ChemFOnt: Showing chemical card for N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine (CFc000001477)

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

CFc000001477

Molecule Identification

Common Name

N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine

Definition

N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine is a cystathione metabolite found in the urine of patients with cystathionuria (PMID 8750604 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-4-(2-acetamido-2-carboxyethylthio)-2-Oxobutanoate	HMDB
(R)-4-(2-acetamido-2-carboxyethylthio)-2-Oxobutanoic acid	HMDB
NAc-OCPC	HMDB, MeSH
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-oxobutanoate	Generator, HMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-oxobutanoate	Generator, HMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-oxobutanoic acid	Generator, HMDB
N-Acetyl-S-(3-oxo-3-carboxy-N-propyl)cysteine	MeSH

Chemical Formula

C₉H₁₃NO₆S

Average Molecular Weight

263.268

Monoisotopic Molecular Weight

263.046357843

IUPAC Name

4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid

Traditional Name

4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid

CAS Registry Number

622368-00-7

SMILES

CC(=O)N[C@@H](CSCCC(=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C9H13NO6S/c1-5(11)10-6(8(13)14)4-17-3-2-7(12)9(15)16/h6H,2-4H2,1H3,(H,10,11)(H,13,14)(H,15,16)/t6-/m0/s1

InChI Key

AHFWWWFNCBRMIV-LURJTMIESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Short-chain keto acid
Thia fatty acid
Alpha-keto acid
Dicarboxylic acid or derivatives
Keto acid
Fatty acyl
Acetamide
Alpha-hydroxy ketone
Carboxamide group
Secondary carboxylic acid amide
Ketone
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0002194)

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	1.22 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-0.42	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.73	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	120.77 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	58.5 m³·mol⁻¹	ChemAxon
Polarizability	24.81 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

HMDB0002194

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022896

KNApSAcK ID

Not Available

Chemspider ID

13628313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6537

PubChem Compound

20849151

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Pankau, Wolf Matthias; Moenninghoff, Sven; von Kiedrowski, Guenter. Thermostable and monoconjugable gold clusters with a dodecadentate thioether ligand gripper. Angewandte Chemie, International Edition (2006), 45(12), 1889-1891.

Showing chemical card for N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine (CFc000001477)

MOL for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D MOL for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D SDF for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D-SDF for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

PDB for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D PDB for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

SMILES for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

INCHI for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

Structure for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D Structure for CFc000001477 (N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)