Showing metabocard for Cysteamine (MMDBc0032009)

Human
Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-18 01:58:29 UTC
Update Date2025-11-05 17:13:02 UTC
Metabolite IDMMDBc0032009
Metabolite Identification
Common NameCysteamine
DescriptionCysteamine is a thiolamine compound belonging to the class of amines and thiols. Its chemical structure is characterized by the presence of a free thiol group (-SH) and an amino group (-NH2), specifically represented as SH-(CH2)2-NH2. This unique configuration allows cysteamine to participate in various biochemical pathways, including the reduction of disulfide bonds, as evidenced by its use in preparing monovalent mouse anti-trinitrophenyl IgG1 through the reduction of disulfide bonds (PMID:41165797 ). Additionally, cysteamine is instrumental in the development of functionalized nanomaterials, such as nanoparticles and quantum dots, which are utilized for the detection and quantification of biomedical, biomolecular, and environmental analytes (PMID:41156391 ). Experimental studies have shown that cysteamine hydrochloride can ameliorate ocular dysplasia in zebrafish by maintaining ocular redox homeostasis, highlighting its role in modulating oxidative stress through the upregulation of superoxide dismutase activity and glutathione content (PMID:41150835 ). Overall, cysteamine's chemical properties and its involvement in various biological processes underscore its significance in both chemistry and biology.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9aa1e8dbc0>

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 #<Metabolite:0x00007f9aa1e8dbc0>

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 #<Metabolite:0x00007f9aa1e8dbc0>

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>
MMDBc0032009

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f9aa1e8dbc0>

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 #<Metabolite:0x00007f9aa1e8dbc0>

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 #<Metabolite:0x00007f9aa1e8dbc0>

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 #<Metabolite:0x00007f9aa1e8dbc0>

NCCS
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INCHI for #<Metabolite:0x00007f9aa1e8dbc0>

InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
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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
Molecular FormulaC2H7NS
Average Mass77.149
Monoisotopic Mass77.029919919
IUPAC Name2-aminoethane-1-thiol
Traditional Namecysteamine
CAS Registry NumberNot Available
SMILES
NCCS
InChI Identifier
InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
InChI KeyUFULAYFCSOUIOV-UHFFFAOYSA-N