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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:46:33 UTC

Update Date

2021-09-26 23:17:39 UTC

HMDB ID

HMDB0259838

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vismodegib

Description

Vismodegib, also known as erivedge, belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene. Based on a literature review a significant number of articles have been published on Vismodegib. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vismodegib is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vismodegib is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

 
  Mrv0541 05281322232D          
 
 27 29  0  0  0  0            999 V2000
    7.6725  -10.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6725  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3870  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1015  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1015  -10.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3870  -10.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8269  -10.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5371  -10.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2515  -10.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2515   -9.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5413   -8.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8269   -9.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1082   -8.9836    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.9773  -10.6398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6794  -10.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3803  -10.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6793   -9.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3805  -11.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0951  -11.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8095  -11.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8093  -10.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0947  -10.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0946   -9.4051    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5237  -11.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.2381  -12.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9362  -11.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1112  -12.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 16 22  2  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  2  0  0  0  0
M  END

HMDB0259838
     RDKit          3D
Vismodegib
 41 43  0  0  0  0  0  0  0  0999 V2000
    7.7241   -0.8387   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3338   -1.6665   -0.7283 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.3194   -3.0725   -0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5662   -1.7622   -2.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342   -0.8275   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.1288    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086   -0.4751    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176    0.4985    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369    1.1949    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    2.2368    1.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    0.6609    0.0098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380    1.1940    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5731    2.4633    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    2.8777    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327    2.0581    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5752    2.6015    0.7943 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326    0.7684    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9063   -0.0860   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7712   -1.3629   -0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9039   -2.1447   -0.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1423   -1.5865   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2319   -0.3073   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1367    0.4069    0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    0.3654   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    0.7996   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    2.0363   -2.0423 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3389    0.1485   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5473   -1.5535    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4727   -0.2650    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575   -0.1280   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895   -1.9070    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -0.7369    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162   -0.2322   -0.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593    3.1577    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0235    3.8898    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010   -1.7970   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7718   -3.1528   -1.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0532   -2.1769   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2240    0.0987   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436   -0.6430   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.3942   -2.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  2  0
  8 25  1  0
 25 26  1  0
 25 27  2  0
 27  5  1  0
 24 12  1  0
 23 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  1  0
 27 41  1  0
M  END

 
  Mrv0541 05281322232D          
 
 27 29  0  0  0  0            999 V2000
    7.6725  -10.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6725  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3870  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1015  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1015  -10.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3870  -10.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8269  -10.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5371  -10.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2515  -10.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2515   -9.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5413   -8.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8269   -9.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1082   -8.9836    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.9773  -10.6398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6794  -10.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3803  -10.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6793   -9.4051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3805  -11.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0951  -11.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8095  -11.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8093  -10.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0947  -10.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0946   -9.4051    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5237  -11.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.2381  -12.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9362  -11.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1112  -12.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 16 22  2  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259838

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)

> <INCHI_KEY>
BPQMGSKTAYIVFO-UHFFFAOYSA-N

> <FORMULA>
C19H14Cl2N2O3S

> <MOLECULAR_WEIGHT>
421.297

> <EXACT_MASS>
420.010218428

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.49217152940425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-methanesulfonylbenzamide

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
3.9289317773333328

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.697470171450448

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.269496925484273

> <JCHEM_PKA_STRONGEST_BASIC>
3.703528641105209

> <JCHEM_POLAR_SURFACE_AREA>
76.13

> <JCHEM_REFRACTIVITY>
107.81199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vismodegib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259838
     RDKit          3D
Vismodegib
 41 43  0  0  0  0  0  0  0  0999 V2000
    7.7241   -0.8387   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3338   -1.6665   -0.7283 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.3194   -3.0725   -0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5662   -1.7622   -2.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342   -0.8275   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.1288    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086   -0.4751    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176    0.4985    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369    1.1949    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    2.2368    1.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    0.6609    0.0098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380    1.1940    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5731    2.4633    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    2.8777    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327    2.0581    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5752    2.6015    0.7943 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326    0.7684    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9063   -0.0860   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7712   -1.3629   -0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9039   -2.1447   -0.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1423   -1.5865   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2319   -0.3073   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1367    0.4069    0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    0.3654   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    0.7996   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    2.0363   -2.0423 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3389    0.1485   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5473   -1.5535    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4727   -0.2650    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575   -0.1280   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895   -1.9070    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -0.7369    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162   -0.2322   -0.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593    3.1577    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0235    3.8898    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010   -1.7970   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7718   -3.1528   -1.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0532   -2.1769   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2240    0.0987   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436   -0.6430   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.3942   -2.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  2  0
  8 25  1  0
 25 26  1  0
 25 27  2  0
 27  5  1  0
 24 12  1  0
 23 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  1  0
 27 41  1  0
M  END

