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Showing metabocard for S-(2-carboxypropyl)-Cysteamine (HMDB0002169)

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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2019-07-29 16:01:50 UTC
HMDB IDHMDB0002169
Secondary Accession Numbers
  • HMDB02169
Metabolite Identification
Common NameS-(2-carboxypropyl)-Cysteamine
DescriptionS-(2-carboxypropyl)-Cysteamine, also known as S-2-CPCT, belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group. Thus, S-(2-carboxypropyl)-cysteamine is considered to be a fatty acid lipid molecule. S-(2-carboxypropyl)-Cysteamine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563860721
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-((2-Aminoethyl)thio)-2-methyl-propanoateHMDB
3-((2-Aminoethyl)thio)-2-methyl-propanoic acidHMDB
S-(2-Carboxypropyl)cysteamineHMDB
S-2-CPCTHMDB
Chemical FormulaC6H13NO2S
Average Molecular Weight163.238
Monoisotopic Molecular Weight163.066699355
IUPAC Name3-[(2-aminoethyl)sulfanyl]-2-methylpropanoic acid
Traditional NameS-(2-carboxypropyl)cysteamine
CAS Registry Number80186-81-8
SMILES
CC(CSCCN)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2S/c1-5(6(8)9)4-10-3-2-7/h5H,2-4,7H2,1H3,(H,8,9)
InChI KeyUFRVABODKAYFCB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAmino acids
Alternative Parents
Substituents
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.4 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)9.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity42.45 m³·mol⁻¹ChemAxon
Polarizability17.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9100000000-0447bd8d116e61e293e3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-008c-9300000000-bedc2a0a8f76ea0c2b83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p5-9800000000-c6733a564418ac2b4504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9200000000-9816d95e1976aa2a45a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-4de7100324d7fa79b6c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-9500000000-97e149fe7b01f81a841dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9300000000-ca9a8f5b9ccd0b88e7daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-42347241982b8a17a93bSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified<10 umol/mmol creatinineNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified14-30 umol/mmol creatinineInfant (0-1 year old)Both
Short-chain enoyl-CoA hydratase deficiency		 details
UrineDetected and Quantified1.2-2.7 umol/mmol creatinineNot SpecifiedNot Specified
Propionic acidemia		 details
UrineDetected and Quantified13-16 umol/mmol creatinineChildren (1-13 years old)Female3-Hydroxyisobutyryl-coa hydrolase deficiency details
Associated Disorders and Diseases
Disease References
3-Hydroxyisobutyryl-coa hydrolase deficiency
  1. Peters H, Ferdinandusse S, Ruiter JP, Wanders RJ, Boneh A, Pitt J: Metabolite studies in HIBCH and ECHS1 defects: Implications for screening. Mol Genet Metab. 2015 Aug;115(4):168-73. doi: 10.1016/j.ymgme.2015.06.008. Epub 2015 Jun 24. [PubMed:26163321 ]
Associated OMIM IDs
  • 250620 (3-Hydroxyisobutyryl-coa hydrolase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022881
KNApSAcK IDNot Available
Chemspider ID117681
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6522
PubChem Compound133402
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brown GK, Hunt SM, Scholem R, Fowler K, Grimes A, Mercer JF, Truscott RM, Cotton RG, Rogers JG, Danks DM: beta-hydroxyisobutyryl coenzyme A deacylase deficiency: a defect in valine metabolism associated with physical malformations. Pediatrics. 1982 Oct;70(4):532-8. [PubMed:7122152 ]
  2. Truscott RJ, Malegan D, McCairns E, Halpern B, Hammond J, Cotton RG, Mercer JF, Hunt S, Rogers JG, Danks DM: Two new sulphur-containing amino acids in man. Biomed Mass Spectrom. 1981 Mar;8(3):99-104. [PubMed:7236859 ]
  3. Aly AM, Arai M, Hoyer LW: Cysteamine enhances the procoagulant activity of Factor VIII-East Hartford, a dysfunctional protein due to a light chain thrombin cleavage site mutation (arginine-1689 to cysteine). J Clin Invest. 1992 May;89(5):1375-81. [PubMed:1569180 ]
  4. Aly AM, Hoyer LW: Factor VIII-East Hartford (arginine 1689 to cysteine) has procoagulant activity when separated from von Willebrand factor. J Clin Invest. 1992 May;89(5):1382-7. [PubMed:1569181 ]