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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:28 UTC
HMDB IDHMDB0000965
Secondary Accession Numbers
  • HMDB00965
Metabolite Identification
Common NameHypotaurine
DescriptionHypotaurine belongs to the class of organic compounds known as sulfinic acids. Sulfinic acids are compounds containing a sulfinic acid functional group, with the general structure RS(=O)OH (R = organyl, not H). Hypotaurine exists in all living species, ranging from bacteria to humans. Within humans, hypotaurine participates in a number of enzymatic reactions. In particular, hypotaurine can be biosynthesized from cysteamine; which is catalyzed by the enzyme 2-aminoethanethiol dioxygenase. In addition, hypotaurine can be biosynthesized from 3-sulfinoalanine through its interaction with the enzyme cysteine sulfinic acid decarboxylase. In humans, hypotaurine is involved in taurine and hypotaurine metabolism.
Structure
Data?1582752168
Synonyms
ValueSource
2-Aminoethanesulfinic acidChEBI
2-AminoethanesulfinateGenerator
2-AminoethanesulphinateGenerator
2-Aminoethanesulphinic acidGenerator
2-Amino-ethanesulfinateHMDB
2-Amino-ethanesulfinic acidHMDB
2-AminoethylsulfinateHMDB
2-Aminoethylsulfinic acidHMDB
CystaminesulfinateHMDB
Cystaminesulfinic acidHMDB
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
Description Belongs to the class of organic compounds known as sulfinic acids. Sulfinic acids are compounds containing a sulfinic acid functional group, with the general structure RS(=O)OH (R = organyl, not H).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassSulfinic acids and derivatives
Sub ClassSulfinic acids
Direct ParentSulfinic acids
Alternative Parents
Substituents
  • Sulfinic acid
  • Alkanesulfinic acid
  • Alkanesulfinic acid or derivatives
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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)1.68ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.16 m³·mol⁻¹ChemAxon
Polarizability10.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udr-0900000000-6d1ec3a7649c0e7a704b2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f79-0900000000-468e3da761e4d86223b12014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fki-5900000000-0569fb6d8502d22d2b7e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f79-0900000000-457c0f4ff1563d09a2082014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-0900000000-31e0a7f3a4c3fd20ce3c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-0900000000-6d1ec3a7649c0e7a704b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-0900000000-468e3da761e4d86223b12017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-5900000000-0569fb6d8502d22d2b7e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f79-0900000000-457c0f4ff1563d09a2082017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9000000000-ebfa02ce7482006f53d12016-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000x-9000000000-82443a9d90e05fad8df22021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-9800000000-f121cbb956b42fc5e20e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9300000000-eec8c8d22a33d4e8da3b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-f461253126e9b74c7d802012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0940100000-886905799c16b4d25a5f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-a34ee572b02492eaefef2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-ff53f17dcba5f9b8c5072012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-a3ccc18b5af8fddfdffa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0920000000-9c1032a24816a62214772012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-6354cd263d6d293f1d612012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-45a36787ef1f002747352012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-004i-0900000000-318c8a0e0325b2e98a062012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-2900000000-123846d2dc8e7cf971372012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-9000000000-6b0caea8d77740b01ec02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-9000000000-a5ce3fbe0fd14222c3c82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-03di-9000000000-32fdc560d98f6fd6be252012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-03di-9000000000-5d74861c832bbb4f97fc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-6900000000-26d55a4c69512ce8ae792012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-9100000000-8fec2539fc653f7bc4d72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-6efe1a9b61e6af3e4d542012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-519623b6e74aa699cb3b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-6f298f33310e539b113f2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0900000000-6f2416e3d3c5aa1f0fff2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-9300000000-85302e310b341400f0792012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-6900000000-b26fa2070e91be8f87922016-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-2252807899b1b8ebfc8e2016-09-14View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
  • Placenta
  • Prostate
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022342
KNApSAcK IDNot Available
Chemspider ID96959
KEGG Compound IDC00519
BioCyc IDHYPOTAURINE
BiGG ID35230
Wikipedia LinkHypotaurine
METLIN ID281
PubChem Compound107812
PDB IDNot Available
ChEBI ID16668
Food Biomarker OntologyNot Available
VMH IDHYPTAUR
MarkerDB IDNot Available
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. 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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