MiMeDB: Showing metabocard for Cibaric acid (MMDBc0013525)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 04:49:16 UTC

Update Date

2022-12-15 22:51:44 UTC

Metabolite ID

MMDBc0013525

Metabolite Identification

Common Name

Cibaric acid

Description

Cibaric acid, also known as cibarate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review very few articles have been published on Cibaric acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152106492D          

 28 27  0  0  0  0            999 V2000
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 24  5  1  0  0  0  0
 25  7  1  0  0  0  0
 26  9  1  0  0  0  0
 27 12  1  0  0  0  0
 28 15  1  0  0  0  0
M  END


  Mrv1652305152106492D          

 28 27  0  0  0  0            999 V2000
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    2.1434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 24  5  1  0  0  0  0
 25  7  1  0  0  0  0
 26  9  1  0  0  0  0
 27 12  1  0  0  0  0
 28 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0013525

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCC(O)=O)=C(/[H])CC(=O)C(\[H])=C(/O)\C(\[H])=C(/[H])CCO

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O5/c19-14-10-9-12-17(21)15-16(20)11-7-5-3-1-2-4-6-8-13-18(22)23/h5,7,9,12,15,19,21H,1-4,6,8,10-11,13-14H2,(H,22,23)/b7-5-,12-9+,17-15-

> <INCHI_KEY>
LFTUCYCUYUJMJB-YXCOHMLOSA-N

> <FORMULA>
C18H28O5

> <MOLECULAR_WEIGHT>
324.417

> <EXACT_MASS>
324.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.364059165853774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,13Z,15E)-14,18-dihydroxy-12-oxooctadeca-9,13,15-trienoic acid

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.1329570429999993

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.894827784995456

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988161946244245

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9811717168112888

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
94.07449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,13Z,15E)-14,18-dihydroxy-12-oxooctadeca-9,13,15-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.470  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.400   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.170   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.860   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.710   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.550   1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.780  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.090   1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.480   5.335   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.550  -1.334   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.860  -0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       6.160  -2.667   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       9.240  -2.667   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      16.170   1.334   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      13.090   4.001   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      10.780   2.667   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7   24                                                  
CONECT    6    4    8                                                       
CONECT    7    5   11   25                                                  
CONECT    8    6   13                                                       
CONECT    9   10   12   26                                                  
CONECT   10    9   14                                                       
CONECT   11    7   16                                                       
CONECT   12    9   17   27                                                  
CONECT   13    8   18                                                       
CONECT   14   10   19                                                       
CONECT   15   16   17   28                                                  
CONECT   16   11   15   20                                                  
CONECT   17   12   15   21                                                  
CONECT   18   13   22   23                                                  
CONECT   19   14                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   18                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    9                                                            
CONECT   27   12                                                            
CONECT   28   15                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

Synonyms

Value	Source
Cibarate	Generator
14,18-Dihydroxy-12-oxo-9,13,15-octadecatrienoic acid	MeSH

Molecular Formula

C₁₈H₂₈O₅

Average Mass

324.417

Monoisotopic Mass

324.193674002

IUPAC Name

(9Z,13Z,15E)-14,18-dihydroxy-12-oxooctadeca-9,13,15-trienoic acid

Traditional Name

(9Z,13Z,15E)-14,18-dihydroxy-12-oxooctadeca-9,13,15-trienoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC(O)=O)=C(/[H])CC(=O)C(\[H])=C(/O)\C(\[H])=C(/[H])CCO

InChI Identifier

InChI=1S/C18H28O5/c19-14-10-9-12-17(21)15-16(20)11-7-5-3-1-2-4-6-8-13-18(22)23/h5,7,9,12,15,19,21H,1-4,6,8,10-11,13-14H2,(H,22,23)/b7-5-,12-9+,17-15-

InChI Key

LFTUCYCUYUJMJB-YXCOHMLOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Acryloyl-group
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	3.23	ALOGPS
logP	3.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	94.07 m³·mol⁻¹	ChemAxon
Polarizability	37.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	3	Human feces	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00055090

Chemspider ID

4943077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438613

PDB ID

Not Available

ChEBI ID

177569

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Cibaric acid (MMDBc0013525)

MOL for #<Metabolite:0x00007fdb4c5edb78>

3D MOL for #<Metabolite:0x00007fdb4c5edb78>

3D SDF for #<Metabolite:0x00007fdb4c5edb78>

3D-SDF for #<Metabolite:0x00007fdb4c5edb78>

PDB for #<Metabolite:0x00007fdb4c5edb78>

3D PDB for #<Metabolite:0x00007fdb4c5edb78>

SMILES for #<Metabolite:0x00007fdb4c5edb78>

INCHI for #<Metabolite:0x00007fdb4c5edb78>

Structure for #<Metabolite:0x00007fdb4c5edb78>

3D Structure for #<Metabolite:0x00007fdb4c5edb78>