Home > Compound List > Compound details
11056-06-7 molecular structure
click picture or here to close

(3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-[(3-{[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: 175
Molecular Formular: C55H84N17O21S3+
Molecular Mass: 1415.55176
Monoisotopic Mass: 1414.51898079
SMILES and InChIs

SMILES:
s1c(nc(c1)c1scc(n1)C(=O)NCCC[S+](C)C)CCNC(=O)[C@@H](NC(=O)[C@H]([C@H](O)[C@H](NC(=O)[C@@H](NC(=O)c1nc(nc(N)c1C)[C@@H](NC[C@H](N)C(=O)N)CC(=O)N)[C@@H](OC1OC(C(O)C(O)C1OC1OC(C(O)C(OC(=O)N)C1O)CO)CO)c1[nH]cnc1)C)C)[C@H](O)C
Canonical SMILES:
OCC1OC(O[C@H]([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(C(C1O)O)OC1OC(CO)C(C(C1O)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-WXFSZRTFSA-O

Cite this record

CBID:175 http://www.chembase.cn/molecule-175.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3-{[2-(2-{2-[(2S,3R)-2-[(2S,3S,4R)-4-[(2S,3R)-2-({6-amino-2-[(1S)-1-{[(2S)-2-amino-2-carbamoylethyl]amino}-2-carbamoylethyl]-5-methylpyrimidin-4-yl}formamido)-3-[(3-{[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
bleomycin
Brand Name
Blenoxane
Bleo
Synonyms
BLM
Bleomycin sulfate
Bleomicin
Bleomicina [INN-Spanish]
Bleomycine [INN-French]
Bleomycinum [INN-Latin]
Bleocin
Bleomycin A2
Bleomycin B2
Bleomycin
CAS Number
11056-06-7
PubChem SID
160963638
46509116
PubChem CID
5360373

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 132.3702 Å3
Polar Surface Area 627.07 Å2 Rotatable Bonds 36 
Lipinski's Rule of Five false 
Log P -0.52  LOG S -4.71 
Solubility (Water) 2.82e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Soluble expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00290 external link
Item Information
Drug Groups approved
Description A complex of related glycopeptide antibiotics from Streptomyces verticillus consisting of bleomycin A2 and B2 (B2 CAS # 9060-10-0). It inhibits DNA metabolism and is used as an antineoplastic, especially for solid tumors. Bleomycin A2 is used as the representative structure for Bleomycin.
Indication For palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas.
Pharmacology Bleomycin is an antibiotic which has been shown to have antitumor activity. Bleomycin selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of mitomycin-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. Bleomycin has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2. The antibiotic antitumor drugs are cell cycle-nonspecific except for Bleomycin (which has major effects in G2 and M phases).
Toxicity Excessive exposure may cause fever, chills, nausea, vomiting, mental, confusion, and wheezing. Bleomycin may cause irritation to eyes, skin and respiratory tract. It may also cause a darkening or thickening of the skin. It may cause an allergic reaction.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Systemic absorption is approximately 45%.
Half Life 115 minutes
Protein Binding 1%
Elimination It was reported that patients with moderately severe renal failure excreted less than 20% of the dose in the urine.
References
Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle