ChemFOnt: Showing chemical card for L-Glyceric acid (CFc000002737)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:41 UTC

Chemfont ID

CFc000002737

Molecule Identification

Common Name

L-Glyceric acid

Definition

L-glyceric acid is a human urinary metabolite present in patients with L-Glyceric aciduria. The formation of L-glyceric acid from accumulated hydroxypyruvate is due to deficiency of human glyoxylate reductase/hydroxypyruvate reductase (GRHPR, EC 1.1.1.81), a D-2-hydroxy-acid dehydrogenase that plays a critical role in the removal of the metabolic by-product glyoxylate from within the liver. Deficiency of this enzyme is the underlying cause of primary hyperoxaluria type 2 (PH2) and leads to increased urinary oxalate levels, formation of kidney stones and renal failure. (PMID: 16756993 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-Glyceric acid	ChEBI
(S)-Glycerate	Generator
L-Glycerate	Generator
(2S)-2,3-Dihydroxy-propanoate	HMDB
(2S)-2,3-Dihydroxy-propanoic acid	HMDB
(S)-2,3-Dihydroxy-propanoate	HMDB
(S)-2,3-Dihydroxy-propanoic acid	HMDB
(S)-2,3-Dihydroxypropanoate	HMDB
(S)-2,3-Dihydroxypropanoic acid	HMDB

Chemical Formula

C₃H₆O₄

Average Molecular Weight

106.0773

Monoisotopic Molecular Weight

106.02660868

IUPAC Name

(2S)-2,3-dihydroxypropanoic acid

Traditional Name

L-glycerate

CAS Registry Number

28305-26-2

SMILES

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

InChI Identifier

InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m0/s1

InChI Key

RBNPOMFGQQGHHO-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Glyceric_acid
Sugar acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
1,2-diol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glyceric acid (CHEBI:74324 )

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Nontypified gene mutation

Organic acidemia

Glycolic aciduria (HMDB: HMDB0006372)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1458609)

Excreta

Biofluid or Excreta

Urine (PMID: 9267307)

Cellular substructure

Cytoplasm (HMDB: HMDB0006372)
Extracellular (HMDB: HMDB0006372)

Source

Endogenous

Endogenous (HMDB: HMDB0006372)

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

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	639 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	0.78	ALOGPS
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	20.38 m³·mol⁻¹	ChemAxon
Polarizability	8.94 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

HMDB0006372

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023907

KNApSAcK ID

Not Available

Chemspider ID

4885497

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2226325

Wikipedia Link

Glyceric acid

METLIN ID

Not Available

PubChem Compound

6326776

PDB ID

Not Available

ChEBI ID

74324

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Lok, C. M.; Ward, J. P.; Van Dorp, D. A. The synthesis of chiral glycerides starting from D- and L-serine. Actes Congr. Mond. - Soc. Int. Etude Corps Gras, 13th (1976), Sect. E 15-20.

Showing chemical card for L-Glyceric acid (CFc000002737)

MOL for CFc000002737 (L-Glyceric acid)

3D MOL for CFc000002737 (L-Glyceric acid)

3D SDF for CFc000002737 (L-Glyceric acid)

3D-SDF for CFc000002737 (L-Glyceric acid)

PDB for CFc000002737 (L-Glyceric acid)

3D PDB for CFc000002737 (L-Glyceric acid)

SMILES for CFc000002737 (L-Glyceric acid)

INCHI for CFc000002737 (L-Glyceric acid)

Structure for CFc000002737 (L-Glyceric acid)

3D Structure for CFc000002737 (L-Glyceric acid)