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Showing NP-Card for Cysteamine (NP0000997)

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Record Information
Version2.0
Created at2006-05-22 15:12:24 UTC
Updated at2021-06-29 00:47:39 UTC
NP-MRD IDNP0000997
Secondary Accession NumbersNone
Natural Product Identification
Common NameCysteamine
DescriptionCysteamine is a product of the constitutive degradation of coenzyme A, a process that occurs in all tissues, although some tissues such as brain and heart may have exceptionally high coenzyme A turnover rates. Cysteamine has only one known function, and that is as a precursor for the formation of hypotaurine, which is subsequently oxidized to taurine. The rate of cysteamine production as a result of coenzyme A breakdown is not well understood but it is clear that cysteamine levels are not as dramatically affected by dietary habits as are cysteine levels. Cysteamine is generated from hypotaurine by cysteamine dioxygenase (EC:1.13.11.19), An enzyme that was recently identified in mammals (PMID: 17581819 ). Cysteamine is the simplest stable aminothiol found in the body. It is used in the treatment of disorders of cystine excretion. Cysteamine cleaves the disulfide bond with cysteine to produce molecules that can escape the metabolic defect in cystinosis and cystinuria. Cyst(e)amine may also serve as an endogenous regulator of immune system activity as well as a potential therapeutic agent for the treatment of Huntington disease. Cysteamine is also used as a radiation-protective agent that oxidizes in air to form cystamine. It can be given intravenously or orally to treat radiation sickness.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000997 (Cysteamine)

847
  Mrv1652305271900072D          

  4  3  0  0  0  0            999 V2000
    4.2369    0.4620    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0933    0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
M  END
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3D MOL for NP0000997 (Cysteamine)

HMDB0002991
     RDKit          3D
Cysteamine
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.2556    0.6396    0.3763 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5440   -0.2606   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -0.5714    0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6748    0.9710    0.4177 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058    0.4311    1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    0.5228    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107   -1.2142   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    0.2656   -1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678   -1.3151   -0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4977   -0.9495    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442    1.4807   -0.7375 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
  1  5  1  0
  1  6  1  0
  2  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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3D SDF for NP0000997 (Cysteamine)

847
  Mrv1652305271900072D          

  4  3  0  0  0  0            999 V2000
    4.2369    0.4620    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0933    0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCS

> <INCHI_IDENTIFIER>
InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2

> <INCHI_KEY>
UFULAYFCSOUIOV-UHFFFAOYSA-N

> <FORMULA>
C2H7NS

> <MOLECULAR_WEIGHT>
77.149

> <EXACT_MASS>
77.029919919

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
8.651056413998477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminoethane-1-thiol

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
-0.41661316428888157

> <ALOGPS_LOGS>
-0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.422940354198866

> <JCHEM_PKA_STRONGEST_BASIC>
10.398577468244163

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
22.393700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cysteamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0000997 (Cysteamine)

HMDB0002991
     RDKit          3D
Cysteamine
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.2556    0.6396    0.3763 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5440   -0.2606   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -0.5714    0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6748    0.9710    0.4177 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058    0.4311    1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    0.5228    0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107   -1.2142   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    0.2656   -1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3678   -1.3151   -0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4977   -0.9495    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442    1.4807   -0.7375 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
  1  5  1  0
  1  6  1  0
  2  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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PDB for NP0000997 (Cysteamine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 847                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0       7.909   0.862   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       3.907   0.092   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.241   0.862   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.575   0.092   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    3                                                            
CONECT    3    2    4                                                       
CONECT    4    1    3                                                       
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for NP0000997 (Cysteamine)

COMPND    HMDB0002991
HETATM    1  N1  UNL     1      -1.256   0.640   0.376  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.544  -0.261  -0.517  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.788  -0.571   0.181  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.675   0.971   0.418  1.00  0.00           S  
HETATM    5  H1  UNL     1      -1.006   0.431   1.369  1.00  0.00           H  
HETATM    6  H2  UNL     1      -2.278   0.523   0.294  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.111  -1.214  -0.684  1.00  0.00           H  
HETATM    8  H4  UNL     1      -0.379   0.266  -1.479  1.00  0.00           H  
HETATM    9  H5  UNL     1       1.368  -1.315  -0.407  1.00  0.00           H  
HETATM   10  H6  UNL     1       0.498  -0.950   1.187  1.00  0.00           H  
HETATM   11  H7  UNL     1       2.244   1.481  -0.738  1.00  0.00           H  
CONECT    1    2    5    6
CONECT    2    3    7    8
CONECT    3    4    9   10
CONECT    4   11
END
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SMILES for NP0000997 (Cysteamine)

