MiMeDB: Showing metabocard for (9Z)-octadecenoic acid (MMDBc0054081)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:51:48 UTC

Update Date

2025-10-07 16:08:22 UTC

Metabolite ID

MMDBc0054081

Metabolite Identification

Common Name

(9Z)-octadecenoic acid

Description

(9Z)-octadecenoic acid is a monounsaturated fatty acid belonging to the class of unsaturated fatty acids. Its chemical structure features a long hydrocarbon chain of 18 carbon atoms with a cis double bond at the ninth position, which contributes to its fluidity and biological functions. This fatty acid is involved in various metabolic pathways, notably the biosynthesis of unsaturated fatty acids, where it plays a role alongside other key metabolites such as linoleic acid and arachidonic acid derivatives. Enrichment analysis has shown that pathways related to these fatty acids are significantly affected, with an adjusted p-value of 0.007 highlighting the importance of (9Z)-octadecenoic acid in lipid metabolism and cellular functions. The presence of (9Z)-octadecenoic acid in metabolic studies underscores its relevance in maintaining cellular homeostasis and influencing biological processes. (PMID:39998092 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222532D          

 20 19  0  0  0  0            999 V2000
   -1.2888    7.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 18 20  2  0  0  0  0
M  CHG  1  19  -1
M  END
> <DATABASE_ID>
MMDBc0054081

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/p-1/b10-9-

> <INCHI_KEY>
ZQPPMHVWECSIRJ-KTKRTIGZSA-M

> <FORMULA>
C18H33O2

> <MOLECULAR_WEIGHT>
281.4534

> <EXACT_MASS>
281.2480553

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60698293885545

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-octadec-9-enoate

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
6.783798451000001

> <ALOGPS_LOGS>
-6.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
40.129999999999995

> <JCHEM_REFRACTIVITY>
98.2393

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.406  14.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.072  13.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.072  11.701   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.262  10.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.262   9.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.595   8.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

Synonyms

Value	Source
(9Z)-Octadecenoate	ChEBI
(Z)-9-Octadecenoic acid, ion(1-)	ChEBI
cis-9-Octadecenoate	ChEBI
Oleat	ChEBI
Oleic acid anion	ChEBI
(9Z)-Octadecenoic acid	Generator
(Z)-9-Octadecenoate, ion(1-)	Generator
cis-9-Octadecenoic acid	Generator
Oleate anion	Generator
Oleic acid	Generator

Molecular Formula

C₁₈H₃₃O₂

Average Mass

281.4534

Monoisotopic Mass

281.2480553

IUPAC Name

(9Z)-octadec-9-enoate

Traditional Name

oleate

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCC([O-])=O

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/p-1/b10-9-

InChI Key

ZQPPMHVWECSIRJ-KTKRTIGZSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid anion (CHEBI:30823 )
unsaturated fatty acid anion (CHEBI:30823 )
octadecenoate (CHEBI:30823 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.1e-05 g/L	ALOGPS
logP	7.71	ALOGPS
logP	6.78	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	98.24 m³·mol⁻¹	ChemAxon
Polarizability	36.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-71e618da168ffaa9204d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4190000000-c53cfc55518cc6a1fd9a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9210000000-c8b1985b0e96593e5d41	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-4a7b76ecd62c26e9a13e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-0090000000-4413d771cbd2cb37d92b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-6490000000-d1664201637755434f0a	2016-09-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	217.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	39.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	763.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1083.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1197.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	861.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	3485.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	125.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	611.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	983.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	775.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	546.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	325.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	8.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	852.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	662.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	636.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	2161.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	2579.4

