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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:53:46 UTC

Update Date

2021-09-26 23:01:05 UTC

HMDB ID

HMDB0249930

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide

Description

N-hydroxy3-[1-(benzenesulfonyl)-1H-indol-5-yl]prop-2-enimidic acid belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Based on a literature review very few articles have been published on N-hydroxy3-[1-(benzenesulfonyl)-1H-indol-5-yl]prop-2-enimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (e)-3-[1-(benzenesulfonyl)indol-5-yl]-n-hydroxyprop-2-enamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 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

HMDB0249930
     RDKit          3D
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.9000   -1.8969   -0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.2169   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.6663   -0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.8984    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548   -0.4218    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844    0.3402   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    0.7857    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688    0.4958    1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -0.2814    2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356   -0.4509    3.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228    0.2261    3.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086    0.8044    2.1184 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252    1.7336    1.5107 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.8406    1.9076    2.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308    3.1241    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    0.9997    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4935   -0.0114    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.5999   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7865   -0.1871   -2.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.8139   -2.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2547    1.4013   -1.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787   -0.7258    1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -0.9872   -2.5131 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -1.4919   -2.7974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112   -0.0821   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -1.5114    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    0.5946   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    1.3949   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1096   -1.0077    4.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160    0.3127    4.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7606   -0.3557    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8250   -1.3851   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2884   -0.6762   -2.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310    1.1221   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    2.1881   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -1.3251    2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541   -0.4150   -3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6884   -1.6505   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  2  0
  2 23  1  0
 23 24  1  0
 22  5  1  0
 12  8  1  0
 21 16  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
 24 38  1  0
M  END


  Mrv1652309112108542D          

 24 26  0  0  0  0            999 V2000
   -1.1633    3.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563    2.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6534    1.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153    2.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    0.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862    1.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -3.5854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 19 17  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249930

> <DATABASE_NAME>
hmdb

> <SMILES>
ONC(=O)C=CC1=CC2=C(C=C1)N(C=C2)S(=O)(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O4S/c20-17(18-21)9-7-13-6-8-16-14(12-13)10-11-19(16)24(22,23)15-4-2-1-3-5-15/h1-12,21H,(H,18,20)

> <INCHI_KEY>
NBHWQUHEYOFBKG-UHFFFAOYSA-N

> <FORMULA>
C17H14N2O4S

> <MOLECULAR_WEIGHT>
342.37

> <EXACT_MASS>
342.067428113

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
34.37393039306836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[1-(benzenesulfonyl)-1H-indol-5-yl]-N-hydroxyprop-2-enamide

