Human Metabolome Database: Showing metabocard for 2-Hydroxyhexadecanoylcarnitine (HMDB0013337)

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

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2010-02-22 12:06:16 UTC

Update Date

2019-07-23 05:58:46 UTC

HMDB ID

HMDB0013337

Secondary Accession Numbers

HMDB13337

Metabolite Identification

Common Name

2-Hydroxyhexadecanoylcarnitine

Description

2-hydroxyhexadecanoylcarnitine, also known as a-Hydroxypalmitoylcarnitine, is classified as a member of the fatty acid esters. Fatty acid esters are carboxylic ester derivatives of a fatty acid. 2-hydroxyhexadecanoylcarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. 2-hydroxyhexadecanoylcarnitine is a fatty ester lipid molecule. 2-hydroxyhexadecanoylcarnitine can be found in blood. Within a cell, 2-hydroxyhexadecanoylcarnitine is primarily located in the extracellular space and near the membrane.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-9(Z)-octadecenoylcarnitine	HMDB

Chemical Formula

C₂₅H₄₇NO₄

Average Molecular Weight

425.654

Monoisotopic Molecular Weight

425.350508997

IUPAC Name

(3S)-3-[(11Z)-octadec-11-enoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-[(11Z)-octadec-11-enoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/CCCCCCCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C25H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h10-11,23H,5-9,12-22H2,1-4H3/b11-10-/t23-/m0/s1

InChI Key

HOAMADDCQBUDDY-JCKUYFFHSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organooxygen compound
Organonitrogen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

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
Water Solubility	5.4e-05 g/L	ALOGPS
logP	2	ALOGPS
logP	2.56	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	147.4 m³·mol⁻¹	ChemAxon
Polarizability	52.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-057i-2226900000-f147392e4965ea75d0bc	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-3930000000-88ead31bcec3fbf14892	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-7970000000-f8339eb9ecb2414c2129	JSpectraViewer \| MoNA

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Feces	Detected and Quantified	0.26 +/- 0.14 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.24 +/- 0.1 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029400

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481699

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-Hydroxyhexadecanoylcarnitine (HMDB0013337)

Structure for HMDB0013337 (2-Hydroxyhexadecanoylcarnitine)