phleomycin   Click here for help

GtoPdb Ligand ID: 10954

Synonyms: NSC 61586 | NSC-61586
Compound class: Natural product or derivative
Comment: Phleomycins are a group of glycopeptide antibacterials 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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Phleomycin
Other databases
CAS Registry No. 11006-33-0 (source: PubChem)
GtoPdb PubChem SID 405560395
PubChem CID 72511
Search Google for chemical match using the InChIKey QRBLKGHRWFGINE-UGWAGOLRSA-N
Search Google for chemicals with the same backbone QRBLKGHRWFGINE
UniChem Compound Search for chemical match using the InChIKey QRBLKGHRWFGINE-UGWAGOLRSA-N
UniChem Connectivity Search for chemical match using the InChIKey QRBLKGHRWFGINE-UGWAGOLRSA-N