NP-MRD: Showing NP-Card for 5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid (NP0217367)

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Record Information

Version

2.0

Created at

2022-09-05 17:41:50 UTC

Updated at

2022-09-05 17:41:50 UTC

NP-MRD ID

NP0217367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid

Description

5-(2,5,5,8A-tetramethyl-6-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-2-enoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid is found in Brickellia laciniata. 5-(2,5,5,8A-tetramethyl-6-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191521382D          

 23 24  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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  4  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1C(C)=CCC2C(C)(C)C(=O)CCC12C)=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h7,12,15-16H,6,8-11H2,1-5H3,(H,22,23)

> <INCHI_KEY>
ZDGKOLMZPXXBIZ-UHFFFAOYSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.385257429324106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2,5,5,8a-tetramethyl-6-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-2-enoic acid

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
4.754367952666668

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.911993462821936

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.852768021358771

> <JCHEM_PKA_STRONGEST_BASIC>
-7.47109114243759

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
93.68689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1H-naphthalen-1-yl)-3-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    9   13   22                                             
CONECT   22   21                                                            
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
5-(2,5,5,8a-Tetramethyl-6-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-2-enoate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

5-(2,5,5,8a-tetramethyl-6-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-2-enoic acid

Traditional Name

5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1H-naphthalen-1-yl)-3-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC1C(C)=CCC2C(C)(C)C(=O)CCC12C)=CC(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h7,12,15-16H,6,8-11H2,1-5H3,(H,22,23)

InChI Key

ZDGKOLMZPXXBIZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brickellia laciniata	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

Labdane diterpenoid
Diterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
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	4.86	ALOGPS
logP	4.75	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-7.5	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	4	ChemAxon
Refractivity	93.69 m³·mol⁻¹	ChemAxon
Polarizability	36.39 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 5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid (NP0217367)

MOL for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

3D MOL for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

3D SDF for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

3D-SDF for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

PDB for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

3D PDB for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

SMILES for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

INCHI for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

Structure for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)

3D Structure for NP0217367 (5-(2,5,5,8a-tetramethyl-6-oxo-4,4a,7,8-tetrahydro-1h-naphthalen-1-yl)-3-methylpent-2-enoic acid)