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Showing NP-Card for 3-(2-Methylpropylidene)-1(3H)-isobenzofuranone (NP0047359)

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Record Information
Version2.0
Created at2022-03-17 20:38:53 UTC
Updated at2022-03-17 20:38:53 UTC
NP-MRD IDNP0047359
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(2-Methylpropylidene)-1(3H)-isobenzofuranone
Description(E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone, also known as (e)-3-isobutylidenephthalide or 2-methylpropylidenephthalide (e), belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone has been detected, but not quantified in, celery stalks and wild celeries. This could make (e)-3-(2-methylpropylidene)-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)


  Mrv0541 02241215552D          

 14 15  0  0  0  0            999 V2000
   -0.5772    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    1.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -1.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950   -1.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8974   -1.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  2  0  0  0  0
  3  8  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
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3D MOL for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

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3D SDF for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

  Mrv0541 02241215552D          

 14 15  0  0  0  0            999 V2000
   -0.5772    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    1.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -1.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950   -1.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8974   -1.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  2  0  0  0  0
  3  8  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)\C=C1\OC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O2/c1-8(2)7-11-9-5-3-4-6-10(9)12(13)14-11/h3-8H,1-2H3/b11-7+

> <INCHI_KEY>
LYSNVWBBICAAMS-YRNVUSSQSA-N

> <FORMULA>
C12H12O2

> <MOLECULAR_WEIGHT>
188.2225

> <EXACT_MASS>
188.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.478997397697192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-3-(2-methylpropylidene)-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.866378659333333

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.059439725631429

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.2237

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-3-(2-methylpropylidene)-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)
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PDB for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.077   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.077   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.461  -0.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.077  -1.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.617  -2.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.542  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.772   0.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.386   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.461   2.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.924   3.388   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.309  -0.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.155  -2.463   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.924  -3.388   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.542  -3.233   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)
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SMILES for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)
CC(C)\C=C1\OC(=O)C2=CC=CC=C12
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INCHI for NP0047359 (3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)
InChI=1S/C12H12O2/c1-8(2)7-11-9-5-3-4-6-10(9)12(13)14-11/h3-8H,1-2H3/b11-7+
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Synonyms
ValueSource
(e)-3-IsobutylidenephthalideHMDB
2-Methylpropylidenephthalide (e)HMDB
3-(2-Methylpropylidene)-(3E)-1(3H)-isobenzofuranoneHMDB
Chemical FormulaC12H12O2
Average Mass188.2225 Da
Monoisotopic Mass188.08373 Da
IUPAC Name(3E)-3-(2-methylpropylidene)-1,3-dihydro-2-benzofuran-1-one
Traditional Name(3E)-3-(2-methylpropylidene)-2-benzofuran-1-one
CAS Registry Number56014-69-8
SMILES
CC(C)\C=C1\OC(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C12H12O2/c1-8(2)7-11-9-5-3-4-6-10(9)12(13)14-11/h3-8H,1-2H3/b11-7+
InChI KeyLYSNVWBBICAAMS-YRNVUSSQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIsocoumarans  
Sub ClassIsobenzofuranones  
Direct ParentIsobenzofuranones  
Alternative Parents
Substituents
  • Isobenzofuranone
    • 

  • Benzenoid
    • 

  • Enol ester
    • 

  • 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
logP2.98ALOGPS
logP2.87ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.22 m³·mol⁻¹ChemAxon
Polarizability20.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032028  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008727  
KNApSAcK IDNot Available
Chemspider ID4941245  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6436620  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available