ChemFOnt: Showing chemical card for L-Homocysteic acid (CFc000001488)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:07 UTC

Chemfont ID

CFc000001488

Molecule Identification

Common Name

L-Homocysteic acid

Definition

L-homocysteic acid is a homocysteic acid with L-configuration. It has a role as a NMDA receptor agonist. It is an enantiomer of a D-homocysteic acid. L-Homocysteic acid is a sulfur-containing glutamic acid analog and a potent NMDA receptor agonist. It is related to homocysteine, a by-product of methionine metabolism. It belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Amino-4-sulfobutyric acid	ChEBI
(S)-2-Amino-4-sulfobutanoic acid	ChEBI
(S)-2-Amino-4-sulfobutyric acid	ChEBI
Homocysteic acid	ChEBI
L-2-Amino-4-sulfobutyric acid	ChEBI
(2S)-2-Amino-4-sulfobutanoic acid	Kegg
(2S)-2-Amino-4-sulfobutyrate	Generator
(2S)-2-Amino-4-sulphobutyrate	Generator
(2S)-2-Amino-4-sulphobutyric acid	Generator
(S)-2-Amino-4-sulfobutanoate	Generator
(S)-2-Amino-4-sulphobutanoate	Generator
(S)-2-Amino-4-sulphobutanoic acid	Generator
(S)-2-Amino-4-sulfobutyrate	Generator
(S)-2-Amino-4-sulphobutyrate	Generator
(S)-2-Amino-4-sulphobutyric acid	Generator
Homocysteate	Generator
L-2-Amino-4-sulfobutyrate	Generator
L-2-Amino-4-sulphobutyrate	Generator
L-2-Amino-4-sulphobutyric acid	Generator
(2S)-2-Amino-4-sulfobutanoate	Generator
(2S)-2-Amino-4-sulphobutanoate	Generator
(2S)-2-Amino-4-sulphobutanoic acid	Generator
L-Homocysteate	Generator

Chemical Formula

C₄H₉NO₅S

Average Molecular Weight

183.183

Monoisotopic Molecular Weight

183.020143093

IUPAC Name

(2S)-2-amino-4-sulfobutanoic acid

Traditional Name

L-homocysteic acid

CAS Registry Number

14857-77-3

SMILES

N[C@@H](CCS(O)(=O)=O)C(O)=O

InChI Identifier

InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1

InChI Key

VBOQYPQEPHKASR-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:80543 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0002205)

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	64.3 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.9	ChemAxon
logS	-0.45	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.3 m³·mol⁻¹	ChemAxon
Polarizability	15.69 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

HMDB0002205

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022905

KNApSAcK ID

Not Available

Chemspider ID

154529

KEGG Compound ID

C16511

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Homocysteic_acid

METLIN ID

6545

PubChem Compound

177491

PDB ID

Not Available

ChEBI ID

132223

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Jolles-Bergeret, Bernadette. Synthesis and properties of L- and DL-homocysteine sulfinic and L-homocysteic acids. Bulletin de la Societe de Chimie Biologique (1966), 48(11), 1265-78.

Showing chemical card for L-Homocysteic acid (CFc000001488)

MOL for CFc000001488 (L-Homocysteic acid)

3D MOL for CFc000001488 (L-Homocysteic acid)

3D SDF for CFc000001488 (L-Homocysteic acid)

3D-SDF for CFc000001488 (L-Homocysteic acid)

PDB for CFc000001488 (L-Homocysteic acid)

3D PDB for CFc000001488 (L-Homocysteic acid)

SMILES for CFc000001488 (L-Homocysteic acid)

INCHI for CFc000001488 (L-Homocysteic acid)

Structure for CFc000001488 (L-Homocysteic acid)

3D Structure for CFc000001488 (L-Homocysteic acid)