ChemFOnt: Showing chemical card for Cystathionine ketimine (CFc000001348)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:57 UTC

Chemfont ID

CFc000001348

Molecule Identification

Common Name

Cystathionine ketimine

Definition

Cystathionine ketimine (CT) is a cyclic amino acid that was found to have a priming effect on superoxide generation in human neutrophils (PMID: 10708546 ). D-Cystathionine ketimine and L-cystathionine ketimine enhance superoxide generation by human neutrophils in two different manners. D-Cystathionine ketimine enhanced seryl phosphorylation of 16.5-kDa protein in human neutrophils, while L-cystathionine ketimine enhanced tyrosyl phosphorylation of 45-kDa protein (PMID: 10049498 ). Cystathionine ketimine was found in the urine of a cystathioninuria patient (PMID: 8373176 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5R)-1-Thia-4-azacyclohepta-3-ene-3,5-dicarboxylic acid	ChEBI
(R)-2,5,6,7-Tetrahydro-1,4-thiazepine-3,5-dicarboxylic acid	ChEBI
(5R)-1-Thia-4-azacyclohepta-3-ene-3,5-dicarboxylate	Generator
(R)-2,5,6,7-Tetrahydro-1,4-thiazepine-3,5-dicarboxylate	Generator
(5R)-2,5,6,7-tetrahydro-1,4-Thiazepine-3,5-dicarboxylic acid	HMDB
(5R)-2,5,6,7-Tetrahydro-1,4-thiazepine-3,5-dicarboxylate	Generator, HMDB
Cystathionine ketimine	MeSH
CT	HMDB

Chemical Formula

C₇H₉NO₄S

Average Molecular Weight

203.216

Monoisotopic Molecular Weight

203.025228471

IUPAC Name

(5R)-2,5,6,7-tetrahydro-1,4-thiazepine-3,5-dicarboxylic acid

Traditional Name

cystathionine ketimine

CAS Registry Number

87254-95-3

SMILES

OC(=O)[C@H]1CCSCC(=N1)C(O)=O

InChI Identifier

InChI=1S/C7H9NO4S/c9-6(10)4-1-2-13-3-5(8-4)7(11)12/h4H,1-3H2,(H,9,10)(H,11,12)/t4-/m1/s1

InChI Key

XJUQJVUYGRTQGI-SCSAIBSYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Ketimine
Carboxylic acid
Thioether
Azacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Imine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002015)

Excreta

Biofluid or Excreta

Urine (PMID: 3254164)

Cellular substructure

Cytoplasm (HMDB: HMDB0002015)

Source

Endogenous

Endogenous (HMDB: HMDB0002015)

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	4.81 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	0.39	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.96 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.2 m³·mol⁻¹	ChemAxon
Polarizability	18.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon