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Chemistry

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Also known as: Maytansinoid dm 1, Maytansinoid dm1, 139504-50-0, Mertansine (dm1), N2'-deacetyl-n2'-(3-mercapto-1-oxopropyl)-maytansine, Ddz29hgh0e

Molecular Formula

C₃₅H₄₈ClN₃O₁₀S

Molecular Weight

738.3 g/mol

InChI Key

ANZJBCHSOXCCRQ-FKUXLPTCSA-N

FDA UNII

DDZ29HGH0E

An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.

1 2D Structure

Maytansinoid DM1

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] (2S)-2-[methyl(3-sulfanylpropanoyl)amino]propanoate

2.1.2 InChI

InChI=1S/C35H48ClN3O10S/c1-19-10-9-11-26(46-8)35(44)18-25(47-33(43)37-35)20(2)31-34(4,49-31)27(48-32(42)21(3)38(5)28(40)12-13-50)17-29(41)39(6)23-15-22(14-19)16-24(45-7)30(23)36/h9-11,15-16,20-21,25-27,31,44,50H,12-14,17-18H2,1-8H3,(H,37,43)/b11-9+,19-10+/t20-,21+,25+,26-,27+,31+,34+,35+/m1/s1

2.1.3 InChI Key

ANZJBCHSOXCCRQ-FKUXLPTCSA-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)N(C)C(=O)CCS)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@H](C)N(C)C(=O)CCS)C)\C)OC)(NC(=O)O2)O

2.2 Other Identifiers

2.2.1 UNII

DDZ29HGH0E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dm1, Maytansinoid

2. Dm4, Maytansinoid

3. Dmmo Maytansine

4. Dmmo-maytansine

5. Emtansine

6. Maitansine

7. Maytansine

8. Maytansinoid Dm1

9. Maytansinoid Dm4

10. N2'-deacetyl-n2'-(4-mercapto-4-methyl-1-oxopentyl)maytansine

11. Ravtansine

12. Soravtansine

2.3.2 Depositor-Supplied Synonyms

1. Maytansinoid Dm 1

2. Maytansinoid Dm1

3. 139504-50-0

4. Mertansine (dm1)

5. N2'-deacetyl-n2'-(3-mercapto-1-oxopropyl)-maytansine

6. Ddz29hgh0e

7. Dm1

8. Dm 1

9. [(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] (2s)-2-[methyl(3-sulfanylpropanoyl)amino]propanoate

10. Maytansine, N2'-deacetyl-n2'-(3-mercapto-1-oxopropyl)-

11. N2'-deacetyl-n2'-(3-mercapto-1-oxopropyl)-maytansine, L-

12. Dm1 [maytansinoid]

13. Dm 1 [maytansinoid]

14. Unii-ddz29hgh0e

15. Mertasine

16. Dm1;maytansinoid

17. Maytansinoid Dm1

18. Maytansinoid Dm1 [mi]

19. Chembl4802230

20. Schembl13558634

21. Chebi:82755

22. Mfcd28398157

23. S6773

24. Zinc95627837

25. Cs-5804

26. Da-48536

27. Hy-19792

28. J3.653.420f

29. Q4515649

30. (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 (2s)-2-[methyl(3-sulfanylpropanoyl)amino]propanoate

31. (3s)-3-o-de[2-(acetylmethylamino)-1-oxopropyl]-3-o-[(2s)-2-(methyl 3-mercaptopropanoylamino)propanoyl]maytansine

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₄₈ClN₃O₁₀S
Molecular Weight	738.3 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	8
Exact Mass	737.2748936 g/mol
Monoisotopic Mass	737.2748936 g/mol
Topological Polar Surface Area	158 Å²
Heavy Atom Count	50
Formal Charge	0
Complexity	1340
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Tubulin Modulators

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)

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