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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:59:14 UTC

Update Date

2021-09-26 23:01:12 UTC

HMDB ID

HMDB0250015

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid

Description

(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid, also known as 6,7,8,9-tetrahydro-5-(H)-benzocycloheptene-5-ol-4-ylideneacetic acid or NCS 382, belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings. Based on a literature review very few articles have been published on (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (s,e)-2-(5-hydroxy-8,9-dihydro-5h-benzo[7]annulen-6(7h)-ylidene)acetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 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

HMDB0255489
     RDKit          3D
6,7,8,9-Tetrahydro-5-hydroxy-5H-benzocyclohept-6-ylideneacetic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.0465   -0.8799    2.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -0.3884    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    0.7784    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863   -1.0658    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559   -0.6740   -0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    0.5197   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    1.7649   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    1.5100    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229    0.5924    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    1.1725    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909    0.4589    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -0.8589   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2671   -1.4618   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -0.7229   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546   -1.5797   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -2.6434    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960    1.3102    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730   -1.9942    1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774    0.3693   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    0.6991   -1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    2.4502   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    2.3733   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653    2.4679    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4474    1.1343    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553    2.1907    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.8716    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -1.4364   -0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197   -2.4905   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534   -1.9488   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3631   -2.5189    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15  5  1  0
 14  9  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
M  END

  Mrv1652309112108592D          

 16 17  0  0  0  0            999 V2000
    2.0408    0.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915    1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374    1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374    2.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    2.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915    2.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    2.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    3.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    3.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    3.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682    4.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988    1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    3.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
  1 15  1  0  0  0  0
  9 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250015

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C2=CC=CC=C2CCCC1=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)

> <INCHI_KEY>
UADPGHINQMWEAG-UHFFFAOYSA-N

> <FORMULA>
C13H14O3

> <MOLECULAR_WEIGHT>
218.252

> <EXACT_MASS>
218.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.811408699441504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{5-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-ylidene}acetic acid

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.160676741333334

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.888707555325698

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.647623230855477

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3144179084065737

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
61.144400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-hydroxy-5,7,8,9-tetrahydrobenzo[7]annulen-6-ylidene}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255489
     RDKit          3D
6,7,8,9-Tetrahydro-5-hydroxy-5H-benzocyclohept-6-ylideneacetic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.0465   -0.8799    2.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -0.3884    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    0.7784    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863   -1.0658    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559   -0.6740   -0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    0.5197   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    1.7649   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    1.5100    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229    0.5924    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    1.1725    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909    0.4589    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -0.8589   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2671   -1.4618   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -0.7229   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546   -1.5797   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -2.6434    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960    1.3102    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730   -1.9942    1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774    0.3693   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    0.6991   -1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    2.4502   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    2.3733   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653    2.4679    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4474    1.1343    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553    2.1907    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.8716    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -1.4364   -0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197   -2.4905   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534   -1.9488   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3631   -2.5189    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15  5  1  0
 14  9  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  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       3.810   1.675   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.308   1.333   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.104   2.293   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.230   1.523   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.563   2.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.563   3.833   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.230   4.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.104   3.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.308   4.793   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.810   4.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.770   5.654   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.207   7.088   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.684   7.317   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.167   8.292   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.478   3.063   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.965   6.294   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10    1                                                       
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0255489
HETATM    1  O1  UNL     1       4.047  -0.880   2.013  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.298  -0.388   1.074  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.698   0.778   0.451  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.086  -1.066   0.715  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.256  -0.674  -0.213  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.450   0.520  -1.020  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.841   1.765  -0.442  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.109   1.510   0.681  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.223   0.592   0.293  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.469   1.172   0.404  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.591   0.459   0.085  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.489  -0.859  -0.354  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.267  -1.462  -0.475  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.147  -0.723  -0.147  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.055  -1.580  -0.355  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.101  -2.643   0.503  1.00  0.00           O  
HETATM   17  H1  UNL     1       4.496   1.310   0.775  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.873  -1.994   1.295  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.877   0.369  -2.004  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.479   0.699  -1.379  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.626   2.450  -0.077  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.275   2.373  -1.207  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.565   2.468   0.972  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.447   1.134   1.565  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.555   2.191   0.743  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.581   0.872   0.157  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.379  -1.436  -0.611  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.220  -2.490  -0.820  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.053  -1.949  -1.399  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.363  -2.519   1.354  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5   18
CONECT    5    6   15
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   10   14
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15
CONECT   15   16   29
CONECT   16   30
END

