NP-MRD: Showing NP-Card for 2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate (NP0164308)

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Record Information

Version

2.0

Created at

2022-09-02 23:09:43 UTC

Updated at

2022-09-02 23:09:43 UTC

NP-MRD ID

NP0164308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate

Description

4B,8,8-trimethyl-2-(propan-2-yl)-3,4,4a,4b,5,6,7,8,8a,9-decahydrophenanthren-8a-yl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate is found in Solidago nemoralis. 4B,8,8-trimethyl-2-(propan-2-yl)-3,4,4a,4b,5,6,7,8,8a,9-decahydrophenanthren-8a-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241501072D          

 24 26  0  0  0  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6021    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    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
  7  8  1  0  0  0  0
  8  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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  6 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
M  END
> <DATABASE_ID>
NP0164308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=CCC3(OC(C)=O)C(C)(C)CCCC3(C)C2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O2/c1-15(2)17-8-9-19-18(14-17)10-13-22(24-16(3)23)20(4,5)11-7-12-21(19,22)6/h10,14-15,19H,7-9,11-13H2,1-6H3

> <INCHI_KEY>
QXGOVOYQEWWNSG-UHFFFAOYSA-N

> <FORMULA>
C22H34O2

> <MOLECULAR_WEIGHT>
330.512

> <EXACT_MASS>
330.255880335

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.700764095551534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4b,8,8-trimethyl-2-(propan-2-yl)-3,4,4a,4b,5,6,7,8,8a,9-decahydrophenanthren-8a-yl acetate

> <ALOGPS_LOGP>
7.04

> <JCHEM_LOGP>
5.198605566666666

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.014491047971035

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
100.02259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3H-phenanthren-8a-yl acetate

> <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       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.185   2.461   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.645   2.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.955   3.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.457   1.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.172   0.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.565  -2.874   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   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14   20                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    9   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    4                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
4b,8,8-Trimethyl-2-(propan-2-yl)-3,4,4a,4b,5,6,7,8,8a,9-decahydrophenanthren-8a-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₂

Average Mass

330.5120 Da

Monoisotopic Mass

330.25588 Da

IUPAC Name

4b,8,8-trimethyl-2-(propan-2-yl)-3,4,4a,4b,5,6,7,8,8a,9-decahydrophenanthren-8a-yl acetate

Traditional Name

2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3H-phenanthren-8a-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=CCC3(OC(C)=O)C(C)(C)CCCC3(C)C2CC1

InChI Identifier

InChI=1S/C22H34O2/c1-15(2)17-8-9-19-18(14-17)10-13-22(24-16(3)23)20(4,5)11-7-12-21(19,22)6/h10,14-15,19H,7-9,11-13H2,1-6H3

InChI Key

QXGOVOYQEWWNSG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solidago nemoralis	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
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	7.04	ALOGPS
logP	5.2	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.02 m³·mol⁻¹	ChemAxon
Polarizability	39.7 Å³	ChemAxon
Number of Rings	3	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

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 2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate (NP0164308)

MOL for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

3D MOL for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

3D SDF for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

3D-SDF for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

PDB for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

3D PDB for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

SMILES for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

INCHI for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

Structure for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)

3D Structure for NP0164308 (2-isopropyl-4b,8,8-trimethyl-4,4a,5,6,7,9-hexahydro-3h-phenanthren-8a-yl acetate)