Molecular Identity
L-Proline
(2S)-pyrrolidine-2-carboxylic acid
PubChem CID: 145742
L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a member of compatible osmolytes, a micronutrient, a nutraceutical, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and an algal metabolite. It is a L-alpha-amino acid, a glutamine family amino acid, a proline and a proteinogenic amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion.
2D Structure
Properties
C5H9NO2
Molecular Formula
115.13
Molecular Weight
g/mol
115.0633
Exact Mass
Da
-2.5
XLogP
Drug-like (Lipinski: < 5)
49.3
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
3
H-Bond Acceptors
103
Complexity
SMILES
Canonical SMILES
SMILES: C1CC(NC1)C(=O)OIsomeric SMILES
SMILES: C1C[C@H](NC1)C(=O)OSynonyms(20)
L-proline147-85-3prolineL-(-)-Proline(2S)-pyrrolidine-2-carboxylic acid(S)-Pyrrolidine-2-carboxylic acid(-)-Proline2-pyrrolidinecarboxylic acid(-)-(S)-Proline(S)-2-Pyrrolidinecarboxylic acidprolinaProlinum(S)-Proline(-)-2-Pyrrolidinecarboxylic acidL-Prolin
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to L-Proline
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