HEADER    PROTEIN                                 28-MAY-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-13         0                                  
HETATM    1  C   UNK     0      14.322 -19.866   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.322 -21.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.656 -22.176   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.989 -21.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.989 -19.866   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      15.656 -19.096   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      18.344 -19.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.669 -19.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.003 -19.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.003 -17.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.677 -16.774   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.344 -17.544   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      17.002 -16.769   0.000  0.00  0.00          Cl+0
HETATM   14  N   UNK     0      22.358 -19.861   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      23.668 -19.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.977 -19.859   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      23.668 -17.556   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      24.977 -21.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.311 -22.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.644 -21.405   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.644 -19.859   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.310 -19.089   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0      26.310 -17.556   0.000  0.00  0.00          Cl+0
HETATM   24  S   UNK     0      28.978 -22.175   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0      30.311 -22.945   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      29.748 -20.841   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      28.208 -23.508   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   18   22                                                  
CONECT   17   15                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0259838
HETATM    1  C1  UNL     1       7.724  -0.839  -0.011  1.00  0.00           C  
HETATM    2  S1  UNL     1       6.334  -1.666  -0.728  1.00  0.00           S  
HETATM    3  O1  UNL     1       6.319  -3.072  -0.200  1.00  0.00           O  
HETATM    4  O2  UNL     1       6.566  -1.762  -2.223  1.00  0.00           O  
HETATM    5  C2  UNL     1       4.834  -0.828  -0.394  1.00  0.00           C  
HETATM    6  C3  UNL     1       4.102  -1.129   0.734  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.909  -0.475   1.019  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.418   0.498   0.181  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.137   1.195   0.493  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.161   2.237   1.179  1.00  0.00           O  
HETATM   11  N1  UNL     1      -0.050   0.661   0.010  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.338   1.194   0.208  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.573   2.463   0.674  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.882   2.878   0.848  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.933   2.058   0.567  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -5.575   2.602   0.794  1.00  0.00          CL  
HETATM   17  C11 UNL     1      -3.733   0.768   0.093  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.906  -0.086  -0.198  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.771  -1.363  -0.667  1.00  0.00           C  
HETATM   20  C14 UNL     1      -5.904  -2.145  -0.933  1.00  0.00           C  
HETATM   21  C15 UNL     1      -7.142  -1.587  -0.708  1.00  0.00           C  
HETATM   22  C16 UNL     1      -7.232  -0.307  -0.239  1.00  0.00           C  
HETATM   23  N2  UNL     1      -6.137   0.407   0.003  1.00  0.00           N  
HETATM   24  C17 UNL     1      -2.447   0.365  -0.076  1.00  0.00           C  
HETATM   25  C18 UNL     1       3.148   0.800  -0.945  1.00  0.00           C  
HETATM   26 CL2  UNL     1       2.558   2.036  -2.042  1.00  0.00          CL  
HETATM   27  C19 UNL     1       4.339   0.148  -1.231  1.00  0.00           C  
HETATM   28  H1  UNL     1       8.547  -1.554   0.242  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.473  -0.265   0.890  1.00  0.00           H  
HETATM   30  H3  UNL     1       8.158  -0.128  -0.767  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.489  -1.907   1.409  1.00  0.00           H  
HETATM   32  H5  UNL     1       2.351  -0.737   1.922  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.016  -0.232  -0.568  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.759   3.158   0.902  1.00  0.00           H  
HETATM   35  H8  UNL     1      -3.023   3.890   1.220  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.801  -1.797  -0.842  1.00  0.00           H  
HETATM   37  H10 UNL     1      -5.772  -3.153  -1.303  1.00  0.00           H  
HETATM   38  H11 UNL     1      -8.053  -2.177  -0.907  1.00  0.00           H  
HETATM   39  H12 UNL     1      -8.224   0.099  -0.074  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.244  -0.643  -0.446  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.916   0.394  -2.131  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6    6   27
CONECT    6    7   31
CONECT    7    8    8   32
CONECT    8    9   25
CONECT    9   10   10   11
CONECT   11   12   33
CONECT   12   13   13   24
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   17
CONECT   17   18   24   24
CONECT   18   19   19   23
CONECT   19   20   36
CONECT   20   21   21   37
CONECT   21   22   38
CONECT   22   23   23   39
CONECT   24   40
CONECT   25   26   27   27
CONECT   27   41
END

