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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Tnp-470, 129298-91-5, Agm-1470, Tnp 470, Agm 1470, O-chloroacetylcarbamoylfumagillol

Molecular Formula

C₁₉H₂₈ClNO₆

Molecular Weight

401.9 g/mol

InChI Key

MSHZHSPISPJWHW-PVDLLORBSA-N

FDA UNII

X47GR46481

Semisynthetic analog of fumagillin (a cyclohexane-sesquiterpene antibiotic isolated from ASPERGILLUS FUMIGATUS) that inhibits angiogenesis.

1 2D Structure

O-Chloroacetylcarbamoyl-Fumagillol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(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

2.1.2 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

2.1.3 InChI Key

MSHZHSPISPJWHW-PVDLLORBSA-N

2.1.4 Canonical SMILES

CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)NC(=O)CCl)OC)C

2.1.5 Isomeric 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)C

2.2 Other Identifiers

2.2.1 UNII

X47GR46481

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2,5)oct-6-yl(chloroacetyl) Carbamate

2. Agm 1470

3. Agm-1470

4. Agm1470

5. Caplostatin

6. Tnp 470

7. Tnp-470

8. Tnp470

2.3.2 Depositor-Supplied Synonyms

1. Tnp-470

2. 129298-91-5

3. Agm-1470

4. Tnp 470

5. Agm 1470

6. O-chloroacetylcarbamoylfumagillol

7. Drg-0148

8. Nsc642492

9. Nsc-642492

10. Chembl424278

11. (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 (2-chloroacetyl)carbamate

12. Chebi:90748

13. X47gr46481

14. Carbamic Acid, N-(2-chloroacetyl)-, (3r,4s,5s,6r)-5-methoxy-4-[(2r,3r)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl Ester

15. (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

16. Nsc 642492

17. Ccris 8049

18. Unii-x47gr46481

19. Carbamic Acid, N-(2-chloroacetyl)-, (3r,4s,5s,6r)-5-methoxy-4-((2r,3r)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl)-1-oxaspiro(2.5)oct-6-yl Ester

20. Schembl1652694

21. Dtxsid0041141

22. Bdbm17446

23. Tnp-470 [mi]

24. Zinc3914617

25. Ccg-208103

26. Cs-8106

27. Db08633

28. (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

29. [(3r,6r,7s,8s)-7-methoxy-8-[(2r,3r)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-2-oxaspiro[2.5]octan-6-yl] N-(2-chloroacetyl)carbamate

30. Nci60_014346

31. Agm-1470; Nsc 642492

32. Hy-101932

33. Tnp-470, >=98% (hplc)

34. 298t915

35. J-005665

36. Brd-k53597484-001-01-9

37. Q27097825

38. (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 Ester

39. [(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

40. 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

41. Carbamic Acid, (chloroacetyl)-, (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

42. Carbamic Acid, (chloroacetyl)-, 5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl)-1-oxaspiro(2.5)oct-6-yl Ester, (3r-(3alpha,4alpha(2r*,3r*),5beta,6beta))-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₈ClNO₆
Molecular Weight	401.9 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	401.1605153 g/mol
Monoisotopic Mass	401.1605153 g/mol
Topological Polar Surface Area	89.7 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	636
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

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