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Showing NP-Card for 1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone (NP0226271)

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Record Information
Version2.0
Created at2022-09-06 05:15:13 UTC
Updated at2022-09-06 05:15:14 UTC
NP-MRD IDNP0226271
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone
Description112936-03-5 Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone is found in Ageratum houstonianum and Eupatorium cannabinum. 112936-03-5 Is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)


  Mrv1533004251513402D          

 16 17  0  0  0  0            999 V2000
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    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
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -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
    4.0668   -1.5229    0.0000 O   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
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  2  0  0  0  0
M  END
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3D MOL for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)

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3D SDF for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)

  Mrv1533004251513402D          

 16 17  0  0  0  0            999 V2000
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    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
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -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
    4.0668   -1.5229    0.0000 O   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
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1=CC2=CC(O)=C(C=C2O1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O3/c1-7(2)12-5-9-4-11(15)10(8(3)14)6-13(9)16-12/h4-6,15H,1H2,2-3H3

> <INCHI_KEY>
WCOLFOJRDDQQEN-UHFFFAOYSA-N

> <FORMULA>
C13H12O3

> <MOLECULAR_WEIGHT>
216.236

> <EXACT_MASS>
216.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.415995333449146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethan-1-one

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.9925492103333333

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.032076779801884

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.734046547490287

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9454946466308902

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
61.128600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)
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PDB for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)
HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+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
HETATM   16  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)
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SMILES for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)
CC(=C)C1=CC2=CC(O)=C(C=C2O1)C(C)=O
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INCHI for NP0226271 (1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone)
InChI=1S/C13H12O3/c1-7(2)12-5-9-4-11(15)10(8(3)14)6-13(9)16-12/h4-6,15H,1H2,2-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H12O3
Average Mass216.2360 Da
Monoisotopic Mass216.07864 Da
IUPAC Name1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethan-1-one
Traditional Name1-[5-hydroxy-2-(prop-1-en-2-yl)-1-benzofuran-6-yl]ethanone
CAS Registry NumberNot Available
SMILES
CC(=C)C1=CC2=CC(O)=C(C=C2O1)C(C)=O
InChI Identifier
InChI=1S/C13H12O3/c1-7(2)12-5-9-4-11(15)10(8(3)14)6-13(9)16-12/h4-6,15H,1H2,2-3H3
InChI KeyWCOLFOJRDDQQEN-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ageratum houstonianumLOTUS Database
Eupatorium cannabinumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassNot Available
Direct ParentBenzofurans  
Alternative Parents
Substituents
  • Acetophenone
    • 

  • Benzofuran
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Furan
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP2.67ALOGPS
logP2.99ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.13 m³·mol⁻¹ChemAxon
Polarizability23.42 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 Compound71336886  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]