ChemFOnt: Showing chemical card for (5R)-5-Hydroxyhexanoic acid (CFc000000308)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:40 UTC

Chemfont ID

CFc000000308

Molecule Identification

Common Name

(5R)-5-Hydroxyhexanoic acid

Definition

5-hydroxyhexanoic acid is produced during omega-oxidation of fatty acids in people unable to beta-oxidize fatty acids properly. Excessive excretion of 5-hydroxyhexanoic acid appears to be a part of Reye's syndrome.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-5-Hydroxycaproic acid	ChEBI
(-)-5-Hydroxyhexanoic acid	ChEBI
(5R)-5-Hydroxycaproic acid	ChEBI
(R)-(-)-5-Hydroxyhexanoic acid	ChEBI
(-)-5-Hydroxycaproate	Generator
(-)-5-Hydroxyhexanoate	Generator
(5R)-5-Hydroxycaproate	Generator
(R)-(-)-5-Hydroxyhexanoate	Generator
(5R)-5-Hydroxyhexanoate	Generator
(5R)-5-Hydroxy-hexanoate	HMDB
(5R)-5-Hydroxy-hexanoic acid	HMDB
HMBA	HMDB
5R-Hydroxy-hexanoate	HMDB

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

(5R)-5-hydroxyhexanoic acid

Traditional Name

HMBA

CAS Registry Number

83972-61-6

SMILES

C[C@@H](O)CCCC(O)=O

InChI Identifier

InChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1

InChI Key

YDCRNMJQROAWFT-RXMQYKEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Hydroxy fatty 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

medium-chain fatty acid (CHEBI:78842 )
(omega-1)-hydroxy fatty acid (CHEBI:78842 )
Hydroxy fatty acids (LMFA01050376 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000409)
Cell membrane (HMDB: HMDB0000409)

Organelle

Adiposome (HMDB: HMDB0000409)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000409)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000409)

Source

Endogenous

Endogenous (HMDB: HMDB0000409)

Animal

Animal (HMDB: HMDB0000409)

Exogenous

Food

Food (HMDB: HMDB0000409)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000409)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000409)

Lipid metabolism pathway (HMDB: HMDB0000409)

Biochemical process

Lipid transport (HMDB: HMDB0000409)

Role

Biological role

Energy source (HMDB: HMDB0000409)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	128 g/L	ALOGPS
logP	0.32	ALOGPS
logP	0.35	ChemAxon
logS	-0.02	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-1.6	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	4	ChemAxon
Refractivity	32.82 m³·mol⁻¹	ChemAxon
Polarizability	14.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000409

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022025

KNApSAcK ID

Not Available

Chemspider ID

5474600

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5398

PubChem Compound

7131043

PDB ID

Not Available

ChEBI ID

78842

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Fazio, Fabio; Schneider, Manfred P. FA-catalyzed trimerization of R-(+)-6-methyltetrahydro-2-pyranone. FB 9-Bergische Universitat-GH-Wuppertal, Wuppertal, Germany. Tetrahedron Letters (2002), 43(5), 811-814.

Showing chemical card for (5R)-5-Hydroxyhexanoic acid (CFc000000308)

MOL for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

3D MOL for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

3D SDF for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

3D-SDF for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

PDB for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

3D PDB for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

SMILES for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

INCHI for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

Structure for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)

3D Structure for CFc000000308 ((5R)-5-Hydroxyhexanoic acid)