   68  H24 UNL     1       1.565  -2.187   2.611  1.00  0.00           H  
HETATM   69  H25 UNL     1       1.764  -0.447   2.918  1.00  0.00           H  
HETATM   70  H26 UNL     1       1.392  -0.001   0.450  1.00  0.00           H  
HETATM   71  H27 UNL     1       1.469  -1.727   0.121  1.00  0.00           H  
HETATM   72  H28 UNL     1      -2.638  -0.985   1.577  1.00  0.00           H  
HETATM   73  H29 UNL     1      -2.347   1.316   0.879  1.00  0.00           H  
HETATM   74  H30 UNL     1      -3.044   0.264  -1.926  1.00  0.00           H  
HETATM   75  H31 UNL     1      -1.449   0.503  -1.220  1.00  0.00           H  
HETATM   76  H32 UNL     1      -2.446   1.924  -1.483  1.00  0.00           H  
HETATM   77  H33 UNL     1      -4.010   0.898   2.325  1.00  0.00           H  
HETATM   78  H34 UNL     1      -4.642  -0.892   1.617  1.00  0.00           H  
HETATM   79  H35 UNL     1      -6.932  -1.133   1.691  1.00  0.00           H  
HETATM   80  H36 UNL     1      -9.431  -0.674  -0.254  1.00  0.00           H  
HETATM   81  H37 UNL     1      -9.416   0.768   0.787  1.00  0.00           H  
HETATM   82  H38 UNL     1      -8.895  -1.939   1.517  1.00  0.00           H  
HETATM   83  H39 UNL     1      -6.837   0.251  -1.818  1.00  0.00           H  
HETATM   84  H40 UNL     1      -8.235   1.249  -1.388  1.00  0.00           H  
HETATM   85  H41 UNL     1      -6.950   2.538  -2.574  1.00  0.00           H  
HETATM   86  H42 UNL     1      -5.275   5.756   0.352  1.00  0.00           H  
HETATM   87  H43 UNL     1      -4.592   5.116   1.856  1.00  0.00           H  
HETATM   88  H44 UNL     1      -6.363   5.236   1.758  1.00  0.00           H  
HETATM   89  H45 UNL     1      -3.515   3.600  -0.204  1.00  0.00           H  
HETATM   90  H46 UNL     1      -4.487   1.633  -1.570  1.00  0.00           H  
HETATM   91  H47 UNL     1      -5.346  -1.814  -1.139  1.00  0.00           H  
HETATM   92  H48 UNL     1      -4.482  -4.971   0.224  1.00  0.00           H  
HETATM   93  H49 UNL     1      -3.253  -4.625  -0.962  1.00  0.00           H  
HETATM   94  H50 UNL     1      -5.034  -4.082  -1.175  1.00  0.00           H  
HETATM   95  H51 UNL     1      -3.559  -2.459   2.334  1.00  0.00           H  
HETATM   96  H52 UNL     1      -4.071  -4.092   1.964  1.00  0.00           H  
HETATM   97  H53 UNL     1      -5.260  -2.806   1.836  1.00  0.00           H  
HETATM   98  H54 UNL     1      -1.092  -1.443  -3.870  1.00  0.00           H  
HETATM   99  H55 UNL     1      -1.549  -3.089  -4.564  1.00  0.00           H  
HETATM  100  H56 UNL     1      -0.452  -2.931  -3.098  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3   48   49
CONECT    3    4   50   51
CONECT    4    5   52   53
CONECT    5    6   54   55
CONECT    6    7   56   57
CONECT    7    8   58   59
CONECT    8    9   60   61
CONECT    9   10   62   63
CONECT   10   11   64   65
CONECT   11   12   66   67
CONECT   12   13   68   69
CONECT   13   14   70   71
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   40   72
CONECT   18   19   20   73
CONECT   19   74   75   76
CONECT   20   21   22   35
CONECT   21   77
CONECT   22   23   36   78
CONECT   23   24   24   79
CONECT   24   25   27
CONECT   25   26   80   81
CONECT   26   82
CONECT   27   28   83   84
CONECT   28   29   30   35
CONECT   29   85
CONECT   30   31   31   32
CONECT   32   33   34   34
CONECT   33   86   87   88
CONECT   34   35   89
CONECT   35   90
CONECT   36   37   40   91
CONECT   37   38   39   40
CONECT   38   92   93   94
CONECT   39   95   96   97
CONECT   40   41
CONECT   41   42
CONECT   42   43   44   44
CONECT   43   98   99  100
END

