NP-MRD: Showing NP-Card for Cacolic acid A (NP0331169)

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Record Information

Version

1.0

Created at

2022-11-21 18:05:34 UTC

Updated at

2024-04-19 09:31:56 UTC

NP-MRD ID

NP0331169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cacolic acid A

Description

(2E,6R,10E,14E)-17-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-2,6,10,14-tetramethyl-4-oxoheptadeca-2,10,14-trienoic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on (2E,6R,10E,14E)-17-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-2,6,10,14-tetramethyl-4-oxoheptadeca-2,10,14-trienoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311212219052D          

 31 31  0  0  1  0            999 V2000
   -3.6287   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -6.8020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0871   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2305   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -6.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -5.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -7.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7721   -8.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -8.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -9.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0778   -8.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5258   -7.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6973   -6.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0008   -9.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 21  2  0  0  0  0
  2 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 27 31  2  0  0  0  0
M  END


  Mrv1652311212219052D          

 31 31  0  0  1  0            999 V2000
   -3.6287   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4853   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3726   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -6.8020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0871   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2305   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9450   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -6.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -5.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -7.6270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -6.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -6.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576   -7.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7721   -8.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8583   -8.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6653   -9.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0778   -8.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5258   -7.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6973   -6.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0008   -9.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 21  2  0  0  0  0
  2 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 27 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331169

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CC(=O)OC1O)CC(=O)\C=C(/C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O6/c1-17(10-6-12-19(3)14-22(26)15-20(4)24(28)29)8-5-9-18(2)11-7-13-21-16-23(27)31-25(21)30/h8,11,15-16,19,25,30H,5-7,9-10,12-14H2,1-4H3,(H,28,29)/b17-8+,18-11+,20-15+/t19-,25?/m1/s1

> <INCHI_KEY>
QHAMYSLUETZYER-FKXDZBODSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.557

> <EXACT_MASS>
432.251188879

$$$$

HEADER    PROTEIN                                 21-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-22         0                                  
HETATM    1  C   UNK     0      -6.774 -14.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.774 -12.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.440 -11.927   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.106 -12.697   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.772 -11.927   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.439 -12.697   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.439 -14.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.105 -11.927   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.229 -12.697   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.562 -11.927   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896 -12.697   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.896 -14.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.230 -11.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.563 -12.697   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.897 -11.927   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.231 -12.697   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.231 -14.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.564 -11.927   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.898 -12.697   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.564 -10.387   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.563 -14.237   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.107 -11.927   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.441 -12.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.441 -14.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.775 -15.007   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.936 -16.539   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.442 -16.859   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -13.212 -15.525   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -12.181 -14.381   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -12.502 -12.874   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -13.068 -18.266   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14                                                            
CONECT   22    2   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   25   30                                                  
CONECT   30   29                                                            
CONECT   31   27                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
(2E,6R,10E,14E)-17-(2-Hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-2,6,10,14-tetramethyl-4-oxoheptadeca-2,10,14-trienoate	Generator

Chemical Formula

C₂₅H₃₆O₆

Average Mass

432.5570 Da

Monoisotopic Mass

432.25119 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCC\C(C)=C\CC\C(C)=C\CCC1=CC(=O)OC1O)CC(=O)\C=C(/C)C(O)=O

InChI Identifier

InChI=1S/C25H36O6/c1-17(10-6-12-19(3)14-22(26)15-20(4)24(28)29)8-5-9-18(2)11-7-13-21-16-23(27)31-25(21)30/h8,11,15-16,19,25,30H,5-7,9-10,12-14H2,1-4H3,(H,28,29)/b17-8+,18-11+,20-15+/t19-,25?/m1/s1

InChI Key

QHAMYSLUETZYER-FKXDZBODSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.92 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Long-chain fatty acid
Methyl-branched fatty acid
Keto fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Dihydrofuran
Acryloyl-group
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

70999840

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163112609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cacolic acid A (NP0331169)

MOL for NP0331169 (Cacolic acid A)

3D MOL for NP0331169 (Cacolic acid A)

3D SDF for NP0331169 (Cacolic acid A)

3D-SDF for NP0331169 (Cacolic acid A)

PDB for NP0331169 (Cacolic acid A)

3D PDB for NP0331169 (Cacolic acid A)

SMILES for NP0331169 (Cacolic acid A)

INCHI for NP0331169 (Cacolic acid A)

Structure for NP0331169 (Cacolic acid A)

3D Structure for NP0331169 (Cacolic acid A)