phleomycin   Click here for help

GtoPdb Ligand ID: 10954

Synonyms: NSC 61586 | NSC-61586
Comment: Phleomycins are a group of glycopeptide antibiotics found in Streptomyces species. They also possess anti-cancer activity through intercalation into DNA and disruption of the double helix.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 37
Hydrogen bond donors 20
Rotatable bonds 35
Topological polar surface area 701.91
Molecular weight 1325.48
XLogP -10
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@@H]1O[C@@H](OC(C(C(=O)NC(C(C(C(=O)NC(C(=O)NCCC2=NC(CS2)c2scc(n2)C(=O)N)C(=O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)C(CC(=O)N)NCC(C(=O)N)N)c2[nH]cnc2)[C@@]([C@H]([C@@H]1O)O)(C)O[C@@H]1OC(CO)[C@@H]([C@]([C@H]1O)(O)C(=O)N)O
Isomeric SMILES OC[C@@H]1O[C@@H](OC(C(C(=O)NC(C(C(C(=O)NC(C(=O)NCCC2=NC(CS2)c2scc(n2)C(=O)N)C(=O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)C(CC(=O)N)NCC(C(=O)N)N)c2[nH]cnc2)[C@@]([C@H]([C@@H]1O)O)(C)O[C@@H]1OC(CO)[C@@H]([C@]([C@H]1O)(O)C(=O)N)O
InChI InChI=1S/C51H75N17O21S2/c1-16-29(65-41(68-38(16)54)21(8-27(53)72)60-9-20(52)39(55)78)44(82)67-31(34(22-10-58-15-61-22)88-49-50(5,36(76)33(74)25(11-69)87-49)89-47-37(77)51(85,48(57)84)35(75)26(12-70)86-47)45(83)62-18(3)32(73)17(2)42(80)66-30(19(4)71)43(81)59-7-6-28-63-24(14-90-28)46-64-23(13-91-46)40(56)79/h10,13,15,17-18,20-21,24-26,30-37,47,49,60,69-70,73-77,85H,6-9,11-12,14,52H2,1-5H3,(H2,53,72)(H2,55,78)(H2,56,79)(H2,57,84)(H,58,61)(H,59,81)(H,62,83)(H,66,80)(H,67,82)(H2,54,65,68)/t17?,18?,20?,21?,24?,25-,26?,30?,31?,32?,33+,34?,35-,36-,37-,47-,49-,50-,51+/m0/s1
InChI Key QRBLKGHRWFGINE-UGWAGOLRSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2R,3S,4S,5S,6S)-3-[(2S,3R,4R,5S)-4-carbamoyl-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxy-2-methylpentanoyl]amino]-3-oxobutanoyl]amino]ethyl]-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxamide
Synonyms Click here for help
NSC 61586 | NSC-61586
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 988
Other databases
CAS Registry No. 11006-33-0 (source: PubChem)
GtoPdb PubChem SID 405560395
PubChem CID 72511
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