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Showing metabocard for 3-Acetoxyindole (HMDB0245796)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:50:54 UTC
Update Date2021-09-26 22:54:29 UTC
HMDB IDHMDB0245796
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Acetoxyindole
Description3-Acetoxyindole, also known as indoxyl acetate, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Based on a literature review very few articles have been published on 3-Acetoxyindole. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-acetoxyindole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Acetoxyindole 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0245796 (3-Acetoxyindole)

  Mrv1533004191516412D          

 13 14  0  0  0  0            999 V2000
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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
  2  4  1  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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
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3D MOL for HMDB0245796 (3-Acetoxyindole)

HMDB0245796
     RDKit          3D
3-Acetoxyindole
 22 23  0  0  0  0  0  0  0  0999 V2000
    4.0057   -0.6911    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6557   -0.1991    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -0.2401    1.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854    0.3141   -0.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166    0.7728   -0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1652    2.0399    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    2.1276    0.2811 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.9086    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    0.4583    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636   -0.8707   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679   -1.7598   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -1.2772   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    0.0333   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440   -1.3791    0.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499    0.1314   -0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0534   -1.3038   -0.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8813    2.8542    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835    2.9854    0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7930    1.1305    0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897   -1.2626   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701   -2.8093   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -1.9633   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  5  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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3D SDF for HMDB0245796 (3-Acetoxyindole)

  Mrv1533004191516412D          

 13 14  0  0  0  0            999 V2000
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   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
  2  4  1  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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245796

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3

> <INCHI_KEY>
JBOPQACSHPPKEP-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.187

> <EXACT_MASS>
175.063328534

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.204171622294034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1H-indol-3-yl acetate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
1.6792687833333333

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.889798755155624

> <JCHEM_PKA_STRONGEST_BASIC>
-7.1479538039739765

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
48.276900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0245796 (3-Acetoxyindole)

HMDB0245796
     RDKit          3D
3-Acetoxyindole
 22 23  0  0  0  0  0  0  0  0999 V2000
    4.0057   -0.6911    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6557   -0.1991    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -0.2401    1.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854    0.3141   -0.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166    0.7728   -0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1652    2.0399    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    2.1276    0.2811 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778    0.9086    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881    0.4583    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636   -0.8707   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2679   -1.7598   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -1.2772   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    0.0333   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440   -1.3791    0.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499    0.1314   -0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0534   -1.3038   -0.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8813    2.8542    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835    2.9854    0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7930    1.1305    0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897   -1.2626   -0.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701   -2.8093   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -1.9633   -0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  5  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0245796 (3-Acetoxyindole)

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0245796 (3-Acetoxyindole)

COMPND    HMDB0245796
HETATM    1  C1  UNL     1       4.006  -0.691   0.100  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.656  -0.199   0.384  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.240  -0.240   1.578  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.785   0.314  -0.561  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.517   0.773  -0.273  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.165   2.040   0.070  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.169   2.128   0.281  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.678   0.909   0.072  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.988   0.458   0.155  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.264  -0.871  -0.114  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.268  -1.760  -0.462  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.978  -1.277  -0.534  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.642   0.033  -0.279  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.344  -1.379   0.902  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.750   0.131  -0.069  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.053  -1.304  -0.844  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.881   2.854   0.156  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.684   2.985   0.553  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.793   1.131   0.425  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.290  -1.263  -0.058  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.470  -2.809  -0.676  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.174  -1.963  -0.808  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6   13
CONECT    6    7   17
CONECT    7    8   18
CONECT    8    9    9   13
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   12   21
CONECT   12   13   13   22
END
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SMILES for HMDB0245796 (3-Acetoxyindole)

CC(=O)OC1=CNC2=CC=CC=C12
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INCHI for HMDB0245796 (3-Acetoxyindole)

InChI=1S/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Indoxyl acetateHMDB
Chemical FormulaC10H9NO2
Average Molecular Weight175.187
Monoisotopic Molecular Weight175.063328534
IUPAC Name1H-indol-3-yl acetate
Traditional Nameindole acetic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3
InChI KeyJBOPQACSHPPKEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID11348
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11841
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]