S-Mercaptocysteine

Identification

Name
S-Mercaptocysteine
Accession Number
DB02761  (EXPT01038)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
3RZ74WA9J2
CAS number
5652-32-4
Weight
Average: 153.223
Monoisotopic: 152.991819853
Chemical Formula
C3H7NO2S2
InChI Key
XBKONSCREBSMCS-REOHCLBHSA-N
InChI
InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
IUPAC Name
(2R)-2-amino-3-disulfanylpropanoic acid
SMILES
N[[email protected]@H](CSS)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCysteine desulfuraseNot AvailableEscherichia coli (strain K12)
UThiosulfate sulfurtransferase GlpENot AvailableShigella flexneri
UHydroxylamine reductaseNot AvailableDesulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
U3-mercaptopyruvate sulfurtransferaseNot AvailableLeishmania major
UL-cysteine/cystine lyase C-DESNot AvailableSynechocystis sp. (strain PCC 6714)
U3-mercaptopyruvate sulfurtransferaseNot AvailableEscherichia coli (strain K12)
UHydroxylamine reductaseNot AvailableDesulfovibrio vulgaris (strain Hildenborough / ATCC 29579 / NCIMB 8303)
UThiosulfate sulfurtransferaseNot AvailableHuman
USulfurtransferaseNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C01962
PubChem Compound
165331
PubChem Substance
46505635
ChemSpider
144934
ChEBI
58591
HET
CSS
PDB Entries
1bi0 / 1bi1 / 1bi3 / 1boh / 1boi / 1dp2 / 1e0c / 1e2u / 1e9v / 1elu
show 94 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 mg/mLALOGPS
logP-2ALOGPS
logP-2.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.04ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.99 m3·mol-1ChemAxon
Polarizability14.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9052
Blood Brain Barrier+0.7597
Caco-2 permeable-0.6714
P-glycoprotein substrateNon-substrate0.8103
P-glycoprotein inhibitor INon-inhibitor0.9805
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9454
CYP450 2C9 substrateNon-substrate0.874
CYP450 2D6 substrateNon-substrate0.8216
CYP450 3A4 substrateNon-substrate0.7887
CYP450 1A2 substrateNon-inhibitor0.8708
CYP450 2C9 inhibitorNon-inhibitor0.9116
CYP450 2D6 inhibitorNon-inhibitor0.9304
CYP450 2C19 inhibitorNon-inhibitor0.927
CYP450 3A4 inhibitorNon-inhibitor0.7694
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9781
Ames testAMES toxic0.7513
CarcinogenicityNon-carcinogens0.7382
BiodegradationReady biodegradable0.6889
Rat acute toxicity2.0402 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9797
hERG inhibition (predictor II)Non-inhibitor0.9622
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-cysteine-S-conjugates
Alternative Parents
L-alpha-amino acids / Amino acids / Sulfenyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
L-cysteine-s-conjugate / Alpha-amino acid / L-alpha-amino acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Sulfenyl compound / Organic nitrogen compound / Hydrocarbon derivative / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
S-substituted L-cysteine (CHEBI:28839)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Selenocysteine lyase activity
Specific Function
Cysteine desulfurases mobilize the sulfur from L-cysteine to yield L-alanine, an essential step in sulfur metabolism for biosynthesis of a variety of sulfur-containing biomolecules. Component of th...
Gene Name
sufS
Uniprot ID
P77444
Uniprot Name
Cysteine desulfurase
Molecular Weight
44433.435 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
Thiosulfate sulfurtransferase activity
Specific Function
Catalyzes, although with low efficiency, the sulfur transfer reaction from thiosulfate to cyanide.
Gene Name
glpE
Uniprot ID
P0A6V7
Uniprot Name
Thiosulfate sulfurtransferase GlpE
Molecular Weight
12082.415 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Desulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the reduction of hydroxylamine to form NH(3) and H(2)O.
Gene Name
hcp
Uniprot ID
Q01770
Uniprot Name
Hydroxylamine reductase
Molecular Weight
58658.78 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Leishmania major
Pharmacological action
Unknown
General Function
3-mercaptopyruvate sulfurtransferase activity
Specific Function
Not Available
Gene Name
MST
Uniprot ID
Q7K9G0
Uniprot Name
3-mercaptopyruvate sulfurtransferase
Molecular Weight
40154.325 Da
Kind
Protein
Organism
Synechocystis sp. (strain PCC 6714)
Pharmacological action
Unknown
General Function
Lyase activity
Specific Function
Not Available
Gene Name
c-des
Uniprot ID
Q9ZHG9
Uniprot Name
L-cysteine/cystine lyase C-DES
Molecular Weight
43153.73 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thiosulfate sulfurtransferase activity
Specific Function
Transfers a sulfur ion to cyanide or to other thiol compounds. Also has weak rhodanese activity (130-fold lower). Its participation in detoxification of cyanide may be small. May be involved in the...
Gene Name
sseA
Uniprot ID
P31142
Uniprot Name
3-mercaptopyruvate sulfurtransferase
Molecular Weight
30811.55 Da
Kind
Protein
Organism
Desulfovibrio vulgaris (strain Hildenborough / ATCC 29579 / NCIMB 8303)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the reduction of hydroxylamine to form NH(3) and H(2)O.
Gene Name
hcp
Uniprot ID
P31101
Uniprot Name
Hydroxylamine reductase
Molecular Weight
59978.4 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thiosulfate sulfurtransferase activity
Specific Function
Formation of iron-sulfur complexes, cyanide detoxification or modification of sulfur-containing enzymes. Other thiol compounds, besides cyanide, can act as sulfur ion acceptors. Also has weak merca...
Gene Name
TST
Uniprot ID
Q16762
Uniprot Name
Thiosulfate sulfurtransferase
Molecular Weight
33428.69 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Thiosulfate sulfurtransferase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q5SJI0
Uniprot Name
Sulfurtransferase
Molecular Weight
32924.91 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:02