NP-MRD: Showing NP-Card for (3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate (NP0233012)

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Record Information

Version

2.0

Created at

2022-09-06 14:27:06 UTC

Updated at

2022-09-06 14:27:06 UTC

NP-MRD ID

NP0233012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062216272D          

 32 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062216272D          

 32 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0233012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1[C@H]2[C@@H](C[C@@H](C)[C@@H]3[C@@H](O)C[C@@H](OC(=O)CC(C)C)[C@@]13C)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O7/c1-8-13(4)23(28)32-22-20-15(6)24(29)30-17(20)10-14(5)21-16(26)11-18(25(21,22)7)31-19(27)9-12(2)3/h8,12,14,16-18,20-22,26H,6,9-11H2,1-5,7H3/b13-8-/t14-,16+,17-,18-,20-,21-,22+,25-/m1/s1

> <INCHI_KEY>
MLTRRVPOGLBRTK-HCYONVALSA-N

> <FORMULA>
C25H36O7

> <MOLECULAR_WEIGHT>
448.556

> <EXACT_MASS>
448.246103499

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.962483417074054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,4aS,5R,7S,7aS,8R,9aR)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.9901831763333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.829722651518491

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8732793122258116

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
117.6588

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.065  -0.412   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.110   0.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.606   0.219   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.190  -1.206   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.416   1.529   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.420   2.703   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.852   4.182   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.965   5.441   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.715   6.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.572   5.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.342   6.867   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.715   8.273   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.848   6.546   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.009   5.015   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.343   4.245   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.676   5.015   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.676   6.555   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.010   4.245   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.344   5.015   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.677   4.245   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.344   6.555   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.602   4.389   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.820   3.446   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.350   2.869   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.609   1.983   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.471   0.449   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.721  -0.896   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.730  -0.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.128   0.210   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.592  -1.971   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.195  -2.619   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.005   2.119   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   14   10   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   24    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(3AR,4S,4as,5R,7S,7as,8R,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-4-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₆O₇

Average Mass

448.5560 Da

Monoisotopic Mass

448.24610 Da

IUPAC Name

(3aR,4S,4aS,5R,7S,7aS,8R,9aR)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-dodecahydroazuleno[6,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3aR,4S,4aS,5R,7S,7aS,8R,9aR)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3aH-azuleno[6,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1[C@H]2[C@@H](C[C@@H](C)[C@@H]3[C@@H](O)C[C@@H](OC(=O)CC(C)C)[C@@]13C)OC(=O)C2=C

InChI Identifier

InChI=1S/C25H36O7/c1-8-13(4)23(28)32-22-20-15(6)24(29)30-17(20)10-14(5)21-16(26)11-18(25(21,22)7)31-19(27)9-12(2)3/h8,12,14,16-18,20-22,26H,6,9-11H2,1-5,7H3/b13-8-/t14-,16+,17-,18-,20-,21-,22+,25-/m1/s1

InChI Key

MLTRRVPOGLBRTK-HCYONVALSA-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 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
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
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	3.99	ChemAxon
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	-2.9	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	7	ChemAxon
Refractivity	117.66 m³·mol⁻¹	ChemAxon
Polarizability	47.96 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

163017544

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate (NP0233012)

MOL for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

PDB for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

Structure for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0233012 ((3ar,4s,4as,5r,7s,7as,8r,9ar)-7-hydroxy-4a,8-dimethyl-5-[(3-methylbutanoyl)oxy]-3-methylidene-2-oxo-octahydro-3ah-azuleno[6,5-b]furan-4-yl (2z)-2-methylbut-2-enoate)