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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014334

Secondary Accession Numbers

HMDB14334

Metabolite Identification

Common Name

Bortezomib

Description

Bortezomib, also known as velcade or PS 341, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Bortezomib is a drug which is used for treatment of multiple myeloma in patients who have not been successfully treated with at least two previous therapies. Bortezomib is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 04191212102D          

 28 29  0  0  1  0            999 V2000
    6.9269  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9269  -18.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2124  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2124  -19.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979  -17.7973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979  -18.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3558  -17.7973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414  -16.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0703  -17.3848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7848  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0703  -16.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -16.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -15.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -16.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4994  -14.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -16.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -15.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -18.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -17.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -17.7973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9282  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6427  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3572  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6427  -18.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -18.6223    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -19.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9282  -19.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  2  0  0  0  0
 12 13  1  0  0  0  0
 11 19  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END

HMDB0014334
     RDKit          3D
Bortezomib
 53 54  0  0  0  0  0  0  0  0999 V2000
   -3.3189   -1.3735   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3456   -0.2734   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6847   -0.8632   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456    0.9193    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.6183   -0.1604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5517    1.0170   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    0.3788    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039   -0.3513    1.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    0.5179   -0.9134 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8639   -0.7037   -1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856   -1.9531   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878   -2.8624   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289   -4.0386   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -4.3153    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -3.4342   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -2.2584   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160    0.7010   -0.1733 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9803    1.7038   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575    2.5308   -1.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975    1.8448    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849    2.7342    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    2.8337    0.8698 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067    2.0622    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    1.1505    2.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236    1.0581    1.4396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801    2.9415    0.7828 B   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3735    4.2103    0.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946    2.7114    2.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -2.3177   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -1.1028   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478   -1.5990    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050    0.0134   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -1.2953   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5191   -1.6713    0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3240   -0.0761    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257    0.7324    1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8453    1.6781   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    2.0114   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9056    0.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    1.3883   -1.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -0.5833   -2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -0.8086   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7679   -2.7029   -0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -4.7478    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -5.2311    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9399   -3.6776   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357   -1.6174   -1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947    0.0511    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    3.3569   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000    2.1955    2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5090    0.5194    3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1796    4.6661   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947    1.7815    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 26 28  1  0
 16 11  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  9 40  1  6
 10 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
 28 53  1  0
M  END


  Mrv0541 04191212102D          

 28 29  0  0  1  0            999 V2000
    6.9269  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9269  -18.6223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2124  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2124  -19.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979  -17.7973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4979  -18.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3558  -17.7973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414  -16.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0703  -17.3848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7848  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0703  -16.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -16.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -15.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -16.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4994  -14.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -16.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -15.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -18.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -17.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -17.7973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9282  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6427  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3572  -17.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6427  -18.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2138  -18.6223    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -19.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9282  -19.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  2  0  0  0  0
 12 13  1  0  0  0  0
 11 19  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014334

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)B(O)O

> <INCHI_IDENTIFIER>
InChI=1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1

> <INCHI_KEY>
GXJABQQUPOEUTA-RDJZCZTQSA-N

> <FORMULA>
C19H25BN4O4

> <MOLECULAR_WEIGHT>
384.237

> <EXACT_MASS>
384.196885774

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.47959960860195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R)-3-methyl-1-[(2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanamido]butyl]boronic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.5303000000000004

