NP-MRD: Showing NP-Card for (3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate (NP0191781)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 08:50:51 UTC

Updated at

2022-09-04 08:50:51 UTC

NP-MRD ID

NP0191781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate

Description

Erigerolide belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. (3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate is found in Inula aspera. Based on a literature review very few articles have been published on Erigerolide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042210502D          

 26 28  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  1  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  0  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  0  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
    5.5587    0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9605   -0.3983    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  0  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
    4.8362   -2.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5108   -2.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9101   -3.6652    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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26  2  1  6  0  0  0
  6 26  1  0  0  0  0
M  END


  Mrv1652309042210502D          

 26 28  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  1  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  0  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  0  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
    5.5587    0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    1.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9605   -0.3983    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  0  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
    4.8362   -2.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5108   -2.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9101   -3.6652    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  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26  2  1  6  0  0  0
  6 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C[C@@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@]2(C)C(CC(OC(C)=O)C12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O7/c1-8-6-12-15(9(2)18(23)26-12)17(22)19(5)14(25-11(4)21)7-13(16(8)19)24-10(3)20/h8,12-17,22H,2,6-7H2,1,3-5H3/t8?,12-,13?,14?,15+,16?,17-,19+/m0/s1

> <INCHI_KEY>
QFJNAUKGMNMIGV-KTQHVISUSA-N

> <FORMULA>
C19H26O7

> <MOLECULAR_WEIGHT>
366.41

> <EXACT_MASS>
366.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.63401391973489

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.7862477436666676

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.227921202516228

> <JCHEM_PKA_STRONGEST_BASIC>
-3.136507266019401

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
89.20400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,4aR,9aS)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3aH-azuleno[6,5-b]furan-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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      10.376   0.601   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.166   1.923   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.126  -0.744   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.652  -2.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.492  -3.127   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.630  -4.661   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.028  -5.308   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.287  -4.422   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.166  -6.842   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.170  -2.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.101  -3.875   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.783  -3.005   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.783  -4.545   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.395  -2.337   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   10   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₇

Average Mass

366.4100 Da

Monoisotopic Mass

366.16785 Da

IUPAC Name

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

Traditional Name

(3aS,4S,4aR,9aS)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3aH-azuleno[6,5-b]furan-7-yl acetate

CAS Registry Number

Not Available

SMILES

CC1C[C@@H]2OC(=O)C(=C)[C@H]2[C@H](O)[C@]2(C)C(CC(OC(C)=O)C12)OC(C)=O

InChI Identifier

InChI=1S/C19H26O7/c1-8-6-12-15(9(2)18(23)26-12)17(22)19(5)14(25-11(4)21)7-13(16(8)19)24-10(3)20/h8,12-17,22H,2,6-7H2,1,3-5H3/t8?,12-,13?,14?,15+,16?,17-,19+/m0/s1

InChI Key

QFJNAUKGMNMIGV-KTQHVISUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Inula aspera	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
Tricarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
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	0.79	ChemAxon
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.2 m³·mol⁻¹	ChemAxon
Polarizability	37.63 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

102059023

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,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate (NP0191781)

MOL for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

3D MOL for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

3D SDF for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

3D-SDF for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

PDB for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

3D PDB for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

SMILES for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

INCHI for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

Structure for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)

3D Structure for NP0191781 ((3as,4s,4ar,9as)-5-(acetyloxy)-4-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl acetate)