(3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2R,3S,4S,5S,6S)-3-{[(2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-(1H-imidazol-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium

• ChemBase ID: 126191
• Molecular Formular: C55H84N17O21S3+
• Molecular Mass: 1415.55176
• Monoisotopic Mass: 1414.51898079
• SMILES: Cc1c(nc(nc1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@@H](C(c1cnc[nH]1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCc1nc(cs1)c1nc(cs1)C(=O)NCCC[S+](C)C)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC([C@@H](C(=O)N[C@@H]([C@H]([C@@H](C(=O)N[C@H](C(=O)NCCc2scc(n2)c2scc(n2)C(=O)NCCC[S+](C)C)[C@H](O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)c2[nH]cnc2)[C@H]([C@H]([C@@H]1O)O)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@@H]1O)OC(=O)N)O
• InChI: InChI=1S/C55H83N17O21S3/c1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-65-26)91-54-43(39(80)37(78)29(15-73)90-54)92-53-40(81)42(93-55(60)88)38(79)30(16-74)89-53)51(87)66-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-67-28(18-94-32)52-68-27(17-95-52)48(84)62-9-7-11-96(5)6/h14,17-19,21-25,29-30,34-43,53-54,64,73-75,77-81H,7-13,15-16,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,65,66,69,70,71,72,76,82,83,84,85,86,87,88)/p+1/t21-,22+,23+,24-,25-,29-,30+,34-,35-,36-,37+,38+,39-,40-,41?,42-,43-,53+,54-/m0/s1
• InChIKey: OYVAGSVQBOHSSS-QRQYLRPSSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2R,3S,4S,5S,6S)-3-{[(2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-(1H-imidazol-5-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium
• IUPAC Traditional name: (3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-{[(2R,3S,4S,5S,6S)-3-{[(2R,3S,4S,5R,6R)-4-(carbamoyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-(3H-imidazol-4-yl)propanamido]-3-hydroxy-2-methylpentanamido]-3-hydroxybutanamido]ethyl}-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]formamido}propyl)dimethylsulfanium
• Brand Name: Blenoxane
• Synonyms: Bleomycin

Database IDs

• CAS Number: 11056-06-7
• PubChem SID: 162220532
• PubChem CID: 456190
• ATC CODE: L01DC01
• CHEMBL: 403664
• Chemspider ID: 401687
• DrugBank ID: DB00290
• KEGG ID: D07535
• Unique Ingredient Identifier: 40S1VHN69B
• Wikipedia Title: Bleomycin
• Medline Plus: a682125

CALCULATED PROPERTIES

• Acid pKa: 11.34357
• H Acceptors: 28
• H Donor: 20
• LogD (pH = 5.5): -9.303759
• LogD (pH = 7.4): -8.932185
• Log P: -9.710223
• Molar Refractivity: 344.1594 cm^3
• Polarizability: 132.3702 Å^3
• Polar Surface Area: 627.07 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: intravenous, intramuscular, subcutaneous, intrapleural, intratumoral
• Bioavailability: well absorbed
• Excretion: renal (60-70%)
• Half Life: 2 hours
• Legal Status: Rx-only (US)
• Pregnancy Category: D (US)