Lodamin
[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate
Molecular Identity
Lodamin
[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate
PubChem CID: 369976
O-(chloroacetylcarbamoyl)fumagillol is a carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative. It has a role as an antineoplastic agent, an angiogenesis inhibitor, an EC 1.5.1.3 (dihydrofolate reductase) inhibitor, a methionine aminopeptidase 2 inhibitor and a retinoic acid receptor alpha antagonist. It is a spiro-epoxide, a carbamate ester, a sesquiterpenoid, an organochlorine compound and a semisynthetic derivative. It is functionally related to a fumagillol.
2D Structure
Properties
C19H28ClNO6
Molecular Formula
401.90
Molecular Weight
g/mol
401.1605
Exact Mass
Da
2.5
XLogP
Drug-like (Lipinski: < 5)
89.7
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
6
H-Bond Acceptors
636
Complexity
SMILES
Canonical SMILES
SMILES: CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)NC(=O)CCl)OC)CIsomeric SMILES
SMILES: CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)NC(=O)CCl)OC)CSynonyms(20)
Tnp-470129298-91-5O-(chloroacetylcarbamoyl)fumagillolO-ChloroacetylcarbamoylfumagillolNSC642492DRG-0148LODAMINDTXSID0041141NSC-642492X47GR46481CHEBI:90748DTXCID00819891(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[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate((3R,4S,5S,6R)-5-methoxy-4-((2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl)-1-oxaspiro(2.5)octan-6-yl) N-(2-chloroacetyl)carbamate
Data from PubChem (NCBI)
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