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TMC-52A

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An epoxide which is a carboxamide obtained by the formal condensation of one of the carboxy groups of oxirane-2,3-dicarboxylic acid with N-{3-[(4-aminobutyl)amino]propyl}-L-tyrosinamide. It is a natural product, isolated from Gliocladium sp. F-2665. TMC-52A acts as an inhibitor of cysteine proteinases, particularly cathepsin B (EC 3.4.22.1), cathepsin L (EC 3.4.22.15), and papain (EC 3.4.22.2); IC50 values are 320 nM, 13 nM, and 44 nM, respectively. The epoxide group has trans configuration but its exact stereochemistry is uncertain: it is either (2R,3R) or (2S,3S).

Term info

Label

TMC-52A

Synonyms
  • (2R*,3R*)-3-{[(2S)-1-({3-[(4-aminobutyl)amino]propyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl}oxirane-2-carboxylic acid
database cross reference
Subsets

3_STAR

IUPAC NAME
(2R*,3R*)-3-{[(2S)-1-({3-[(4-aminobutyl)amino]propyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl}oxirane-2-carboxylic acid [ IUPAC ]

charge

0

formula

C20H30N4O6

has obo namespace

chebi_ontology

id

CHEBI:66238

inchi

InChI=1S/C20H30N4O6/c21-8-1-2-9-22-10-3-11-23-18(26)15(12-13-4-6-14(25)7-5-13)24-19(27)16-17(30-16)20(28)29/h4-7,15-17,22,25H,1-3,8-12,21H2,(H,23,26)(H,24,27)(H,28,29)/t15-,16?,17?/m0/s1

inchikey

PRCZPOBZJVCPKL-GTPINHCMSA-N

mass

422.47540

monoisotopicmass

422.21653

smiles

NCCCCNCCCNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)C1OC1C(O)=O