NP-MRD: Showing NP-Card for methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate (NP0266302)

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Record Information

Version

2.0

Created at

2022-09-08 10:36:26 UTC

Updated at

2022-09-08 10:36:26 UTC

NP-MRD ID

NP0266302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate

Description

Methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-1,3,4,5,6,7,8,8a-octahydroacenaphthylene-5-carboxylate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate is found in Cladogynos orientalis. Methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-1,3,4,5,6,7,8,8a-octahydroacenaphthylene-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171504002D          

 25 28  0  0  0  0            999 V2000
   -0.4611   -2.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324   -1.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -2.5352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    0.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    2.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0489    3.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    2.7160    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  2  0  0  0  0
  3  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
  8 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
 13 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
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 10 20  1  0  0  0  0
 13 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 25  1  0  0  0  0
M  END


  Mrv1533004171504002D          

 25 28  0  0  0  0            999 V2000
   -0.4611   -2.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1324   -1.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -2.5352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    0.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4614    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    2.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0489    3.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    2.7160    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  2  0  0  0  0
  3  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
  8 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
 13 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
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 10 20  1  0  0  0  0
 13 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)CC(=O)C2=C(CC3(C)C(C)CCC1=C23)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O4/c1-12-5-6-15-18-17(16(22)10-21(15,3)19(23)24-4)14(9-20(12,18)2)13-7-8-25-11-13/h7-8,11-12H,5-6,9-10H2,1-4H3

> <INCHI_KEY>
UZOFSGSGPZZHSD-UHFFFAOYSA-N

> <FORMULA>
C21H24O4

> <MOLECULAR_WEIGHT>
340.419

> <EXACT_MASS>
340.167459253

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.14077328494167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-1,3,4,5,6,7,8,8a-octahydroacenaphthylene-5-carboxylate

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
3.4229369370000002

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.574700139235766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.868827650869782

> <JCHEM_POLAR_SURFACE_AREA>
56.510000000000005

> <JCHEM_REFRACTIVITY>
94.9487

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1H-acenaphthylene-5-carboxylate

> <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      -0.861  -3.883   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.247  -2.814   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.727  -3.238   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.100  -4.732   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.696  -3.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.504   1.174   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.633   2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.793   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.302   1.174   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.728   3.605   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.188   3.605   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.712   5.070   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.958   5.975   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.204   5.070   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   19                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5   20                                                  
CONECT   20   19   10   13                                                  
CONECT   21   11   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-1,3,4,5,6,7,8,8a-octahydroacenaphthylene-5-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄O₄

Average Mass

340.4190 Da

Monoisotopic Mass

340.16746 Da

IUPAC Name

methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-1,3,4,5,6,7,8,8a-octahydroacenaphthylene-5-carboxylate

Traditional Name

methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1H-acenaphthylene-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)CC(=O)C2=C(CC3(C)C(C)CCC1=C23)C1=COC=C1

InChI Identifier

InChI=1S/C21H24O4/c1-12-5-6-15-18-17(16(22)10-21(15,3)19(23)24-4)14(9-20(12,18)2)13-7-8-25-11-13/h7-8,11-12H,5-6,9-10H2,1-4H3

InChI Key

UZOFSGSGPZZHSD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cladogynos orientalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Cyclohexenone
Furan
Methyl ester
Heteroaromatic compound
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.01	ALOGPS
logP	3.42	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.57	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.95 m³·mol⁻¹	ChemAxon
Polarizability	37.14 Å³	ChemAxon
Number of Rings	4	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

12302909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate (NP0266302)

MOL for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

3D MOL for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

3D SDF for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

3D-SDF for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

PDB for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

3D PDB for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

SMILES for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

INCHI for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

Structure for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)

3D Structure for NP0266302 (methyl 2-(furan-3-yl)-5,8,8a-trimethyl-3-oxo-4,6,7,8-tetrahydro-1h-acenaphthylene-5-carboxylate)