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0024990	TG(18:1(9Z)/18:1(9Z)/18:1(9Z))	(9Z)-octadecenoic acid	Triacylglycerol lipase	Reduction	RHEA	34755880
MMDBr0024991	TG(18:1(9Z)/18:1(9Z)/18:1(9Z))	(9Z)-octadecenoic acid	Triacylglycerol lipase 4	Reduction	RHEA	34755880
MMDBr0025583	(9Z)-octadecenoic acid	(12R)-hydroxy-(9Z)-octadecenoic acid	Oleate hydroxylase FAH12	Hydroxylation	RHEA	34755880
MMDBr0028211	CL(10:0/18:1(9Z)/10:0/18:1(9Z))	2-MLCL(10:0/0:0/10:0/18:1(9Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028212	CL(10:0/18:1(9Z)/18:1(11Z)/18:1(11Z))	2-MLCL(10:0/0:0/18:1(11Z)/18:1(11Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028213	CL(10:0/18:1(9Z)/18:1(11Z)/18:1(9Z))	2-MLCL(10:0/0:0/18:1(11Z)/18:1(9Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028214	CL(10:0/18:1(9Z)/18:1(11Z)/20:0)	2-MLCL(10:0/0:0/18:1(11Z)/20:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028215	CL(10:0/18:1(9Z)/18:1(11Z)/20:1(11Z))	2-MLCL(10:0/0:0/18:1(11Z)/20:1(11Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028216	CL(10:0/18:1(9Z)/18:1(11Z)/20:1(13Z))	2-MLCL(10:0/0:0/18:1(11Z)/20:1(13Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028217	CL(10:0/18:1(9Z)/18:1(11Z)/22:0)	2-MLCL(10:0/0:0/18:1(11Z)/22:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028218	CL(10:0/18:1(9Z)/18:1(11Z)/22:1(11Z))	2-MLCL(10:0/0:0/18:1(11Z)/22:1(11Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028219	CL(10:0/18:1(9Z)/18:1(11Z)/22:1(9Z))	2-MLCL(10:0/0:0/18:1(11Z)/22:1(9Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028220	CL(10:0/18:1(9Z)/18:1(11Z)/24:0)	2-MLCL(10:0/0:0/18:1(11Z)/24:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028221	CL(10:0/18:1(9Z)/18:1(11Z)/24:1(11Z))	2-MLCL(10:0/0:0/18:1(11Z)/24:1(11Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028222	CL(10:0/18:1(9Z)/18:1(11Z)/24:1(9Z))	2-MLCL(10:0/0:0/18:1(11Z)/24:1(9Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028223	CL(10:0/18:1(9Z)/18:1(11Z)/26:0)	2-MLCL(10:0/0:0/18:1(11Z)/26:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028224	CL(10:0/18:1(9Z)/18:1(11Z)/26:1(11Z))	2-MLCL(10:0/0:0/18:1(11Z)/26:1(11Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028225	CL(10:0/18:1(9Z)/18:1(9Z)/18:1(11Z))	2-MLCL(10:0/0:0/18:1(9Z)/18:1(11Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028226	CL(10:0/18:1(9Z)/18:1(9Z)/18:1(9Z))	2-MLCL(10:0/0:0/18:1(9Z)/18:1(9Z))	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880
MMDBr0028227	CL(10:0/18:1(9Z)/18:1(9Z)/20:0)	2-MLCL(10:0/0:0/18:1(9Z)/20:0)	Cardiolipin-specific deacylase 1, mitochondrial	Deacylation	RHEA	34755880

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
Bacteria/Eubacteria	Bacteroidetes	1	Human
Bacteria/Eubacteria	Firmicutes	2	Human
Bacteria/Eubacteria	Actinobacteria	2	Human
Eukaryota/Fungi	Ascomycota	2
Bacteria	Proteobacteria	2	Human ; Human sputum; Human subgingival plaque; Human feces; Human feces; pleural fluid plaque; bal
Bacteria/Eubacteria	Proteobacteria	4	Human ; Human sputum; Human subgingival plaque; Human feces; Human feces; pleural fluid plaque; bal

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleic acid

METLIN ID

Not Available

PubChem Compound

5460221

PDB ID

Not Available

ChEBI ID

30823

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (9Z)-octadecenoic acid (MMDBc0054081)

MOL for #<Metabolite:0x00007f2e50af4c10>

3D MOL for #<Metabolite:0x00007f2e50af4c10>

3D SDF for #<Metabolite:0x00007f2e50af4c10>

3D-SDF for #<Metabolite:0x00007f2e50af4c10>

PDB for #<Metabolite:0x00007f2e50af4c10>

3D PDB for #<Metabolite:0x00007f2e50af4c10>

SMILES for #<Metabolite:0x00007f2e50af4c10>

INCHI for #<Metabolite:0x00007f2e50af4c10>

Structure for #<Metabolite:0x00007f2e50af4c10>

3D Structure for #<Metabolite:0x00007f2e50af4c10>