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Showing NP-Card for (3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one (NP0303975)

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Record Information
Version2.0
Created at2022-09-10 18:44:47 UTC
Updated at2022-09-10 18:44:47 UTC
NP-MRD IDNP0303975
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one
DescriptionCleroindicin C 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. (3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one is found in Clerodendrum bungei and Clerodendrum indicum. (3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one was first documented in 2014 (PMID: 24383986). Based on a literature review very few articles have been published on Cleroindicin C.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)


  Mrv1652309102220442D          

 11 12  0  0  1  0            999 V2000
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8371    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.6726   -0.3921   -2.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812   -0.3104   -1.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239    0.5904   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3418    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    0.4723    0.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2545    0.8166   -1.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.3782    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.9454    0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725   -1.6072    0.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0459   -1.0117   -0.0555 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6528   -1.1887   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    0.0354    0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8185    1.3426   -0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6879    2.1707   -0.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    1.8191    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0223    1.3511   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    1.2063    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6081    0.2503    2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207   -0.6474    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1871   -1.5200    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6108   -1.1876    0.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9000   -2.2330   -1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0211   -0.7310   -2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
 10  5  1  0
  4  5  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
  8 19  1  0
  8 20  1  0
 10 21  1  1
 11 22  1  0
 11 23  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
M  END
Download

3D SDF for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)


  Mrv1652309102220442D          

 11 12  0  0  1  0            999 V2000
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8371    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@]12CCO[C@H]1CC(=O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O3/c9-6-1-2-8(10)3-4-11-7(8)5-6/h7,10H,1-5H2/t7-,8-/m0/s1

> <INCHI_KEY>
ZCBQZDMJIVJQLX-YUMQZZPRSA-N

> <FORMULA>
C8H12O3

> <MOLECULAR_WEIGHT>
156.181

> <EXACT_MASS>
156.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.870537915828622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,7aS)-3a-hydroxy-octahydro-1-benzofuran-6-one

> <JCHEM_LOGP>
-0.3621903963333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.739058365417087

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.717097265955616

> <JCHEM_PKA_STRONGEST_BASIC>
-3.359020378788472

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
38.66159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,7aS)-3a-hydroxy-hexahydro-1-benzofuran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)

Download
PDB for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.429   0.541   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   10                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)
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SMILES for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)
O[C@@]12CCO[C@H]1CC(=O)CC2
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INCHI for NP0303975 ((3as,7as)-3a-hydroxy-hexahydro-1-benzofuran-6-one)
InChI=1S/C8H12O3/c9-6-1-2-8(10)3-4-11-7(8)5-6/h7,10H,1-5H2/t7-,8-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H12O3
Average Mass156.1810 Da
Monoisotopic Mass156.07864 Da
IUPAC Name(3aS,7aS)-3a-hydroxy-octahydro-1-benzofuran-6-one
Traditional Name(3aS,7aS)-3a-hydroxy-hexahydro-1-benzofuran-6-one
CAS Registry NumberNot Available
SMILES
O[C@@]12CCO[C@H]1CC(=O)CC2
InChI Identifier
InChI=1S/C8H12O3/c9-6-1-2-8(10)3-4-11-7(8)5-6/h7,10H,1-5H2/t7-,8-/m0/s1
InChI KeyZCBQZDMJIVJQLX-YUMQZZPRSA-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
Clerodendrum bungeiLOTUS Database
Clerodendrum indicumLOTUS 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
  • Benzofuran
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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
logP-0.36ChemAxon
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.66 m³·mol⁻¹ChemAxon
Polarizability15.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00050346  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124349842  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mousouri E, Melliou E, Magiatis P: Isolation of megaritolactones and other bioactive metabolites from 'megaritiki' table olives and debittering water. J Agric Food Chem. 2014 Jan 22;62(3):660-7. doi: 10.1021/jf404685h. Epub 2014 Jan  8. [PubMed:24383986  ] 
  2. LOTUS database [Link]