sulfuric acid (2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-{2-[(6-amino-2-{1-[(2-amino-2-carbamoylethyl)amino]-2-carbamoylethyl}-5-methylpyrimidin-4-yl)formamido]-2-({3-hydroxy-4-[(2-hydroxy-1-{[2-(4-{4-[(3-{[(1R)-1-phenylethyl]amino}propyl)carbamoyl]-1,3-thiazol-2-yl}-1,3-thiazol-2-yl)ethyl]carbamoyl}propyl)carbamoyl]-4-methylbutan-2-yl}carbamoyl)-1-(1H-imidazol-4-yl)ethoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl carbamate

• ChemBase ID: 176358
• Molecular Formular: C61H90N18O25S3
• Molecular Mass: 1571.6679
• Monoisotopic Mass: 1570.54866347
• SMILES: n1c(c(c(nc1C(NCC(C(=O)N)N)CC(=O)N)C(=O)NC(C(=O)NC(C(C(C(=O)NC(C(=O)NCCc1scc(n1)c1scc(n1)C(=O)NCCCN[C@@H](c1ccccc1)C)C(O)C)C)O)C)C(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)c1c[nH]cn1)C)N.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.OC[C@@H]1O[C@@H](OC(C(C(=O)NC(C(C(C(=O)NC(C(=O)NCCc2scc(n2)c2scc(n2)C(=O)NCCCN[C@@H](c2ccccc2)C)C(O)C)C)O)C)NC(=O)c2nc(nc(c2C)N)C(CC(=O)N)NCC(C(=O)N)N)c2nc[nH]c2)[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/C61H88N18O21S2.H2O4S/c1-24-39(76-52(79-50(24)64)31(16-37(63)83)71-17-30(62)51(65)89)56(93)78-41(47(32-18-67-23-72-32)98-60-49(45(87)43(85)35(19-80)97-60)99-59-46(88)48(100-61(66)95)44(86)36(20-81)96-59)57(94)73-27(4)42(84)25(2)53(90)77-40(28(5)82)55(92)70-15-12-38-74-34(22-101-38)58-75-33(21-102-58)54(91)69-14-9-13-68-26(3)29-10-7-6-8-11-29;1-5(2,3)4/h6-8,10-11,18,21-23,25-28,30-31,35-36,40-49,59-60,68,71,80-82,84-88H,9,12-17,19-20,62H2,1-5H3,(H2,63,83)(H2,65,89)(H2,66,95)(H,67,72)(H,69,91)(H,70,92)(H,73,94)(H,77,90)(H,78,93)(H2,64,76,79);(H2,1,2,3,4)/t25?,26-,27?,28?,30?,31?,35+,36-,40?,41?,42?,43-,44-,45+,46+,47?,48+,49+,59-,60+;/m1./s1
• InChIKey: ZHHIHQFAUZZMTG-PZSJMQSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid (2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-{2-[(6-amino-2-{1-[(2-amino-2-carbamoylethyl)amino]-2-carbamoylethyl}-5-methylpyrimidin-4-yl)formamido]-2-({3-hydroxy-4-[(2-hydroxy-1-{[2-(4-{4-[(3-{[(1R)-1-phenylethyl]amino}propyl)carbamoyl]-1,3-thiazol-2-yl}-1,3-thiazol-2-yl)ethyl]carbamoyl}propyl)carbamoyl]-4-methylbutan-2-yl}carbamoyl)-1-(1H-imidazol-4-yl)ethoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl carbamate
• IUPAC Traditional name: sulfuric acid (2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-{2-[(6-amino-2-{1-[(2-amino-2-carbamoylethyl)amino]-2-carbamoylethyl}-5-methylpyrimidin-4-yl)formamido]-2-({3-hydroxy-4-[(2-hydroxy-1-{[2-(4-{4-[(3-{[(1R)-1-phenylethyl]amino}propyl)carbamoyl]-1,3-thiazol-2-yl}-1,3-thiazol-2-yl)ethyl]carbamoyl}propyl)carbamoyl]-4-methylbutan-2-yl}carbamoyl)-1-(1H-imidazol-4-yl)ethoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl carbamate
• Synonyms: N1-[3-[[(1S)-1-phenylethyl]amino]propyl]bleomycinamide Sulfate; NK 631; Pepleo; Pepleomycin Sulfate; Peplomycin Sulfate

Database IDs

• CAS Number: 70384-29-1
• PubChem SID: 164232268
• PubChem CID: 71751515

CALCULATED PROPERTIES

• Acid pKa: 11.409381
• H Acceptors: 29
• H Donor: 21
• LogD (pH = 5.5): -13.115734
• LogD (pH = 7.4): -9.973542
• Log P: -7.37387
• Molar Refractivity: 365.1073 cm^3
• Polarizability: 139.94193 Å^3
• Polar Surface Area: 639.1 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol; Water
• Apperance: Pale Yellow Amorphous Powder
• Melting Point: 196-198°C

DETAILS

Toronto Research Chemicals - P285250

A derivative of Bleomycin with cytostatic activity and less pulmonary toxicity than the natural Bleomycin mixture.

REFERENCES

• Takahashi, K., et al.: J. Antibiot., 32, 36 (1979)
• Sikic, B.I., et al.: Cancer Treat. Rep., 64, 659 (1979)