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

2018-05-20 10:11:21 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
a-Hydroxyhexadecanoylcarnitine	HMDB
a-Hydroxypalmitoylcarnitine	HMDB
alpha-Hydroxyhexadecanoylcarnitine	HMDB
alpha-Hydroxypalmitoylcarnitine	HMDB

Chemical Formula

C₂₃H₄₅NO₅

Average Molecular Weight

415.6071

Monoisotopic Molecular Weight

415.329773555

IUPAC Name

(4S)-4-[(2-hydroxyhexadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(4S)-4-[(2-hydroxyhexadecanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC(O)C(=O)O[C@@H](CCC([O-])=O)[N+](C)(C)C

InChI Identifier

InChI=1S/C23H45NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-20(25)23(28)29-21(24(2,3)4)18-19-22(26)27/h20-21,25H,5-19H2,1-4H3/t20?,21-/m0/s1

InChI Key

ALAYOLIEZSXQPY-LBAQZLPGSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Monosaccharide
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
Organic nitrogen compound
Carbonyl group
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	0.86	ALOGPS
logP	1.49	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	138.5 m³·mol⁻¹	ChemAxon
Polarizability	51.17 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5941000000-b0319f34aab020f87950	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-7901100000-886b24348ed9b0208b50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-1319400000-68a89a529efd18a22a07	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-2910000000-07bf145106b7f6ac1036	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-4910000000-e28111f8f3c8bb2b560b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-0060900000-46e188163b0c92c9599a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0192100000-606c9e0fbb8dd9eb3ee3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-4490000000-058a49553e8417b2864d	View in MoNA

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Location

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

FDB029397

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

53481693

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)