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Showing NP-Card for Hypotaurine (NP0000528)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:11 UTC
NP-MRD IDNP0000528
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000528 (Hypotaurine)


  Mrv1652305271900162D          

  6  5  0  0  0  0            999 V2000
   -0.1178   -0.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967    0.0684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324    0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -0.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    0.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506   -0.3459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
M  END
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3D MOL for NP0000528 (Hypotaurine)

HMDB0000965
     RDKit          3D
Hypotaurine
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.0357    0.5711   -0.1955 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714    0.4410   -0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203   -0.5709    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -0.8541   -0.3195 S   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3422   -1.7942    0.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5369    0.6289   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700    1.0418   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -0.3977    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    1.4516   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    0.1569   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -0.0924    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780   -1.4932    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446    0.9111    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  6 13  1  0
M  END
Download

3D SDF for NP0000528 (Hypotaurine)


  Mrv1652305271900162D          

  6  5  0  0  0  0            999 V2000
   -0.1178   -0.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967    0.0684    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324    0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -0.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    0.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506   -0.3459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000528

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C2H7NO2S

> <MOLECULAR_WEIGHT>
109.147

> <EXACT_MASS>
109.019749163

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
10.155904259627393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminoethane-1-sulfinic acid

> <ALOGPS_LOGP>
-1.19

> <JCHEM_LOGP>
-2.7011833506339884

> <ALOGPS_LOGS>
-0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6837092025855522

> <JCHEM_PKA_STRONGEST_BASIC>
9.639469196544843

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
23.162200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hypotaurine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000528 (Hypotaurine)

HMDB0000965
     RDKit          3D
Hypotaurine
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.0357    0.5711   -0.1955 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714    0.4410   -0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203   -0.5709    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028   -0.8541   -0.3195 S   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3422   -1.7942    0.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5369    0.6289   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700    1.0418   -0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -0.3977    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    1.4516   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    0.1569   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -0.0924    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780   -1.4932    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446    0.9111    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  6 13  1  0
M  END
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PDB for NP0000528 (Hypotaurine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.220  -0.646   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       1.114   0.128   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.554   0.121   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.462  -0.631   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.093   1.674   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      -2.894  -0.646   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    6                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for NP0000528 (Hypotaurine)

COMPND    HMDB0000965
HETATM    1  N1  UNL     1       2.036   0.571  -0.195  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.671   0.441  -0.723  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.020  -0.571   0.179  1.00  0.00           C  
HETATM    4  S1  UNL     1      -1.703  -0.854  -0.319  1.00  0.00           S  
HETATM    5  O1  UNL     1      -2.342  -1.794   0.702  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.537   0.629  -0.234  1.00  0.00           O  
HETATM    7  H1  UNL     1       2.670   1.042  -0.857  1.00  0.00           H  
HETATM    8  H2  UNL     1       2.392  -0.398   0.045  1.00  0.00           H  
HETATM    9  H3  UNL     1       0.200   1.452  -0.576  1.00  0.00           H  
HETATM   10  H4  UNL     1       0.653   0.157  -1.774  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.053  -0.092   1.200  1.00  0.00           H  
HETATM   12  H6  UNL     1       0.578  -1.493   0.226  1.00  0.00           H  
HETATM   13  H7  UNL     1      -2.545   0.911   0.712  1.00  0.00           H  
CONECT    1    2    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5    5    6
CONECT    6   13
END
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SMILES for NP0000528 (Hypotaurine)

NCCS(O)=O
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INCHI for NP0000528 (Hypotaurine)

InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)
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View in JSmol
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 Mass109.1470 Da
Monoisotopic Mass109.01975 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point354.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-2.030 (est)The Good Scents Company Information System
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
HMDB IDHMDB0000965
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022342
KNApSAcK IDNot Available
Chemspider ID96959
KEGG Compound IDC00519
BioCyc IDHYPOTAURINE
BiGG ID35230
Wikipedia LinkHypotaurine
METLIN ID281
PubChem Compound107812
PDB IDNot Available
ChEBI ID16668
Good Scents IDrw1684611
References
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 ]