NP-MRD: Showing NP-Card for (3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate (NP0282322)

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Record Information

Version

2.0

Created at

2022-09-09 09:06:41 UTC

Updated at

2022-09-09 09:06:41 UTC

NP-MRD ID

NP0282322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate

Description

(3AS,6aS,8S,9aR,9bS)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 2-methylpropanoate 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. Based on a literature review very few articles have been published on (3aS,6aS,8S,9aR,9bS)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 2-methylpropanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092211062D          

 24 26  0  0  1  0            999 V2000
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -2.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7053   -1.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782    0.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -0.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668    0.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2348    0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3439    1.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  2  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  6  0  0  0
  6 24  1  0  0  0  0
 12 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1C[C@]2(O)[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3CCC2=C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-9(2)17(20)23-14-8-19(22)10(3)6-7-13-11(4)18(21)24-16(13)15(19)12(14)5/h9,13-16,22H,3-8H2,1-2H3/t13-,14-,15+,16-,19+/m0/s1

> <INCHI_KEY>
LUUJHRSUAVIZOX-KSPMYQCISA-N

> <FORMULA>
C19H24O5

> <MOLECULAR_WEIGHT>
332.396

> <EXACT_MASS>
332.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.42192910782386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6aS,8S,9aR,9bS)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 2-methylpropanoate

> <JCHEM_LOGP>
2.338554641999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.763814605677524

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3395074914766507

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
87.2255

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6aS,8S,9aR,9bS)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3aH-azuleno[4,5-b]furan-8-yl 2-methylpropanoate

> <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      10.530  -1.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.380   1.393   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.691   0.843   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.482  -4.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.183  -2.660   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.766   1.393   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.333   0.831   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.103  -0.692   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.871   1.791   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.305   1.228   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.642   3.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.455   0.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.996   2.285   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    6   12                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(3AS,6as,8S,9ar,9BS)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₉H₂₄O₅

Average Mass

332.3960 Da

Monoisotopic Mass

332.16237 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1C[C@]2(O)[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3CCC2=C)C1=C

InChI Identifier

InChI=1S/C19H24O5/c1-9(2)17(20)23-14-8-19(22)10(3)6-7-13-11(4)18(21)24-16(13)15(19)12(14)5/h9,13-16,22H,3-8H2,1-2H3/t13-,14-,15+,16-,19+/m0/s1

InChI Key

LUUJHRSUAVIZOX-KSPMYQCISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

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

14262457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate (NP0282322)

MOL for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

3D MOL for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

3D SDF for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

3D-SDF for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

PDB for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

3D PDB for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

SMILES for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

INCHI for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

Structure for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)

3D Structure for NP0282322 ((3as,6as,8s,9ar,9bs)-6a-hydroxy-3,6,9-trimethylidene-2-oxo-hexahydro-3ah-azuleno[4,5-b]furan-8-yl 2-methylpropanoate)