NP-MRD: Showing NP-Card for (3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate (NP0179120)

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Record Information

Version

2.0

Created at

2022-09-03 17:15:13 UTC

Updated at

2022-09-03 17:15:13 UTC

NP-MRD ID

NP0179120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate

Description

(3AR,4aR,6S,7aS,9aS)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-6-yl propanoate 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. (3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate is found in Arctotis fastuosa. Based on a literature review very few articles have been published on (3aR,4aR,6S,7aS,9aS)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-6-yl propanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032219152D          

 23 25  0  0  1  0            999 V2000
    2.7580    1.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1159    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9409    0.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    0.3230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2770    0.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6013   -0.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4056   -0.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717   -0.4813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5284   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851   -0.4813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8222   -1.3055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769   -0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0030   -1.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556   -0.3617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6513   -0.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4082   -1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -1.9383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962   -1.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -2.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7799    0.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016    0.3230    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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  1  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 23 22  1  1  0  0  0
  2 23  1  0  0  0  0
 12 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179120

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O5/c1-5-16(19)22-14-7-13-9(2)6-15-12(10(3)17(20)23-15)8-18(13,21)11(14)4/h12-15,21H,2-8H2,1H3/t12-,13+,14+,15+,18+/m1/s1

> <INCHI_KEY>
PKSIZINMGNWSOJ-ZVZLPEGASA-N

> <FORMULA>
C18H22O5

> <MOLECULAR_WEIGHT>
318.369

> <EXACT_MASS>
318.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.817043981328794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aR,6S,7aS,9aS)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-6-yl propanoate

> <JCHEM_LOGP>
1.826805642666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.846223514265812

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3034618348601326

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
82.79339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4aR,6S,7aS,9aS)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3aH-azuleno[6,5-b]furan-6-yl propanoate

> <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       5.148   3.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.816   1.807   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.356   1.807   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.317   0.603   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.850   0.741   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.456  -0.675   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.957  -1.018   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.296  -1.688   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.434  -3.222   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.974  -0.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.586  -1.567   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.199  -0.898   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.268  -2.437   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.877  -1.688   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.739  -3.222   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.717  -0.675   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.216  -1.018   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.762  -2.489   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.809  -3.618   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.739  -2.832   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.193  -4.304   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.322   0.741   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.856   0.603   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   23                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   16   23                                                       
CONECT   23   22    2   12                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4ar,6S,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-6-yl propanoic acid	Generator

Chemical Formula

C₁₈H₂₂O₅

Average Mass

318.3690 Da

Monoisotopic Mass

318.14672 Da

IUPAC Name

(3aR,4aR,6S,7aS,9aS)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-6-yl propanoate

Traditional Name

(3aR,4aR,6S,7aS,9aS)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3aH-azuleno[6,5-b]furan-6-yl propanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H22O5/c1-5-16(19)22-14-7-13-9(2)6-15-12(10(3)17(20)23-15)8-18(13,21)11(14)4/h12-15,21H,2-8H2,1H3/t12-,13+,14+,15+,18+/m1/s1

InChI Key

PKSIZINMGNWSOJ-ZVZLPEGASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arctotis fastuosa	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
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
logP	1.83	ChemAxon
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.79 m³·mol⁻¹	ChemAxon
Polarizability	33.82 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

162954022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate (NP0179120)

MOL for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

3D MOL for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

3D SDF for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

3D-SDF for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

PDB for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

3D PDB for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

SMILES for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

INCHI for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

Structure for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)

3D Structure for NP0179120 ((3ar,4ar,6s,7as,9as)-4a-hydroxy-3,5,8-trimethylidene-2-oxo-hexahydro-3ah-azuleno[6,5-b]furan-6-yl propanoate)