Identification
NameS-Hydroxycysteine
Accession NumberDB01915  (EXPT01035, DB03398)
TypeSmall Molecule
GroupsExperimental
Description

S-hydroxycysteine is a solid. This compound belongs to the 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. It targets the proteins subtilisin BPN', glutathione S-transferase A1, glutathione S-transferase p, myelin P2 protein, and complement c3.

Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients 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
CategoriesNot Available
UNIIFB8KIA847T
CAS numberNot Available
WeightAverage: 137.158
Monoisotopic: 137.014663785
Chemical FormulaC3H7NO3S
InChI KeyFXIRVRPOOYSARH-REOHCLBHSA-N
InChI
InChI=1S/C3H7NO3S/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
IUPAC Name
(2R)-2-amino-3-(hydroxysulfanyl)propanoic acid
SMILES
N[C@@H](CSO)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Complement C3ProteinunknownNot AvailableHumanP01024 details
AzurinProteinunknownNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)P00282 details
Glutathione S-transferase PProteinunknownNot AvailableHumanP09211 details
Acetyl-CoA acetyltransferase, cytosolicProteinunknownNot AvailableHumanQ9BWD1 details
Glutathione S-transferase A1ProteinunknownNot AvailableHumanP08263 details
Myelin P2 proteinProteinunknownNot AvailableHumanP02689 details
Acetyl-CoA acetyltransferaseProteinunknownNot AvailableZoogloea ramigeraP07097 details
Subtilisin BPN'ProteinunknownNot AvailableBacillus amyloliquefaciensP00782 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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not 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
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility342.0 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.2ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30 m3·mol-1ChemAxon
Polarizability12.41 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8453
Blood Brain Barrier+0.5259
Caco-2 permeable-0.6772
P-glycoprotein substrateNon-substrate0.851
P-glycoprotein inhibitor INon-inhibitor0.9663
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9559
CYP450 2C9 substrateNon-substrate0.8657
CYP450 2D6 substrateNon-substrate0.8234
CYP450 3A4 substrateNon-substrate0.7518
CYP450 1A2 substrateNon-inhibitor0.9113
CYP450 2C9 inhibitorNon-inhibitor0.9226
CYP450 2D6 inhibitorNon-inhibitor0.9312
CYP450 2C19 inhibitorNon-inhibitor0.9253
CYP450 3A4 inhibitorNon-inhibitor0.9184
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9899
Ames testAMES toxic0.5133
CarcinogenicityNon-carcinogens0.7528
BiodegradationReady biodegradable0.8925
Rat acute toxicity1.9007 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9754
hERG inhibition (predictor II)Non-inhibitor0.9547
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-cysteine-S-conjugates
Alternative ParentsL-alpha-amino acids / Amino acids / Sulfenyl compounds / SO-thioperoxols / S-alkylsulfenates / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
SubstituentsL-cysteine-s-conjugate / Alpha-amino acid / L-alpha-amino acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / So-thioperoxol / Sulfenyl compound / S-alkylsulfenate / Carbonyl group
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsnon-proteinogenic L-alpha-amino acid, L-cysteine derivative (CHEBI:41710 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Receptor binding
Specific Function:
C3 plays a central role in the activation of the complement system. Its processing by C3 convertase is the central reaction in both classical and alternative complement pathways. After activation C3b can bind covalently, via its reactive thioester, to cell surface carbohydrates or immune aggregates.Derived from proteolytic degradation of complement C3, C3a anaphylatoxin is a mediator of local i...
Gene Name:
C3
Uniprot ID:
P01024
Uniprot Name:
Complement C3
Molecular Weight:
187146.73 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 ]
  3. 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
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Transfers electrons from cytochrome c551 to cytochrome oxidase.
Gene Name:
azu
Uniprot ID:
P00282
Uniprot Name:
Azurin
Molecular Weight:
16008.315 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
Human
Pharmacological action
unknown
General Function:
S-nitrosoglutathione binding
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Uniprot Name:
Glutathione S-transferase P
Molecular Weight:
23355.625 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
Human
Pharmacological action
unknown
General Function:
Acetyl-coa c-acetyltransferase activity
Specific Function:
Not Available
Gene Name:
ACAT2
Uniprot ID:
Q9BWD1
Uniprot Name:
Acetyl-CoA acetyltransferase, cytosolic
Molecular Weight:
41350.5 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
Human
Pharmacological action
unknown
General Function:
Glutathione transferase activity
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA1
Uniprot ID:
P08263
Uniprot Name:
Glutathione S-transferase A1
Molecular Weight:
25630.785 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 ]
  3. 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
Human
Pharmacological action
unknown
General Function:
Transporter activity
Specific Function:
May play a role in lipid transport protein in Schwann cells. May bind cholesterol.
Gene Name:
PMP2
Uniprot ID:
P02689
Uniprot Name:
Myelin P2 protein
Molecular Weight:
14909.305 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 ]
  3. 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
Zoogloea ramigera
Pharmacological action
unknown
General Function:
Acetyl-coa c-acetyltransferase activity
Specific Function:
Not Available
Gene Name:
phbA
Uniprot ID:
P07097
Uniprot Name:
Acetyl-CoA acetyltransferase
Molecular Weight:
40472.955 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
Bacillus amyloliquefaciens
Pharmacological action
unknown
General Function:
Serine-type endopeptidase activity
Specific Function:
Subtilisin is an extracellular alkaline serine protease, it catalyzes the hydrolysis of proteins and peptide amides. Has a high substrate specificity to fibrin.
Gene Name:
apr
Uniprot ID:
P00782
Uniprot Name:
Subtilisin BPN'
Molecular Weight:
39180.935 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 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:37