HMDB0255489
     RDKit          3D
6,7,8,9-Tetrahydro-5-hydroxy-5H-benzocyclohept-6-ylideneacetic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.0465   -0.8799    2.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -0.3884    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6980    0.7784    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863   -1.0658    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559   -0.6740   -0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    0.5197   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    1.7649   -0.4418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    1.5100    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229    0.5924    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4693    1.1725    0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5909    0.4589    0.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885   -0.8589   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2671   -1.4618   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467   -0.7229   -0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546   -1.5797   -0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009   -2.6434    0.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960    1.3102    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730   -1.9942    1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774    0.3693   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    0.6991   -1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    2.4502   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752    2.3733   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5653    2.4679    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4474    1.1343    1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5553    2.1907    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    0.8716    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3793   -1.4364   -0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197   -2.4905   -0.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534   -1.9488   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3631   -2.5189    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15  5  1  0
 14  9  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S,e)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetate	Generator
6,7,8,9-Tetrahydro-5-(H)-benzocycloheptene-5-ol-4-ylideneacetic acid	HMDB
NCS 382	HMDB

Chemical Formula

C₁₃H₁₄O₃

Average Molecular Weight

218.252

Monoisotopic Molecular Weight

218.094294311

IUPAC Name

2-{5-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-ylidene}acetic acid

Traditional Name

{5-hydroxy-5,7,8,9-tetrahydrobenzo[7]annulen-6-ylidene}acetic acid

CAS Registry Number

Not Available

SMILES

OC1C2=CC=CC=C2CCCC1=CC(O)=O

InChI Identifier

InChI=1S/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)

InChI Key

UADPGHINQMWEAG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Not Available

Sub Class

Not Available

Direct Parent

Benzenoids

Alternative Parents

Substituents

Benzenoid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	1.98	ALOGPS
logP	2.16	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	61.14 m³·mol⁻¹	ChemAxon
Polarizability	22.81 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
DeepCCS	[M+H]+	144.019	30932474
DeepCCS	[M-H]-	140.257	30932474
DeepCCS	[M-2H]-	177.774	30932474
DeepCCS	[M+Na]+	153.312	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TMS,isomer #1	C[Si](C)(C)OC1C(=CC(=O)O)CCCC2=CC=CC=C21	2150.0	Semi standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TMS,isomer #1	C[Si](C)(C)OC1C(=CC(=O)O)CCCC2=CC=CC=C21	1861.1	Standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TMS,isomer #1	C[Si](C)(C)OC1C(=CC(=O)O)CCCC2=CC=CC=C21	2496.8	Standard polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O	2078.0	Semi standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O	1918.7	Standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O	2571.4	Standard polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O[Si](C)(C)C	2086.8	Semi standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O[Si](C)(C)C	1994.0	Standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O[Si](C)(C)C	2329.8	Standard polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=CC(=O)O)CCCC2=CC=CC=C21	2406.0	Semi standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=CC(=O)O)CCCC2=CC=CC=C21	2121.8	Standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(=CC(=O)O)CCCC2=CC=CC=C21	2674.3	Standard polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O	2326.1	Semi standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O	2187.9	Standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O	2723.0	Standard polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O[Si](C)(C)C(C)(C)C	2518.4	Semi standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O[Si](C)(C)C(C)(C)C	2474.4	Standard non polar	33892256
(S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C=C1CCCC2=CC=CC=C2C1O[Si](C)(C)C(C)(C)C	2579.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uyj-2920000000-831a11ec3ad95816b881	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 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 - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 10V, Positive-QTOF	splash10-0udi-0390000000-e7ced85749d8a32a855f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 20V, Positive-QTOF	splash10-0kai-0940000000-adf20a1e23dbee5d6264	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 40V, Positive-QTOF	splash10-0a5c-3900000000-ebb2cae9c1ca6411be53	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 10V, Negative-QTOF	splash10-0002-0900000000-f1973619adefb9e41197	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 20V, Negative-QTOF	splash10-00di-0900000000-d4e7d4c76bef76306bef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid 40V, Negative-QTOF	splash10-053r-0900000000-0f4a554dcfb9304014a3	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

116153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131414

PDB ID

Not Available

ChEBI ID

91816

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 (S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid (HMDB0250015)

MOL for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

3D MOL for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

3D SDF for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

3D-SDF for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

PDB for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

3D PDB for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

SMILES for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

INCHI for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

Structure for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

3D Structure for HMDB0250015 ((S,E)-2-(5-Hydroxy-8,9-dihydro-5H-benzo[7]annulen-6(7H)-ylidene)acetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra