Sansanmycin

Class: MraY inhibitor (nucleoside antibiotic)

Spectrum of activity:	Gram-positive
Details of activity:	Interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate. Activity against Mycobacterium tuberculosis
Description:	Natural product produced by Streptomyces; structurally similar to pacidamycin; synthetic dihydrosansanmycin, several synthetic analogues
Year first mentioned:	2007
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	CC(C(C(=O)N/C=C/1\C[C@H]([C@H](N2C=CC(=O)NC2=O)O1)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CNC4=C3C=CC=C4)C(=O)O)N(C)C(=O)C(CC5=CC=CC(=C5)O)N
Isomeric SMILES:	CC(C(C(=O)N/C=C/1\C[C@H]([C@@H](O1)N2C=CC(=O)NC2=O)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O)N(C)C(=O)C(CC5=CC(=CC=C5)O)N
InChI:	InChI=1S/C40H49N9O11S/c1-21(48(2)36(55)27(41)16-22-7-6-8-24(50)15-22)33(35(54)43-20-25-18-31(51)37(60-25)49-13-11-32(52)46-40(49)59)47-34(53)29(12-14-61-3)44-39(58)45-30(38(56)57)17-23-19-42-28-10-5-4-9-26(23)28/h4-11,13,15,19-21,27,29-31,33,37,42,50-51H,12,14,16-18,41H2,1-3H3,(H,43,54)(H,47,53)(H,56,57)(H2,44,45,58)(H,46,52,59)/b25-20+/t21?,27?,29?,30?,31-,33?,37-/m1/s1
InChI Key:	JTNZPPUDLUHMKK-OXOXDDDLSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/57395472

External links:
Guide to Pharmacology:	sansanmycin A
Main Source:	https://www.nature.com/articles/ncomms14414
Citations:	https://pubmed.ncbi.nlm.nih.gov/34845906/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5337940/