NP-MRD: Showing NP-Card for 3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate (NP0253991)

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Record Information

Version

2.0

Created at

2022-09-07 18:01:26 UTC

Updated at

2022-09-07 18:01:26 UTC

NP-MRD ID

NP0253991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate

Description

3,4A,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl 3-methylbutanoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate is found in Roldana aschenborniana. 3,4A,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl 3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251513322D          

 24 26  0  0  0  0            999 V2000
    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
    2.8579    0.0000    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
    4.2868    0.8250    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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0497    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7578    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808   -0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OC1C2=C(OC=C2C)C(=O)C2=CCCC(C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-11(2)9-15(21)24-19-16-12(3)10-23-18(16)17(22)14-8-6-7-13(4)20(14,19)5/h8,10-11,13,19H,6-7,9H2,1-5H3

> <INCHI_KEY>
FWENKENVKHNNFP-UHFFFAOYSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.11381544671352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl 3-methylbutanoate

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
4.346008832333334

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9408238601480843

> <JCHEM_POLAR_SURFACE_AREA>
56.51

> <JCHEM_REFRACTIVITY>
92.47079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H-naphtho[2,3-b]furan-4-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.323   3.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.293   4.961   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.855   3.977   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.481   2.570   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.804  -0.931   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    8   17   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
3,4a,5-Trimethyl-9-oxo-4H,4ah,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,9H-naphtho[2,3-b]furan-4-yl 3-methylbutanoate

Traditional Name

3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H-naphtho[2,3-b]furan-4-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OC1C2=C(OC=C2C)C(=O)C2=CCCC(C)C12C

InChI Identifier

InChI=1S/C20H26O4/c1-11(2)9-15(21)24-19-16-12(3)10-23-18(16)17(22)14-8-6-7-13(4)20(14,19)5/h8,10-11,13,19H,6-7,9H2,1-5H3

InChI Key

FWENKENVKHNNFP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Roldana aschenborniana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Aryl ketone
Fatty acid ester
Fatty acyl
Heteroaromatic compound
Furan
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	4.37	ALOGPS
logP	4.35	ChemAxon
logS	-4.3	ALOGPS
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	4	ChemAxon
Refractivity	92.47 m³·mol⁻¹	ChemAxon
Polarizability	36.11 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

14287052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate (NP0253991)

MOL for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

3D MOL for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

3D SDF for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

3D-SDF for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

PDB for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

3D PDB for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

SMILES for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

INCHI for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

Structure for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)

3D Structure for NP0253991 (3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h-naphtho[2,3-b]furan-4-yl 3-methylbutanoate)