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Showing NP-Card for 7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one (NP0330595)

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Record Information
Version2.0
Created at2022-09-12 16:05:37 UTC
Updated at2022-09-12 16:05:37 UTC
NP-MRD IDNP0330595
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one
Description7-Ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-tetradecahydrophenanthren-9-one belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one is found in Vellozia compacta. 7-Ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-tetradecahydrophenanthren-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)


  Mrv1533004191514482D          

 22 24  0  0  0  0            999 V2000
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    0.6606    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 13 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
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3D MOL for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)

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3D SDF for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)

  Mrv1533004191514482D          

 22 24  0  0  0  0            999 V2000
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5178    0.6606    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 13 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0330595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(C)C1CC(=O)C1(O)CC(C)(CCC21)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-6-18(4)11-8-14-19(5)10-7-9-17(2,3)15(19)12-16(21)20(14,22)13-18/h6,14-15,22H,1,7-13H2,2-5H3

> <INCHI_KEY>
LYKJEJVAXSGWAJ-UHFFFAOYSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.474

> <EXACT_MASS>
304.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.16310036603272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-tetradecahydrophenanthren-9-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.532442065

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.400197048613617

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.808427636141555

> <JCHEM_PKA_STRONGEST_BASIC>
-3.757391603873942

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.9119

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.43e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2H-phenanthren-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)
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PDB for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-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       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -1.897   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.833   1.233   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   13                                                  
CONECT   21   16   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

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3D PDB for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)
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SMILES for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)
CC1(C)CCCC2(C)C1CC(=O)C1(O)CC(C)(CCC21)C=C
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INCHI for NP0330595 (7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2h-phenanthren-9-one)
InChI=1S/C20H32O2/c1-6-18(4)11-8-14-19(5)10-7-9-17(2,3)15(19)12-16(21)20(14,22)13-18/h6,14-15,22H,1,7-13H2,2-5H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H32O2
Average Mass304.4740 Da
Monoisotopic Mass304.24023 Da
IUPAC Name7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-tetradecahydrophenanthren-9-one
Traditional Name7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-octahydro-2H-phenanthren-9-one
CAS Registry NumberNot Available
SMILES
CC1(C)CCCC2(C)C1CC(=O)C1(O)CC(C)(CCC21)C=C
InChI Identifier
InChI=1S/C20H32O2/c1-6-18(4)11-8-14-19(5)10-7-9-17(2,3)15(19)12-16(21)20(14,22)13-18/h6,14-15,22H,1,7-13H2,2-5H3
InChI KeyLYKJEJVAXSGWAJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vellozia compactaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentDiterpenoids  
Alternative Parents
Substituents
  • Pimarane diterpenoid
    • 

  • Diterpenoid
    • 

  • Phenanthrene
    • 

  • Hydrophenanthrene
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP4.08ALOGPS
logP4.53ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)12.81ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.91 m³·mol⁻¹ChemAxon
Polarizability36.16 ųChemAxon
Number of Rings3ChemAxon
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 Compound14191477  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]