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ACTIVE PHARMA INGREDIENTS

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Also known as: Ansamitocin p3, 66584-72-3, Ansamitomicin p-3, Maytansinol isobutyrate, Antibiotic c 15003p3, 2'-de(acetylmethylamino)-2'-methylmaytansine

Molecular Formula

C₃₂H₄₃ClN₂O₉

Molecular Weight

635.1 g/mol

InChI Key

OPQNCARIZFLNLF-JBHFWYGFSA-N

FDA UNII

7SUK7876BG

Ansamitomicin P-3 is an ansamacrolide and maytansine analogue originally isolated from the Ethiopian shrub Maytenus serrata with antineoplastic activity. Ansamitomicin P-3 binds to tubulin at the maytansine-binding site, thereby inhibiting microtubule assembly, inducing microtubule disassembly, and disrupting mitosis.

1 2D Structure

Ansamitocin P3

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-methylpropanoate

2.1.2 InChI

InChI=1S/C32H43ClN2O9/c1-17(2)29(37)43-25-15-26(36)35(6)21-13-20(14-22(40-7)27(21)33)12-18(3)10-9-11-24(41-8)32(39)16-23(42-30(38)34-32)19(4)28-31(25,5)44-28/h9-11,13-14,17,19,23-25,28,39H,12,15-16H2,1-8H3,(H,34,38)/b11-9+,18-10+/t19-,23+,24-,25+,28+,31+,32+/m1/s1

2.1.3 InChI Key

OPQNCARIZFLNLF-JBHFWYGFSA-N

2.1.4 Canonical SMILES

CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)C)C)C)OC)(NC(=O)O2)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)C(C)C)C)\C)OC)(NC(=O)O2)O

2.2 Other Identifiers

2.2.1 UNII

7SUK7876BG

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ansamitocin P 3

2. Ansamitocin P 3'

3. Ansamitocin P 4

4. Ansamitocins

5. Ansamitomicin P-3

2.3.2 Depositor-Supplied Synonyms

1. Ansamitocin P3

2. 66584-72-3

3. Ansamitomicin P-3

4. Maytansinol Isobutyrate

5. Antibiotic C 15003p3

6. 2'-de(acetylmethylamino)-2'-methylmaytansine

7. Antibiotic C15003p3

8. 7suk7876bg

9. Chebi:29515

10. C15003p3

11. [(1s,2r,3s,5s,6s,16e,18e,20r,21s)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-methylpropanoate

12. Ansamitocin P 3

13. Maytansine, 2'-de(acetylmethylamino)-2'-methyl-

14. Ansamitosin P3

15. Ansamitosin P 3

16. Ansamitocin-p-3

17. Ansamitosin P-3

18. Nsc-292222

19. Maytansinol-isobutyrate

20. Nsc 292222

21. C 15003p3

22. Unii-7suk7876bg

23. Chembl507305

24. Schembl15706083

25. Ex-a492

26. Zinc4102313

27. Lmpk04000039

28. S2447

29. Cs-1568

30. Ac-35339

31. Hy-15739

32. Q27110111

33. (1s,2r,3s,5s,6s,16e,18e,20r,21s)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1(10,14).0(3,5)]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2-methylpropanoate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₄₃ClN₂O₉
Molecular Weight	635.1 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	634.2657086 g/mol
Monoisotopic Mass	634.2657086 g/mol
Topological Polar Surface Area	136 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	1150
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1