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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015310

Secondary Accession Numbers

HMDB15310

Metabolite Identification

Common Name

Podofilox

Description

Podofilox, also known as condylox or podophyllotoxin 7, belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Podofilox is a drug which is used for treatment of external genital warts (condyloma acuminatum). Podofilox is an extremely weak basic (essentially neutral) compound (based on its pKa). Podofilox is a potentially toxic compound.

Structure

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

1179
  Mrv0541 09041214372D          

 32 36  0  0  1  0            999 V2000
    4.7435    2.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    1.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8850    1.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8478   -2.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986   -2.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276    0.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -1.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    1.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4697    1.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4697    0.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0407    1.2066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7552   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0777    1.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7684   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -0.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834   -0.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986   -1.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9982   -2.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131   -2.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276    1.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0420   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218    2.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.9389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  6  0  0  0
  3 16  2  0  0  0  0
  4 20  1  0  0  0  0
  4 27  1  0  0  0  0
  5 21  1  0  0  0  0
  5 27  1  0  0  0  0
  6 24  1  0  0  0  0
  6 28  1  0  0  0  0
  7 25  1  0  0  0  0
  7 29  1  0  0  0  0
  8 26  1  0  0  0  0
  8 30  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 31  1  6  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 10 32  1  1  0  0  0
 11 13  1  0  0  0  0
 11 17  1  6  0  0  0
 12 15  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  2  0  0  0  0
 15 19  2  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

HMDB0015310
     RDKit          3D
Podofilox
 52 56  0  0  0  0  0  0  0  0999 V2000
    3.4028   -2.1772   -2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8014   -1.2983   -1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384   -0.8177   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170   -1.2104   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921   -0.7851    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -1.2665    0.1228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5564   -0.3987   -0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.1396   -1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    0.9518   -2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    1.2528   -2.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6112    0.7156   -1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.0931   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -0.6102    0.8985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5373    0.1045    1.3065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026   -0.5616    1.8961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6169   -1.1191    3.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061   -1.5240    3.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5229   -1.8347    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -2.2126    2.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468   -1.6361    1.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7424    2.0868   -3.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7035    2.5186   -4.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248    1.6032   -3.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    0.0817    1.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    0.4933    1.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    1.3666    2.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    1.8840    3.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.0489    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    0.4452    0.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293    1.6161   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -3.1910   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -2.2274   -3.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -1.7913   -3.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -1.8904   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -2.2345   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691   -0.0704   -2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146    0.9466   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6835   -1.6968    0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315    0.7646    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    0.4341    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.0489    3.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740   -0.4076    3.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.5501    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793    3.5195   -3.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    2.5125   -5.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    0.4463    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    2.6615    2.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    2.2976    4.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    1.0399    3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    2.4794    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    1.7245   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248    1.5185   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  6
  8 36  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
 15 40  1  1
 16 41  1  0
 16 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  END

1179
  Mrv0541 09041214372D          

 32 36  0  0  1  0            999 V2000
    4.7435    2.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263    1.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8850    1.5868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8478   -2.1607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986   -2.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276    0.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -1.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7552    1.6191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4697    1.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4697    0.3816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0407    1.2066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7552   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0777    1.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7684   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -0.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834   -0.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8986   -1.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9982   -2.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6131   -2.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276    1.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0420   -0.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218    2.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.9389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 16  1  0  0  0  0
 12  2  1  6  0  0  0
  3 16  2  0  0  0  0
  4 20  1  0  0  0  0
  4 27  1  0  0  0  0
  5 21  1  0  0  0  0
  5 27  1  0  0  0  0
  6 24  1  0  0  0  0
  6 28  1  0  0  0  0
  7 25  1  0  0  0  0
  7 29  1  0  0  0  0
  8 26  1  0  0  0  0
  8 30  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 31  1  6  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 10 32  1  1  0  0  0
 11 13  1  0  0  0  0
 11 17  1  6  0  0  0
 12 15  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  2  0  0  0  0
 15 19  2  0  0  0  0
 17 22  2  0  0  0  0
 17 23  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 21  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 24 26  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015310

