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CHEBI:142822 - andrastin B(1−)

ChEBI IDCHEBI:142822
ChEBI Nameandrastin B(1−)
Stars
ASCII Nameandrastin B(1-)
DefinitionAn enolate anion resulting from the deprotonation of the enol group of andrastin B. Major species at pH 7.3. Published in Tetrahedron, 2013, 69(38), 8199-8204. http://dx.doi.org/10.1016/j.tet.2013.07.029
Last Modified9 January 2019
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC28H39O7
Net Charge-1
Average Mass487.613
Monoisotopic Mass487.27013
SMILES[H][C@@]12C=C(C)[C@@]3(C)C(=O)C(C)=C([O-])[C@@]3(C(=O)OC)[C@@]1(C)CC[C@]1([H])C(C)(C)[C@@H](OC(C)=O)CC[C@@]21CO
InChIInChI=1S/C28H40O7/c1-15-13-19-25(6,28(23(33)34-8)22(32)16(2)21(31)26(15,28)7)11-9-18-24(4,5)20(35-17(3)30)10-12-27(18,19)14-29/h13,18-20,29,32H,9-12,14H2,1-8H3/p-1/t18-,19-,20+,25+,26+,27+,28-/m1/s1
InChIKeyHWVZMVZNLKRRLT-OXILWVMOSA-M
Roles Classification
Biological Role:
EC 2.5.1.58 (protein farnesyltransferase) inhibitor  An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group.
ChEBI Ontology
Outgoing Relation(s)
andrastin B(1−) (CHEBI:142822) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
andrastin B(1−) (CHEBI:142822) is a enolate (CHEBI:142839)
andrastin B(1−) (CHEBI:142822) is conjugate base of andrastin B (CHEBI:142862)
Incoming Relation(s)
andrastin B (CHEBI:142862) is conjugate acid of andrastin B(1−) (CHEBI:142822)
IUPAC Name 
3β-(acetyloxy)-14-(methoxycarbonyl)-4,4,8α,12,16-pentamethyl-17,19-dioxo-5β,9β,10α,13α-androsta-11,15-dien-15-olate
Synonym  Source
(3β,5β,8α,9β,10α,13α)-3-(acetyloxy)-14-(methoxycarbonyl)-4,4,8,12,16-pentamethyl-17,19-dioxoandrosta-11,15-dien-15-olateIUPAC
UniProt Name  Source
andrastin BUniProt