Compound: Monomethyl auristatin E
SMILES: O=C(N([C@H]([C@H](OC)CC(=O)N1[C@H]([C@H](OC)[C@H](C(=O)N[C@@H]([C@@H](O)c2ccccc2)C)C)CCC1)[C@H](CC)C)C)[C@@H](NC(=O)[C@@H](NC)C(C)C)C(C)C
InChIKey: DASWEROEPLKSEI-UIJRFTGLSA-N
Synonyms: Monomethyl auristatin E, 474645-27-7, MMAE, Monomethylauristatin E, MMAE peptide, V7I58RC5EJ, SGD-1010, DTXSID101028844, (S)-N-((3R,4S,5S)-1-((S)-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)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamide, N-Methyl-L-valyl-N-((1S,2R)-4-((2S)-2-((1R,2R)-3-(((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-2-methoxy-1-((1S)-1-methylpropyl)-4-oxobutyl)-N-methyl-L-valinamide, RefChem:159590, DTXCID801514480, L-Valinamide, N-methyl-L-valyl-N-((1S,2R)-4-((2S)-2-((1R,2R)-3-(((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)amino)-1-methoxy-2-methyl-3-oxopropyl)-1-pyrrolidinyl)-2-methoxy-1-((1S)-1-methylpropyl)-4-oxobutyl)-N-methyl-, N(sup 2)-(N-methyl-L-valyl)-N(sup 1)-((1S,2R)-4-((2S)-2-((1R,2R)-3-(((1R,2S)-2-hydroxy-1-methyl-2-phenylethyl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-2-methoxy-1-((1S)-1-methylpropyl)-4-oxobutyl)-N(sup 1)-methyl-L-valinamide, MFCD22124498, MMAE (Monomethyl auristatin E), Monomethyl auristatin E (GMP), [3H]-Vedotin, (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, N-methyl-L-valyl-N-[(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]-N-methyl-L-valinamide, UNII-V7I58RC5EJ, Monomethyl auristatin E (MMAE), 4Q5, N-Methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide; MMAE; Monomethylauristatin E; Monomethylauristatin Norephedrine;, MMAE, monomethyl auristatin E, SCHEMBL5402144, CHEMBL2103835, GLXC-06285, Monomethyl auristatin E (Standard), MONOMETHYLAURISTATIN E [MI], (S)-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1R,2R)-1-Hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxohe, Monomethyl auristatin E (vedotin)?, FD9056, HY-15162G, HY-15162R, MSK169050, NSC791792, NSC832263, s7721, AKOS025312191, CCG-270400, CS-0837, FM63498, NSC-791792, NSC-832263, MonoMethyl auristatin E(MMAE, vedotin), (2S)-N-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-2-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]carbamoyl}-1-methoxy-2-methylethyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N,3-dimethyl-2-[(2S)-3-methyl-2-(methylamino)butanamido]butanamide, BP-22278, HY-15162, SY034481, CS-0899132, Q6901739, (2S)-N-[(1S)-1-[[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl]amino]-1-methoxy-2-methyl-3-oxo-propyl]pyrrolidin-1-yl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxo-butyl]-methyl-carbamoyl]-2-methyl-propyl]-3-methyl-2-(methylamino)butanamide, (S)-2-(((3R,4S,5S)-1-((S)-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)(methyl)amino)-3-methyl-N-(methyl-L-valyl)butanamide, L-Valinamide, N-methyl-L-valyl-N-((1S,2R)-4-((2S)-2-((1R,2R)-3-(((1R,2S)-2-hydroxy-1- methyl-2-phenylethyl)amino)-1-methoxy-2-methyl-3-oxopropyl)-1-pyrrolidinyl)-2- methoxy-1-((1S)-1-methylpropyl)-4-oxobutyl)-N-methyl-, N(sup 2)-(N-Methyl-L-valyl)-N(sup 1)-((1S,2R)-4-((2S)-2-((1R,2R)-3-(((1R,2S)-2-hydroxy-1-methyl-2- phenylethyl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-2-methoxy-1-((1S)- 1-methylpropyl)-4-oxobutyl)-N(sup 1)-methyl-L-valinamide
Theoretical properties:
molecular_formula: C39H67N5O7
molecular_weight: 718.0 g/mol
exact_mass: 717.50404949 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 20
heavy_atom_count: 51
topological_polar_surface_area: 150 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chebi: A synthetic antineoplastic agent; vedotin refers to MMAE plus its linking structure to the antibody and as an antibody–drug conjugate, it targets various proteins or glycoproteins involved in tumors.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Monomethyl auristatin E (MMAE) is a synthetic antineoplastic agent. Because of its toxicity, it cannot be used as a drug itself; instead, it is linked to a monoclonal antibody (MAB) which directs it to the cancer cells. In International Nonproprietary Names for MMAE-MAB-conjugates, the name vedotin refers to MMAE plus its linking structure to the antibody. It is a potent antimitotic drug derived from peptides occurring in marine shell-less mollusc Dolabella auricularia called dolastatins which show potent activity in preclinical studies, both in vitro and in vivo, against a range of lymphomas, leukemia and solid tumors. These drugs show potency of up to 200 times that of vinblastine, another antimitotic drug used for Hodgkin lymphoma as well as other types of cancer.
MMAE is actually desmethyl-auristatin E; that is, the N-terminal amino group has only one methyl substituent instead of two as in auristatin E itself.