TN4

(1R,2S,3S,4R)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (chloroacetyl)carbamate

Created:	2003-04-24
Last modified:	2024-09-27

Find Related PDB Entry
2 entries where TN4 is found as a standalone ligand2 entries where TN4 is covalently linked to polymer or other heterogen groups

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	57
Chiral Atom Count	6
Bond Count	58
Aromatic Bond Count	0

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	(1R,2S,3S,4R)-4-hydroxy-2-methoxy-4-methyl-3-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (chloroacetyl)carbamate
Synonyms	TNP-470 (Open form)
Systematic Name (OpenEye OEToolkits)	[(1R,2S,3S,4R)-2-methoxy-4-methyl-3-[(3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-4-oxidanyl-cyclohexyl] N-(2-chloranylethanoyl)carbamate
Formula	C₁₉ H₃₀ Cl N O₆
Molecular Weight	403.898
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	ClCC(=O)NC(=O)OC2CCC(O)(C(C1(OC1C/C=C(/C)C)C)C2OC)C
SMILES	CACTVS	3.370	CO[CH]1[CH](CC[C](C)(O)[CH]1[C]2(C)O[CH]2CC=C(C)C)OC(=O)NC(=O)CCl
SMILES	OpenEye OEToolkits	1.7.2	CC(=CCC1C(O1)(C)C2C(C(CCC2(C)O)OC(=O)NC(=O)CCl)OC)C
Canonical SMILES	CACTVS	3.370	CO[C@@H]1[C@@H](CC[C@@](C)(O)[C@H]1[C@@]2(C)O[C@@H]2CC=C(C)C)OC(=O)NC(=O)CCl
Canonical SMILES	OpenEye OEToolkits	1.7.2	CC(=CC[C@@H]1C(O1)(C)[C@H]2[C@@H]([C@@H](CC[C@@]2(C)O)OC(=O)NC(=O)CCl)OC)C
InChI	InChI	1.03	InChI=1S/C19H30ClNO6/c1-11(2)6-7-13-19(4,27-13)16-15(25-5)12(8-9-18(16,3)24)26-17(23)21-14(22)10-20/h6,12-13,15-16,24H,7-10H2,1-5H3,(H,21,22,23)/t12-,13-,15-,16+,18-,19+/m1/s1
InChIKey	InChI	1.03	OUUSPVSSNHLIGE-AGYLCKTBSA-N

Drug Info: DrugBank

DrugBank ID	DB08633
Name	TNP-470
Groups	investigational
Description	O-(chloroacetylcarbamoyl)fumagillol (TNP-470) has been used in trials studying the treatment of HIV Infections, Sarcoma, Kaposi, and Pancreatic Neoplasms.
Synonyms	O-chloroacetylcarbamoylfumagillol O-(chloroacetylcarbamoyl)fumagillol TNP-470
Categories	Angiogenesis Inhibitors Angiogenesis Modulating Agents Antibiotics, Antineoplastic Antineoplastic Agents Cyclohexanes Cycloparaffins Growth Inhibitors Growth Substances Sesquiterpenes Terpenes
CAS number	129298-91-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Methionine aminopeptidase 2	MAGVEEVAASGSHLNGDLDPDDREEGAASTAEEAAKKKRRKKKKSKGPSA...	unknown	inhibitor

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