ChemFOnt: Showing chemical card for L-Homocystine (CFc000000533)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:57 UTC

Chemfont ID

CFc000000533

Molecule Identification

Common Name

L-Homocystine

Definition

Homocystine is the oxidized form of homocysteine. Homocystine is a dipeptide consisting of two homocysteine molecules joined by a disulfide bond. Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Homocystine occurs only transiently before being reduced to homocysteine and converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfides account for >98% of total homocysteine in plasma from healthy individuals (PMID 11592966 ). Homocystine has been shown to stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells, thereby inducing a vascular cell type-specific oxidative stress. This vascular stress is associated with atherothrombotic cardiovascular disease (PMID: 14980706 ). High levels of homocysteine (and homocysteine) can be found in individuals suffering from homocystinura due to cystathionine synthase deficiency (PMID: 4685596 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4,4'-Dithiobis(2-aminobutyric acid)	HMDB
4,4'-Dithiobis-2-amino-L-butyrate	HMDB
4,4'-Dithiobis-2-amino-L-butyric acid	HMDB
[S-(R,r)]-4,4'-dithiobis-2-amino-butanoate	HMDB
[S-(R,r)]-4,4'-dithiobis-2-amino-butanoic acid	HMDB
2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoate	HMDB
2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoate	HMDB
2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoic acid	HMDB

Chemical Formula

C₈H₁₆N₂O₄S₂

Average Molecular Weight

268.354

Monoisotopic Molecular Weight

268.05514839

IUPAC Name

2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

Traditional Name

2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

CAS Registry Number

626-72-2

SMILES

NC(CCSSCC[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1

InChI Key

ZTVZLYBCZNMWCF-ZBHICJROSA-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
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Amino acid
Organic disulfide
Dialkyldisulfide
Carboxylic acid
Sulfenyl compound
Organic oxygen compound
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Homocystinuria (HMDB: HMDB0000676)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8745393)
Cerebrospinal Fluid (CSF) (PMID: 14264314)
Cerebrospinal fluid (HMDB: HMDB0000676)

Excreta

Biofluid or Excreta

Urine (PMID: 2026685)

Cellular substructure

Cytoplasm (HMDB: HMDB0000676)
Membrane (HMDB: HMDB0000676)

Source

Endogenous

Endogenous (HMDB: HMDB0000676)

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

Biochemical pathway

Disease pathway

Cystathionine beta-Synthase Deficiency (HMDB: HMDB0000676)

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000215)
Homocystinuria (MarkerDB: MDB00000215)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.5 g/L	ALOGPS
logP	-4.2	ALOGPS
logP	-5.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.38 m³·mol⁻¹	ChemAxon
Polarizability	26.92 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