NP-MRD: Showing NP-Card for (4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate (NP0307378)

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Record Information

Version

2.0

Created at

2022-09-11 00:28:11 UTC

Updated at

2022-09-11 00:28:11 UTC

NP-MRD ID

NP0307378

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate

Description

(4AS,8R,8aS)-3,5,8a-trimethyl-2-oxo-2H,4H,4aH,7H,8H,8aH-naphtho[2,3-b]furan-8-yl acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate is found in Smyrnium perfoliatum. Based on a literature review very few articles have been published on (4aS,8R,8aS)-3,5,8a-trimethyl-2-oxo-2H,4H,4aH,7H,8H,8aH-naphtho[2,3-b]furan-8-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112202282D          

 21 23  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    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  1  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0307378

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1CC=C(C)[C@@H]2CC3=C(C)C(=O)OC3=C[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O4/c1-9-5-6-15(20-11(3)18)17(4)8-14-12(7-13(9)17)10(2)16(19)21-14/h5,8,13,15H,6-7H2,1-4H3/t13-,15+,17+/m0/s1

> <INCHI_KEY>
ZNVXNYHXQCEWBS-YSVLISHTSA-N

> <FORMULA>
C17H20O4

> <MOLECULAR_WEIGHT>
288.343

> <EXACT_MASS>
288.136159124

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.434528196585973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,8R,8aS)-3,5,8a-trimethyl-2-oxo-2H,4H,4aH,7H,8H,8aH-naphtho[2,3-b]furan-8-yl acetate

> <JCHEM_LOGP>
2.154461627000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.706849359123151

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
80.15920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,8R,8aS)-3,5,8a-trimethyl-2-oxo-4H,4aH,7H,8H-naphtho[2,3-b]furan-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.609   1.171   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.578  -1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -3.850   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   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   10    5   21                                             
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(4AS,8R,8as)-3,5,8a-trimethyl-2-oxo-2H,4H,4ah,7H,8H,8ah-naphtho[2,3-b]furan-8-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₄

Average Mass

288.3430 Da

Monoisotopic Mass

288.13616 Da

IUPAC Name

(4aS,8R,8aS)-3,5,8a-trimethyl-2-oxo-2H,4H,4aH,7H,8H,8aH-naphtho[2,3-b]furan-8-yl acetate

Traditional Name

(4aS,8R,8aS)-3,5,8a-trimethyl-2-oxo-4H,4aH,7H,8H-naphtho[2,3-b]furan-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1CC=C(C)[C@@H]2CC3=C(C)C(=O)OC3=C[C@@]12C

InChI Identifier

InChI=1S/C17H20O4/c1-9-5-6-15(20-11(3)18)17(4)8-14-12(7-13(9)17)10(2)16(19)21-14/h5,8,13,15H,6-7H2,1-4H3/t13-,15+,17+/m0/s1

InChI Key

ZNVXNYHXQCEWBS-YSVLISHTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Smyrnium perfoliatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.15	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.16 m³·mol⁻¹	ChemAxon
Polarizability	31.43 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

162910517

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate (NP0307378)

MOL for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

3D MOL for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

3D SDF for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

3D-SDF for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

PDB for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

3D PDB for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

SMILES for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

INCHI for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

Structure for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)

3D Structure for NP0307378 ((4as,8r,8as)-3,5,8a-trimethyl-2-oxo-4h,4ah,7h,8h-naphtho[2,3-b]furan-8-yl acetate)