HMDB0244744
     RDKit          3D
Phorbol 12-myristate 13-acetate
100103  0  0  0  0  0  0  0  0999 V2000
   13.1328    0.7006   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7563    1.3049   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7421    0.1985   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3604    0.8135   -0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3635   -0.2947   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9342    0.1225   -0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6039    1.1513    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944    1.6201    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    0.4910    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.1871    1.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -1.3321    2.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344   -1.2551    2.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -0.9726    0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -1.0077    1.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520   -1.2398    2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0813   -0.7688    0.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760   -0.7742    0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    0.6439    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173    0.8818   -1.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474    0.8094    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5607    1.4471    1.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554   -0.5236    0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5185   -0.5589    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4918    0.0199    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8898   -0.1788    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9834   -0.9802    1.7143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2711    0.8776   -1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3720    1.9981   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5060    2.9414   -1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6714    2.7531    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5752    2.7084    1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5099    3.6757    0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4663    5.0470    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4957    3.1093   -0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9345    1.7621   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082   -1.5794   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9273   -2.8606    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1554   -4.1628   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1977   -2.9987    1.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864   -1.7537   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956   -1.9312   -1.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4741   -2.5275   -2.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274   -2.5206   -3.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128   -3.0945   -3.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0945   -0.3416   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6831    1.3255    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6157    0.6747   -1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6119    1.7609   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5487    2.0754    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9218   -0.5526   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7693   -0.2853    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2290    1.2764   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2151    1.5377    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5526   -1.1032   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4765   -0.7513    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7173    0.5366   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3039   -0.7640   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2465    2.0450    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8275    0.7402    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9641    2.0723   -0.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9672    2.3381    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1951    1.0913    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1436   -0.1588   -0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    0.6556    2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4081   -0.5240    1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924   -1.8317    3.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096   -2.1491    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650   -2.1868    2.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645   -0.4471    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.0006    0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4693   -1.7265    0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382   -0.9850    1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471    1.3157    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    0.2639   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.5034   -1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464    1.9236   -1.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0101    0.8985    2.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6416   -0.8919    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321   -1.1328    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4315   -0.6745   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4163    0.7685    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8953   -1.9394    1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8368    0.2510   -1.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2353    1.2493   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9497    2.5380   -2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2750    5.7555    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5922    5.1163    1.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3625    5.2357    1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150    3.6005   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870    1.6328   -1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3465   -1.8138   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4822   -4.9713    0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -4.6254   -0.9616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0340   -4.0816   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -2.4589    2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -4.0917    1.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2602   -2.8061    1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0922   -1.4426   -3.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5488   -3.0887   -4.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4524   -2.9310   -3.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-(Acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-14-yl tetradecanoic acid	Generator
Phorbol acetic acid, myristic acid	Generator
12 Myristoyl 13 acetylphorbol	MeSH
12 O Tetradecanoyl phorbol 13 acetate	MeSH
12-Myristoyl-13-acetylphorbol	MeSH
12-O-Tetradecanoyl phorbol 13-acetate	MeSH
13-Acetate, 12-O-tetradecanoyl phorbol	MeSH
Acetate, phorbol myristate	MeSH
Acetate, tetradecanoylphorbol	MeSH
Myristate acetate, phorbol	MeSH
Phorbol 13-acetate, 12-O-tetradecanoyl	MeSH
Phorbol myristate acetate	MeSH
Tetradecanoylphorbol acetate	MeSH
Tetradecanoylphorbol acetate, 4a alpha isomer	MeSH
Tetradecanoylphorbol acetate, 4a alpha-isomer	MeSH