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.82409734011327

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.037310355452274

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6960069020998824

> <JCHEM_POLAR_SURFACE_AREA>
124.44000000000001

> <JCHEM_REFRACTIVITY>
99.37379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bortezomib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014334
     RDKit          3D
Bortezomib
 53 54  0  0  0  0  0  0  0  0999 V2000
   -3.3189   -1.3735   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3456   -0.2734   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6847   -0.8632   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456    0.9193    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.6183   -0.1604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5517    1.0170   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    0.3788    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039   -0.3513    1.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    0.5179   -0.9134 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8639   -0.7037   -1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856   -1.9531   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878   -2.8624   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289   -4.0386   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -4.3153    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -3.4342   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -2.2584   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160    0.7010   -0.1733 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9803    1.7038   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575    2.5308   -1.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975    1.8448    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849    2.7342    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    2.8337    0.8698 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067    2.0622    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    1.1505    2.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236    1.0581    1.4396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801    2.9415    0.7828 B   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3735    4.2103    0.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946    2.7114    2.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -2.3177   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -1.1028   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478   -1.5990    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050    0.0134   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -1.2953   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5191   -1.6713    0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3240   -0.0761    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257    0.7324    1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8453    1.6781   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    2.0114   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9056    0.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    1.3883   -1.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -0.5833   -2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -0.8086   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7679   -2.7029   -0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -4.7478    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -5.2311    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9399   -3.6776   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357   -1.6174   -1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947    0.0511    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    3.3569   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000    2.1955    2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5090    0.5194    3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1796    4.6661   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947    1.7815    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 26 28  1  0
 16 11  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  9 40  1  6
 10 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
 28 53  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      12.930 -33.222   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      12.930 -34.762   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      11.596 -32.452   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.596 -35.532   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      10.263 -33.222   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      10.263 -34.762   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.264 -32.452   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      15.597 -33.222   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      14.264 -30.912   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.931 -32.452   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.265 -33.222   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.931 -30.912   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.265 -30.142   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.265 -28.601   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.599 -30.912   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.599 -27.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.932 -30.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.932 -28.601   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.265 -34.762   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      19.599 -32.452   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      20.932 -33.222   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.266 -32.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.600 -33.222   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.933 -32.452   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.600 -34.762   0.000  0.00  0.00           C+0
HETATM   26  B   UNK     0      20.932 -34.762   0.000  0.00  0.00           B+0
HETATM   27  O   UNK     0      19.599 -35.532   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.266 -35.532   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    1    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10   19   20                                                  
CONECT   12   10   13                                                       
CONECT   13   14   15   12                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
CONECT   19   11                                                            
CONECT   20   11   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0014334
HETATM    1  C1  UNL     1      -3.319  -1.373  -0.562  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.346  -0.273  -0.672  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.685  -0.863  -0.231  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.046   0.919   0.157  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.728   1.618  -0.160  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.552   1.017  -0.035  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.303   0.379   0.098  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.004  -0.351   1.078  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.779   0.518  -0.913  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.864  -0.704  -1.792  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.186  -1.953  -1.118  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.288  -2.862  -0.654  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.629  -4.039  -0.007  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.955  -4.315   0.186  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.888  -3.434  -0.262  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.542  -2.258  -0.909  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.016   0.701  -0.173  1.00  0.00           N  
HETATM   18  C15 UNL     1       2.980   1.704  -0.453  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.858   2.531  -1.393  1.00  0.00           O  
HETATM   20  C16 UNL     1       4.198   1.845   0.347  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.185   2.734   0.071  1.00  0.00           C  
HETATM   22  N3  UNL     1       6.272   2.834   0.870  1.00  0.00           N  
HETATM   23  C18 UNL     1       6.407   2.062   1.950  1.00  0.00           C  
HETATM   24  C19 UNL     1       5.416   1.151   2.250  1.00  0.00           C  
HETATM   25  N4  UNL     1       4.324   1.058   1.440  1.00  0.00           N  
HETATM   26  B1  UNL     1      -2.780   2.942   0.783  1.00  0.00           B  
HETATM   27  O3  UNL     1      -2.373   4.210   0.207  1.00  0.00           O  
HETATM   28  O4  UNL     1      -2.695   2.711   2.222  1.00  0.00           O  
HETATM   29  H1  UNL     1      -3.676  -2.318  -1.032  1.00  0.00           H  
HETATM   30  H2  UNL     1      -2.409  -1.103  -1.101  1.00  0.00           H  
HETATM   31  H3  UNL     1      -3.148  -1.599   0.490  1.00  0.00           H  
HETATM   32  H4  UNL     1      -4.505   0.013  -1.745  1.00  0.00           H  
HETATM   33  H5  UNL     1      -6.208  -1.295  -1.092  1.00  0.00           H  
HETATM   34  H6  UNL     1      -5.519  -1.671   0.512  1.00  0.00           H  
HETATM   35  H7  UNL     1      -6.324  -0.076   0.244  1.00  0.00           H  
HETATM   36  H8  UNL     1      -4.126   0.732   1.242  1.00  0.00           H  
HETATM   37  H9  UNL     1      -4.845   1.678  -0.067  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.878   2.011  -1.242  1.00  0.00           H  
HETATM   39  H11 UNL     1      -1.906   0.530   1.177  1.00  0.00           H  
HETATM   40  H12 UNL     1       0.598   1.388  -1.532  1.00  0.00           H  
HETATM   41  H13 UNL     1       1.525  -0.583  -2.646  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.176  -0.809  -2.238  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.768  -2.703  -0.776  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.101  -4.748   0.352  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.214  -5.231   0.695  1.00  0.00           H  
HETATM   46  H18 UNL     1       3.940  -3.678  -0.095  1.00  0.00           H  
HETATM   47  H19 UNL     1       3.336  -1.617  -1.232  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.195   0.051   0.611  1.00  0.00           H  
HETATM   49  H21 UNL     1       5.084   3.357  -0.798  1.00  0.00           H  
HETATM   50  H22 UNL     1       7.300   2.195   2.547  1.00  0.00           H  
HETATM   51  H23 UNL     1       5.509   0.519   3.130  1.00  0.00           H  
HETATM   52  H24 UNL     1      -3.180   4.666  -0.185  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.895   1.782   2.456  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   26   38
CONECT    6    7   39
CONECT    7    8    8    9
CONECT    9   10   17   40
CONECT   10   11   41   42
CONECT   11   12   12   16
CONECT   12   13   43
CONECT   13   14   14   44
CONECT   14   15   45
CONECT   15   16   16   46
CONECT   16   47
CONECT   17   18   48
CONECT   18   19   19   20
CONECT   20   21   21   25
CONECT   21   22   49
CONECT   22   23   23
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   26   27   28
CONECT   27   52
CONECT   28   53
END