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

> <INCHI_KEY>
YJGVMLPVUAXIQN-XVVDYKMHSA-N

> <FORMULA>
C22H22O8

> <MOLECULAR_WEIGHT>
414.4053

> <EXACT_MASS>
414.13146768

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
41.70556165338746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.6227982693333332

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.015751296514601

> <JCHEM_PKA_STRONGEST_BASIC>
-3.229310382904514

> <JCHEM_POLAR_SURFACE_AREA>
92.68000000000002

> <JCHEM_REFRACTIVITY>
103.905

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
condylox

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015310
     RDKit          3D
Podofilox
 52 56  0  0  0  0  0  0  0  0999 V2000
    3.4028   -2.1772   -2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8014   -1.2983   -1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384   -0.8177   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170   -1.2104   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921   -0.7851    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -1.2665    0.1228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5564   -0.3987   -0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.1396   -1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    0.9518   -2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    1.2528   -2.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6112    0.7156   -1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.0931   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -0.6102    0.8985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5373    0.1045    1.3065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026   -0.5616    1.8961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6169   -1.1191    3.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061   -1.5240    3.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5229   -1.8347    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -2.2126    2.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468   -1.6361    1.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7424    2.0868   -3.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7035    2.5186   -4.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248    1.6032   -3.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    0.0817    1.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    0.4933    1.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    1.3666    2.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    1.8840    3.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.0489    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    0.4452    0.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293    1.6161   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -3.1910   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -2.2274   -3.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -1.7913   -3.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -1.8904   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -2.2345   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691   -0.0704   -2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146    0.9466   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6835   -1.6968    0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315    0.7646    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    0.4341    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.0489    3.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740   -0.4076    3.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.5501    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793    3.5195   -3.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    2.5125   -5.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    0.4463    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    2.6615    2.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    2.2976    4.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    1.0399    3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    2.4794    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    1.7245   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248    1.5185   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  6
  8 36  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
 15 40  1  1
 16 41  1  0
 16 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  END

