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Showing NP-Card for 3-butylidene-4,5-dihydro-2-benzofuran-1-one (NP0232870)

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Record Information
Version2.0
Created at2022-09-06 14:15:15 UTC
Updated at2022-09-06 14:15:16 UTC
NP-MRD IDNP0232870
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-butylidene-4,5-dihydro-2-benzofuran-1-one
Description3-Butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety. 3-butylidene-4,5-dihydro-2-benzofuran-1-one is found in Angelica acutiloba, Angelica glauca, Angelica sinensis, Levisticum officinale and Ligusticum porteri. 3-Butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)


  Mrv1533004191522062D          

 14 15  0  0  0  0            999 V2000
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
Download

3D MOL for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.2768   -0.5566   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2608    0.4404    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4345    1.6307    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0132    1.3790    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    0.2582    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -0.9305    0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202   -1.8929    0.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0214   -3.0779    1.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.2544    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -0.0190    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082    0.9214   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4828    0.3878   -0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6688   -0.9941   -0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975   -1.7594    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4330   -0.3819   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2878   -1.5698   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2237   -0.3975   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -0.0568    1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    0.7499    0.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    2.4608    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    2.0450   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3807    2.1964   -0.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783    1.2369   -1.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1247    1.8718    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8828    0.4451   -1.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2083    1.0238    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6859   -1.3934   -0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802   -2.7629    0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 10  5  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
M  END
Download

3D SDF for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)


  Mrv1533004191522062D          

 14 15  0  0  0  0            999 V2000
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC=C1OC(=O)C2=C1CCC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3

> <INCHI_KEY>
IQVQXVFMNOFTMU-UHFFFAOYSA-N

> <FORMULA>
C12H14O2

> <MOLECULAR_WEIGHT>
190.242

> <EXACT_MASS>
190.099379691

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.41854046754161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
2.7349952670000004

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.084769885719521

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
58.04110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-butylidene-4,5-dihydro-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)

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PDB for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)
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      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.173  -1.303   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.744  -4.013   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)
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SMILES for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)
CCCC=C1OC(=O)C2=C1CCC=C2
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INCHI for NP0232870 (3-butylidene-4,5-dihydro-2-benzofuran-1-one)
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3
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View in JSmol
Synonyms
ValueSource
LigustilideMeSH
Ligustilide, (e)-isomerMeSH
Ligustilide, (Z)-isomerMeSH
Chemical FormulaC12H14O2
Average Mass190.2420 Da
Monoisotopic Mass190.09938 Da
IUPAC Name3-butylidene-1,3,4,5-tetrahydro-2-benzofuran-1-one
Traditional Name3-butylidene-4,5-dihydro-2-benzofuran-1-one
CAS Registry NumberNot Available
SMILES
CCCC=C1OC(=O)C2=C1CCC=C2
InChI Identifier
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3
InChI KeyIQVQXVFMNOFTMU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica acutilobaLOTUS Database
Angelica glaucaLOTUS Database
Angelica sinensisLOTUS Database
Levisticum officinaleLOTUS Database
Ligusticum porteriLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isobenzofurans. These are organic aromatic compounds containing an isobenzofuran moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIsobenzofurans  
Sub ClassNot Available
Direct ParentIsobenzofurans  
Alternative Parents
Substituents
  • Isobenzofuran
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Enol ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP3.48ALOGPS
logP2.73ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.04 m³·mol⁻¹ChemAxon
Polarizability21.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound529865  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]