Molecule ID: 6438394

IUPAC Name: (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid

Description: The molecule is an amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity. It has a role as an antimicrobial agent, an antifungal agent, an immunosuppressive agent, an EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor, an apoptosis inducer, an antineoplastic agent and a fungal metabolite. It is a sphingoid, an alpha-amino fatty acid and a non-proteinogenic alpha-amino acid.

SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@@H](O)[C@H](O)[C@@](N)(CO)C(=O)O

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

InChI: InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1

Molecular Properties:
- Polar Surface Area: 141.0 Ų
- LogP: -0.1