Maytansinoid DM4

Synopsis, Chemistry

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Also known as: Dm4, 796073-69-3, Wob38vs2ni, Ravtansine, (14s,16s,32s,33s,2r,4s,10e,12e,14r)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl n-(4-mercapto-4-methylpentanoyl)-n-methyl-l-alaninate, Unii-wob38vs2ni

Molecular Formula

C₃₈H₅₄ClN₃O₁₀S

Molecular Weight

780.4 g/mol

InChI Key

JFCFGYGEYRIEBE-YVLHJLIDSA-N

FDA UNII

WOB38VS2NI

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

1 2D Structure

Maytansinoid DM4

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-(4-methyl-4-sulfanylpentanoyl)amino]propanoate

2.1.2 InChI

InChI=1S/C38H54ClN3O10S/c1-21-12-11-13-28(49-10)38(47)20-27(50-35(46)40-38)22(2)33-37(6,52-33)29(51-34(45)23(3)41(7)30(43)14-15-36(4,5)53)19-31(44)42(8)25-17-24(16-21)18-26(48-9)32(25)39/h11-13,17-18,22-23,27-29,33,47,53H,14-16,19-20H2,1-10H3,(H,40,46)/b13-11+,21-12+/t22-,23+,27+,28-,29+,33+,37+,38+/m1/s1

2.1.3 InChI Key

JFCFGYGEYRIEBE-YVLHJLIDSA-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)CCC(C)(C)S)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)CCC(C)(C)S)C)\C)OC)(NC(=O)O2)O

2.2 Other Identifiers

2.2.1 UNII

WOB38VS2NI

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. Mertansine

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

12. Ravtansine

13. Soravtansine

2.3.2 Depositor-Supplied Synonyms

1. Dm4

2. 796073-69-3

3. Wob38vs2ni

4. Ravtansine

5. (14s,16s,32s,33s,2r,4s,10e,12e,14r)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-(4-mercapto-4-methylpentanoyl)-n-methyl-l-alaninate

6. Unii-wob38vs2ni

7. Maytansinoid Dm 4

8. Dm 4

9. Schembl12719514

10. Ex-a3441

11. Zinc161601616

12. Cs-6866

13. Ac-36376

14. Hy-12454

15. Ds-028663

16. D94659

17. Q27292749

18. Maytansine, N2'-deacetyl-n2'-(4-mercapto-4-methyl-1-oxopentyl)

19. [(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-(4-methyl-4-sulfanylpentanoyl)amino]propanoate

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₃₈H₅₄ClN₃O₁₀S
Molecular Weight	780.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	779.3218438 g/mol
Monoisotopic Mass	779.3218438 g/mol
Topological Polar Surface Area	158 Å²
Heavy Atom Count	53
Formal Charge	0
Complexity	1430
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.)