ChemFOnt: Showing chemical card for (R)-3-Hydroxy-hexadecanoic acid (CFc000006739)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:49 UTC

Chemfont ID

CFc000006739

Molecule Identification

Common Name

(R)-3-Hydroxy-hexadecanoic acid

Definition

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-hexadecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC: 2.3.1.41).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-3-Hydroxy-hexadecanoate	Generator
(R)-beta-Hydroxypalmitic acid	ChEBI
(R)-b-Hydroxypalmitate	Generator
(R)-b-Hydroxypalmitic acid	Generator
(R)-beta-Hydroxypalmitate	Generator
(R)-β-hydroxypalmitate	Generator
(R)-β-hydroxypalmitic acid	Generator
3-Hydroxypalmitic acid	MeSH, HMDB
beta-Hydroxypalmitic acid	MeSH, HMDB
3-Hydroxypalmitic acid, (+-)-isomer	MeSH, HMDB
beta-Hydroxypalmitate	MeSH, HMDB

Chemical Formula

C₁₆H₃₂O₃

Average Molecular Weight

272.4235

Monoisotopic Molecular Weight

272.23514489

IUPAC Name

(3R)-3-hydroxyhexadecanoic acid

Traditional Name

(R)-3-hydroxypalmitic acid

CAS Registry Number

2398-34-7

SMILES

[H][C@@](O)(CCCCCCCCCCCCC)CC(O)=O

InChI Identifier

InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15(17)14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m1/s1

InChI Key

CBWALJHXHCJYTE-OAHLLOKOSA-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
Hydroxy fatty acid
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

(3R)-3-hydroxy fatty acid (CHEBI:38247 )
3-hydroxypalmitic acid (CHEBI:38247 )
Hydroxy fatty acids (LMFA01050366 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0010734)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010734)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010734)

Source

Endogenous

Endogenous (HMDB: HMDB0010734)

Animal

Animal (HMDB: HMDB0010734)

Exogenous

Food

Food (HMDB: HMDB0010734)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0010734)

Process

Role

Biological role

Energy source (HMDB: HMDB0010734)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010734)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0056 g/L	ALOGPS
logP	5.75	ALOGPS
logP	5.03	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	78.6 m³·mol⁻¹	ChemAxon
Polarizability	35.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010734

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027881

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

15569776

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (R)-3-Hydroxy-hexadecanoic acid (CFc000006739)

MOL for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

3D MOL for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

3D SDF for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

3D-SDF for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

PDB for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

3D PDB for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

SMILES for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

INCHI for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

Structure for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)

3D Structure for CFc000006739 ((R)-3-Hydroxy-hexadecanoic acid)