NP-MRD: Showing NP-Card for (3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate (NP0159514)

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Record Information

Version

2.0

Created at

2022-09-02 17:16:49 UTC

Updated at

2022-09-02 17:16:49 UTC

NP-MRD ID

NP0159514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(3AS,4R,4aS,5R,7S,7aS,8S,9R,9aR)-4-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-7-yl acetate belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. Based on a literature review very few articles have been published on (3aS,4R,4aS,5R,7S,7aS,8S,9R,9aR)-4-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-7-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022219162D          

 27 29  0  0  1  0            999 V2000
    4.0876    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392    1.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890    2.3296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3054    1.5253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5621    1.1673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5621    0.3423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0971   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    1.5253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8558    0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352    2.3296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8136    2.4036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3904    3.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    3.8077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.1022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0366    0.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    2.9746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7917    3.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    2.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3326    3.7179    0.0000 O   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  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  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  6  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END


  Mrv1652309022219162D          

 27 29  0  0  1  0            999 V2000
    4.0876    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392    1.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890    2.3296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3054    1.5253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5621    1.1673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5621    0.3423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0971   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188    1.5253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8558    0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352    2.3296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8136    2.4036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3904    3.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345    3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    3.8077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.1022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0366    0.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    2.9746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7917    3.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    2.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3326    3.7179    0.0000 O   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  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  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  6  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0159514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2[C@H](C[C@@H](O)[C@@]2(C)[C@H](OC(C)=O)[C@H]2[C@@H](OC(=O)C2=C)[C@@H]1O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-7-13-16(27-18(7)24)15(23)8(2)14-11(25-9(3)20)6-12(22)19(14,5)17(13)26-10(4)21/h8,11-17,22-23H,1,6H2,2-5H3/t8-,11-,12+,13+,14+,15+,16+,17+,19+/m0/s1

> <INCHI_KEY>
FQCOUKWLWDFEQU-DWVBCWGVSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.409

> <EXACT_MASS>
382.162767797

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.43431080363884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
-0.21070213333333312

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.622529507707817

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.808788922710384

> <JCHEM_PKA_STRONGEST_BASIC>
-3.003910590876104

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
90.4885

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       7.630   0.524   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.492   2.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.652   3.071   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.153   2.728   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.047   4.487   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.513   4.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.170   2.847   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.783   2.179   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.783   0.639   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.116  -0.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.648  -0.292   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.116  -1.671   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.395   2.847   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.464   1.309   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.052   4.349   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.519   4.487   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.729   5.809   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.811   5.786   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.561   4.441   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.601   7.108   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.913   3.071   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.073   2.057   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.935   0.524   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.013   5.553   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.344   6.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.553   5.553   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.221   6.940   0.000  0.00  0.00           O+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   26                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22                                                            
CONECT   24   15   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    6   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(3AS,4R,4as,5R,7S,7as,8S,9R,9ar)-4-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-7-yl acetic acid	Generator

Chemical Formula

C₁₉H₂₆O₈

Average Mass

382.4090 Da

Monoisotopic Mass

382.16277 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2[C@H](C[C@@H](O)[C@@]2(C)[C@H](OC(C)=O)[C@H]2[C@@H](OC(=O)C2=C)[C@@H]1O)OC(C)=O

InChI Identifier

InChI=1S/C19H26O8/c1-7-13-16(27-18(7)24)15(23)8(2)14-11(25-9(3)20)6-12(22)19(14,5)17(13)26-10(4)21/h8,11-17,22-23H,1,6H2,2-5H3/t8-,11-,12+,13+,14+,15+,16+,17+,19+/m0/s1

InChI Key

FQCOUKWLWDFEQU-DWVBCWGVSA-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 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
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen 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
logP	0.62	ALOGPS
logP	-0.21	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.49 m³·mol⁻¹	ChemAxon
Polarizability	38.43 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

162875164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate (NP0159514)

MOL for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

3D MOL for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

3D SDF for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

3D-SDF for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

PDB for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

3D PDB for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

SMILES for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

INCHI for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

Structure for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)

3D Structure for NP0159514 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-7-(acetyloxy)-5,9-dihydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl acetate)