NCCS
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INCHI for NP0000997 (Cysteamine)

InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
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View in JSmol
Synonyms
ValueSource
2-Amino-1-ethanethiolChEBI
2-AMINO-ethanethiolChEBI
2-AminoethanethiolChEBI
beta-AminoethanethiolChEBI
beta-AminoethylthiolChEBI
beta-MEAChEBI
beta-MercaptoethylamineChEBI
MEAChEBI
MercaptaminaChEBI
MercaptamineChEBI
MercaptaminumChEBI
ThioethanolamineChEBI
b-AminoethanethiolGenerator
Β-aminoethanethiolGenerator
b-AminoethylthiolGenerator
Β-aminoethylthiolGenerator
b-MEAGenerator
Β-meaGenerator
b-MercaptoethylamineGenerator
Β-mercaptoethylamineGenerator
(2-Mercaptoethyl)amineHMDB
2-Aminoethyl mercaptanHMDB
2-MercaptoethanamineHMDB
Aminoethyl mercaptanHMDB
BecaptanHMDB
CASHHMDB
CisteaminaHMDB
CysteamideHMDB
CysteaminHMDB
CysteaminiumHMDB
CysteinamineHMDB
DecarboxycysteineHMDB
EthanethiolamineHMDB
LambratenHMDB
LambrateneHMDB
MecramineHMDB
MercaminHMDB
MercamineHMDB
MercaptaminHMDB
MerkaminHMDB
RiaconHMDB
35S-Labeled cysteamineHMDB
CystagonHMDB
Cysteamine hydrobromideHMDB
Hydrochloride, cysteamineHMDB
Tosylate, cysteamineHMDB
Cysteamine dihydrochlorideHMDB
Cysteamine hydrochlorideHMDB
Cysteamine maleate (1:1)HMDB
Cysteamine tosylateHMDB
MercaptoethylamineHMDB
2 AminoethanethiolHMDB
Cysteamine bitartrateHMDB
Cysteamine tartrateHMDB
Cysteamine tartrate (1:1)HMDB
Hydrobromide, cysteamineHMDB
Tartrate, cysteamineHMDB
beta MercaptoethylamineHMDB
Bitartrate, cysteamineHMDB
Cysteamine, 35S labeledHMDB
Cysteamine, 35S-labeledHMDB
Dihydrochloride, cysteamineHMDB
Chemical FormulaC2H7NS
Average Mass77.1490 Da
Monoisotopic Mass77.02992 Da
IUPAC Name2-aminoethane-1-thiol
Traditional Namecysteamine
CAS Registry Number60-23-1
SMILES
NCCS
InChI Identifier
InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
InChI KeyUFULAYFCSOUIOV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
Ipomoea nilKNApSAcK Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point98 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.5 g/LALOGPS
logP0.01ALOGPS
logP-0.42ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m³·mol⁻¹ChemAxon
Polarizability8.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002991
DrugBank IDDB00847
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023091
KNApSAcK IDC00006768
Chemspider ID5834
KEGG Compound IDC01678
BioCyc IDCPD-239
BiGG ID1808054
Wikipedia LinkCysteamine
METLIN ID3222
PubChem Compound6058
PDB IDNot Available
ChEBI ID17141
Good Scents IDNot Available
References
General References
  1. Dominy JE Jr, Simmons CR, Hirschberger LL, Hwang J, Coloso RM, Stipanuk MH: Discovery and characterization of a second mammalian thiol dioxygenase, cysteamine dioxygenase. J Biol Chem. 2007 Aug 31;282(35):25189-98. Epub 2007 Jun 20. [PubMed:17581819 ]
  2. Pastore A, Massoud R, Motti C, Lo Russo A, Fucci G, Cortese C, Federici G: Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine. Clin Chem. 1998 Apr;44(4):825-32. [PubMed:9554495 ]
  3. Sonies BC, Almajid P, Kleta R, Bernardini I, Gahl WA: Swallowing dysfunction in 101 patients with nephropathic cystinosis: benefit of long-term cysteamine therapy. Medicine (Baltimore). 2005 May;84(3):137-46. [PubMed:15879904 ]
