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Showing NP-Card for 6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one (NP0252133)

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Record Information
Version2.0
Created at2022-09-07 15:33:10 UTC
Updated at2022-09-07 15:33:10 UTC
NP-MRD IDNP0252133
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one
Description6,16-Dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]Hexadeca-1(14),4-dien-2-one belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. 6,16-Dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]Hexadeca-1(14),4-dien-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)


  Mrv1533004161521362D          

 23 25  0  0  0  0            999 V2000
    4.9748    2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506    1.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2904    1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5839    0.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4046    0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526   -0.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9317   -1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4148   -1.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1607   -1.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7065   -0.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134   -0.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544    0.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    0.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815    0.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1213    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    0.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236    1.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9999    1.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790    2.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405   -0.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2626   -0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.0985    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
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
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3D MOL for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)

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3D SDF for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)

  Mrv1533004161521362D          

 23 25  0  0  0  0            999 V2000
    4.9748    2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6506    1.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2904    1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5839    0.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4046    0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526   -0.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9317   -1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4148   -1.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1607   -1.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3462   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7065   -0.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134   -0.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544    0.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    0.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815    0.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1213    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    0.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8236    1.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9999    1.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4790    2.3307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405   -0.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2626   -0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.0985    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
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252133

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)CC(=C)CCC2CCC3=C(C(=O)C1C3O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-11-5-6-13-7-8-15-17(20(13,3)4)19(23)16(18(15)22)12(2)10-14(21)9-11/h10,13-14,16,18,21-22H,1,5-9H2,2-4H3

> <INCHI_KEY>
PYHGXJSOVZVBAF-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.52740773340571

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.797059517333334

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.218094968373773

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.20218242370029

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3574292660587748

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
92.72989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)
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PDB for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       9.286   4.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.681   3.048   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.875   2.076   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.423   0.637   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.955   0.793   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.178  -0.884   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.206  -2.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.108  -3.326   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.767  -2.626   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.246  -2.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.052  -1.408   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.758  -0.573   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.835   0.965   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.205   1.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.499   0.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.693   1.805   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.182   1.410   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.137   3.241   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.600   3.156   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.627   4.351   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.422  -0.706   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.957  -0.836   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.173  -2.050   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   15   11   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

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3D PDB for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)
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SMILES for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)
CC1=CC(O)CC(=C)CCC2CCC3=C(C(=O)C1C3O)C2(C)C
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INCHI for NP0252133 (6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one)
InChI=1S/C20H28O3/c1-11-5-6-13-7-8-15-17(20(13,3)4)19(23)16(18(15)22)12(2)10-14(21)9-11/h10,13-14,16,18,21-22H,1,5-9H2,2-4H3
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SynonymsNot Available
Chemical FormulaC20H28O3
Average Mass316.4410 Da
Monoisotopic Mass316.20384 Da
IUPAC Name6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one
Traditional Name6,16-dihydroxy-4,15,15-trimethyl-8-methylidenetricyclo[9.3.1.1³,¹⁴]hexadeca-1(14),4-dien-2-one
CAS Registry NumberNot Available
SMILES
CC1=CC(O)CC(=C)CCC2CCC3=C(C(=O)C1C3O)C2(C)C
InChI Identifier
InChI=1S/C20H28O3/c1-11-5-6-13-7-8-15-17(20(13,3)4)19(23)16(18(15)22)12(2)10-14(21)9-11/h10,13-14,16,18,21-22H,1,5-9H2,2-4H3
InChI KeyPYHGXJSOVZVBAF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentCyclic alcohols and derivatives  
Alternative Parents
Substituents
  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • 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
logP2.39ALOGPS
logP2.8ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.73 m³·mol⁻¹ChemAxon
Polarizability35.53 ųChemAxon
Number of Rings3ChemAxon
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 Compound73837299  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]