NP-MRD: Showing NP-Card for (3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate (NP0256597)

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Record Information

Version

2.0

Created at

2022-09-07 21:28:56 UTC

Updated at

2022-09-07 21:28:56 UTC

NP-MRD ID

NP0256597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate

Description

(3R,4aR,5S,8R,8aR)-3,4a,5-trimethyl-2-oxo-2H,3H,4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate 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. (3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate is found in Parasenecio petasitoides. Based on a literature review very few articles have been published on (3R,4aR,5S,8R,8aR)-3,4a,5-trimethyl-2-oxo-2H,3H,4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072223282D          

 24 26  0  0  1  0            999 V2000
    0.0000   -4.9500    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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  2  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  1  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
    3.5724   -0.4125    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
    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
    4.3570   -1.4924    0.0000 O   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   -0.1576    0.0000 C   0  0  2  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
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
  8 19  1  0  0  0  0
 13 19  1  0  0  0  0
 17 20  1  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
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0256597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)O[C@@H]1CC[C@H](C)[C@@]2(C)CC3=C(C[C@@H]12)OC(=O)[C@@H]3C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-6-11(2)18(21)23-16-8-7-12(3)20(5)10-14-13(4)19(22)24-17(14)9-15(16)20/h6,12-13,15-16H,7-10H2,1-5H3/t12-,13+,15-,16+,20+/m0/s1

> <INCHI_KEY>
QPYNKFVRSIYHQA-FKVACTLWSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.67632342192122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4aR,5S,8R,8aR)-3,4a,5-trimethyl-2-oxo-2H,3H,4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate

> <JCHEM_LOGP>
4.014270708666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.460521769571532

> <JCHEM_PKA_STRONGEST_BASIC>
-6.706040081538241

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
93.34259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aR,5S,8R,8aR)-3,4a,5-trimethyl-2-oxo-3H,4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   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       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.578  -1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.609   1.171   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                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    8   13                                                  
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(3R,4AR,5S,8R,8ar)-3,4a,5-trimethyl-2-oxo-2H,3H,4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(3R,4aR,5S,8R,8aR)-3,4a,5-trimethyl-2-oxo-2H,3H,4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate

Traditional Name

(3R,4aR,5S,8R,8aR)-3,4a,5-trimethyl-2-oxo-3H,4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)O[C@@H]1CC[C@H](C)[C@@]2(C)CC3=C(C[C@@H]12)OC(=O)[C@@H]3C

InChI Identifier

InChI=1S/C20H28O4/c1-6-11(2)18(21)23-16-8-7-12(3)20(5)10-14-13(4)19(22)24-17(14)9-15(16)20/h6,12-13,15-16H,7-10H2,1-5H3/t12-,13+,15-,16+,20+/m0/s1

InChI Key

QPYNKFVRSIYHQA-FKVACTLWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Parasenecio petasitoides	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
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.01	ChemAxon
pKa (Strongest Acidic)	16.46	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	3	ChemAxon
Refractivity	93.34 m³·mol⁻¹	ChemAxon
Polarizability	37.68 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

163008534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate (NP0256597)

MOL for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

3D MOL for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

3D SDF for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

3D-SDF for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

PDB for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

3D PDB for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

SMILES for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

INCHI for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

Structure for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)

3D Structure for NP0256597 ((3r,4ar,5s,8r,8ar)-3,4a,5-trimethyl-2-oxo-3h,4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl 2-methylbut-2-enoate)