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Showing NP-Card for 1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one (NP0256102)

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Record Information
Version1.0
Created at2022-09-07 20:49:25 UTC
Updated at2022-09-07 20:49:25 UTC
NP-MRD IDNP0256102
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one
Description1-(6,7-Dihydroxy-6-methyl-3-methylidene-octahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one is found in Pleurotus cystidiosus. Based on a literature review very few articles have been published on 1-(6,7-dihydroxy-6-methyl-3-methylidene-octahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)


  Mrv1652309072222492D          

 19 20  0  0  0  0            999 V2000
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    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
    2.8825   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522   -1.8857    0.0000 O   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
    1.3556   -2.3479    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
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 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
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3D MOL for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)

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3D SDF for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)

  Mrv1652309072222492D          

 19 20  0  0  0  0            999 V2000
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    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
    2.8825   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522   -1.8857    0.0000 O   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
    1.3556   -2.3479    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC(=O)C1OC2C(CCC(C)(O)C2O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8(2)7-11(16)12-9(3)10-5-6-15(4,18)14(17)13(10)19-12/h7,10,12-14,17-18H,3,5-6H2,1-2,4H3

> <INCHI_KEY>
RIXLJEHCUPAPRJ-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.163488485518858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(6,7-dihydroxy-6-methyl-3-methylidene-octahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one

> <JCHEM_LOGP>
1.4471645016666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.826785530152861

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.0058875851648

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2443292129556793

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
72.28420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)
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PDB for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.483  -2.637   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.793  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.793   1.365   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.268  -2.549   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.381  -1.805   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.391  -3.520   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   11   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

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3D PDB for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)
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SMILES for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)
CC(C)=CC(=O)C1OC2C(CCC(C)(O)C2O)C1=C
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INCHI for NP0256102 (1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one)
InChI=1S/C15H22O4/c1-8(2)7-11(16)12-9(3)10-5-6-15(4,18)14(17)13(10)19-12/h7,10,12-14,17-18H,3,5-6H2,1-2,4H3
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SynonymsNot Available
Chemical FormulaC15H22O4
Average Mass266.3370 Da
Monoisotopic Mass266.15181 Da
IUPAC Name1-(6,7-dihydroxy-6-methyl-3-methylidene-octahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one
Traditional Name1-(6,7-dihydroxy-6-methyl-3-methylidene-hexahydro-1-benzofuran-2-yl)-3-methylbut-2-en-1-one
CAS Registry NumberNot Available
SMILES
CC(C)=CC(=O)C1OC2C(CCC(C)(O)C2O)C1=C
InChI Identifier
InChI=1S/C15H22O4/c1-8(2)7-11(16)12-9(3)10-5-6-15(4,18)14(17)13(10)19-12/h7,10,12-14,17-18H,3,5-6H2,1-2,4H3
InChI KeyRIXLJEHCUPAPRJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pleurotus cystidiosusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Benzofuran
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Enone
    • 

  • Cyclic alcohol
    • 

  • Acryloyl-group
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • 1,2-diol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • 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
logP1.45ChemAxon
pKa (Strongest Acidic)13.01ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity72.28 m³·mol⁻¹ChemAxon
Polarizability29.16 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 Compound162909084  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]