Common NameD-cysteine
DescriptionD-cysteine is an optically active form of cysteine having D-configuration. It is a cysteine and a D-alpha-amino acid. It is a conjugate base of a D-cysteinium. It is a conjugate acid of a D-cysteinate(1-). It is an enantiomer of a L-cysteine. It is a tautomer of a D-cysteine zwitterion. D-Cysteine, also known as D-cystein or DCY, 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. It is a non-proteogenic sulfur-containing amino acid. D-Cysteine is known to be toxic to bacteria and several bacteria (and plants) have developed and enzyme called D-cysteine desulfhydrase (EC4.1.99.4). D-cysteine can be generated from D-Cysteine via cysteine racemase. D-Cysteine is a naturally occurring enantiomer of L-Cysteine. Cysteine is named after cystine, which comes from the Greek word kustis meaning bladder -cystine was first isolated from kidney stones. D-Cysteine exists in all living species, ranging from bacteria to humans. Outside of the human body, D-Cysteine has been detected, but not quantified in several different foods, such as chervils, fruits, lichee, nuts, and cherimoya.
Structure
Molecular FormulaC3H7NO2S
Average Mass121.15000
Monoisotopic Mass121.01975
IUPAC Name(2S)-2-amino-3-sulfanylpropanoic acid
Traditional NameD-cysteine
CAS Registry Number0921-01-07
SMILES[NH3+][C@H](CS)C(=O)[O-]
InChI IdentifierInChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1
InChI KeyXUJNEKJLAYXESH-UWTATZPHSA-N
CHEBI IDCHEBI:35236
HMDB IDHMDB0003417
StateSolid
Water Solubility2.31e+01 g/l
logP-2.57
logS-0.72
pKa (Strongest Acidic)2.35
pKa (Strongest Basic)9.05
Hydrogen Acceptor Count3
Hydrogen Donor Count3
Polar Surface Area63.32 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity28.22 m³·mol⁻¹
Polarizability11.40

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