HMDB0014334
     RDKit          3D
Bortezomib
 53 54  0  0  0  0  0  0  0  0999 V2000
   -3.3189   -1.3735   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3456   -0.2734   -0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6847   -0.8632   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456    0.9193    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    1.6183   -0.1604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5517    1.0170   -0.0349 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    0.3788    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039   -0.3513    1.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    0.5179   -0.9134 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8639   -0.7037   -1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856   -1.9531   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878   -2.8624   -0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289   -4.0386   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -4.3153    0.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -3.4342   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422   -2.2584   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160    0.7010   -0.1733 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9803    1.7038   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575    2.5308   -1.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1975    1.8448    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1849    2.7342    0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    2.8337    0.8698 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4067    2.0622    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158    1.1505    2.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236    1.0581    1.4396 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7801    2.9415    0.7828 B   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3735    4.2103    0.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946    2.7114    2.2221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6756   -2.3177   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -1.1028   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1478   -1.5990    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050    0.0134   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -1.2953   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5191   -1.6713    0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3240   -0.0761    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257    0.7324    1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8453    1.6781   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8785    2.0114   -1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9056    0.5305    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    1.3883   -1.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -0.5833   -2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -0.8086   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7679   -2.7029   -0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -4.7478    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140   -5.2311    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9399   -3.6776   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3357   -1.6174   -1.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947    0.0511    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0839    3.3569   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3000    2.1955    2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5090    0.5194    3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1796    4.6661   -0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8947    1.7815    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  5 26  1  0
 26 27  1  0
 26 28  1  0
 16 11  1  0
 25 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  9 40  1  6
 10 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
 28 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[(1R)-1-(DIHYDROXYBORYL)-3-methylbutyl]-N-(pyrazin-2-ylcarbonyl)-L-phenylalaninamide	ChEBI
PS 341	ChEBI
PS-341	ChEBI
Velcade	ChEBI
341, PS	HMDB
LDP 341	HMDB
LDP-341	HMDB

Chemical Formula

C₁₉H₂₅BN₄O₄

Average Molecular Weight

384.237

Monoisotopic Molecular Weight

384.196885774

IUPAC Name

[(1R)-3-methyl-1-[(2S)-3-phenyl-2-(pyrazin-2-ylformamido)propanamido]butyl]boronic acid

