Compound ID | 2667

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Pholipomycin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Proteus vulgaris, and Klebsiella pneumoniae
Description: Natural product from Streptomyces lividoclavatus; low toxicity observed in mice (LD50 600 mg/kg); shows growth-promoting activity observed in broiler and pigs; protects mice from Staphylococcus infection when administered subcutaneously; contains a phosphoglycolipid scaffold
Institute where first reported: Central Research Laboratories, Sankyo Co., Ltd. 2-58, 1-chome, Hiromachi, Shinagawa-ku, Tokyo 140, Japan
Year first mentioned: 1977
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1436.44
Iso. SMILES: CC(=CCC/C(=C/CC(=C)CCC(C)(C)/C=C/CC/C(=C\CO[C@H](COP(=O)(O)O[C@@H]1[C@H]([C@@H]([C@]([C@H](O1)C(=O)N)(C)O)OC(=O)N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@H]([C@@H](O4)C(=O)NC5=C(CCC5=O)O)O)O)O)O)NC(=O)C)O)NC(=O)C)C(=O)O)/C)/C)C
InChI Key: XYJIXNBDVDMTFA-QGROGYFUSA-N
Can. SMILES: CC(=CCC/C(=C/CC(=C)CCC(C)(C)/C=C/CC/C(=C\CO[C@H](COP(=O)(O)O[C@@H]1[C@H]([C@@H]([C@@](C)([C@@H](C(=O)N)O1)O)OC(=O)N)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O[C@H]4[C@@H]([C@H]([C@H]([C@H](C(=O)NC5=C(CCC5=O)O)O4)O)O)O)O)NC(=O)C)O)NC(=O)C)C(=O)O)/C)/C)C
InChI: InChI=1S/C63H98N5O30P/c1-29(2)14-13-16-30(3)17-18-32(5)21-24-62(8,9)23-12-11-15-31(4)22-25-88-39(56(82)83)28-89-99(86,87)98-60-51(52(97-61(65)84)63(10,85)53(96-60)54(64)80)95-58-42(67-34(7)72)43(75)48(37(26-69)91-58)92-57-41(66-33(6)71)44(76)49(38(27-70)90-57)93-59-47(79)45(77)46(78)50(94-59)55(81)68-40-35(73)19-20-36(40)74/h12,14,17,22-23,37-39,41-53,57-60,69-70,73,75-79,85H,5,11,13,15-16,18-21,24-28H2,1-4,6-10H3,(H2,64,80)(H2,65,84)(H,66,71)(H,67,72)(H,68,81)(H,82,83)(H,86,87)/b23-12+,30-17+,31-22-/t37-,38-,39-,41-,42-,43-,44-,45+,46-,47-,48-,49-,50-,51+,52+,53-,57+,58+,59-,60-,63+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/139589144
Citation: https://www.jstage.jst.go.jp/article/antibiotics1968/30/12/30_12_1060/_pdf/-char/en

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