NP-MRD: Showing NP-Card for 8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one (NP0219644)

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Record Information

Version

2.0

Created at

2022-09-05 20:42:35 UTC

Updated at

2022-09-05 20:42:35 UTC

NP-MRD ID

NP0219644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one

Description

8-Hydroxy-6,10,12a-trimethyl-3-(propan-2-yl)-1H,3aH,4H,5H,8H,9H,12H,12aH-cyclopenta[11]annulen-1-one belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton. 8-Hydroxy-6,10,12a-trimethyl-3-(propan-2-yl)-1H,3aH,4H,5H,8H,9H,12H,12aH-cyclopenta[11]annulen-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251505542D          

 22 23  0  0  0  0            999 V2000
   -0.7051   -3.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5790   -3.9916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799   -2.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234   -0.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188   -0.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5511   -1.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091   -1.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223   -2.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3573   -3.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421   -3.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924   -2.4232    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 15  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
  8 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC(=O)C2(C)CC=C(C)CC(O)C=C(C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13(2)17-12-19(22)20(5)9-8-15(4)11-16(21)10-14(3)6-7-18(17)20/h8,10,12-13,16,18,21H,6-7,9,11H2,1-5H3

> <INCHI_KEY>
HQCVRJOFBONDTQ-UHFFFAOYSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.25863460341074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-6,10,12a-trimethyl-3-(propan-2-yl)-1H,3aH,4H,5H,8H,9H,12H,12aH-cyclopenta[11]annulen-1-one

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
4.582740714333333

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.22782435115175

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.1463730732605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3868527483018847

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
94.51289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3aH,4H,5H,8H,9H,12H-cyclopenta[11]annulen-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -1.316  -6.281   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.220  -6.174   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.081  -7.451   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.896  -4.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.173  -3.430   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.244  -2.323   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.977  -0.806   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.628  -2.998   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.649  -1.458   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.161  -2.300   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.837  -0.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.362  -1.132   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.432  -0.024   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.629  -2.648   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.910  -3.743   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.350  -3.198   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.695  -5.268   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.267  -5.844   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.052  -7.369   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.054  -4.896   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.626  -5.472   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.413  -4.523   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   22                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

8-hydroxy-6,10,12a-trimethyl-3-(propan-2-yl)-1H,3aH,4H,5H,8H,9H,12H,12aH-cyclopenta[11]annulen-1-one

Traditional Name

8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3aH,4H,5H,8H,9H,12H-cyclopenta[11]annulen-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC(=O)C2(C)CC=C(C)CC(O)C=C(C)CCC12

InChI Identifier

InChI=1S/C20H30O2/c1-13(2)17-12-19(22)20(5)9-8-15(4)11-16(21)10-14(3)6-7-18(17)20/h8,10,12-13,16,18,21H,6-7,9,11H2,1-5H3

InChI Key

HQCVRJOFBONDTQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Dolabellane and neodolabellane diterpenoids

Alternative Parents

Substituents

Dolabellane diterpenoid
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.96	ALOGPS
logP	4.58	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.15	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.51 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73880676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one (NP0219644)

MOL for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

3D MOL for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

3D SDF for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

3D-SDF for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

PDB for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

3D PDB for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

SMILES for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

INCHI for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

Structure for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)

3D Structure for NP0219644 (8-hydroxy-3-isopropyl-6,10,12a-trimethyl-3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one)