MMAE (Monomethyl auristatin E)

Chemical Information
Monomethyl Auristatin E is a dolastatin-10 peptide derivative with potent antimitotic activity and potential antineoplastic activity as part of an antibody-drug conjugate (ADC). Monomethyl auristatin E (MMAE) binds to tubulin, blocks tubulin polymerization, and inhibits microtubule formation, which results in both disruption of mitotic spindle assembly and arrest of tumor cells in the M phase of the cell cycle. To minimize toxicity and maximize efficacy, MMAE is conjugated, via a cleavable peptide linker, to a monoclonal antibody that specifically targets a patient's tumor. The linker is stable in the extracellular milieu but is readily cleaved to release MMAE following binding and internalization of the ADC by the target cells.
| CAS Number | 474645-27-7 |
| PubChem CID | 11542188 |
| IUPAC Name | (2S)-N-[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamide |
| Molecular Formula | C39H67N5O7 |
| Molecular Weight | 718.0 |
| XLogP | 4.1 |
| Topological Polar Surface Area | 150 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 20 |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Complexity | 1100 |
| Property | Value |
|---|---|
| Molecular Weight | 718.0 |
| XLogP3 | 4.1 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 20 |
| Exact Mass | 717.50404949 |
| Monoisotopic Mass | 717.50404949 |
| Topological Polar Surface Area | 150 Ų |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Complexity | 1100 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 10 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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