NP-MRD: Showing NP-Card for 5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid (NP0248802)

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Record Information

Version

2.0

Created at

2022-09-07 11:11:43 UTC

Updated at

2022-09-07 11:11:43 UTC

NP-MRD ID

NP0248802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid

Description

5,6,8A-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a,5,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid is found in Scapania nemorea. 5,6,8A-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a,5,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171501292D          

 24 26  0  0  0  0            999 V2000
   -1.4289    0.0000    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
   -0.7145   -1.2375    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    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
    2.1434   -1.2375    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    1.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4161    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594    2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009    2.7746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8309    2.8003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    2.2272    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)C(C=CC=C2C(O)=O)C1(C)CCC1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-13-7-9-20(3)15(18(22)23)5-4-6-16(20)19(13,2)10-8-14-11-17(21)24-12-14/h4-6,11,13,16H,7-10,12H2,1-3H3,(H,22,23)

> <INCHI_KEY>
XVTYNOXQGXBEAH-UHFFFAOYSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.05652576437575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,8a-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a,5,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
3.8684555576666666

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.472339184495049

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.80288000353797

> <JCHEM_PKA_STRONGEST_BASIC>
-6.822540393452907

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
94.10999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.262   1.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.985   2.773   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.510   2.988   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.777   4.504   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.162   5.179   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.418   5.227   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.310   4.157   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
5,6,8a-Trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a,5,6,7,8,8a-hexahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

5,6,8a-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a,5,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

Traditional Name

5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(C=CC=C2C(O)=O)C1(C)CCC1=CC(=O)OC1

InChI Identifier

InChI=1S/C20H26O4/c1-13-7-9-20(3)15(18(22)23)5-4-6-16(20)19(13,2)10-8-14-11-17(21)24-12-14/h4-6,11,13,16H,7-10,12H2,1-3H3,(H,22,23)

InChI Key

XVTYNOXQGXBEAH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Scapania nemorea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Clerodane diterpenoid
Diterpenoid
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.41	ALOGPS
logP	3.87	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	36.06 Å³	ChemAxon
Number of Rings	3	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 5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid (NP0248802)

MOL for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

3D MOL for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

3D SDF for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

3D-SDF for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

PDB for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

3D PDB for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

SMILES for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

INCHI for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

Structure for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)

3D Structure for NP0248802 (5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-4a,6,7,8-tetrahydronaphthalene-1-carboxylic acid)