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CHEBI:90748 - O-(chloroacetylcarbamoyl)fumagillol

ChEBI IDCHEBI:90748
ChEBI NameO-(chloroacetylcarbamoyl)fumagillol
Stars
ASCII NameO-(chloroacetylcarbamoyl)fumagillol
DefinitionA carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative.
Secondary ChEBI IDCHEBI:47708
Last Modified24 August 2016
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H28ClNO6
Net Charge0
Average Mass401.887
Monoisotopic Mass401.16052
SMILES[H][C@]1([C@@]2(C)O[C@]2([H])CC=C(C)C)[C@H](OC)[C@H](OC(=O)NC(=O)CCl)CC[C@]12CO2
InChIInChI=1S/C19H28ClNO6/c1-11(2)5-6-13-18(3,27-13)16-15(24-4)12(7-8-19(16)10-25-19)26-17(23)21-14(22)9-20/h5,12-13,15-16H,6-10H2,1-4H3,(H,21,22,23)/t12-,13-,15-,16-,18+,19+/m1/s1
InChIKeyMSHZHSPISPJWHW-PVDLLORBSA-N
Roles Classification
Biological Roles:
retinoic acid receptor alpha antagonist  A retinoic acid receptor antagonist that antagonises retinoic acid receptor α.
methionine aminopeptidase 2 inhibitor  Any methionyl aminopeptidase inhibitor that inhibits the action of methionyl aminopeptidase 2.
EC 1.5.1.3 (dihydrofolate reductase) inhibitor  An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3).
Applications:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
retinoic acid receptor alpha antagonist  A retinoic acid receptor antagonist that antagonises retinoic acid receptor α.
ChEBI Ontology
Outgoing Relation(s)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) has functional parent fumagillol (CHEBI:324935)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) has role angiogenesis inhibitor (CHEBI:48422)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) has role antineoplastic agent (CHEBI:35610)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) has role methionine aminopeptidase 2 inhibitor (CHEBI:73361)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) has role retinoic acid receptor α antagonist (CHEBI:90713)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) is a carbamate ester (CHEBI:23003)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) is a organochlorine compound (CHEBI:36683)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) is a semisynthetic derivative (CHEBI:72588)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) is a sesquiterpenoid (CHEBI:26658)
O-(chloroacetylcarbamoyl)fumagillol (CHEBI:90748) is a spiro-epoxide (CHEBI:133131)
IUPAC Name 
(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl (chloroacetyl)carbamate
Synonyms  Source
(CHLOROACETYL)CARBAMIC ACID (3R,4S,5S,5R)-5-METHOXY-4-[(2R,3R)-2-METHYL-3-(3-METHYL-2-BUTENYL)OXIRANYL]-1-OXASPIRO[2.5]OCT-6-YL ESTERPDBeChem
Agm 1470ChemIDplus
O-chloroacetylcarbamoylfumagillolChemIDplus
AGM-1470ChEBI
DRG-0148ChemIDplus
TNP-470ChEBI
Manual XrefsDatabases
TN4PDBeChem
DB08633DrugBank
LSM-37119LINCS
Registry NumbersSources
Reaxys:5358869Reaxys
CAS:129298-91-5ChemIDplus
Citations