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Identification
NameS-Mercaptocysteine
Accession NumberDB02761  (EXPT01038)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS number5652-32-4
WeightAverage: 153.223
Monoisotopic: 152.991819853
Chemical FormulaC3H7NO2S2
InChI KeyXBKONSCREBSMCS-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[C@@H](CSS)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Cysteine desulfuraseProteinunknownNot AvailableEscherichia coli (strain K12)P77444 details
Thiosulfate sulfurtransferase GlpEProteinunknownNot AvailableShigella flexneriP0A6V7 details
Hydroxylamine reductaseProteinunknownNot AvailableDesulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)Q01770 details
3-mercaptopyruvate sulfurtransferaseProteinunknownNot AvailableLeishmania majorQ7K9G0 details
L-cysteine/cystine lyase C-DESProteinunknownNot AvailableSynechocystis sp. (strain PCC 6714)Q9ZHG9 details
3-mercaptopyruvate sulfurtransferaseProteinunknownNot AvailableEscherichia coli (strain K12)P31142 details
Hydroxylamine reductaseProteinunknownNot AvailableDesulfovibrio vulgaris (strain Hildenborough / ATCC 29579 / NCIMB 8303)P31101 details
Thiosulfate sulfurtransferaseProteinunknownNot AvailableHumanQ16762 details
SulfurtransferaseProteinunknownNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)Q5SJI0 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Sulfenyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

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 the suf operon, which is activated and required under specific conditions such as oxidative stress and iron limitation. Acts as a potent selenocysteine lyase in vitro, that mobilizes selenium from L-sel...
Gene Name:
sufS
Uniprot ID:
P77444
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
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
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
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
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 enhancement of serine sensitivity.
Gene Name:
sseA
Uniprot ID:
P31142
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
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 mercaptopyruvate sulfurtransferase (MST) activity (By similarity). Together with MRPL18, acts as a mitochondrial import factor for the cytosolic 5S rRNA. Only the nascent unfolded cytoplasmic form is able ...
Gene Name:
TST
Uniprot ID:
Q16762
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
Molecular Weight:
32924.91 Da
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23