ChemFOnt: Showing chemical card for Allocystathionine (CFc000000348)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:43 UTC

Chemfont ID

CFc000000348

Molecule Identification

Common Name

Allocystathionine

Definition

Allocystathionine belongs to the class of organic compounds known as cysteines and cysteine derivatives. Cysteine and cysteine derivatives are compounds containing cysteine or a derivative thereof resulting from the reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Allocystathionine is a stereo-isomer of cystathionine. Both cystathionine and allocystathionine are modified amino acids generated by enzymic means from homocysteine and serine. Allocystathionine is a product of enzyme cystathionine synthetase (EC 2.5.1.48) which converts homocysteine into allocystathionine in the sulfur metabolism pathway. It is also the substrate of enzyme cystathionine beta-lyase (EC 4.4.1.8) in the same pathway (KEGG). Cystathionine and allocystathionine can be used by the enzymes cystathionine gamma-lyase (CTH), cysteine dioxygenase (CDO), and sulfinoalanine decarboxylase to produce hypotaurine and then taurine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-Amino-g-(2-amino-2-carboxyethylmercapto)-butyric acid	HMDB
alpha-Amino-gamma-(2-amino-2-carboxyethylmercapto)-butyric acid	HMDB
DL-Allocystathionine	HMDB
DL-S-(2-Amino-2-carboxyethyl)-homocysteine	HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoate	HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoate	HMDB
(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoic acid	HMDB

Chemical Formula

C₇H₁₄N₂O₄S

Average Molecular Weight

222.262

Monoisotopic Molecular Weight

222.067427636

IUPAC Name

(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

Traditional Name

(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

CAS Registry Number

535-34-2

SMILES

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

InChI Identifier

InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5?/m0/s1

InChI Key

ILRYLPWNYFXEMH-ROLXFIACSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Amino acid
Carboxylic acid
Thioether
Dialkylthioether
Sulfenyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000455)

Source

Endogenous

Endogenous (HMDB: HMDB0000455)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	17.3 g/L	ALOGPS
logP	-4	ALOGPS
logP	-5.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.66	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	7	ChemAxon
Refractivity	51.57 m³·mol⁻¹	ChemAxon
Polarizability	22.24 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

HMDB0000455

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022055

KNApSAcK ID

Not Available

Chemspider ID

8280480

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10104953

PDB ID

Not Available

ChEBI ID

165853

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Mary L. Snow, Roy S. Dombro, and Charlotte Ressler. Synthesis of L-cystathionine and D-allocystathionine. J. Org. Chem., 1967, 32 (1), pp 246–248

Showing chemical card for Allocystathionine (CFc000000348)

MOL for CFc000000348 (Allocystathionine)

3D MOL for CFc000000348 (Allocystathionine)

3D SDF for CFc000000348 (Allocystathionine)

3D-SDF for CFc000000348 (Allocystathionine)

PDB for CFc000000348 (Allocystathionine)

3D PDB for CFc000000348 (Allocystathionine)

SMILES for CFc000000348 (Allocystathionine)

INCHI for CFc000000348 (Allocystathionine)

Structure for CFc000000348 (Allocystathionine)

3D Structure for CFc000000348 (Allocystathionine)