S-Hydroxycysteine

Identification

Name
S-Hydroxycysteine
Accession Number
DB01915  (EXPT01035, DB03398)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
Categories
Not Available
UNII
FB8KIA847T
CAS number
Not Available
Weight
Average: 137.158
Monoisotopic: 137.014663785
Chemical Formula
C3H7NO3S
InChI Key
FXIRVRPOOYSARH-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[[email protected]@H](CSO)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UComplement C3Not AvailableHuman
UAzurinNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UGlutathione S-transferase PNot AvailableHuman
UAcetyl-CoA acetyltransferase, cytosolicNot AvailableHuman
UGlutathione S-transferase A1Not AvailableHuman
UMyelin P2 proteinNot AvailableHuman
UAcetyl-CoA acetyltransferaseNot AvailableZoogloea ramigera
USubtilisin BPN'Not AvailableBacillus amyloliquefaciens
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
PubChem Compound
165339
PubChem Substance
46507482
ChemSpider
144942
ChEBI
41710
HET
CSO
PDB Entries
1cxp / 1d2v / 1d5l / 1d7w / 1dmp / 1dnu / 1dnw / 1eq2 / 1f3b / 1fnj
show 550 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 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
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 / SO-thioperoxols / S-alkylsulfenates / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
L-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
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-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 C...
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 December 01, 2017 14:50