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Showing NP-Card for 3-(2-hydroxybutylidene)-2-benzofuran-1-one (NP0184977)

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Record Information
Version1.0
Created at2022-09-04 00:14:59 UTC
Updated at2022-09-04 00:14:59 UTC
NP-MRD IDNP0184977
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(2-hydroxybutylidene)-2-benzofuran-1-one
DescriptionCTK6C6198 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. 3-(2-hydroxybutylidene)-2-benzofuran-1-one is found in Angelica acutiloba. CTK6C6198 is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)


  Mrv0541 04121517362D          

 15 16  0  0  0  0            999 V2000
    1.7329   -4.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 10 15  1  0  0  0  0
M  END
Download

3D MOL for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -4.5029    0.0019    0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -0.7685    0.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284    0.2413   -0.2641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0532    1.1363    0.7836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094   -0.3817   -0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2674    0.3021   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240    1.5804    0.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.9507    0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9777    3.0391    1.1797 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068    0.8625    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.7488    0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655   -0.4156   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450   -1.4176   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2677   -1.2824   -0.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -0.1293   -0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9774   -0.1909    1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3427    1.1048    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1823   -0.2426   -0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462   -1.2440    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127   -1.5588   -0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4184    0.7142   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614    0.6130    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6600   -1.3706   -0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441    1.5654    0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5351   -0.4782   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -2.3122   -0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6373   -2.0684   -1.0332 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  6  1  0
 15 10  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  6
  4 22  1  0
  5 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
M  END
Download

3D SDF for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)


  Mrv0541 04121517362D          

 15 16  0  0  0  0            999 V2000
    1.7329   -4.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)C=C1OC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O3/c1-2-8(13)7-11-9-5-3-4-6-10(9)12(14)15-11/h3-8,13H,2H2,1H3

> <INCHI_KEY>
RAGLCXMIVOLFJJ-UHFFFAOYSA-N

> <FORMULA>
C12H12O3

> <MOLECULAR_WEIGHT>
204.225

> <EXACT_MASS>
204.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.59814452766613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.7931171609999996

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.772715357493983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.898214302632132

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
57.791600000000024

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxybutylidene)-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)

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PDB for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)
HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       3.235  -7.767   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.187  -4.838   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)
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SMILES for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)
CCC(O)C=C1OC(=O)C2=CC=CC=C12
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INCHI for NP0184977 (3-(2-hydroxybutylidene)-2-benzofuran-1-one)
InChI=1S/C12H12O3/c1-2-8(13)7-11-9-5-3-4-6-10(9)12(14)15-11/h3-8,13H,2H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H12O3
Average Mass204.2250 Da
Monoisotopic Mass204.07864 Da
IUPAC Name3-(2-hydroxybutylidene)-1,3-dihydro-2-benzofuran-1-one
Traditional Name3-(2-hydroxybutylidene)-2-benzofuran-1-one
CAS Registry NumberNot Available
SMILES
CCC(O)C=C1OC(=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C12H12O3/c1-2-8(13)7-11-9-5-3-4-6-10(9)12(14)15-11/h3-8,13H,2H2,1H3
InChI KeyRAGLCXMIVOLFJJ-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
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
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP1.93ALOGPS
logP1.79ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.77ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.79 m³·mol⁻¹ChemAxon
Polarizability21.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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 Compound57374725  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]