ChemFOnt: Showing chemical card for 6-Hydroxyhexanoic acid (CFc000008094)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:44 UTC

Chemfont ID

CFc000008094

Molecule Identification

Common Name

6-Hydroxyhexanoic acid

Definition

6-Hydroxyhexanoate was identified as the immediate product of hexanoate w-hydroxylation by whole cells and was further oxidized into adipic acid and an unexpected metabolite identified as 2-tetrahydrofuranacetic acid. This same metabolite, together with adipic acid, was also detected when similarly induced cells were incubated with hexanoate or 1,6-hexanediol, but not with 6-oxohexanoate (adipic semialdehyde).Cells grown on hexanoate and incubated with 6-hydroxyhexanoate were also found to accumulate 2-tetrahydrofuranacetic acid, which was not further degraded. Utilization of 6-hydroxyhexanoate for growth was restricted to those organisms also able to utilize adipate. Similar observations were made with 1,6-hexanediol serving as the carbon source and cells obtained from one organism,Pseudomonas aeruginosa PAO, grown either on 1,6-hexanediol or 6-hydroxyhexanoate,were found to be well induced for both 6-oxohexanoate and adipate oxidation. The results indicate that 6-hydroxyhexanoate and 1,6-hexanediol are susceptible to both 1B- and w-oxidative attack; however, the former pathway appears to be of no physiological significance since it generates 2-tetrahydrofuranacetic acid as a nonmetabolizable intermediate, making w-oxidation via adipate the exclusive pathway for degradation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Carboxypentanol	ChEBI
5-Hydroxypentanecarboxylic acid	ChEBI
6-Hydroxy caproic acid	ChEBI
6-Hydroxycaproic acid	ChEBI
6-Hydroxyhexanoate	ChEBI
epsilon-Hydroxycaproic acid	ChEBI
epsilon-Hydroxyhexanoic acid	ChEBI
5-Hydroxypentanecarboxylate	Generator
6-Hydroxy caproate	Generator
6-Hydroxycaproate	Generator
epsilon-Hydroxycaproate	Generator
epsilon-Hydroxyhexanoate	Generator
6-Hydroxyhexanoic acid	Generator

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

6-hydroxyhexanoic acid

Traditional Name

6-hydroxyhexanoic acid

CAS Registry Number

1191-25-9

SMILES

OCCCCCC(O)=O

InChI Identifier

InChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9)

InChI Key

IWHLYPDWHHPVAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Straight chain fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:17869 )
straight-chain fatty acid (CHEBI:17869 )
omega-hydroxy fatty acid (CHEBI:17869 )
6-hydroxy monocarboxylic acid (CHEBI:17869 )
Hydroxy fatty acids (C06103 )
Hydroxy fatty acids (LMFA01050015 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0012843)

Source

Endogenous

Endogenous (HMDB: HMDB0012843)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	69.7 g/L	ALOGPS
logP	0.29	ALOGPS
logP	0.37	ChemAxon
logS	-0.28	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-2	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	5	ChemAxon
Refractivity	33 m³·mol⁻¹	ChemAxon
Polarizability	14.24 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

HMDB0012843

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029184

KNApSAcK ID

Not Available

Chemspider ID

13835

KEGG Compound ID

C06103

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14490

PDB ID

Not Available

ChEBI ID

17869

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-Hydroxyhexanoic acid (CFc000008094)

MOL for CFc000008094 (6-Hydroxyhexanoic acid)

3D MOL for CFc000008094 (6-Hydroxyhexanoic acid)

3D SDF for CFc000008094 (6-Hydroxyhexanoic acid)

3D-SDF for CFc000008094 (6-Hydroxyhexanoic acid)

PDB for CFc000008094 (6-Hydroxyhexanoic acid)

3D PDB for CFc000008094 (6-Hydroxyhexanoic acid)

SMILES for CFc000008094 (6-Hydroxyhexanoic acid)

INCHI for CFc000008094 (6-Hydroxyhexanoic acid)

Structure for CFc000008094 (6-Hydroxyhexanoic acid)

3D Structure for CFc000008094 (6-Hydroxyhexanoic acid)