NP-MRD: Showing NP-Card for (3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one (NP0176006)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 13:35:59 UTC

Updated at

2022-09-03 13:35:59 UTC

NP-MRD ID

NP0176006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one

Description

(3AS,4S,4aS,5R,7S,8R,9aR)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. (3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one is found in Gaillardia aristata. Based on a literature review very few articles have been published on (3aS,4S,4aS,5R,7S,8R,9aR)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032215362D          

 20 22  0  0  1  0            999 V2000
    1.0366   -2.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -1.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136   -0.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352   -0.4476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1496    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    0.1974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3326    0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -0.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -0.3737    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7338    0.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0876   -2.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054   -1.2519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2684   -2.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -1.6099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5621   -2.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -1.2519    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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20  2  1  6  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@]2(C)[C@H](O)C[C@H](O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-6-4-9-11(7(2)14(19)20-9)13(18)15(3)10(17)5-8(16)12(6)15/h6,8-13,16-18H,2,4-5H2,1,3H3/t6-,8+,9-,10-,11-,12?,13+,15-/m1/s1

> <INCHI_KEY>
CHHJAEIMNOFHLW-HTUURHGYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.97378662107581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,4aS,5R,7S,8R,9aR)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
-0.09600307700000062

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.600698523856117

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.987567978007284

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8725325813319413

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
70.901

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,4aS,5R,7S,8R,9aR)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3aH-azuleno[6,5-b]furan-2-one

> <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       1.935  -4.661   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.073  -3.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.913  -2.114   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.588  -2.456   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.519  -0.698   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.052  -0.836   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.013   0.368   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.553   0.368   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.221   1.756   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.513  -0.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.047  -0.698   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.836   0.625   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.652  -2.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.492  -3.127   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.630  -4.661   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.170  -2.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.101  -3.875   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.783  -3.005   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.783  -4.545   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.395  -2.337   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

(3aS,4S,4aS,5R,7S,8R,9aR)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one

Traditional Name

(3aS,4S,4aS,5R,7S,8R,9aR)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3aH-azuleno[6,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@]2(C)[C@H](O)C[C@H](O)C12

InChI Identifier

InChI=1S/C15H22O5/c1-6-4-9-11(7(2)14(19)20-9)13(18)15(3)10(17)5-8(16)12(6)15/h6,8-13,16-18H,2,4-5H2,1,3H3/t6-,8+,9-,10-,11-,12?,13+,15-/m1/s1

InChI Key

CHHJAEIMNOFHLW-HTUURHGYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gaillardia aristata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Sesquiterpene lactones

Alternative Parents

Substituents

Helenalin-skeleton
Ambrosanolide
Sesquiterpenoid
Pseudoguaiane sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.08	ALOGPS
logP	-0.096	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	13.99	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.9 m³·mol⁻¹	ChemAxon
Polarizability	28.97 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

163080696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one (NP0176006)

MOL for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

3D MOL for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

3D SDF for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

3D-SDF for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

PDB for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

3D PDB for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

SMILES for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

INCHI for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

Structure for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)

3D Structure for NP0176006 ((3as,4s,4as,5r,7s,8r,9ar)-4,5,7-trihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3ah-azuleno[6,5-b]furan-2-one)