Traditional Name

bortezomib

CAS Registry Number

179324-69-7

SMILES

CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)B(O)O

InChI Identifier

InChI=1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17-/m0/s1

InChI Key

GXJABQQUPOEUTA-RDJZCZTQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Amphetamine or derivatives
Pyrazine carboxylic acid or derivatives
Pyrazinecarboxamide
2-heteroaryl carboxamide
Monocyclic benzene moiety
Fatty amide
Pyrazine
Benzenoid
Fatty acyl
Heteroaromatic compound
Boronic acid derivative
Boronic acid
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organic metalloid salt
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organoboron compound
Organopnictogen compound
Alkylborane
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Monoalkylborane
Organic salt
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazines (CHEBI:52717 )
amino acid amide (CHEBI:52717 )
L-phenylalanine derivative (CHEBI:52717 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014334)
Membrane (HMDB: HMDB0014334)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.053 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.053 g/L	ALOGPS
logP	0.89	ALOGPS
logP	1.53	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-0.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	99.37 m³·mol⁻¹	ChemAxon
Polarizability	40.48 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	192.2	32859911
AllCCS	[M+H-H2O]+	189.6	32859911
AllCCS	[M+NH4]+	194.7	32859911
AllCCS	[M+Na]+	195.4	32859911
AllCCS	[M-H]-	190.0	32859911
AllCCS	[M+Na-2H]-	190.5	32859911
AllCCS	[M+HCOO]-	191.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bortezomib	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)B(O)O	3686.5	Standard polar	33892256
Bortezomib	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)B(O)O	2470.4	Standard non polar	33892256
Bortezomib	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)B(O)O	3183.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bortezomib,1TMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)[Si](C)(C)C	2901.8	Semi standard non polar	33892256
Bortezomib,1TMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)[Si](C)(C)C	2732.2	Standard non polar	33892256
Bortezomib,1TMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)[Si](C)(C)C	4729.1	Standard polar	33892256
Bortezomib,1TMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C)B(O)O	2934.1	Semi standard non polar	33892256
Bortezomib,1TMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C)B(O)O	2598.7	Standard non polar	33892256
Bortezomib,1TMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C)B(O)O	4643.1	Standard polar	33892256
Bortezomib,2TMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C)[Si](C)(C)C	2901.7	Semi standard non polar	33892256
Bortezomib,2TMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C)[Si](C)(C)C	2737.0	Standard non polar	33892256
Bortezomib,2TMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C)[Si](C)(C)C	4311.6	Standard polar	33892256
Bortezomib,1TBDMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C	3121.2	Semi standard non polar	33892256
Bortezomib,1TBDMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C	2898.7	Standard non polar	33892256
Bortezomib,1TBDMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)NC(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C	4714.1	Standard polar	33892256
Bortezomib,1TBDMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C)B(O)O	3141.5	Semi standard non polar	33892256
Bortezomib,1TBDMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C)B(O)O	2783.1	Standard non polar	33892256
Bortezomib,1TBDMS,isomer #2	CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C)B(O)O	4615.6	Standard polar	33892256
Bortezomib,2TBDMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3287.2	Semi standard non polar	33892256
Bortezomib,2TBDMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3066.9	Standard non polar	33892256
Bortezomib,2TBDMS,isomer #1	CC(C)C[C@@H](B(O)O)N(C(=O)[C@H](CC1=CC=CC=C1)N(C(=O)C1=CN=CC=N1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4352.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bortezomib GC-MS (Non-derivatized) - 70eV, Positive	splash10-002e-9242000000-9fa602d07e0566dc1738	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bortezomib GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bortezomib 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 - Bortezomib LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0035900000-122163b342b985220f63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bortezomib LC-ESI-qTof , Positive-QTOF	splash10-016r-1397000000-e168634cfe7e1453d742	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bortezomib , positive-QTOF	splash10-0a4i-0035900000-122163b342b985220f63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bortezomib , positive-QTOF	splash10-016r-1397000000-e168634cfe7e1453d742	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 10V, Positive-QTOF	splash10-0040-0945000000-717d35ff034d0823a60b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 20V, Positive-QTOF	splash10-040r-2920000000-7cf2f714cdc618ca8e8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 40V, Positive-QTOF	splash10-0a59-9500000000-a64c45db287441805ffc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 10V, Negative-QTOF	splash10-00lr-4369000000-54da8c6f6ac19bc3a537	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 20V, Negative-QTOF	splash10-0a7i-7696000000-a8904f81583ba4b00fd9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 40V, Negative-QTOF	splash10-00b9-9830000000-fb072cbf98c79ced110d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 10V, Positive-QTOF	splash10-000i-0019000000-738c7318d1c90ad3d40e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 20V, Positive-QTOF	splash10-002r-2497000000-05ce46c969a07d400170	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 40V, Positive-QTOF	splash10-0a4i-2910000000-b1c62abf177f3ec176c5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 10V, Negative-QTOF	splash10-00kr-0009000000-f57a7486c4cab88316bf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 20V, Negative-QTOF	splash10-0006-9012000000-f47b8deb96b3fec82f1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bortezomib 40V, Negative-QTOF	splash10-0006-9100000000-8c4defe85755665f03f3	2021-09-24	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 DB00188	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00188	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00188