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1179                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  O   UNK     0       8.855   4.678   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.342   3.022   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.985   2.962   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.316  -4.033   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.080  -2.742   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.011  -3.908   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.678   0.712   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.678  -2.368   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.010   3.022   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.343   2.252   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.343   0.712   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.676   2.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.010  -0.058   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.332   4.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.676   0.712   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.478   3.280   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.677  -0.058   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.034  -1.662   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.275  -0.068   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.652  -2.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.262  -1.672   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.011   0.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.677  -1.598   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.011  -2.368   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.344  -0.058   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.344  -1.598   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.730  -4.199   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.344  -4.678   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.678   2.252   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.012  -1.598   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       6.014   3.748   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.469   1.753   0.000  0.00  0.00           H+0
CONECT    1   14   16                                                       
CONECT    2   12                                                            
CONECT    3   16                                                            
CONECT    4   20   27                                                       
CONECT    5   21   27                                                       
CONECT    6   24   28                                                       
CONECT    7   25   29                                                       
CONECT    8   26   30                                                       
CONECT    9   10   12   14   31                                             
CONECT   10    9   11   16   32                                             
CONECT   11   10   13   17                                                  
CONECT   12    2    9   15                                                  
CONECT   13   11   15   18                                                  
CONECT   14    1    9                                                       
CONECT   15   12   13   19                                                  
CONECT   16    1    3   10                                                  
CONECT   17   11   22   23                                                  
CONECT   18   13   20                                                       
CONECT   19   15   21                                                       
CONECT   20    4   18   21                                                  
CONECT   21    5   19   20                                                  
CONECT   22   17   25                                                       
CONECT   23   17   24                                                       
CONECT   24    6   23   26                                                  
CONECT   25    7   22   26                                                  
CONECT   26    8   24   25                                                  
CONECT   27    4    5                                                       
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0015310
HETATM    1  C1  UNL     1       3.403  -2.177  -2.701  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.801  -1.298  -1.690  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.938  -0.818  -0.711  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.617  -1.210  -0.711  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.692  -0.785   0.219  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.702  -1.266   0.123  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.556  -0.399  -0.701  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.072   0.140  -1.890  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.851   0.952  -2.684  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.149   1.253  -2.309  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.611   0.716  -1.136  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.830  -0.093  -0.349  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.438  -0.610   0.898  1.00  0.00           C  
HETATM   14  O2  UNL     1      -4.537   0.104   1.306  1.00  0.00           O  
HETATM   15  C13 UNL     1      -2.303  -0.562   1.896  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.617  -1.119   3.237  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.306  -1.524   3.669  1.00  0.00           O  
HETATM   18  C15 UNL     1      -0.523  -1.835   2.565  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.666  -2.213   2.610  1.00  0.00           O  
HETATM   20  C16 UNL     1      -1.347  -1.636   1.385  1.00  0.00           C  
HETATM   21  O5  UNL     1      -3.742   2.087  -3.261  1.00  0.00           O  
HETATM   22  C17 UNL     1      -2.704   2.519  -4.100  1.00  0.00           C  
HETATM   23  O6  UNL     1      -1.625   1.603  -3.885  1.00  0.00           O  
HETATM   24  C18 UNL     1       1.162   0.082   1.185  1.00  0.00           C  
HETATM   25  C19 UNL     1       2.481   0.493   1.212  1.00  0.00           C  
HETATM   26  O7  UNL     1       2.963   1.367   2.182  1.00  0.00           O  
HETATM   27  C20 UNL     1       2.124   1.884   3.201  1.00  0.00           C  
HETATM   28  C21 UNL     1       3.388   0.049   0.263  1.00  0.00           C  
HETATM   29  O8  UNL     1       4.718   0.445   0.264  1.00  0.00           O  
HETATM   30  C22 UNL     1       5.029   1.616  -0.480  1.00  0.00           C  
HETATM   31  H1  UNL     1       3.197  -3.191  -2.310  1.00  0.00           H  
HETATM   32  H2  UNL     1       4.173  -2.227  -3.496  1.00  0.00           H  
HETATM   33  H3  UNL     1       2.468  -1.791  -3.172  1.00  0.00           H  
HETATM   34  H4  UNL     1       1.314  -1.890  -1.494  1.00  0.00           H  
HETATM   35  H5  UNL     1      -0.639  -2.234  -0.484  1.00  0.00           H  
HETATM   36  H6  UNL     1      -0.069  -0.070  -2.217  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.615   0.947  -0.843  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.683  -1.697   0.745  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.232   0.765   1.981  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.871   0.434   1.943  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.203  -2.049   3.112  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.074  -0.408   3.938  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.005  -2.550   1.273  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.379   3.519  -3.749  1.00  0.00           H  
HETATM   45  H15 UNL     1      -2.979   2.513  -5.180  1.00  0.00           H  
HETATM   46  H16 UNL     1       0.504   0.446   1.931  1.00  0.00           H  
HETATM   47  H17 UNL     1       1.440   2.662   2.854  1.00  0.00           H  
HETATM   48  H18 UNL     1       2.763   2.298   4.014  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.569   1.040   3.630  1.00  0.00           H  
HETATM   50  H20 UNL     1       4.627   2.479   0.075  1.00  0.00           H  
HETATM   51  H21 UNL     1       6.099   1.725  -0.679  1.00  0.00           H  
HETATM   52  H22 UNL     1       4.525   1.519  -1.481  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    4   28
CONECT    4    5   34
CONECT    5    6   24   24
CONECT    6    7   20   35
CONECT    7    8    8   12
CONECT    8    9   36
CONECT    9   10   10   23
CONECT   10   11   21
CONECT   11   12   12   37
CONECT   12   13
CONECT   13   14   15   38
CONECT   14   39
CONECT   15   16   20   40
CONECT   16   17   41   42
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   43
CONECT   21   22
CONECT   22   23   44   45
CONECT   24   25   46
CONECT   25   26   28   28
CONECT   26   27
CONECT   27   47   48   49
CONECT   28   29
CONECT   29   30
CONECT   30   50   51   52
END

