NP-MRD: Showing NP-Card for (4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione (NP0180579)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 18:57:54 UTC

Updated at

2022-09-03 18:57:54 UTC

NP-MRD ID

NP0180579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione

Description

(4AS,5R,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione is found in Ligularia fischeri, Senecio flavus and Senecio nemorensis. Based on a literature review very few articles have been published on (4aS,5R,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032220572D          

 20 22  0  0  1  0            999 V2000
    3.2190   -0.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516   -0.7025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  1  6  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12C[C@@H]3C=CC(=O)[C@H](C)[C@@]3(C)CC1=C(C)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O4/c1-9-12-8-15(3)10(2)13(17)6-5-11(15)7-16(12,19-4)20-14(9)18/h5-6,10-11H,7-8H2,1-4H3/t10-,11-,15+,16+/m0/s1

> <INCHI_KEY>
OJVOYGHFOFCKMO-DPDCMNJDSA-N

> <FORMULA>
C16H20O4

> <MOLECULAR_WEIGHT>
276.332

> <EXACT_MASS>
276.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.375325132249735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,5R,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

> <JCHEM_LOGP>
2.9812973103333342

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.188500865287924

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2416385808727295

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
75.2383

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,5R,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-4H,5H,8aH,9H-naphtho[2,3-b]furan-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       6.009  -0.406   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.763  -1.311   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.592  -5.153   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.014  -3.613   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.459  -2.367   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15   20                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₄

Average Mass

276.3320 Da

Monoisotopic Mass

276.13616 Da

IUPAC Name

(4aS,5R,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2,6-dione

Traditional Name

(4aS,5R,8aR,9aR)-9a-methoxy-3,4a,5-trimethyl-4H,5H,8aH,9H-naphtho[2,3-b]furan-2,6-dione

CAS Registry Number

Not Available

SMILES

CO[C@@]12C[C@@H]3C=CC(=O)[C@H](C)[C@@]3(C)CC1=C(C)C(=O)O2

InChI Identifier

InChI=1S/C16H20O4/c1-9-12-8-15(3)10(2)13(17)6-5-11(15)7-16(12,19-4)20-14(9)18/h5-6,10-11H,7-8H2,1-4H3/t10-,11-,15+,16+/m0/s1

InChI Key

OJVOYGHFOFCKMO-DPDCMNJDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia fischeri	LOTUS Database	35616633
Senecio flavus	LOTUS Database	35616633
Senecio nemorensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
Ketal
Cyclohexenone
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Aldehyde
Hydrocarbon derivative
Organic oxygen compound
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	2.98	ChemAxon
pKa (Strongest Acidic)	16.19	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.24 m³·mol⁻¹	ChemAxon
Polarizability	29.38 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

8146263

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9970671

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione (NP0180579)

MOL for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

3D MOL for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

3D SDF for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

3D-SDF for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

PDB for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

3D PDB for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

SMILES for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

INCHI for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

Structure for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)

3D Structure for NP0180579 ((4as,5r,8ar,9ar)-9a-methoxy-3,4a,5-trimethyl-4h,5h,8ah,9h-naphtho[2,3-b]furan-2,6-dione)