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

343402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bortezomib

METLIN ID

Not Available

PubChem Compound

387447

PDB ID

BO2

ChEBI ID

52717

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

Voorhees PM, Dees EC, O'Neil B, Orlowski RZ: The proteasome as a target for cancer therapy. Clin Cancer Res. 2003 Dec 15;9(17):6316-25. [PubMed:14695130 ]
Adams J, Kauffman M: Development of the proteasome inhibitor Velcade (Bortezomib). Cancer Invest. 2004;22(2):304-11. [PubMed:15199612 ]
Oakervee HE, Popat R, Curry N, Smith P, Morris C, Drake M, Agrawal S, Stec J, Schenkein D, Esseltine DL, Cavenagh JD: PAD combination therapy (PS-341/bortezomib, doxorubicin and dexamethasone) for previously untreated patients with multiple myeloma. Br J Haematol. 2005 Jun;129(6):755-62. [PubMed:15953001 ]
Bonvini P, Zorzi E, Basso G, Rosolen A: Bortezomib-mediated 26S proteasome inhibition causes cell-cycle arrest and induces apoptosis in CD-30+ anaplastic large cell lymphoma. Leukemia. 2007 Apr;21(4):838-42. Epub 2007 Feb 1. [PubMed:17268529 ]

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. 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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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. Cytochrome P450 2C9

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

4. 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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

6. Cytochrome P450 1A1

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

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

7. Cytochrome P450 1A2

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

8. Cytochrome P450 2C8

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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 ]

Transporters

Enzyme Details

1. High affinity copper uptake protein 1

General function:: Involved in copper ion transmembrane transporter activity
Specific function:: Involved in high-affinity copper uptake
Gene Name:: SLC31A1
Uniprot ID:: O15431
Molecular weight:: 21090.5

References

Jandial DD, Farshchi-Heydari S, Larson CA, Elliott GI, Wrasidlo WJ, Howell SB: Enhanced delivery of cisplatin to intraperitoneal ovarian carcinomas mediated by the effects of bortezomib on the human copper transporter 1. Clin Cancer Res. 2009 Jan 15;15(2):553-60. doi: 10.1158/1078-0432.CCR-08-2081. [PubMed:19147760 ]

Showing metabocard for Bortezomib (HMDB0014334)

MOL for HMDB0014334 (Bortezomib)

3D MOL for HMDB0014334 (Bortezomib)

3D SDF for HMDB0014334 (Bortezomib)

3D-SDF for HMDB0014334 (Bortezomib)

PDB for HMDB0014334 (Bortezomib)

3D PDB for HMDB0014334 (Bortezomib)

SMILES for HMDB0014334 (Bortezomib)

INCHI for HMDB0014334 (Bortezomib)

Structure for HMDB0014334 (Bortezomib)

3D Structure for HMDB0014334 (Bortezomib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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