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.354097935

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.087096276975451

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.55537992538388

> <JCHEM_PKA_STRONGEST_BASIC>
-5.129130019136366

> <JCHEM_POLAR_SURFACE_AREA>
88.4

> <JCHEM_REFRACTIVITY>
90.75349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[1-(benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249930
     RDKit          3D
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.9000   -1.8969   -0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.2169   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.6663   -0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.8984    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548   -0.4218    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844    0.3402   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    0.7857    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688    0.4958    1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -0.2814    2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356   -0.4509    3.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228    0.2261    3.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086    0.8044    2.1184 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252    1.7336    1.5107 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.8406    1.9076    2.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308    3.1241    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    0.9997    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4935   -0.0114    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.5999   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7865   -0.1871   -2.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.8139   -2.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2547    1.4013   -1.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787   -0.7258    1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -0.9872   -2.5131 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -1.4919   -2.7974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112   -0.0821   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -1.5114    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    0.5946   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    1.3949   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1096   -1.0077    4.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160    0.3127    4.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7606   -0.3557    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8250   -1.3851   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2884   -0.6762   -2.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310    1.1221   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    2.1881   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -1.3251    2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541   -0.4150   -3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6884   -1.6505   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  2  0
  2 23  1  0
 23 24  1  0
 22  5  1  0
 12  8  1  0
 21 16  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
 24 38  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.171   5.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.665   5.481   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.189   4.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.220   2.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.202   4.657   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -0.744   1.408   0.000  0.00  0.00           S+0
HETATM    8  O   UNK     0      -2.208   0.932   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.721   1.884   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.865  -4.383   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       6.531  -6.693   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       7.865  -7.463   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0249930
HETATM    1  O1  UNL     1       5.900  -1.897  -0.409  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.309  -1.217  -1.263  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.004  -0.666  -0.989  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.446  -0.898   0.191  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.155  -0.422   0.617  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.384   0.340  -0.213  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.147   0.786   0.221  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.369   0.496   1.481  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.448  -0.281   2.291  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.236  -0.451   3.484  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.423   0.226   3.338  1.00  0.00           C  
HETATM   12  N1  UNL     1      -1.509   0.804   2.118  1.00  0.00           N  
HETATM   13  S1  UNL     1      -2.825   1.734   1.511  1.00  0.00           S  
HETATM   14  O2  UNL     1      -3.841   1.908   2.635  1.00  0.00           O  
HETATM   15  O3  UNL     1      -2.331   3.124   1.217  1.00  0.00           O  
HETATM   16  C11 UNL     1      -3.559   1.000   0.121  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.494  -0.011   0.251  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.101  -0.600  -0.839  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.786  -0.187  -2.112  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.863   0.814  -2.274  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.255   1.401  -1.158  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.679  -0.726   1.863  1.00  0.00           C  
HETATM   23  N2  UNL     1       5.932  -0.987  -2.513  1.00  0.00           N  
HETATM   24  O4  UNL     1       7.156  -1.492  -2.797  1.00  0.00           O  
HETATM   25  H1  UNL     1       3.511  -0.082  -1.740  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.004  -1.511   0.931  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.730   0.595  -1.194  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.490   1.395  -0.403  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.110  -1.008   4.348  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.216   0.313   4.075  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.761  -0.356   1.233  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.825  -1.385  -0.693  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.288  -0.676  -2.959  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.631   1.122  -3.283  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.536   2.188  -1.299  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.280  -1.325   2.521  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.454  -0.415  -3.255  1.00  0.00           H  
HETATM   38  H14 UNL     1       7.688  -1.650  -1.965  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   22
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   12
CONECT    9   10   22   22
CONECT   10   11   11   29
CONECT   11   12   30
CONECT   12   13
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   17   17   21
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21   34
CONECT   21   35
CONECT   22   36
CONECT   23   24   37
CONECT   24   38
END

HMDB0249930
     RDKit          3D
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide
 38 40  0  0  0  0  0  0  0  0999 V2000
    5.9000   -1.8969   -0.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3089   -1.2169   -1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -0.6663   -0.9886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -0.8984    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548   -0.4218    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844    0.3402   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    0.7857    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3688    0.4958    1.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482   -0.2814    2.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356   -0.4509    3.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228    0.2261    3.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086    0.8044    2.1184 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8252    1.7336    1.5107 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.8406    1.9076    2.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3308    3.1241    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    0.9997    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4935   -0.0114    0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.5999   -0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7865   -0.1871   -2.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.8139   -2.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2547    1.4013   -1.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6787   -0.7258    1.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -0.9872   -2.5131 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -1.4919   -2.7974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5112   -0.0821   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0040   -1.5114    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    0.5946   -1.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    1.3949   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1096   -1.0077    4.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160    0.3127    4.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7606   -0.3557    1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8250   -1.3851   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2884   -0.6762   -2.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310    1.1221   -3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5365    2.1881   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -1.3251    2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541   -0.4150   -3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6884   -1.6505   -1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  2  0
  2 23  1  0
 23 24  1  0
 22  5  1  0
 12  8  1  0
 21 16  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
 23 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Hydroxy3-[1-(benzenesulfonyl)-1H-indol-5-yl]prop-2-enimidate	Generator
N-Hydroxy3-[1-(benzenesulphonyl)-1H-indol-5-yl]prop-2-enimidate	Generator
N-Hydroxy3-[1-(benzenesulphonyl)-1H-indol-5-yl]prop-2-enimidic acid	Generator
(e)-3-[1-(Benzenesulphonyl)indol-5-yl]-N-hydroxyprop-2-enamide	Generator

