NP-MRD: Showing NP-Card for (3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione (NP0286636)

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Record Information

Version

2.0

Created at

2022-09-09 15:17:33 UTC

Updated at

2022-09-09 15:17:33 UTC

NP-MRD ID

NP0286636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione

Description

(3S,3aR,6aS,9R,9aS,9bR)-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione is found in Echinops ritro. Based on a literature review very few articles have been published on (3S,3aR,6aS,9R,9aS,9bR)-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092217172D          

 18 20  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6763   -1.6349    0.0000 C   0  0  0  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  1  0  0  0
  5 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0286636

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2CCC(=C)[C@H]3CC(=O)[C@H](C)[C@H]3[C@@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h8-11,13-14H,1,4-6H2,2-3H3/t8-,9-,10+,11+,13+,14+/m0/s1

> <INCHI_KEY>
QEFUTRKIARMBLC-WKSZEZMPSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.0311508019581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,6aS,9R,9aS,9bR)-3,9-dimethyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

> <JCHEM_LOGP>
2.3579957806666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.1077098782816

> <JCHEM_PKA_STRONGEST_BASIC>
-6.919853870827602

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.05780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,6aS,9R,9aS,9bR)-3,9-dimethyl-6-methylidene-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.530   1.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   12   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2CCC(=C)[C@H]3CC(=O)[C@H](C)[C@H]3[C@@H]2OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h8-11,13-14H,1,4-6H2,2-3H3/t8-,9-,10+,11+,13+,14+/m0/s1

InChI Key

QEFUTRKIARMBLC-WKSZEZMPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Echinops ritro	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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

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

162872679

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione (NP0286636)

MOL for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

3D MOL for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

3D SDF for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

3D-SDF for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

PDB for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

3D PDB for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

SMILES for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

INCHI for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

Structure for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)

3D Structure for NP0286636 ((3s,3ar,6as,9r,9as,9br)-3,9-dimethyl-6-methylidene-octahydro-3h-azuleno[4,5-b]furan-2,8-dione)