Maytansine, N2a(2)-deacetyl-N2a(2)-[4-[[1-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-4-methyl-1-oxopentyl]-
Basic information
- CAS
1228105-52-9- Standard SMILES
COc1cc2cc(c1Cl)N(C)C(=O)CC(OC(=O)[C@H](C)N(C)C(=O)CCC(C)(C)SC1CC(=O)N(CC3CCC(C(=O)ON4C(=O)CCC4=O)CC3)C1=O)[C@]1(C)O[C@H]1[C@H](C)[C@@H]1C[C@@](O)(NC(=O)O1)[C@H](OC)C=CC=C(C)C2- InChIKey
VYNFFBGYRBMGDS-DWVTWXSNSA-N- Molecular formula
- C54H72ClN5O16S
- Average molar mass
- 1,114.7 g/mol
- Monoisotopic mass
- 1,113.4383301
Names & identifiers
- Preferred name
- Maytansine, N2a(2)-deacetyl-N2a(2)-[4-[[1-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-4-methyl-1-oxopentyl]-
- IUPAC
- (2,5-dioxopyrrolidin-1-yl) 4-[[3-[5-[[(2S)-1-[[(1S,2R,3S,5S,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]oxy]-1-oxopropan-2-yl]-methylamino]-2-methyl-5-oxopentan-2-yl]sulfanyl-2,5-dioxopyrrolidin-1-yl]methyl]cyclohexane-1-carboxylate
- English name
- DM4-SMCC
- Molecular formula
- C54H72ClN5O16S
- Molecular weight
- 1114.7
Names & synonyms
DTXSID6011000731228105-52-9Maytansine, N2a(2)-deacetyl-N2a(2)-[4-[[1-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-4-methyl-1-oxopentyl]-DM4-SMCCSMCC-DM4Maytansine, N2'-deacetyl-N2'-[4-[[1-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-4-methyl-1-oxopentyl]-
Database identifiers
- CAS
1228105-52-9- PubChem CID
- 165366359
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 283 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 17
- Rotatable bonds
- 16
- Heavy atoms
- 77
- Formal charge
- 0
- Complexity
- 2,350
Physicochemical properties
- Density
- 1.38 · 1.38±0.1 g/cm3(Predicted)
- pka
- 9.82 · 9.82±0.70(Predicted)
- form
- Solid
- color
- White to off-white
Chemistry & industry
Applications
UsesSMCC-DM4 is a mertansine drug with a reactive linker SMCC to make antibody drug conjugate. DM1 (mertansine), a thiol-containing maytansinoid, is a potent microtubule-disrupting agent.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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