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Showing metabocard for 5-Hydroxybenzofuran-2(3H)-one (HMDB0245720)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:46:27 UTC
Update Date2021-09-26 22:54:20 UTC
HMDB IDHMDB0245720
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Hydroxybenzofuran-2(3H)-one
Description5-Hydroxybenzofuran-2(3H)-one, also known as 5-hydroxy-2(3H)-benzofuranone or homogentisic acid gamma-lactone, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 5-Hydroxybenzofuran-2(3H)-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 5-Hydroxybenzofuran-2(3H)-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-hydroxybenzofuran-2(3h)-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Hydroxybenzofuran-2(3H)-one 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 HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

  Mrv1652309112100462D          

 11 12  0  0  0  0            999 V2000
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   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
   -1.4534   -0.6979    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
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

HMDB0245720
     RDKit          3D
5-Hydroxybenzofuran-2(3H)-one
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.9658   -0.5520   -0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6898   -0.4484   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819    0.3338    0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    0.1360    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    0.6357    0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442    0.3303    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9836    0.8228    1.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574   -0.4925   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.9863   -1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -0.6838   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -1.0284   -1.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909    1.3987    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522   -0.1071    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5013    1.2844    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3381    1.7217    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623   -0.7320   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180   -1.6330   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  2  1  0
 10  4  1  0
  3 12  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

  Mrv1652309112100462D          

 11 12  0  0  0  0            999 V2000
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   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
   -1.4534   -0.6979    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
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245720

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(OC(=O)C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O3/c9-6-1-2-7-5(3-6)4-8(10)11-7/h1-3,9H,4H2

> <INCHI_KEY>
POUITAHNNRJWMA-UHFFFAOYSA-N

> <FORMULA>
C8H6O3

> <MOLECULAR_WEIGHT>
150.133

> <EXACT_MASS>
150.031694053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.210558235309222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2,3-dihydro-1-benzofuran-2-one

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
1.1380354723333332

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.18404698204439

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.382474180316299

> <JCHEM_PKA_STRONGEST_BASIC>
-5.927863707545684

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
37.8352

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3H-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

HMDB0245720
     RDKit          3D
5-Hydroxybenzofuran-2(3H)-one
 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.9658   -0.5520   -0.5532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6898   -0.4484   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819    0.3338    0.5817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5539    0.1360    0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704    0.6357    0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442    0.3303    0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9836    0.8228    1.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574   -0.4925   -0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.9863   -1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508   -0.6838   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -1.0284   -1.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2909    1.3987    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522   -0.1071    1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5013    1.2844    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3381    1.7217    0.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623   -0.7320   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9180   -1.6330   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  2  1  0
 10  4  1  0
  3 12  1  0
  3 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

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      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6                                                            
CONECT    9    3   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

COMPND    HMDB0245720
HETATM    1  O1  UNL     1      -3.966  -0.552  -0.553  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.690  -0.448  -0.446  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.982   0.334   0.582  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.554   0.136   0.282  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.570   0.636   0.922  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.844   0.330   0.482  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.984   0.823   1.113  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.957  -0.492  -0.620  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.835  -0.986  -1.252  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.451  -0.684  -0.816  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.725  -1.028  -1.245  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.291   1.399   0.510  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.252  -0.107   1.572  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.501   1.284   1.791  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.338   1.722   0.763  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.962  -0.732  -0.965  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.918  -1.633  -2.119  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   12   13
CONECT    4    5    5   10
CONECT    5    6   14
CONECT    6    7    8    8
CONECT    7   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11
END
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SMILES for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

OC1=CC2=C(OC(=O)C2)C=C1
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INCHI for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

InChI=1S/C8H6O3/c9-6-1-2-7-5(3-6)4-8(10)11-7/h1-3,9H,4H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,3-Dihydro-5-hydroxybenzofuran-2-oneChEBI
5-Hydroxy-2(3H)-benzofuranoneChEBI
5-Hydroxy-2-coumaranoneChEBI
Homogentisic acid gamma-lactoneChEBI
Homogentisate g-lactoneGenerator
Homogentisate gamma-lactoneGenerator
Homogentisate γ-lactoneGenerator
Homogentisic acid g-lactoneGenerator
Homogentisic acid γ-lactoneGenerator
Chemical FormulaC8H6O3
Average Molecular Weight150.133
Monoisotopic Molecular Weight150.031694053
IUPAC Name5-hydroxy-2,3-dihydro-1-benzofuran-2-one
Traditional Name5-hydroxy-3H-1-benzofuran-2-one
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(OC(=O)C2)C=C1
InChI Identifier
InChI=1S/C8H6O3/c9-6-1-2-7-5(3-6)4-8(10)11-7/h1-3,9H,4H2
InChI KeyPOUITAHNNRJWMA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Coumaran
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 ID68403
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75898
PDB IDNot Available
ChEBI ID141343
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 ]