Livestock Metabolome Database: Showing metabocard for Myristoleic acid (LMDB00370)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:19 UTC

Update Date

2016-09-23 18:45:16 UTC

Lmdb

LMDB00370

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Myristoleic acid

Description

Myristoleic acid, also known as 9-tetradecenoate or myristoleate, 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. Based on a literature review a significant number of articles have been published on Myristoleic acid.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(9Z)-Tetradecenoic acid	ChEBI
(Z)-Tetradec-9-enoic acid	ChEBI
9-Tetradecenoic acid	ChEBI
9Z-Tetradecenoic acid	ChEBI
cis-9-Tetradecenoic acid	ChEBI
cis-Delta(9)-Tetradecenoic acid	ChEBI
cis-Tetradec-9-enoic acid	ChEBI
(9Z)-Tetradecenoate	Generator
(Z)-Tetradec-9-enoate	Generator
9-Tetradecenoate	Generator
9Z-Tetradecenoate	Generator
cis-9-Tetradecenoate	Generator
cis-delta(9)-Tetradecenoate	Generator
cis-Δ(9)-tetradecenoate	Generator
cis-Δ(9)-tetradecenoic acid	Generator
cis-Tetradec-9-enoate	Generator
Myristoleate	Generator
(9Z)-Tetradec-9-enoate	HMDB
(9Z)-Tetradec-9-enoic acid	HMDB
(9Z)-9-Tetradecenoic acid	HMDB
(Z)-9-Tetradecenoic acid	HMDB
9(Z)-Tetradecenoic acid	HMDB
9-cis-Tetradecenoic acid	HMDB
FA(14:1(9Z))	HMDB
FA(14:1n5)	HMDB
Myristoleic acid	HMDB
Myristolenic acid	HMDB
Oleomyristic acid	HMDB
cis-delta9-Tetradecenoic acid	HMDB
cis-Δ9-Tetradecenoic acid	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Molecular Weight

226.355

Monoisotopic Molecular Weight

226.193280076

IUPAC Name

(9Z)-tetradec-9-enoic acid

Traditional Name

myristoleic acid

CAS Registry Number

544-64-9

SMILES

CCCC\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

InChI Key

YWWVWXASSLXJHU-WAYWQWQTSA-N

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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:27781 )
tetradecenoic acid (CHEBI:27781 )
Unsaturated fatty acids (C08322 )
Monounsaturated fatty acids (C08322 )
Unsaturated fatty acids (LMFA01030051 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

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
logP	5.69	ALOGPS
logP	5.01	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	69 m³·mol⁻¹	ChemAxon
Polarizability	28.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-71fb52f9fefd5cb3790e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00a9-9520000000-b85c6ba98a1ce24c3518	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0090000000-57b079c6d11a9714cb51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0090000000-4fcda40660e1f5947eb6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9120000000-50121015a2477be41bec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0595-9000000000-98c3d58fb9e1e7c41c90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004i-0090000000-e588f40ae851251aee81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0390000000-6a2bf4ff780562d5fdd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-6930000000-bd53c7ac25c8930728e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9300000000-cd017bd3efd7fa06ee6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-c6a068748e37ad83d1d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1590000000-999dd13c5871dbb32a3f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-97121a85c8e202172ecf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-6c6d923a7644bf907b73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1090000000-bf30a380076470239567	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-b037435cdbd96f2e828d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7j-9330000000-790a04dc9533b3b6607b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05o1-9000000000-fa6bdbb819001b908171	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9000000000-aaba2dc5fc19c49556c2	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0aou-9100000000-1823acbf402fe87fba5b	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	20855010	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected and Quantified	2100 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	2300 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	2400 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	3700 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002000

FooDB ID

FDB012633

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001229

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6424

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jiang J, Wolk A, Vessby B: Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Am J Clin Nutr. 1999 Jul;70(1):21-7. [10393134 ]
Iguchi K, Okumura N, Usui S, Sajiki H, Hirota K, Hirano K: Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate. 2001 Apr;47(1):59-65. [11304730 ]

Showing metabocard for Myristoleic acid (LMDB00370)

Structure for LMDB00370 (Myristoleic acid)