Showing NP-Card for L-Cysteine (NP0000120)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2025-02-11 15:40:34 UTC
NP-MRD IDNP0000120
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Cysteine
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000120 (L-Cysteine)

  Mrv1652309272007452D          

  7  6  0  0  0  0            999 V2000
    0.6124    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -0.1768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8165    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124    1.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -1.0018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310   -0.1768    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  2  0  0  0  0
  4  1  1  0  0  0  0
  3  2  1  0  0  0  0
  2  6  1  1  0  0  0
  7  3  1  0  0  0  0
M  END
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3D MOL for NP0000120 (L-Cysteine)

HMDB0000574
     RDKit          3D
L-Cysteine
 14 13  0  0  0  0  0  0  0  0999 V2000
   -1.2562   -1.1395    0.5043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694    0.0386    0.3993 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0121   -0.2774    0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453   -1.3589   -0.9942 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630    0.8796   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.5570   -1.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0360    2.0476   -0.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518   -1.2014   -0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6950   -1.2598    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6492    0.6636    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    0.6944    0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.7869    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.4383   -1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429    2.5813   -0.1451 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  1
  3 11  1  0
  3 12  1  0
  4 13  1  0
  7 14  1  0
M  END
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3D SDF for NP0000120 (L-Cysteine)

  Mrv1652309272007452D          

  7  6  0  0  0  0            999 V2000
    0.6124    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -0.1768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8165    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269   -0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124    1.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -1.0018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310   -0.1768    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  2  0  0  0  0
  4  1  1  0  0  0  0
  3  2  1  0  0  0  0
  2  6  1  1  0  0  0
  7  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CS)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

> <INCHI_KEY>
XUJNEKJLAYXESH-REOHCLBHSA-N

> <FORMULA>
C3H7NO2S

> <MOLECULAR_WEIGHT>
121.158

> <EXACT_MASS>
121.019749163

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.40532279226667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-sulfanylpropanoic acid

> <ALOGPS_LOGP>
-2.57

> <JCHEM_LOGP>
-2.7921332976482773

> <ALOGPS_LOGS>
-0.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.171891903949282

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.345995198078135

> <JCHEM_PKA_STRONGEST_BASIC>
9.053809511128133

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
28.2236

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-cysteine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0000120 (L-Cysteine)

HMDB0000574
     RDKit          3D
L-Cysteine
 14 13  0  0  0  0  0  0  0  0999 V2000
   -1.2562   -1.1395    0.5043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694    0.0386    0.3993 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0121   -0.2774    0.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453   -1.3589   -0.9942 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630    0.8796   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.5570   -1.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0360    2.0476   -0.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518   -1.2014   -0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6950   -1.2598    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6492    0.6636    1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    0.6944    0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.7869    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8473   -1.4383   -1.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429    2.5813   -0.1451 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  1
  3 11  1  0
  3 12  1  0
  4 13  1  0
  7 14  1  0
M  END
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PDB for NP0000120 (L-Cysteine)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.143   0.440   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.191  -0.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.524   0.440   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.477  -0.330   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.143   1.980   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      -0.191  -1.870   0.000  0.00  0.00           N+0
HETATM    7  S   UNK     0      -2.858  -0.330   0.000  0.00  0.00           S+0
CONECT    1    2    5    4                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0000120 (L-Cysteine)

COMPND    HMDB0000574
HETATM    1  N1  UNL     1      -1.256  -1.139   0.504  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.469   0.039   0.399  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.012  -0.277   0.404  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.445  -1.359  -0.994  1.00  0.00           S  
HETATM    5  C3  UNL     1      -0.763   0.880  -0.764  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.648   0.557  -1.587  1.00  0.00           O  
HETATM    7  O2  UNL     1      -0.036   2.048  -0.936  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.952  -1.201  -0.269  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.695  -1.260   1.451  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.649   0.664   1.312  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.541   0.694   0.322  1.00  0.00           H  
HETATM   12  H5  UNL     1       1.280  -0.787   1.351  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.847  -1.438  -1.048  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.343   2.581  -0.145  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3    5   10
CONECT    3    4   11   12
CONECT    4   13
CONECT    5    6    6    7
CONECT    7   14
END
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SMILES for NP0000120 (L-Cysteine)

N[C@@H](CS)C(O)=O
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INCHI for NP0000120 (L-Cysteine)

InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
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Synonyms
Chemical FormulaC3H7NO2S
Average Mass121.1580 Da
Monoisotopic Mass121.01975 Da
IUPAC Name(2R)-2-amino-3-sulfanylpropanoic acid
Traditional NameL-cysteine
CAS Registry Number52-90-4
SMILES
N[C@@H](CS)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChI KeyXUJNEKJLAYXESH-REOHCLBHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-07-25View Spectrum
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility277 mg/mL at 25 °CBeilstein Handbook of Organic Chemistry (Handbuch der Organischen Chemie), 4th Edition
LogP-2.49Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP-2.6ALOGPS
logP-2.8ChemAxon
logS-0.72ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.22 m³·mol⁻¹ChemAxon
Polarizability11.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000574
DrugBank IDDB00151
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012678
KNApSAcK IDC00001351
Chemspider ID5653
KEGG Compound IDC00097
BioCyc IDCYS
BiGG ID33843
Wikipedia LinkCysteine
METLIN ID5556
PubChem Compound5862
PDB IDNot Available
ChEBI ID17561
Good Scents IDrw1018061
References
General References