HMDB0015310
     RDKit          3D
Podofilox
 52 56  0  0  0  0  0  0  0  0999 V2000
    3.4028   -2.1772   -2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8014   -1.2983   -1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384   -0.8177   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170   -1.2104   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921   -0.7851    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -1.2665    0.1228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5564   -0.3987   -0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.1396   -1.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8509    0.9518   -2.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491    1.2528   -2.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6112    0.7156   -1.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -0.0931   -0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376   -0.6102    0.8985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5373    0.1045    1.3065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026   -0.5616    1.8961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6169   -1.1191    3.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061   -1.5240    3.6688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5229   -1.8347    2.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -2.2126    2.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468   -1.6361    1.3853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7424    2.0868   -3.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7035    2.5186   -4.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248    1.6032   -3.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    0.0817    1.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810    0.4933    1.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    1.3666    2.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    1.8840    3.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881    0.0489    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7185    0.4452    0.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0293    1.6161   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -3.1910   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -2.2274   -3.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -1.7913   -3.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3137   -1.8904   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -2.2345   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691   -0.0704   -2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6146    0.9466   -0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6835   -1.6968    0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315    0.7646    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    0.4341    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.0489    3.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740   -0.4076    3.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -2.5501    1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793    3.5195   -3.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9793    2.5125   -5.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    0.4463    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    2.6615    2.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7629    2.2976    4.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    1.0399    3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    2.4794    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    1.7245   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5248    1.5185   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
 23  9  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  6 35  1  6
  8 36  1  0
 11 37  1  0
 13 38  1  6
 14 39  1  0
 15 40  1  1
 16 41  1  0
 16 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 24 46  1  0
 27 47  1  0
 27 48  1  0
 27 49  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Podophyllotoxin	ChEBI
9-HYDROXY-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-D][1,3]dioxol-6(5ah)-one	ChEBI
Condylox	ChEBI
Podophyllinic acid lactone	ChEBI
Podophyllotoxin 7	ChEBI
PPT	ChEBI
Podophyllotoxin	Kegg
Podophyllinate lactone	Generator
Ardern brand OF podophyllotoxin	HMDB
Condyline	HMDB
Hamilton brand OF podophyllotoxin	HMDB
Oclassen brand OF podophyllotoxin	HMDB
Wartec	HMDB
CPH86	HMDB
Epipodophyllotoxin	HMDB
Fides ecopharma brand OF podophyllotoxin	HMDB
Paladin brand OF podophyllotoxin	HMDB
PODOCON-25	HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 alpha))-isomer	HMDB
Podophyllotoxin, (5R-(5 alpha,5a beta,8a alpha,9 beta))-isomer	HMDB
Warticon	HMDB
Newport brand OF podophyllotoxin	HMDB
Podofilm	HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a beta,9 alpha))-isomer	HMDB
Wolff brand OF podophyllotoxin	HMDB
Canderm brand OF podophyllotoxin	HMDB
Paddock brand OF podophyllotoxin	HMDB
Podophyllotoxin, (5R-(5 alpha,5a alpha,8a alpha,9 beta))-isomer	HMDB
Stiefel brand OF podophyllotoxin	HMDB
Yamanouchi brand OF podophyllotoxin	HMDB
Podofilox	ChEBI

Chemical Formula

C₂₂H₂₂O₈

Average Molecular Weight

414.4053

Monoisotopic Molecular Weight

414.13146768

IUPAC Name

(10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Traditional Name

condylox

CAS Registry Number

477-47-4

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O

InChI Identifier

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

InChI Key

YJGVMLPVUAXIQN-XVVDYKMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

Podophyllotoxin
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Tetralin
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

