NP-MRD: Showing NP-Card for (3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one (NP0260992)

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Record Information

Version

2.0

Created at

2022-09-08 03:19:31 UTC

Updated at

2022-09-08 03:19:31 UTC

NP-MRD ID

NP0260992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one

Description

(3S,3aS,6aR,9aR,9bS)-3-{[(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-dodecahydroazuleno[4,5-b]furan-2-one belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review very few articles have been published on (3S,3aS,6aR,9aR,9bS)-3-{[(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-dodecahydroazuleno[4,5-b]furan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082205192D          

 37 41  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309082205192D          

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   10.0867    7.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9552    6.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5948    6.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1841    6.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5445    7.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7734    6.8553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4342    4.3037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9797    3.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2696    2.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1844    3.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474    4.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9198    4.9487    0.0000 C   0  0  1  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  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
 20 31  1  0  0  0  0
 16 31  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  1  0  0  0
  2 37  1  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C[C@@]1(C[C@H]2[C@@H]3CC\C(C)=C/CC\C(C)=C/[C@H]3OC2=O)[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O5/c1-18-7-6-8-19(2)15-27-24(12-9-18)25(30(34)36-27)17-32(16-22(5)33)26-14-11-20(3)23-13-10-21(4)28(23)29(26)37-31(32)35/h7,15,23-29H,3-4,6,8-14,16-17H2,1-2,5H3/b18-7-,19-15-/t23-,24-,25-,26+,27+,28-,29-,32+/m0/s1

> <INCHI_KEY>
RAIJJHURLMJTBQ-JWQBYJPESA-N

> <FORMULA>
C32H42O5

> <MOLECULAR_WEIGHT>
506.683

> <EXACT_MASS>
506.303224452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.45673689445512

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aS,6aR,9aR,9bS)-3-{[(3S,3aS,11aS)-6,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-dodecahydroazuleno[4,5-b]furan-2-one

> <JCHEM_LOGP>
5.709784612333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.47707526692666

> <JCHEM_PKA_STRONGEST_BASIC>
-6.688792993432842

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
144.2263

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,6aR,9aR,9bS)-3-{[(3S,3aS,11aS)-6,10-dimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.322  11.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.526  10.739   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.914  11.407   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.301  10.739   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.644   9.238   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.684   8.034   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.532   6.748   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.017   7.158   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.221   6.198   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.086   8.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.622   8.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.484   7.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.020   7.637   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      15.809   6.144   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.789  10.066   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.954  11.361   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.417  11.446   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.980  12.002   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.022  12.934   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.316  13.769   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.562  15.290   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.001  15.837   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.247  17.358   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.195  14.865   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.635  15.412   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.828  14.439   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.583  12.919   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.777  11.946   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.144  12.371   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.950  13.344   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.510  12.797   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.144   8.034   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.295   6.748   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.837   5.306   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.811   7.158   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.742   8.696   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.184   9.238   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11   15                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   20   16                                                  
CONECT   32    6   33   37                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    2   32                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂O₅

Average Mass

506.6830 Da

Monoisotopic Mass

506.30322 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)C[C@@]1(C[C@H]2[C@@H]3CC\C(C)=C/CC\C(C)=C/[C@H]3OC2=O)[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O

InChI Identifier

InChI=1S/C32H42O5/c1-18-7-6-8-19(2)15-27-24(12-9-18)25(30(34)36-27)17-32(16-22(5)33)26-14-11-20(3)23-13-10-21(4)28(23)29(26)37-31(32)35/h7,15,23-29H,3-4,6,8-14,16-17H2,1-2,5H3/b18-7-,19-15-/t23-,24-,25-,26+,27+,28-,29-,32+/m0/s1

InChI Key

RAIJJHURLMJTBQ-JWQBYJPESA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Germacranolide
Sesquiterpenoid
Guaiane sesquiterpenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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

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

163014407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one (NP0260992)

MOL for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

3D MOL for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

3D SDF for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

3D-SDF for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

PDB for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

3D PDB for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

SMILES for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

INCHI for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

Structure for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)

3D Structure for NP0260992 ((3s,3as,6ar,9ar,9bs)-3-{[(3s,3as,11as)-6,10-dimethyl-2-oxo-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-3-yl]methyl}-6,9-dimethylidene-3-(2-oxopropyl)-octahydroazuleno[4,5-b]furan-2-one)