myriocin   Click here for help

GtoPdb Ligand ID: 6664

Synonyms: ISP-1 | thermozymocidin
Compound class: Synthetic organic
Comment: Myriocin is a sphingosine-like potent immunosuppressant acting primarily via inhibition of serine palmitoyltransferase which catalyses the first step of sphingolipid biosynthesis [1]. The compound was originally isolated from the fungus Isaria sinclarii.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 5
Rotatable bonds 18
Topological polar surface area 141.08
Molecular weight 401.28
XLogP 0.12
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCC(=O)CCCCCCC=CCC(C(C(C(=O)O)(CO)N)O)O
Isomeric SMILES CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H]([C@](C(=O)O)(CO)N)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
InChI Key ZZIKIHCNFWXKDY-GNTQXERDSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Synonyms Click here for help
ISP-1 | thermozymocidin
Database Links Click here for help
CAS Registry No. 35891-70-4 (source: Scifinder)
ChEMBL Ligand CHEMBL55076
GtoPdb PubChem SID 178103276
PubChem CID 6438394
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Wikipedia Myriocin