(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 N-(2-chloroacetyl)carbamate

• ChemBase ID: 153673
• Molecular Formular: C19H28ClNO6
• Molecular Mass: 401.88172
• Monoisotopic Mass: 401.1605153
• SMILES: CC(=CC[C@@H]1[C@@](O1)(C)[C@H]1[C@@H]([C@@H](CC[C@@]21CO2)OC(=O)NC(=O)CCl)OC)C
• Canonical SMILES: CO[C@@H]1[C@@H](CC[C@@]2([C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C)CO2)OC(=O)NC(=O)CCl
• InChI: InChI=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
• InChIKey: MSHZHSPISPJWHW-PVDLLORBSA-N

NAMES AND DATABASE IDS

Names

• 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 N-(2-chloroacetyl)carbamate
• IUPAC Traditional 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 N-(2-chloroacetyl)carbamate
• Synonyms: (Chloracetyl) carbamic acid (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl ester; AGM-1470; NSC 642492; O-Chloracetyl-carbamoyl fumagillol; TNP-470

Database IDs

• MDL Number: MFCD00870281
• PubChem SID: 162247812
• PubChem CID: 369976

CALCULATED PROPERTIES

• Acid pKa: 7.3115864
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.2370756
• LogD (pH = 7.4): 1.9021959
• Log P: 2.24365
• Molar Refractivity: 98.4515 cm^3
• Polarizability: 39.307835 Å^3
• Polar Surface Area: 89.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >15 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H28ClNO6

DETAILS

Sigma Aldrich - T1455

Other Notes
TNP-470 is hygroscopic.
Biochem/physiol Actions
TNP-470 is a methionine aminopeptidase-2 (MetAP-2) inhibitor, selective for MetAP-2 over MetAP11. TNP-470 is an antiangiogenic.