NP-MRD: Showing NP-Card for 10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate (NP0187248)

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Record Information

Version

2.0

Created at

2022-09-04 03:21:00 UTC

Updated at

2022-09-04 03:21:00 UTC

NP-MRD ID

NP0187248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate

Description

10-Hydroxy-3a,10-dimethyl-6-methylidene-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,10H,12aH-cyclopenta[11]annulen-7-yl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate is found in Sphaerococcus coronopifolius. 10-Hydroxy-3a,10-dimethyl-6-methylidene-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,10H,12aH-cyclopenta[11]annulen-7-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121513252D          

 25 26  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
    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
    3.4374    0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313   -0.5490    0.0000 O   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
    4.7722   -3.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571   -4.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3070   -4.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920   -4.4560    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
    1.0925   -3.2236    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
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv0541 04121513252D          

 25 26  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
    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
    3.4374    0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313   -0.5490    0.0000 O   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
    4.7722   -3.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571   -4.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3070   -4.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920   -4.4560    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
    1.0925   -3.2236    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
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC2C=CC(C)(O)CCC(OC(C)=O)C(=C)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O3/c1-15(2)19-8-7-18-10-12-21(5,24)13-11-20(25-17(4)23)16(3)9-14-22(18,19)6/h10,12,15,18-20,24H,3,7-9,11,13-14H2,1-2,4-6H3

> <INCHI_KEY>
MSHQCXZTTKTIFR-UHFFFAOYSA-N

> <FORMULA>
C22H36O3

> <MOLECULAR_WEIGHT>
348.527

> <EXACT_MASS>
348.266445019

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.26273844549035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-3a,10-dimethyl-6-methylidene-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,10H,12aH-cyclopenta[11]annulen-7-yl acetate

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
4.601321821000001

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.688532423965292

> <JCHEM_PKA_STRONGEST_BASIC>
-2.93503591775758

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
102.94369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.81e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1H,2H,3H,4H,5H,7H,8H,9H,12aH-cyclopenta[11]annulen-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  C   UNK     0       2.628  -2.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.161  -2.300   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.837  -0.917   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.362  -1.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.416   0.407   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.898  -1.025   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.629  -2.648   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.910  -3.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.695  -5.268   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.908  -6.217   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.693  -7.742   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.906  -8.690   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.265  -8.318   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.267  -5.844   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.052  -7.369   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.054  -4.896   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.626  -5.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.413  -4.523   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.039  -6.017   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    4    7   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
10-Hydroxy-3a,10-dimethyl-6-methylidene-3-(propan-2-yl)-1H,2H,3H,3ah,4H,5H,6H,7H,8H,9H,10H,12ah-cyclopenta[11]annulen-7-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₆O₃

Average Mass

348.5270 Da

Monoisotopic Mass

348.26645 Da

IUPAC Name

10-hydroxy-3a,10-dimethyl-6-methylidene-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,10H,12aH-cyclopenta[11]annulen-7-yl acetate

Traditional Name

10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1H,2H,3H,4H,5H,7H,8H,9H,12aH-cyclopenta[11]annulen-7-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC2C=CC(C)(O)CCC(OC(C)=O)C(=C)CCC12C

InChI Identifier

InChI=1S/C22H36O3/c1-15(2)19-8-7-18-10-12-21(5,24)13-11-20(25-17(4)23)16(3)9-14-22(18,19)6/h10,12,15,18-20,24H,3,7-9,11,13-14H2,1-2,4-6H3

InChI Key

MSHQCXZTTKTIFR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sphaerococcus coronopifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Tertiary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	4.83	ALOGPS
logP	4.6	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.69	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.94 m³·mol⁻¹	ChemAxon
Polarizability	41.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate (NP0187248)

MOL for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

3D MOL for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

3D SDF for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

3D-SDF for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

PDB for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

3D PDB for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

SMILES for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

INCHI for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

Structure for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)

3D Structure for NP0187248 (10-hydroxy-3-isopropyl-3a,10-dimethyl-6-methylidene-1h,2h,3h,4h,5h,7h,8h,9h,12ah-cyclopenta[11]annulen-7-yl acetate)