NP-MRD: Showing NP-Card for (4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one (NP0217429)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 17:46:32 UTC

Updated at

2022-09-05 17:46:33 UTC

NP-MRD ID

NP0217429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one

Description

Atractylenolide I 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,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one is found in Atractylodes japonica, Atractylodes lancea, Atractylodes macrocephala and Solanum lyratum. (4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one was first documented in 2022 (PMID: 35378415). Based on a literature review a small amount of articles have been published on Atractylenolide I (PMID: 35784720) (PMID: 35749964) (PMID: 35643303).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052219462D          

 17 19  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  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
    2.1434   -0.4125    0.0000 C   0  0  2  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
    4.3570   -0.1576    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   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
  2 17  1  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C[C@H]3C(=C)CCC[C@]3(C)C=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1

> <INCHI_KEY>
ZTVSGQPHMUYCRS-SWLSCSKDSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.160209304633113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,8aS)-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-2-one

> <JCHEM_LOGP>
3.0020809539999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.010557037842069

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.4197

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,8aS)-3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.578  -1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
8,9-Dehydroasterolide	MeSH

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

(4aS,8aS)-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-2-one

Traditional Name

(4aS,8aS)-3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1=C2C[C@H]3C(=C)CCC[C@]3(C)C=C2OC1=O

InChI Identifier

InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1

InChI Key

ZTVSGQPHMUYCRS-SWLSCSKDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Atractylodes japonica	LOTUS Database	35616633
Atractylodes lancea	LOTUS Database	35616633
Atractylodes macrocephala	LOTUS Database	35616633
Solanum lyratum	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
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	3	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.42 m³·mol⁻¹	ChemAxon
Polarizability	26.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00012887

Chemspider ID

4478915

KEGG Compound ID

C17885

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321018

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Zhou L, Ge Y, Chen J, Du W, Xiao L, Tong P, Huang J, Shan L, Efferth T: Fuzi decoction ameliorates pain and cartilage degeneration of osteoarthritic rats through PI3K-Akt signaling pathway and its clinical retrospective evidence. Phytomedicine. 2022 Jun;100:154071. doi: 10.1016/j.phymed.2022.154071. Epub 2022 Mar 20. [PubMed:35378415 ]
Shen J, Li J, Yu P, Du G: Research Status and Hotspots of Anticancer Natural Products Based on the Patent Literature and Scientific Articles. Front Pharmacol. 2022 Jun 17;13:903239. doi: 10.3389/fphar.2022.903239. eCollection 2022. [PubMed:35784720 ]
Zhan C, Wang H, Wang Y: Quality evaluation of Atractylodis macrocephalae rhizoma through fingerprint qualitative analysis and quantitative analysis of multi-components by single marker. J Pharm Biomed Anal. 2022 Sep 20;219:114899. doi: 10.1016/j.jpba.2022.114899. Epub 2022 Jun 18. [PubMed:35749964 ]
Li C, Wang C, Guo Y, Wen R, Yan L, Zhang F, Gong Q, Yu H: Research on the effect and underlying molecular mechanism of Cangzhu in the treatment of gouty arthritis. Eur J Pharmacol. 2022 Jul 15;927:175044. doi: 10.1016/j.ejphar.2022.175044. Epub 2022 May 26. [PubMed:35643303 ]
LOTUS database [Link]

Showing NP-Card for (4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one (NP0217429)

MOL for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

3D MOL for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

3D SDF for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

3D-SDF for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

PDB for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

3D PDB for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

SMILES for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

INCHI for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

Structure for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)

3D Structure for NP0217429 ((4as,8as)-3,8a-dimethyl-5-methylidene-4h,4ah,6h,7h,8h-naphtho[2,3-b]furan-2-one)