lignan (CHEBI:50305 )
furonaphthodioxole (CHEBI:50305 )
Phenylpropanoids (C10874 )
Lignans (C10874 )
Phytotoxins (C10874 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.11 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.02	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	41.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	199.371	31661259
DarkChem	[M-H]-	196.323	31661259
DeepCCS	[M-2H]-	222.074	30932474
DeepCCS	[M+Na]+	197.031	30932474
AllCCS	[M+H]+	195.6	32859911
AllCCS	[M+H-H2O]+	193.0	32859911
AllCCS	[M+NH4]+	198.0	32859911
AllCCS	[M+Na]+	198.7	32859911
AllCCS	[M-H]-	199.4	32859911
AllCCS	[M+Na-2H]-	199.4	32859911
AllCCS	[M+HCOO]-	199.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Podofilox	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O	5213.4	Standard polar	33892256
Podofilox	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O	3328.3	Standard non polar	33892256
Podofilox	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(OC)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@@H]2O	3492.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Podofilox,1TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1OC	3327.9	Semi standard non polar	33892256
Podofilox,1TBDMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1OC	3566.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Podofilox GC-EI-TOF (Non-derivatized)	splash10-014i-0932100000-95e1178f6bbdd050862b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Podofilox GC-EI-TOF (Non-derivatized)	splash10-014i-0932100000-95e1178f6bbdd050862b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Podofilox GC-MS (Non-derivatized) - 70eV, Positive	splash10-0040-1109000000-946a81564d6a1db98613	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Podofilox GC-MS (1 TMS) - 70eV, Positive	splash10-0kmi-1003900000-d43e5f990afbda30580d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Podofilox GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox LC-ESI-qTOF , Positive-QTOF	splash10-000j-0963000000-4476c6936a37aa211aa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox LC-ESI-qTof , Positive-QTOF	splash10-0002-0597000000-db51a944dfa407960e8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox LC-ESI-qTof , Positive-QTOF	splash10-00ks-2963000000-b25b106b59de4143117b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox , positive-QTOF	splash10-0002-0597000000-db51a944dfa407960e8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox , positive-QTOF	splash10-000j-0963000000-4476c6936a37aa211aa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox , positive-QTOF	splash10-00ks-2963000000-b25b106b59de4143117b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox , positive-QTOF	splash10-0002-0985000000-53e98e579f100740f337	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox , positive-QTOF	splash10-01q9-0294000000-a3c5accc0b01026c8804	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox , positive-QTOF	splash10-0002-0986000000-0ae140ecf023e899576f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 6V, Positive-QTOF	splash10-000i-0964000000-594e28c58db6c7a23702	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 6V, Positive-QTOF	splash10-0002-0689100000-26e5d1f1c51b5bc8cd1b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 40V, Positive-QTOF	splash10-015j-0941000000-a2536e1570c993ceaf4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 30V, Positive-QTOF	splash10-000j-0963000000-41a101d931c005b8f2a2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 50V, Positive-QTOF	splash10-014r-0940000000-ab1bd1f1613825ab15f6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 20V, Positive-QTOF	splash10-0002-0696000000-ebcc3b8fa151aa4628d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 10V, Positive-QTOF	splash10-0002-0269000000-6681bfe5b9880ae1ea45	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 50V, Positive-QTOF	splash10-014r-0940000000-95cc0fdbff989196786a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 30V, Positive-QTOF	splash10-000i-0943000000-f9628ba88402476de046	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Podofilox 10V, Positive-QTOF	splash10-0002-0689100000-e79bf062b65177d2e409	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Podofilox 10V, Positive-QTOF	splash10-00kb-0009500000-4616d49ee91153709c32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Podofilox 20V, Positive-QTOF	splash10-014j-0029100000-07a109dcecbceb611534	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Podofilox 40V, Positive-QTOF	splash10-0gc0-0029000000-866502321774872dbd1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Podofilox 10V, Negative-QTOF	splash10-03di-0003900000-0a5bb4d2c68362569d3c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Podofilox 20V, Negative-QTOF	splash10-02ta-0009200000-dc7b8f1ae65bdd58832d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Podofilox 40V, Negative-QTOF	splash10-014j-1039000000-d11a736e9337d8575e1e	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01179	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01179	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01179

