Human Metabolome Database Version 3.5

Showing metabocard for Hypotaurine (HMDB00965)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:54 -0600
HMDB ID HMDB00965
Secondary Accession Numbers None
Metabolite Identification
Common Name Hypotaurine
Description Hypotaurine 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C2H7NO2S
Average Molecular Weight 109.147
Monoisotopic Molecular Weight 109.019749163
IUPAC Name 2-aminoethane-1-sulfinic acid
Traditional IUPAC Name hypotaurine
CAS Registry Number 300-84-5
SMILES NCCS(O)=O
InChI Identifier InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
InChI Key VVIUBCNYACGLLV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Sulfinic Acids and Derivatives
Sub Class Sulfinic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • zwitterion(ChEBI)
Substituents
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Sulfinic Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Taurine and hypotaurine metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 38.8 g/L ALOGPS
LogP -1.19 ALOGPS
LogP -2.7 ChemAxon
LogS -0.45 ALOGPS
pKa (strongest acidic) -0.36 ChemAxon
pKa (strongest basic) 9.64 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 63.32 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 23.16 ChemAxon
Polarizability 10.16 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Prostate
  • Sperm
Pathways
Name SMPDB Link KEGG Link
Taurine and Hypotaurine Metabolism SMP00021 map00430 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected and Quantified
0.65 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022342
KNApSAcK ID Not Available
Chemspider ID 96959 Link_out
KEGG Compound ID C00519 Link_out
BioCyc ID HYPOTAURINE Link_out
BiGG ID 35230 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB00965 Link_out
Metagene Link HMDB00965 Link_out
METLIN ID 281 Link_out
PubChem Compound 107812 Link_out
PDB ID Not Available
ChEBI ID 16668 Link_out
References
Synthesis Reference Owen, 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. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out

Enzymes
Name: Glutamate decarboxylase 2
Reactions:
3-Sulfinoalanine unknown Hypotaurine + Carbon dioxide details
Gene Name: GAD2
Uniprot ID: Q05329 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamate decarboxylase 1
Reactions:
3-Sulfinoalanine unknown Hypotaurine + Carbon dioxide details
Gene Name: GAD1
Uniprot ID: Q99259 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cysteine sulfinic acid decarboxylase
Reactions:
3-Sulfinoalanine unknown Hypotaurine + CO(2) details
3-Sulfinoalanine unknown Hypotaurine + Carbon dioxide details
Gene Name: CSAD
Uniprot ID: Q9Y600 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-aminoethanethiol dioxygenase
Reactions:
Cysteamine + Oxygen unknown Hypotaurine details
Gene Name: ADO
Uniprot ID: Q96SZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA