NP-MRD: Showing NP-Card for 1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid (NP0226509)

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Record Information

Version

2.0

Created at

2022-09-06 05:34:34 UTC

Updated at

2022-09-06 05:34:35 UTC

NP-MRD ID

NP0226509

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid

Description

1,4A-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-decahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid is found in Cryptomeria japonica. 1,4A-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-decahydronaphthalene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241515442D          

 26 27  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8340   -0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7842   -1.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
  3  4  1  0  0  0  0
  4  5  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 21  1  0  0  0  0
 22 21  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END


  Mrv1533004241515442D          

 26 27  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0095   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3969   -1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8340   -0.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7842   -1.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
  3  4  1  0  0  0  0
  4  5  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  2 21  1  0  0  0  0
 22 21  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226509

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)CC=CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O3/c1-16(8-6-9-18(3)24)10-12-19-17(2)11-13-20-22(19,4)14-7-15-23(20,5)21(25)26/h6,9,16,19-20H,2,7-8,10-15H2,1,3-5H3,(H,25,26)

> <INCHI_KEY>
KNRXBOCDMJMJJX-UHFFFAOYSA-N

> <FORMULA>
C23H36O3

> <MOLECULAR_WEIGHT>
360.538

> <EXACT_MASS>
360.266445019

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.72942335657663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-decahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.9336982606666675

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.851129818731675

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.92939123049712

> <JCHEM_PKA_STRONGEST_BASIC>
-4.587821206406755

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
106.65809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2H-naphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.484  -3.616   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.207  -2.364   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.024  -1.058   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.930  -3.723   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    2   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
1,4a-Dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-decahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₂₃H₃₆O₃

Average Mass

360.5380 Da

Monoisotopic Mass

360.26645 Da

IUPAC Name

1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-decahydronaphthalene-1-carboxylic acid

Traditional Name

1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2H-naphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(CCC1C(=C)CCC2C1(C)CCCC2(C)C(O)=O)CC=CC(C)=O

InChI Identifier

InChI=1S/C23H36O3/c1-16(8-6-9-18(3)24)10-12-19-17(2)11-13-20-22(19,4)14-7-15-23(20,5)21(25)26/h6,9,16,19-20H,2,7-8,10-15H2,1,3-5H3,(H,25,26)

InChI Key

KNRXBOCDMJMJJX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cryptomeria japonica	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
Labdane diterpenoid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
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	5.69	ALOGPS
logP	5.93	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	106.66 m³·mol⁻¹	ChemAxon
Polarizability	42.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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 1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid (NP0226509)

MOL for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

3D MOL for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

3D SDF for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

3D-SDF for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

PDB for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

3D PDB for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

SMILES for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

INCHI for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

Structure for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)

3D Structure for NP0226509 (1,4a-dimethyl-5-(3-methyl-7-oxooct-5-en-1-yl)-6-methylidene-hexahydro-2h-naphthalene-1-carboxylic acid)