NP-MRD: Showing NP-Card for (3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate (NP0214356)

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Record Information

Version

2.0

Created at

2022-09-05 13:37:55 UTC

Updated at

2022-09-05 13:37:55 UTC

NP-MRD ID

NP0214356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215372D          

 33 35  0  0  1  0            999 V2000
    0.6048    7.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1612    7.1054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6756    5.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6378    5.9561    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.9140    5.1936    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3049    5.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    4.4090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.5101    4.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052215372D          

 33 35  0  0  1  0            999 V2000
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 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0214356

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O9/c1-10(2)8-17(27)32-15-9-16(30-13(5)25)24(7)19(15)12(4)20(28)21-18(11(3)23(29)33-21)22(24)31-14(6)26/h10,12,15-16,18-22,28H,3,8-9H2,1-2,4-7H3/t12-,15-,16+,18+,19+,20+,21+,22+,24+/m0/s1

> <INCHI_KEY>
OHXAYESXJHEHGM-LYGMSERTSA-N

> <FORMULA>
C24H34O9

> <MOLECULAR_WEIGHT>
466.527

> <EXACT_MASS>
466.220282675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.35253284412653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.6625468853333354

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.900061298046143

> <JCHEM_PKA_STRONGEST_BASIC>
-3.279913188234614

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
113.4165

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.129  13.862   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.461  12.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.054  12.199   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.168  13.263   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.261  10.673   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.126  10.005   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.191  11.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.724  10.980   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.514  12.302   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.764  13.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.532  14.571   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.554  14.969   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.573   9.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.303  11.051   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.097   8.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.343   7.325   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.343   5.785   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.676   5.015   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.676   3.475   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.010   5.785   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.344   5.015   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.677   5.785   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.344   3.475   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.589   8.230   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.113   9.695   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.018  10.941   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.549  10.780   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.455  12.025   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.176   9.373   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.655   7.689   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.517   6.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.333   8.479   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.952   7.630   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   32                                                  
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   25                                             
CONECT   14   13                                                            
CONECT   15   13   16   30                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16   25                                                       
CONECT   25   24   13   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   15   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₄H₃₄O₉

Average Mass

466.5270 Da

Monoisotopic Mass

466.22028 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H34O9/c1-10(2)8-17(27)32-15-9-16(30-13(5)25)24(7)19(15)12(4)20(28)21-18(11(3)23(29)33-21)22(24)31-14(6)26/h10,12,15-16,18-22,28H,3,8-9H2,1-2,4-7H3/t12-,15-,16+,18+,19+,20+,21+,22+,24+/m0/s1

InChI Key

OHXAYESXJHEHGM-LYGMSERTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gaillardia pulchella	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
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
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	1.66	ChemAxon
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	113.42 m³·mol⁻¹	ChemAxon
Polarizability	48.35 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	Yes	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

162872005

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)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate (NP0214356)

MOL for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

3D MOL for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

3D SDF for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

3D-SDF for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

PDB for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

3D PDB for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

SMILES for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

INCHI for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

Structure for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)

3D Structure for NP0214356 ((3as,4r,4as,5r,7s,7as,8s,9r,9ar)-4,5-bis(acetyloxy)-9-hydroxy-4a,8-dimethyl-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-7-yl 3-methylbutanoate)