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000610

Chemspider ID

10162

KEGG Compound ID

C10874

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Podophyllotoxin

METLIN ID

Not Available

PubChem Compound

10607

PDB ID

Not Available

ChEBI ID

50305

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

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Tubulin beta chain

General function:: Involved in structural molecule activity
Specific function:: Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:: TUBB
Uniprot ID:: P07437
Molecular weight:: 49670.5

References

Wolff J, Knipling L, Cahnmann HJ, Palumbo G: Direct photoaffinity labeling of tubulin with colchicine. Proc Natl Acad Sci U S A. 1991 Apr 1;88(7):2820-4. [PubMed:2011590 ]

Enzyme Details

4. Tubulin alpha-4A chain

General function:: Involved in structural molecule activity
Specific function:: Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:: TUBA4A
Uniprot ID:: P68366
Molecular weight:: 49924.0

References

Labruere R, Gautier B, Testud M, Seguin J, Lenoir C, Desbene-Finck S, Helissey P, Garbay C, Chabot GG, Vidal M, Giorgi-Renault S: Design, synthesis, and biological evaluation of the first podophyllotoxin analogues as potential vascular-disrupting agents. ChemMedChem. 2010 Dec 3;5(12):2016-25. doi: 10.1002/cmdc.201000305. [PubMed:20979080 ]
Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [PubMed:20814887 ]
Kim ND, Park ES, Kim YH, Moon SK, Lee SS, Ahn SK, Yu DY, No KT, Kim KH: Structure-based virtual screening of novel tubulin inhibitors and their characterization as anti-mitotic agents. Bioorg Med Chem. 2010 Oct 1;18(19):7092-100. doi: 10.1016/j.bmc.2010.07.072. Epub 2010 Aug 6. [PubMed:20810285 ]
Screpanti E, Santaguida S, Nguyen T, Silvestri R, Gussio R, Musacchio A, Hamel E, De Wulf P: A screen for kinetochore-microtubule interaction inhibitors identifies novel antitubulin compounds. PLoS One. 2010 Jul 15;5(7):e11603. doi: 10.1371/journal.pone.0011603. [PubMed:20657644 ]
Alam MA, Naik PK: Applying linear interaction energy method for binding affinity calculations of podophyllotoxin analogues with tubulin using continuum solvent model and prediction of cytotoxic activity. J Mol Graph Model. 2009 Jun-Jul;27(8):930-43. doi: 10.1016/j.jmgm.2009.02.003. Epub 2009 Feb 20. [PubMed:19286405 ]
Clark PI: Clinical pharmacology and schedule dependency of the podophyllotoxin derivatives. Semin Oncol. 1992 Apr;19(2 Suppl 6):20-7. [PubMed:1411635 ]

Enzyme Details

5. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Iida A, Kano M, Kubota Y, Koga K, Tomioka K: Podophyllotoxin aza-analogue, a novel DNA topoisomerase II inhibitor. Chem Pharm Bull (Tokyo). 2000 Apr;48(4):486-9. [PubMed:10783066 ]
Zhang YL, Shen YC, Wang ZQ, Chen HX, Guo X, Cheng YC, Lee KH: Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II. J Nat Prod. 1992 Aug;55(8):1100-11. [PubMed:1331331 ]
Terada T, Fujimoto K, Nomura M, Yamashita J, Kobunai T, Takeda S, Wierzba K, Yamada Y, Yamaguchi H: Antitumor agents. I. DNA topoisomerase II inhibitory activity and the structural relationship of podophyllotoxin derivatives as antitumor agents. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2720-7. [PubMed:1334447 ]
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Showing metabocard for Podofilox (HMDB0015310)

MOL for HMDB0015310 (Podofilox)

3D MOL for HMDB0015310 (Podofilox)

3D SDF for HMDB0015310 (Podofilox)

3D-SDF for HMDB0015310 (Podofilox)

PDB for HMDB0015310 (Podofilox)

3D PDB for HMDB0015310 (Podofilox)

SMILES for HMDB0015310 (Podofilox)

INCHI for HMDB0015310 (Podofilox)

Structure for HMDB0015310 (Podofilox)

3D Structure for HMDB0015310 (Podofilox)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References