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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 21:47:33 UTC
HMDB IDHMDB00965
Secondary Accession NumbersNone
Metabolite Identification
Common NameHypotaurine
DescriptionHypotaurine is a product of enzyme cysteamine dioxygenase [EC 1.13.11.19] in taurine and hypotaurine metabolism pathway (KEGG). It may function as an antioxidant and a protective agent under physiological conditions (PMID 14992269 ).
Structure
Thumb
Synonyms
  1. 2-Amino-Ethanesulfinate
  2. 2-Amino-Ethanesulfinic acid
  3. 2-Aminoethanesulfinate
  4. 2-Aminoethanesulfinic acid
  5. 2-Aminoethylsulfinate
  6. 2-Aminoethylsulfinic acid
  7. Cystaminesulfinate
  8. Cystaminesulfinic acid
  9. Hypotaurine
Chemical FormulaC2H7NO2S
Average Molecular Weight109.147
Monoisotopic Molecular Weight109.019749163
IUPAC Name2-aminoethane-1-sulfinic acid
Traditional Namehypotaurine
CAS Registry Number300-84-5
SMILES
NCCS(O)=O
InChI Identifier
InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
InChI KeyVVIUBCNYACGLLV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassSulfinic Acids and Derivatives
Sub ClassSulfinic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • zwitterion(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentSulfinic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Taurine and hypotaurine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility38.8 g/LALOGPS
logP-1.2ALOGPS
logP-2.7ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)-0.36ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.16ChemAxon
Polarizability10.16ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
  • Prostate
  • Sperm
Pathways
NameSMPDB LinkKEGG Link
Taurine and Hypotaurine MetabolismSMP00021map00430
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
SalivaDetected and Quantified0.842 +/- 1.41 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.240 +/- 0.461 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.614 +/- 0.660 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified0.65 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022342
KNApSAcK IDNot Available
Chemspider ID96959
KEGG Compound IDC00519
BioCyc IDHYPOTAURINE
BiGG ID35230
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00965
Metagene LinkHMDB00965
METLIN ID281
PubChem Compound107812
PDB IDNot Available
ChEBI ID16668
References
Synthesis ReferenceOwen, Terence C.; Wilbraham, A. C. Convenient preparation and characterization of hypotaurine. Journal of the Chemical Society (1965), (Jan.), 826-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Dominy J, Eller S, Dawson R Jr: Building biosynthetic schools: reviewing compartmentation of CNS taurine synthesis. Neurochem Res. 2004 Jan;29(1):97-103. Pubmed: 14992267
  3. Fontana M, Pecci L, Dupre S, Cavallini D: Antioxidant properties of sulfinates: protective effect of hypotaurine on peroxynitrite-dependent damage. Neurochem Res. 2004 Jan;29(1):111-6. Pubmed: 14992269
  4. Pitari G, Dupre S, Spirito A, Antonini G, Amicarelli F: Hypotaurine protection on cell damage by singlet oxygen. Adv Exp Med Biol. 2000;483:157-62. Pubmed: 11787593
  5. Grafe F, Wohlrab W, Neubert RH, Brandsch M: Functional characterization of sodium- and chloride-dependent taurine transport in human keratinocytes. Eur J Pharm Biopharm. 2004 Mar;57(2):337-41. Pubmed: 15018993
  6. Krieg RC, Uihlein D, Murthum T, Endlicher E, Hausmann F, Messmann H, Knuechel R: Improving the use of 5-aminolevulinic acid (ALA)-induced protoporphyrin IX (PPIX) for the gastrointestinal tract by esterification--an in vitro study. Cell Mol Biol (Noisy-le-grand). 2002 Dec;48(8):917-23. Pubmed: 12699251
  7. Guerin P, Menezo Y: Hypotaurine and taurine in gamete and embryo environments: de novo synthesis via the cysteine sulfinic acid pathway in oviduct cells. Zygote. 1995 Nov;3(4):333-43. Pubmed: 8730898
  8. Masuoka N, Yao K, Kinuta M, Ohta J, Wakimoto M, Ubuka T: High-performance liquid chromatographic determination of taurine and hypotaurine using 3,5-dinitrobenzoyl chloride as derivatizing reagent. J Chromatogr B Biomed Appl. 1994 Oct 3;660(1):31-5. Pubmed: 7858721
  9. Guerin P, Guillaud J, Menezo Y: Hypotaurine in spermatozoa and genital secretions and its production by oviduct epithelial cells in vitro. Hum Reprod. 1995 Apr;10(4):866-72. Pubmed: 7650134
  10. Holmes RP, Goodman HO, Shihabi ZK, Jarow JP: The taurine and hypotaurine content of human semen. J Androl. 1992 May-Jun;13(3):289-92. Pubmed: 1601750
  11. Mahadevan MM, Trounson AO: Removal of the cumulus oophorus from the human oocyte for in vitro fertilization. Fertil Steril. 1985 Feb;43(2):263-7. Pubmed: 3967784

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD2
Uniprot ID:
Q05329
Molecular weight:
65410.77
Reactions
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD1
Uniprot ID:
Q99259
Molecular weight:
66896.065
Reactions
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Not Available
Gene Name:
CSAD
Uniprot ID:
Q9Y600
Molecular weight:
55022.79
Reactions
3-Sulfinoalanine → Hypotaurine + CO(2)details
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in cysteamine dioxygenase activity
Specific function:
Not Available
Gene Name:
ADO
Uniprot ID:
Q96SZ5
Molecular weight:
29750.535
Reactions
Cysteamine + Oxygen → Hypotaurinedetails