Molecule ID: 16109784

IUPAC Name: (1R,4R,5R,6R,8S,19R)-4-ethenyl-5-isocyano-4,9,9,20,20-pentamethyl-7-oxa-11-azahexacyclo[14.3.1.05,19.06,8.010,18.012,17]icosa-10(18),12,14,16-tetraen-19-ol

Description: The molecule is an ambiguine that consists of a 5,5,7,10,10-pentamethyl-4,5,5a,6a,6b,7,8,9,9a,10-decahydro-10dH-6-oxa-4-azacyclopropa[6,7]cyclohepta[1,2,3,4-mno]aceanthrylen-10d-ol skeleton with an ethenyl substituent at position 7 and an isocyano group at position 6b (the 5aS,6aR,6bR,7R,9aR,10dR stereoisomer). An antimicrobial agent isolated from the cyanobacterium strain Fischerella. It has a role as an antibacterial agent, an antifungal agent and a bacterial metabolite. It is an isocyanide, an epoxide, an organic heterohexacyclic compound, a tertiary alcohol and an ambiguine.

SMILES: [C-]#[N+][C@]12[C@H]3O[C@H]3C(C)(C)c3[nH]c4cccc5c4c3[C@]1(O)[C@H](CC[C@]2(C)C=C)C5(C)C

SELFIES: [C-1][#N+1][C@][C@H1][O][C@H1][Ring1][Ring1][C][Branch1][C][C][Branch1][C][C][C][NH1][C][=C][C][=C][C][=C][Ring1][=Branch1][C][=Ring1][=Branch2][C@][Ring1][P][Branch1][C][O][C@H1][Branch1][N][C][C][C@][Ring2][Ring1][=Branch1][Branch1][C][C][C][=C][C][Ring1][=N][Branch1][C][C][C]

InChI: InChI=1S/C26H30N2O2/c1-8-24(6)13-12-16-22(2,3)14-10-9-11-15-17(14)18-19(28-15)23(4,5)20-21(30-20)26(24,27-7)25(16,18)29/h8-11,16,20-21,28-29H,1,12-13H2,2-6H3/t16-,20-,21+,24+,25-,26+/m1/s1

Molecular Properties:
- Polar Surface Area: 52.9 Ų
- LogP: 4.4