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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:39 UTC
HMDB IDHMDB0014435
Secondary Accession Numbers
  • HMDB14435
Metabolite Identification
Common NameBleomycin
DescriptionBleomycin, also known as bleomycin sulfate or BLM, belongs to the class of organic compounds known as hybrid glycopeptides. Hybrid glycopeptides are compounds containing a carbohydrate component linked to a hybrid peptide component. Thus, bleomycin is considered to be a non-ribosomal peptide/polyketide hybrid lipid molecule. Bleomycin is a drug which is used for palliative treatment in the management malignant neoplasm (trachea, bronchus, lung), squamous cell carcinoma, and lymphomas. 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. Bleomycin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Bleomycin is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Bleomycin A2 is used as the representative structure for Bleomycin. Bleomycin may cause irritation to eyes, skin and respiratory tract.
Structure
Data?1582753179
Synonyms
ValueSource
BleocinHMDB
BleomicinHMDB
Bleomycin a2HMDB
Bleomycin sulfateHMDB
Bleomycin sulphateHMDB
BLMHMDB
Almirall brand OF bleomycin sulfateHMDB
Bleo cellHMDB
Bleo-cellHMDB
BLEOcellHMDB
Bellon brand OF bleomycin sulfateHMDB
Bellon, bléomycineHMDB
BlanoxanHMDB
BlenoxaneHMDB
BleolemHMDB
BleomicinaHMDB
Bleomycin a(2)HMDB
Bleomycin b(2)HMDB
Bleomycin b2HMDB
BleomycinsHMDB
Bleomycinum mackHMDB
Bléomycine bellonHMDB
Bristol myers squibb brand OF bleomycin sulfateHMDB
Bristol-myers squibb brand OF bleomycin sulfateHMDB
Bull brand OF bleomycin sulfateHMDB
Lemery brand OF bleomycin sulfateHMDB
Lundbeck brand OF bleomycin sulfateHMDB
Mack brand OF bleomycin sulfateHMDB
Mack, bleomycinumHMDB
Sulfate, bleomycinHMDB
Cell pharm brand OF bleomycin sulfateHMDB
BleomycinMeSH
Chemical FormulaC55H84N17O21S3
Average Molecular Weight1415.552
Monoisotopic Molecular Weight1414.518979905
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
Traditional Namebleomycin
CAS Registry Number11056-06-7
SMILES
C[C@@H](O)[C@H](NC(=O)[C@@H](C)[C@H](O)[C@@H](C)NC(=O)[C@@H](NC(=O)C1=C(C)C(N)=NC(=N1)[C@H](CC(N)=O)NC[C@H](N)C(N)=O)[C@@H](OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(OC(N)=O)C1O)C1=CN=CN1)C(=O)NCCC1=NC(=CS1)C1=NC(=CS1)C(=O)NCCC[S+](C)C
InChI Identifier
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
InChI KeyOYVAGSVQBOHSSS-WXFSZRTFSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid glycopeptides. Hybrid glycopeptides are compounds containing a carbohydrate component linked to a hybrid peptide component.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid glycopeptides
Alternative Parents
Substituents
  • Hybrid glycopeptide
  • Histidine or derivatives
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • N-acyl-alpha amino acid or derivatives
  • Gamma amino acid or derivatives
  • Alpha-amino acid amide
  • Beta amino acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyrimidine-6-carboxylic acid or derivatives
  • 2-heteroaryl carboxamide
  • Thiazolecarboxamide
  • Thiazolecarboxylic acid or derivatives
  • Aralkylamine
  • 2,4-disubstituted 1,3-thiazole
  • Aminopyrimidine
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Imidolactam
  • Oxane
  • Pyrimidine
  • Azole
  • Carbamic acid ester
  • Heteroaromatic compound
  • Thiazole
  • Imidazole
  • Secondary alcohol
  • Carboxamide group
  • Carbonic acid derivative
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Organoheterocyclic compound
  • Secondary aliphatic amine
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Primary alcohol
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Biological role:

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point71 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.028 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP-0.52ALOGPS
logP-9.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.34ChemAxon
pKa (Strongest Basic)7.67ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count28ChemAxon
Hydrogen Donor Count20ChemAxon
Polar Surface Area627.07 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity344.16 m³·mol⁻¹ChemAxon
Polarizability142.03 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-5519000000-a9e7e590fae8c464ce36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-5918000000-5ca154887c83cf983142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-5925010000-dfb06a8f5285854a7878Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00290 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00290 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00290
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4514492
KEGG Compound IDC06854
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBleomycin
METLIN IDNot Available
PubChem Compound5360373
PDB IDNot Available
ChEBI ID22907
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Claussen CA, Long EC: Nucleic Acid recognition by metal complexes of bleomycin. Chem Rev. 1999 Sep 8;99(9):2797-816. [PubMed:11749501 ]

Enzymes

General function:
Involved in DNA ligase (ATP) activity
Specific function:
Interacts with DNA-repair protein XRCC1 and can correct defective DNA strand-break repair and sister chromatid exchange following treatment with ionizing radiation and alkylating agents.
Gene Name:
LIG3
Uniprot ID:
P49916
Molecular weight:
106017.03
References
  1. Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [PubMed:17202402 ]
General function:
Involved in DNA ligase (ATP) activity
Specific function:
DNA ligase that seals nicks in double-stranded DNA during DNA replication, DNA recombination and DNA repair.
Gene Name:
LIG1
Uniprot ID:
P18858
Molecular weight:
101735.11
References
  1. Rose JL, Reeves KC, Likhotvorik RI, Hoyt DG: Base excision repair proteins are required for integrin-mediated suppression of bleomycin-induced DNA breakage in murine lung endothelial cells. J Pharmacol Exp Ther. 2007 Apr;321(1):318-26. Epub 2007 Jan 3. [PubMed:17202402 ]