Chemical Formula

C₁₇H₁₄N₂O₄S

Average Molecular Weight

342.37

Monoisotopic Molecular Weight

342.067428113

IUPAC Name

3-[1-(benzenesulfonyl)-1H-indol-5-yl]-N-hydroxyprop-2-enamide

Traditional Name

3-[1-(benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide

CAS Registry Number

Not Available

SMILES

ONC(=O)C=CC1=CC2=C(C=C1)N(C=C2)S(=O)(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H14N2O4S/c20-17(18-21)9-7-13-6-8-16-14(12-13)10-11-19(16)24(22,23)15-4-2-1-3-5-15/h1-12,21H,(H,18,20)

InChI Key

NBHWQUHEYOFBKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Benzenesulfonamide
Benzenesulfonyl group
Indole
Indole or derivatives
Styrene
Monocyclic benzene moiety
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Hydroxamic acid
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.09	ALOGPS
logP	2.35	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.75 m³·mol⁻¹	ChemAxon
Polarizability	34.37 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
DeepCCS	[M+H]+	176.985	30932474
DeepCCS	[M-H]-	174.627	30932474
DeepCCS	[M-2H]-	208.89	30932474
DeepCCS	[M+Na]+	184.535	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide	ONC(=O)C=CC1=CC2=C(C=C1)N(C=C2)S(=O)(=O)C1=CC=CC=C1	5212.6	Standard polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide	ONC(=O)C=CC1=CC2=C(C=C1)N(C=C2)S(=O)(=O)C1=CC=CC=C1	2996.1	Standard non polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide	ONC(=O)C=CC1=CC2=C(C=C1)N(C=C2)S(=O)(=O)C1=CC=CC=C1	3302.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide,1TMS,isomer #1	C[Si](C)(C)N(O)C(=O)C=CC1=CC=C2C(=C1)C=CN2S(=O)(=O)C1=CC=CC=C1	3363.8	Semi standard non polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide,1TMS,isomer #1	C[Si](C)(C)N(O)C(=O)C=CC1=CC=C2C(=C1)C=CN2S(=O)(=O)C1=CC=CC=C1	3012.5	Standard non polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide,1TMS,isomer #1	C[Si](C)(C)N(O)C(=O)C=CC1=CC=C2C(=C1)C=CN2S(=O)(=O)C1=CC=CC=C1	4486.5	Standard polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C(=O)C=CC1=CC=C2C(=C1)C=CN2S(=O)(=O)C1=CC=CC=C1	3586.0	Semi standard non polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C(=O)C=CC1=CC=C2C(=C1)C=CN2S(=O)(=O)C1=CC=CC=C1	3244.7	Standard non polar	33892256
(E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(O)C(=O)C=CC1=CC=C2C(=C1)C=CN2S(=O)(=O)C1=CC=CC=C1	4423.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1944000000-16e4535595e623968e40	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 10V, Positive-QTOF	splash10-03dl-0029000000-6af189a3785d46270be4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 20V, Positive-QTOF	splash10-007o-0965000000-6d24eb81d8fd8badb8f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 40V, Positive-QTOF	splash10-002f-2900000000-d24d4541b93b88ae5bd3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 10V, Negative-QTOF	splash10-0006-1019000000-4f8dc8c1b68f8763b962	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 20V, Negative-QTOF	splash10-052f-9111000000-5d7c0fcfc4e85ddc73fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide 40V, Negative-QTOF	splash10-0006-9610000000-92c4090e7aee28a0a62d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76034973

PDB ID

Not Available

ChEBI ID

Not Available

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 (E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide (HMDB0249930)

MOL for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

3D MOL for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

3D SDF for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

3D-SDF for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

PDB for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

3D PDB for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

SMILES for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

INCHI for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

Structure for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

3D Structure for HMDB0249930 ((E)-3-[1-(Benzenesulfonyl)indol-5-yl]-N-hydroxyprop-2-enamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra