Molecule ID: 90659901

IUPAC Name: (2S)-2-[[(2S)-3-amino-2-[[(2R,3R)-3-carbamoyloxirane-2-carbonyl]amino]propanoyl]amino]-3-methylbutanoic acid

Description: The molecule is a member of the family of dapdiamides consisting of 3-aminoalanylvaline, in which the N-terminus is acylated by a 3-carbamoyloxirane-2-carbonyl group. NB Although the relative configuration of the epoxide moiety has been assigned as trans, it has not yet been established whether the absolute configuration is R,R (as drawn) or S,S. It is a dapdiamide and an epoxide. It is a tautomer of a dapdiamide E zwitterion.

SMILES: CC(C)[C@H](N=C(O)[C@H](CN)N=C(O)[C@@H]1O[C@H]1C(=N)O)C(=O)O

SELFIES: [C][C][Branch1][C][C][C@H1][Branch2][Ring1][#Branch2][N][=C][Branch1][C][O][C@H1][Branch1][Ring1][C][N][N][=C][Branch1][C][O][C@@H1][O][C@H1][Ring1][Ring1][C][=Branch1][C][=N][O][C][=Branch1][C][=O][O]

InChI: InChI=1S/C12H20N4O6/c1-4(2)6(12(20)21)16-10(18)5(3-13)15-11(19)8-7(22-8)9(14)17/h4-8H,3,13H2,1-2H3,(H2,14,17)(H,15,19)(H,16,18)(H,20,21)/t5-,6-,7+,8+/m0/s1

Molecular Properties:
- Polar Surface Area: 177.0 Ų
- LogP: -4.7