NP-MRD: Showing NP-Card for Cacolic acid B (NP0331162)

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Record Information

Version

2.0

Created at

2022-11-21 17:48:40 UTC

Updated at

2024-09-03 04:14:46 UTC

NP-MRD ID

NP0331162

Natural Product DOI

https://doi.org/10.57994/0039

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cacolic acid B

Description

(2R,6E,10E)-13-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-2,6,10-trimethyltrideca-6,10-dienoic acid belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on (2R,6E,10E)-13-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-2,6,10-trimethyltrideca-6,10-dienoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311212218482D          

 25 25  0  0  1  0            999 V2000
   -2.3622   -7.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -6.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6477   -6.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332   -6.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2188   -6.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957   -6.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957   -7.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102   -6.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9247   -6.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -6.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -6.6014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3536   -7.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0681   -6.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7825   -6.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0681   -5.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766   -6.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911   -6.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911   -7.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -7.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5918   -8.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3988   -8.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8113   -8.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2593   -7.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4308   -6.6963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7343   -9.5845    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
 13 15  2  0  0  0  0
  2 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331162

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-14(9-5-11-16(3)19(22)23)7-4-8-15(2)10-6-12-17-13-18(21)25-20(17)24/h7,10,13,16,20,24H,4-6,8-9,11-12H2,1-3H3,(H,22,23)/b14-7+,15-10+/t16-,20?/m1/s1

> <INCHI_KEY>
BRWKDBAXWVCQIQ-SOIRDAQJSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

$$$$

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      -4.409 -13.863   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.409 -12.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.076 -11.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.742 -12.323   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.408 -11.553   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.925 -12.323   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.925 -13.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.259 -11.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.593 -12.323   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.926 -11.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.260 -12.323   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.260 -13.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.594 -11.553   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.927 -12.323   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.594 -10.013   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.743 -11.553   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.077 -12.323   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.077 -13.863   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.410 -14.633   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.571 -16.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.078 -16.484   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -10.848 -15.151   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.817 -14.006   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.137 -12.500   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -10.704 -17.891   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
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   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23                                                            
CONECT   25   21                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
(2R,6E,10E)-13-(2-Hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-2,6,10-trimethyltrideca-6,10-dienoate	Generator

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 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)C(O)=O

InChI Identifier

InChI=1S/C20H30O5/c1-14(9-5-11-16(3)19(22)23)7-4-8-15(2)10-6-12-17-13-18(21)25-20(17)24/h7,10,13,16,20,24H,4-6,8-9,11-12H2,1-3H3,(H,22,23)/b14-7+,15-10+/t16-,20?/m1/s1

InChI Key

BRWKDBAXWVCQIQ-SOIRDAQJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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	¹³C NMR Spectrum (1D, 151 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
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
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-11-21	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Long-chain fatty acid
Methyl-branched 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 carboxylic ester
Enoate ester
Dihydrofuran
Lactone
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

70999841

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163107638

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cacolic acid B (NP0331162)

MOL for NP0331162 (Cacolic acid B)

3D MOL for NP0331162 (Cacolic acid B)

3D SDF for NP0331162 (Cacolic acid B)

3D-SDF for NP0331162 (Cacolic acid B)

PDB for NP0331162 (Cacolic acid B)

3D PDB for NP0331162 (Cacolic acid B)

SMILES for NP0331162 (Cacolic acid B)

INCHI for NP0331162 (Cacolic acid B)

Structure for NP0331162 (Cacolic acid B)

3D Structure for NP0331162 (Cacolic acid B)