EAL

1-((2S)-2-{[(1S)-1-CARBOXY-3-PHENYLPROPYL]AMINO}PROPANOYL)-L-PROLINE

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is present as a standalone ligand in 2 entries

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Chemical Component Summary
Name	1-((2S)-2-{[(1S)-1-CARBOXY-3-PHENYLPROPYL]AMINO}PROPANOYL)-L-PROLINE
Synonyms	ENALAPRILAT INHIBITOR
Identifiers	(2S)-1-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenyl-butan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid
Formula	C₁₈ H₂₄ N₂ O₅
Molecular Weight	348.394
Type	NON-POLYMER
Isomeric SMILES	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@@H](CCc2ccccc2)C(=O)O
InChI	InChI=1S/C18H24N2O5/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25)/t12-,14-,15-/m0/s1
InChIKey	LZFZMUMEGBBDTC-QEJZJMRPSA-N

Chemical Details
Formal Charge	0
Atom Count	49
Chiral Atom Count	3
Bond Count	50
Aromatic Bond Count	6

Drug Info: DrugBank

DrugBank ID	DB09477
Name	Enalaprilat
Groups	approved
Description	Enalaprilat is the active metabolite of the orally available pro-drug, [enalapril]. Used in the treatment of hypertension, enalapril is an ACE inhibitor that prevents Angiotensin Converting Enzyme (ACE) from transforming angiotensin I into angiotensin II. As angiotensin II is responsible for vasoconstriction and sodium reabsorption in the proximal tubule of the kidney, down-regulation of this protein results in reduced blood pressure and blood fluid volume. Enalaprilat was originally created to overcome the limitations of the first ACE inhibitor, captopril, which had numerous side effects and left a metallic taste in the mouth. Removal of the problematic thiol group from captopril resulted in enalaprilat, which was then modified further with an ester to create the orally available pro-drug enalapril. Enalaprilat is poorly orally available and is therefore only available as an intravenous injection for the treatment of hypertension when oral therapy is not possible.
Synonyms	Enalaprilat anhydrous Enalaprilat Enalaprilat dihydrate
Brand Names	Vasotec IV Enalaprilat Enalaprilat Injection USP
Indication	Enalaprilat injection is indicated for the treatment of hypertension when oral therapy is not practical.
Categories	Agents Acting on the Renin-Angiotensin System Agents causing angioedema Agents causing hyperkalemia Amino Acids, Peptides, and Proteins Angiotensin-Converting Enzyme Inhibitors Antihypertensive Agents Antihypertensive Agents Indicated for Hypertension Cardiovascular Agents Decreased Blood Pressure Dipeptides Drugs causing inadvertant photosensitivity Drugs that are Mainly Renally Excreted Enzyme Inhibitors Hypotensive Agents Oligopeptides Peptides Photosensitizing Agents Protease Inhibitors
CAS number	76420-72-9

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Angiotensin-converting enzyme	MGAASGRRGPGLLLPLPLLLLLPPQPALALDPGLQPGNFSADEAGAQLFA...	unknown	inhibitor
B1 bradykinin receptor	MASSWPPLELQSSNQSQLFPQNATACDNAPEAWDLLHRVLPTFIISICFF...	unknown

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682