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Showing metabocard for Phthalide (HMDB0032469)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:58 UTC
Update Date2023-02-21 17:22:14 UTC
HMDB IDHMDB0032469
Secondary Accession Numbers
  • HMDB32469
Metabolite Identification
Common NamePhthalide
DescriptionPhthalide, also known as 1-phthalanone or isobenzofuranone, belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,. Phthalide is a sweet, coconut, and coumarin tasting compound. Phthalide has been detected, but not quantified in, several different foods, such as blackberries (Rubus), celeriacs (Apium graveolens var. rapaceum), celery stalks (Apium graveolens var. dulce), and evergreen blackberries (Rubus laciniatus). This could make phthalide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phthalide.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032469 (Phthalide)

  Mrv0541 05061306322D          

 10 11  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
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3D MOL for HMDB0032469 (Phthalide)

HMDB0032469
     RDKit          3D
Phthalide
 16 17  0  0  0  0  0  0  0  0999 V2000
   -2.5253    2.0095    0.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275    0.9016    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -0.3148   -0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264   -1.3265   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -0.6533   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   -1.1386   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.2996   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    1.0699    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195    1.5511    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    0.7165    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7679   -1.9281   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761   -1.9984    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -2.2254   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -0.7298   -0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630    1.7442    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437    2.6217    0.1689 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  2  1  0
 10  5  1  0
  4 11  1  0
  4 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
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3D SDF for HMDB0032469 (Phthalide)

  Mrv0541 05061306322D          

 10 11  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032469

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1OCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2

> <INCHI_KEY>
WNZQDUSMALZDQF-UHFFFAOYSA-N

> <FORMULA>
C8H6O2

> <MOLECULAR_WEIGHT>
134.132

> <EXACT_MASS>
134.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.05577030289945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
1.527950081333333

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.362232431989053

> <JCHEM_PKA_STRONGEST_BASIC>
-6.922127626530696

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
36.6379

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phthalide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0032469 (Phthalide)

HMDB0032469
     RDKit          3D
Phthalide
 16 17  0  0  0  0  0  0  0  0999 V2000
   -2.5253    2.0095    0.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9275    0.9016    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -0.3148   -0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264   -1.3265   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -0.6533   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   -1.1386   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.2996   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    1.0699    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195    1.5511    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    0.7165    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7679   -1.9281   -1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7761   -1.9984    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -2.2254   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -0.7298   -0.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630    1.7442    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437    2.6217    0.1689 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  2  1  0
 10  5  1  0
  4 11  1  0
  4 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
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PDB for HMDB0032469 (Phthalide)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    6   10                                                       
CONECT    6    3    5    7                                                  
CONECT    7    4    6    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    5    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0032469 (Phthalide)

COMPND    HMDB0032469
HETATM    1  O1  UNL     1      -2.525   2.009   0.107  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.927   0.902   0.040  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.589  -0.315  -0.043  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.626  -1.326  -0.101  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.302  -0.653  -0.047  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.976  -1.139  -0.069  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.091  -0.300  -0.006  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.913   1.070   0.080  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.619   1.551   0.101  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.486   0.717   0.039  1.00  0.00           C  
HETATM   11  H1  UNL     1      -1.768  -1.928  -1.016  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.776  -1.998   0.781  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.122  -2.225  -0.138  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.074  -0.730  -0.027  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.763   1.744   0.130  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.444   2.622   0.169  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4
CONECT    4    5   11   12
CONECT    5    6    6   10
CONECT    6    7   13
CONECT    7    8    8   14
CONECT    8    9   15
CONECT    9   10   10   16
END
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SMILES for HMDB0032469 (Phthalide)

O=C1OCC2=CC=CC=C12
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INCHI for HMDB0032469 (Phthalide)

InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H6O2
Average Molecular Weight134.132
Monoisotopic Molecular Weight134.036779436
IUPAC Name1,3-dihydro-2-benzofuran-1-one
Traditional Namephthalide
CAS Registry Number87-41-2
SMILES
O=C1OCC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
InChI KeyWNZQDUSMALZDQF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsocoumarans
Sub ClassIsobenzofuranones
Direct ParentPhthalides
Alternative Parents
Substituents
  • Phthalide
  • Benzenoid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point75 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.80Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010076
KNApSAcK IDC00014972
Chemspider ID6621
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhthalide
METLIN IDNot Available
PubChem Compound6885
PDB IDNot Available
ChEBI ID38085
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. (). EAFUS: Everything Added to Food in the United States.. .