  4. Lochman P, Adam T, Friedecky D, Hlidkova E, Skopkova Z: High-throughput capillary electrophoretic method for determination of total aminothiols in plasma and urine. Electrophoresis. 2003 Apr;24(7-8):1200-7. [PubMed:12707912 ]
  5. Chakrabarti MC, Le N, Paik CH, De Graff WG, Carrasquillo JA: Prevention of radiolysis of monoclonal antibody during labeling. J Nucl Med. 1996 Aug;37(8):1384-8. [PubMed:8708780 ]
  6. Skov Olsen P: Role of epidermal growth factor in gastroduodenal mucosal protection. J Clin Gastroenterol. 1988;10 Suppl 1:S146-51. [PubMed:3053882 ]
  7. Gahl WA, Schneider JA, Schulman JD, Thoene JG, Reed GF: Predicted reciprocal serum creatinine at age 10 years as a measure of renal function in children with nephropathic cystinosis treated with oral cysteamine. Pediatr Nephrol. 1990 Mar;4(2):129-35. [PubMed:2397178 ]
  8. Smolin LA, Clark KF, Thoene JG, Gahl WA, Schneider JA: A comparison of the effectiveness of cysteamine and phosphocysteamine in elevating plasma cysteamine concentration and decreasing leukocyte free cystine in nephropathic cystinosis. Pediatr Res. 1988 Jun;23(6):616-20. [PubMed:3393396 ]
  9. Levtchenko EN, van Dael CM, de Graaf-Hess AC, Wilmer MJ, van den Heuvel LP, Monnens LA, Blom HJ: Strict cysteamine dose regimen is required to prevent nocturnal cystine accumulation in cystinosis. Pediatr Nephrol. 2006 Jan;21(1):110-3. Epub 2005 Oct 27. [PubMed:16252107 ]
  10. Liu YC, Wang CM, Hsiung KP: Comparison of different protein immobilization methods on quartz crystal microbalance surface in flow injection immunoassay. Anal Biochem. 2001 Dec 15;299(2):130-5. [PubMed:11730334 ]
  11. Yudkoff M, Foreman JW, Segal S: Effects of cysteamine therapy in nephropathic cystinosis. N Engl J Med. 1981 Jan 15;304(3):141-5. [PubMed:7442733 ]
  12. Gahl WA, Charnas L, Markello TC, Bernardini I, Ishak KG, Dalakas MC: Parenchymal organ cystine depletion with long-term cysteamine therapy. Biochem Med Metab Biol. 1992 Dec;48(3):275-85. [PubMed:1476793 ]
  13. Geelen JM, Monnens LA, Levtchenko EN: Follow-up and treatment of adults with cystinosis in the Netherlands. Nephrol Dial Transplant. 2002 Oct;17(10):1766-70. [PubMed:12270982 ]
  14. Stachowicz M, Lehmann B, Tibi A, Prognon P, Daurat V, Pradeau D: Determination of total cysteamine in human serum by a high-performance liquid chromatography with fluorescence detection. J Pharm Biomed Anal. 1998 Aug;17(4-5):767-73. [PubMed:9682161 ]
  15. Orloff S, Butler JD, Towne D, Mukherjee AB, Schulman JD: Pantetheinase activity and cysteamine content in cystinotic and normal fibroblasts and leukocytes. Pediatr Res. 1981 Jul;15(7):1063-7. [PubMed:7254953 ]
  16. de Graaf-Hess A, Trijbels F, Blom H: New method for determining cystine in leukocytes and fibroblasts. Clin Chem. 1999 Dec;45(12):2224-8. [PubMed:10585356 ]
  17. Chmiel J, Kopczynski Z, Rybczynska M: The influence of the known radioprotective compounds on the metabolism of red blood cells. I. Effect of cysteamine on the cellular level of the intermediates and coenzymes. Pol J Pharmacol Pharm. 1976;28(2):113-21. [PubMed:934944 ]
  18. Schneider JA, Clark KF, Greene AA, Reisch JS, Markello TC, Gahl WA, Thoene JG, Noonan PK, Berry KA: Recent advances in the treatment of cystinosis. J Inherit Metab Dis. 1995;18(4):387-97. [PubMed:7494398 ]