ChemFOnt: Showing chemical card for D-Leucic acid (CFc000000485)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:53 UTC

Chemfont ID

CFc000000485

Molecule Identification

Common Name

D-Leucic acid

Definition

D-Leucic acid is an alpha-hydroxycarboxylic acid present in patients affected with Short-bowel syndrome (an Inborn errors of metabolism, OMIM 175200 ) (PMID 9766851 ), and in Maple Syrup Urine Disease (MSUD, an autosomal recessive inherited metabolic disorder of branched-chain amino acid) (PMID 9766851 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2-Hydroxy-4-methylvaleric acid	ChEBI
(R)-2-Hydroxyisocaproic acid	ChEBI
(R)-Leucic acid	ChEBI
2-Hydroxy-4-methyl-D-valeric acid	ChEBI
alpha-Hydroxyisocaproic acid	ChEBI
D-2-Hydroxy-4-methylpentanoic acid	ChEBI
D-2-Hydroxy-4-methylvaleric acid	ChEBI
D-2-Hydroxyisocaproic acid	ChEBI
delta-Leucic acid	ChEBI
Leucic acid	ChEBI
D-2-Hydroxyisocaproate	Kegg
(R)-2-Hydroxy-4-methylpentanoate	Kegg
D-Leucate	Kegg
(R)-2-Hydroxy-4-methylvalerate	Generator
(R)-2-Hydroxyisocaproate	Generator
(R)-Leucate	Generator
2-Hydroxy-4-methyl-D-valerate	Generator
a-Hydroxyisocaproate	Generator
a-Hydroxyisocaproic acid	Generator
alpha-Hydroxyisocaproate	Generator
Α-hydroxyisocaproate	Generator
Α-hydroxyisocaproic acid	Generator
D-2-Hydroxy-4-methylpentanoate	Generator
D-2-Hydroxy-4-methylvalerate	Generator
delta-Leucate	Generator
Δ-leucate	Generator
Δ-leucic acid	Generator
Leucate	Generator
(R)-2-Hydroxy-4-methylpentanoic acid	Generator
(-)-2-Hydroxyisocaproate	HMDB
(-)-2-Hydroxyisocaproic acid	HMDB
(-)-a-Hydroxyisocaproate	HMDB
(-)-a-Hydroxyisocaproic acid	HMDB
(-)-alpha-Hydroxyisocaproate	HMDB
(-)-alpha-Hydroxyisocaproic acid	HMDB
(R)-2-Hydroxy-4-methyl-pentanoate	HMDB
(R)-2-Hydroxy-4-methyl-pentanoic acid	HMDB
2-Hydroxy-4-methyl-delta-valerate	HMDB
2-Hydroxy-4-methyl-delta-valeric acid	HMDB
D-a-Hydroxyisocaproate	HMDB
D-a-Hydroxyisocaproic acid	HMDB
delta-2-Hydroxy-4-methylpentanoate	HMDB
delta-2-Hydroxy-4-methylpentanoic acid	HMDB
delta-2-Hydroxy-4-methylvalerate	HMDB
delta-2-Hydroxy-4-methylvaleric acid	HMDB
delta-2-Hydroxyisocaproate	HMDB
delta-2-Hydroxyisocaproic acid	HMDB
delta-alpha-Hydroxyisocaproate	HMDB
delta-alpha-Hydroxyisocaproic acid	HMDB

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

(2R)-2-hydroxy-4-methylpentanoic acid

Traditional Name

(-)-α-hydroxyisocaproate

CAS Registry Number

20312-37-2

SMILES

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

InChI Identifier

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1

InChI Key

LVRFTAZAXQPQHI-RXMQYKEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Alpha-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

(2R)-2-hydroxy monocarboxylic acid (CHEBI:55534 )
2-hydroxy-4-methylvaleric acid (CHEBI:55534 )
Hydroxy fatty acids (LMFA01050402 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000624)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000624)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000624)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000624)

Source

Endogenous

Endogenous (HMDB: HMDB0000624)

Animal

Animal (HMDB: HMDB0000624)

Exogenous

Food

Food (HMDB: HMDB0000624)

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: HMDB0000624)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000624)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000624)

Lipid metabolism pathway (HMDB: HMDB0000624)

Cellular process

Cell signaling (HMDB: HMDB0000624)

Biochemical process

Lipid transport (HMDB: HMDB0000624)

Role

Biological role

Energy source (HMDB: HMDB0000624)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000624)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	124 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.78	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	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	3	ChemAxon
Refractivity	32.51 m³·mol⁻¹	ChemAxon
Polarizability	13.71 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

HMDB0000624

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022149

KNApSAcK ID

Not Available

Chemspider ID

388986

KEGG Compound ID

C03264

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hydroxyisocaproic acid

METLIN ID

5597

PubChem Compound

439960

PDB ID

Not Available

ChEBI ID

55534

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Kallwass, Helmut K. W. Potential of R-2-hydroxyisocaproate dehydrogenase from Lactobacillus casei for stereospecific reductions. Enzyme and Microbial Technology (1992), 14(1), 28-35.

Showing chemical card for D-Leucic acid (CFc000000485)

MOL for CFc000000485 (D-Leucic acid)

3D MOL for CFc000000485 (D-Leucic acid)

3D SDF for CFc000000485 (D-Leucic acid)

3D-SDF for CFc000000485 (D-Leucic acid)

PDB for CFc000000485 (D-Leucic acid)

3D PDB for CFc000000485 (D-Leucic acid)

SMILES for CFc000000485 (D-Leucic acid)

INCHI for CFc000000485 (D-Leucic acid)

Structure for CFc000000485 (D-Leucic acid)

3D Structure for CFc000000485 (D-Leucic acid)