Chemical Formula

C₃₆H₅₆O₈

Average Molecular Weight

616.836

Monoisotopic Molecular Weight

616.397518763

IUPAC Name

13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl tetradecanoate

Traditional Name

tetradecanoylphorbol acetate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(C)=O

InChI Identifier

InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3

InChI Key

PHEDXBVPIONUQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.53	ALOGPS
logP	5.69	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	12.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	169.32 m³·mol⁻¹	ChemAxon
Polarizability	72.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	275.422	30932474
DeepCCS	[M+Na]+	250.673	30932474
AllCCS	[M+H]+	241.0	32859911
AllCCS	[M+H-H2O]+	240.2	32859911
AllCCS	[M+NH4]+	241.6	32859911
AllCCS	[M+Na]+	241.8	32859911
AllCCS	[M-H]-	232.2	32859911
AllCCS	[M+Na-2H]-	236.3	32859911
AllCCS	[M+HCOO]-	241.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phorbol 12-myristate 13-acetate	CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(C)=O	4187.6	Standard polar	33892256
Phorbol 12-myristate 13-acetate	CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(C)=O	3986.3	Standard non polar	33892256
Phorbol 12-myristate 13-acetate	CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C(C)(C)C12OC(C)=O	3991.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phorbol 12-myristate 13-acetate GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phorbol 12-myristate 13-acetate 10V, Positive-QTOF	splash10-0aor-0000095000-abf292d26130ce402119	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phorbol 12-myristate 13-acetate 20V, Positive-QTOF	splash10-014i-1001194000-6741288a522343a71dde	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phorbol 12-myristate 13-acetate 40V, Positive-QTOF	splash10-066r-9200510000-7e33d7c918ac0a841ee4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phorbol 12-myristate 13-acetate 10V, Negative-QTOF	splash10-014i-0010059000-495c3dd07cc2065fb8bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phorbol 12-myristate 13-acetate 20V, Negative-QTOF	splash10-014i-2000049000-5b5be3fa24f7af36cb7f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phorbol 12-myristate 13-acetate 40V, Negative-QTOF	splash10-00p0-5950434000-af80bd77e5d09beb49ab	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4792

PDB ID

Not Available

ChEBI ID

93813

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Protein kinase C delta type

General function:: Involved in protein serine/threonine kinase activity
Specific function:: This is calcium-independent, phospholipid-dependent, serine- and threonine-specific enzyme. PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters. May play a role in antigen-dependent control of B-cell function. Phosphorylates MUC1 in the C-terminal and regulates the interaction between MUC1 and beta-catenin
Gene Name:: PRKCD
Uniprot ID:: Q05655
Molecular weight:: 77504.4

Enzyme Details

2. Solute carrier family 22 member 6

General function:: Not Available
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of cidofovir, adefovir, 9-(2-phosphonylmethoxyethyl) guanine (PMEG), 9-(2-phosphonylmethoxyethyl) diaminopurine (PMEDAP), ochratoxin (OTA), acyclovir (ACV), 3'-azido-3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS), 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF) and edaravone sulfate (By similarity). Mediates the sodium-independent uptake of p-aminohippurate (PAH) and 2,3-dimercapto-1-propanesulfonic acid (DMPS). PAH uptake is inhibited by p-chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), indomethacin, sulindac, diclofenac, carprofen, okadaic acid, furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, bumetamide, losartan, probenecid, phenol red and glutarate (By similarity). PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), urate, alpha-ketoglutarate and probenecid.
Gene Name:: SLC22A6
Uniprot ID:: Q9TSY7
Molecular weight:: 60588.3

