NP-MRD: Showing NP-Card for 3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one (NP0249705)

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Record Information

Version

2.0

Created at

2022-09-07 12:20:44 UTC

Updated at

2022-09-07 12:20:45 UTC

NP-MRD ID

NP0249705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one

Description

AC1MWM5E 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. 3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one is found in Eunicea calyculata and Eunicea laciniata. AC1MWM5E is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241517492D          

 21 22  0  0  0  0            999 V2000
   -0.2518   -0.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234   -0.4317    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
    1.4076   -1.6062    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
    3.5511   -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
    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
    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
    1.0925   -3.2236    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
   -0.7240   -1.7223    0.0000 O   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
    3.9816   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556    0.0983    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  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  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  4  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 19  1  0  0  0  0
  7 20  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C1C2CCC(C)=CCCC(C)=CCC2(C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O/c1-14(2)19-17-10-9-15(3)7-6-8-16(4)11-12-20(17,5)13-18(19)21/h7,11,17H,6,8-10,12-13H2,1-5H3

> <INCHI_KEY>
YETBHHZORHIONL-UHFFFAOYSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.459

> <EXACT_MASS>
286.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.9520110977686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
6.28

> <JCHEM_LOGP>
5.410148810333332

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.617726951538996

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
92.75409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3a,6,10-trimethyl-1-(propan-2-ylidene)-3H,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.470  -0.279   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.977  -0.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.244  -2.323   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.628  -2.998   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.161  -2.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.837  -0.917   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.362  -1.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.629  -2.648   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.910  -3.743   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.695  -5.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.267  -5.844   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.054  -4.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.626  -5.472   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.413  -4.523   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.039  -6.017   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.896  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.173  -3.430   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.351  -3.215   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.052  -7.369   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.432  -0.024   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.157   0.183   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    4   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17                                                            
CONECT   19   11                                                            
CONECT   20    7                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O

Average Mass

286.4590 Da

Monoisotopic Mass

286.22967 Da

IUPAC Name

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

Traditional Name

3a,6,10-trimethyl-1-(propan-2-ylidene)-3H,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=C1C2CCC(C)=CCCC(C)=CCC2(C)CC1=O

InChI Identifier

InChI=1S/C20H30O/c1-14(2)19-17-10-9-15(3)7-6-8-16(4)11-12-20(17,5)13-18(19)21/h7,11,17H,6,8-10,12-13H2,1-5H3

InChI Key

YETBHHZORHIONL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eunicea calyculata	LOTUS Database	35616633
Eunicea laciniata	LOTUS Database	35616633

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
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.28	ALOGPS
logP	5.41	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.75 m³·mol⁻¹	ChemAxon
Polarizability	34.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

3801455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one (NP0249705)

MOL for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

3D MOL for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

3D SDF for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

3D-SDF for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

PDB for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

3D PDB for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

SMILES for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

INCHI for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

Structure for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)

3D Structure for NP0249705 (3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-2-one)