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Showing NP-Card for 4-Hydroxyphthalide (NP0336870)

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Record Information
Version2.0
Created at2024-09-11 08:13:11 UTC
Updated at2024-09-11 08:13:11 UTC
NP-MRD IDNP0336870
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxyphthalide
Description4-Hydroxyphthalide belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,. 4-Hydroxyphthalide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Hydroxyphthalide has been detected, but not quantified in, cereals and cereal products and oats. This could make 4-hydroxyphthalide a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336870 (4-Hydroxyphthalide)


  Mrv0541 05061306352D          

 11 12  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    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
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
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3D MOL for NP0336870 (4-Hydroxyphthalide)

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3D SDF for NP0336870 (4-Hydroxyphthalide)

  Mrv0541 05061306352D          

 11 12  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    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
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  1  0  0  0  0
 11  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1COC2=O

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

> <INCHI_KEY>
ZSCIMKFWMUXNBS-UHFFFAOYSA-N

> <FORMULA>
C8H6O3

> <MOLECULAR_WEIGHT>
150.1314

> <EXACT_MASS>
150.031694058

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.949857685977534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.2243847596666666

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.48511631417179

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.22834004352244

> <JCHEM_PKA_STRONGEST_BASIC>
-6.102121567549159

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
38.6188

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336870 (4-Hydroxyphthalide)
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PDB for NP0336870 (4-Hydroxyphthalide)
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       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    7                                                       
CONECT    4    6   11                                                       
CONECT    5    2    6    8                                                  
CONECT    6    4    5    7                                                  
CONECT    7    3    6    9                                                  
CONECT    8    5   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0336870 (4-Hydroxyphthalide)
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SMILES for NP0336870 (4-Hydroxyphthalide)
OC1=CC=CC2=C1COC2=O
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INCHI for NP0336870 (4-Hydroxyphthalide)
InChI=1S/C8H6O3/c9-7-3-1-2-5-6(7)4-11-8(5)10/h1-3,9H,4H2
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View in JSmol
Synonyms
ValueSource
4-Hydroxy-1(3H)-isobenzofuranone, 9ciHMDB
Chemical FormulaC8H6O3
Average Mass150.1314 Da
Monoisotopic Mass150.03169 Da
IUPAC Name4-hydroxy-1,3-dihydro-2-benzofuran-1-one
Traditional Name4-hydroxy-3H-2-benzofuran-1-one
CAS Registry NumberNot Available
SMILES
OC1=CC=CC2=C1COC2=O
InChI Identifier
InChI=1S/C8H6O3/c9-7-3-1-2-5-6(7)4-11-8(5)10/h1-3,9H,4H2
InChI KeyZSCIMKFWMUXNBS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 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
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.49ALOGPS
logP1.22ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.62 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032598  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010536  
KNApSAcK IDNot Available
Chemspider ID15585646  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12662077  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available