Enzyme Details

3. Solute carrier family 22 member 6

General function:: Not Available
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS), 9-(2-phosphonylmethoxyethyl) guanine (PMEG), 9-(2-phosphonylmethoxyethyl) diaminopurine (PMEDAP), ochratoxin (OTA), acyclovir (ACV), 3'-azido-3-'deoxythymidine (AZT), cimetidine (CMD) and edaravone sulfate. Mediates the sodium-independent uptake of p-aminohippurate (PAH), cidofovir, adefovir, 2,4-dichloro-phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF). PAH uptake is inhibited by p-chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), indomethacin, sulindac, diclofenac, carprofen, okadaic acid, benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, bumetamide, losartan, phenol red, urate and alpha-ketoglutarate (By similarity). PAH uptake is inhibited by glutarate and probenecid.
Gene Name:: SLC22A6
Uniprot ID:: O35956
Molecular weight:: 60765.66

Enzyme Details

4. mRNA decay activator protein ZFP36L2

General function:: Not Available
Specific function:: Zinc-finger RNA-binding protein that destabilizes several cytoplasmic AU-rich element (ARE)-containing mRNA transcripts by promoting their poly(A) tail removal or deadenylation, and hence provide a mechanism for attenuating protein synthesis (PubMed:25106868, PubMed:14981510). Acts as a 3'-untranslated region (UTR) ARE mRNA-binding adapter protein to communicate signaling events to the mRNA decay machinery (PubMed:25106868). Functions by recruiting the CCR4-NOT deadenylase complex and probably other components of the cytoplasmic RNA decay machinery to the bound ARE-containing mRNAs, and hence promotes ARE-mediated mRNA deadenylation and decay processes (PubMed:25106868). Binds to 3'-UTR ARE of numerous mRNAs (PubMed:20506496, PubMed:25106868, PubMed:14981510). Promotes ARE-containing mRNA decay of the low-density lipoprotein (LDL) receptor (LDLR) mRNA in response to phorbol 12-myristate 13-acetate (PMA) treatment in a p38 MAPK-dependent manner (PubMed:25106868). Positively regulates early adipogenesis by promoting ARE-mediated mRNA decay of immediate early genes (IEGs). Plays a role in mature peripheral neuron integrity by promoting ARE-containing mRNA decay of the transcriptional repressor REST mRNA. Plays a role in ovulation and oocyte meiotic maturation by promoting ARE-mediated mRNA decay of the luteinizing hormone receptor LHCGR mRNA. Acts as a negative regulator of erythroid cell differentiation: promotes glucocorticoid-induced self-renewal of erythroid cells by binding mRNAs that are induced or highly expressed during terminal erythroid differentiation and promotes their degradation, preventing erythroid cell differentiation. In association with ZFP36L1 maintains quiescence on developing B lymphocytes by promoting ARE-mediated decay of several mRNAs encoding cell cycle regulators that help B cells progress through the cell cycle, and hence ensuring accurate variable-diversity-joining (VDJ) recombination process and functional immune cell formation. Together with ZFP36L1 is also necessary for thymocyte development and prevention of T-cell acute lymphoblastic leukemia (T-ALL) transformation by promoting ARE-mediated mRNA decay of the oncogenic transcription factor NOTCH1 mRNA.
Gene Name:: ZFP36L2
Uniprot ID:: P47974
Molecular weight:: 51062.055

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

Showing metabocard for Phorbol 12-myristate 13-acetate (HMDB0244744)

MOL for HMDB0244744 (Phorbol 12-myristate 13-acetate)

3D MOL for HMDB0244744 (Phorbol 12-myristate 13-acetate)

3D SDF for HMDB0244744 (Phorbol 12-myristate 13-acetate)

3D-SDF for HMDB0244744 (Phorbol 12-myristate 13-acetate)

PDB for HMDB0244744 (Phorbol 12-myristate 13-acetate)

3D PDB for HMDB0244744 (Phorbol 12-myristate 13-acetate)

SMILES for HMDB0244744 (Phorbol 12-myristate 13-acetate)

INCHI for HMDB0244744 (Phorbol 12-myristate 13-acetate)

Structure for HMDB0244744 (Phorbol 12-myristate 13-acetate)

3D Structure for HMDB0244744 (Phorbol 12-myristate 13-acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Transporters