HMDB0259838
     RDKit          3D
Vismodegib
 41 43  0  0  0  0  0  0  0  0999 V2000
    7.7241   -0.8387   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3338   -1.6665   -0.7283 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.3194   -3.0725   -0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5662   -1.7622   -2.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342   -0.8275   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.1288    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086   -0.4751    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4176    0.4985    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369    1.1949    0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    2.2368    1.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495    0.6609    0.0098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3380    1.1940    0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5731    2.4633    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    2.8777    0.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327    2.0581    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5752    2.6015    0.7943 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326    0.7684    0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9063   -0.0860   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7712   -1.3629   -0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9039   -2.1447   -0.9325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1423   -1.5865   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2319   -0.3073   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1367    0.4069    0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    0.3654   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479    0.7996   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5576    2.0363   -2.0423 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3389    0.1485   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5473   -1.5535    0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4727   -0.2650    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575   -0.1280   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895   -1.9070    1.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -0.7369    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162   -0.2322   -0.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7593    3.1577    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0235    3.8898    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010   -1.7970   -0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7718   -3.1528   -1.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0532   -2.1769   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2240    0.0987   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436   -0.6430   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9163    0.3942   -2.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 24  2  0
  8 25  1  0
 25 26  1  0
 25 27  2  0
 27  5  1  0
 24 12  1  0
 23 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  1  0
 27 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Erivedge	ChEBI
Vismodegibum	ChEBI
HhAntag691	MeSH
R3616 CPD	MeSH

Chemical Formula

C₁₉H₁₄Cl₂N₂O₃S

Average Molecular Weight

421.297

Monoisotopic Molecular Weight

420.010218428

IUPAC Name

2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-methanesulfonylbenzamide

Traditional Name

vismodegib

CAS Registry Number

Not Available

SMILES

CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1

InChI Identifier

InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)

InChI Key

BPQMGSKTAYIVFO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
2-phenylpyridine
2-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzenesulfonyl group
Benzoyl
Chlorobenzene
Halobenzene
Pyridine
Aryl halide
Aryl chloride
Vinylogous halide
Heteroaromatic compound
Sulfonyl
Sulfone
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone (CHEBI:66903 )
benzamides (CHEBI:66903 )
pyridines (CHEBI:66903 )
monochlorobenzenes (CHEBI:66903 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.22	ALOGPS
logP	3.93	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.81 m³·mol⁻¹	ChemAxon
Polarizability	39.49 Å³	ChemAxon
Number of Rings	3	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]+	192.748	32859911
AllCCS	[M+H-H2O]+	190.059	32859911
AllCCS	[M+Na]+	195.934	32859911
AllCCS	[M+NH4]+	195.225	32859911
AllCCS	[M-H]-	183.962	32859911
AllCCS	[M+Na-2H]-	183.498	32859911
AllCCS	[M+HCOO]-	183.14	32859911
DeepCCS	[M+H]+	189.709	30932474
DeepCCS	[M-H]-	187.351	30932474
DeepCCS	[M-2H]-	220.862	30932474
DeepCCS	[M+Na]+	196.09	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vismodegib	CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1	5262.6	Standard polar	33892256
Vismodegib	CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1	3537.5	Standard non polar	33892256
Vismodegib	CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1	3822.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vismodegib,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C1=CC=C(Cl)C(C2=CC=CC=N2)=C1	3416.4	Semi standard non polar	33892256
Vismodegib,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C1=CC=C(Cl)C(C2=CC=CC=N2)=C1	3467.6	Standard non polar	33892256
Vismodegib,1TMS,isomer #1	C[Si](C)(C)N(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C1=CC=C(Cl)C(C2=CC=CC=N2)=C1	4384.0	Standard polar	33892256
Vismodegib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C1=CC=C(Cl)C(C2=CC=CC=N2)=C1	3626.8	Semi standard non polar	33892256
Vismodegib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C1=CC=C(Cl)C(C2=CC=CC=N2)=C1	3675.6	Standard non polar	33892256
Vismodegib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(S(C)(=O)=O)C=C1Cl)C1=CC=C(Cl)C(C2=CC=CC=N2)=C1	4364.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vismodegib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gdr-4951100000-0071865ba804a5101fbf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vismodegib 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 - Vismodegib , positive-QTOF	splash10-00di-0212900000-190a5fdca2d781122e92	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vismodegib 10V, Positive-QTOF	splash10-00di-0000900000-f9e751cccc530a0515a5	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vismodegib 20V, Positive-QTOF	splash10-00di-0002900000-755a8d6f1218b3807a00	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vismodegib 40V, Positive-QTOF	splash10-0uec-5964100000-0ff4b3037b11c3a0931e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vismodegib 10V, Negative-QTOF	splash10-014i-0000900000-5a5cc27e568fa409d70a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vismodegib 20V, Negative-QTOF	splash10-014i-0121900000-5096c79c2bbcc9c104e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vismodegib 40V, Negative-QTOF	splash10-004i-5892000000-f615821e2284fc031649	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08828

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23337846

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vismodegib

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66903

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Vismodegib (HMDB0259838)

MOL for HMDB0259838 (Vismodegib)

3D MOL for HMDB0259838 (Vismodegib)

3D SDF for HMDB0259838 (Vismodegib)

3D-SDF for HMDB0259838 (Vismodegib)

PDB for HMDB0259838 (Vismodegib)

3D PDB for HMDB0259838 (Vismodegib)

SMILES for HMDB0259838 (Vismodegib)

INCHI for HMDB0259838 (Vismodegib)

Structure for HMDB0259838 (Vismodegib)

3D Structure for HMDB0259838 (Vismodegib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra