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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:18 UTC
HMDB IDHMDB0014764
Secondary Accession Numbers
  • HMDB14764
Metabolite Identification
Common NameBacitracin
DescriptionBacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. Its unique name derives from the fact that the bacillus producing it was first isolated in 1943 from a knee scrape from a girl named Margaret Tracy. As a toxic and difficult-to-use antibiotic, bacitracin doesn't work well orally. However, it is very effective topically. Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis.
Structure
Data?1582753218
Synonyms
ValueSource
Bacitracin a2aChEBI
A.L. labs brand OF bacitracin zinc saltHMDB
Ak tracinHMDB
Akorn brand OF bacitracinHMDB
Lee brand OF bacitracinHMDB
Pharmascience brand OF bacitracinHMDB
Reed and carnrick brand OF bacitracinHMDB
TopitracinHMDB
Zinc bacitracinHMDB
Bacitracin aHMDB
Baci-RXHMDB
Bacitracin pharmascience brandHMDB
Bacitracin zinc complexHMDB
Bacitracine martinetHMDB
McNeil brand OF bacitracinHMDB
OcuTracinHMDB
Baci RXHMDB
Bacitracin akorn brandHMDB
Bacitracin mcneil brandHMDB
Bacitracin zincHMDB
Martinet, bacitracineHMDB
Ocu tracinHMDB
Ocu-tracinHMDB
Ocumed brand OF bacitracinHMDB
Zeba RXHMDB
Zeba-RXHMDB
Zinc, bacitracinHMDB
Ak-tracinHMDB
AltracinHMDB
Baci imHMDB
Baci-imHMDB
BacitinHMDB
Bacitracin dioptic brandHMDB
Bacitracin lee brandHMDB
Bacitracin, zincHMDB
Ciba vision brand OF bacitracinHMDB
Dioptic brand OF bacitracinHMDB
Pharma tek brand OF bacitracinHMDB
Chemical FormulaC66H103N17O16S
Average Molecular Weight1422.693
Monoisotopic Molecular Weight1421.748941023
IUPAC Name(4R)-4-[(2S)-2-{[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-4-yl]formamido}-4-methylpentanamido]-4-{[(1S,2S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-3-(carbamoylmethyl)-6-(carboxymethyl)-9-(1H-imidazol-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
Traditional Namebaciguent
CAS Registry Number1405-87-4
SMILES
CC[C@H](C)[C@H](N)C1=N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]1CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC1=O)[C@@H](C)CC
InChI Identifier
InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1
InChI KeyCLKOFPXJLQSYAH-ABRJDSQDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Cyclic alpha peptide
  • Glutamic acid or derivatives
  • Leucine or derivatives
  • Isoleucine or derivatives
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Thiazolecarboxamide
  • Fatty amide
  • N-acyl-amine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Fatty acyl
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Thiazole
  • Meta-thiazoline
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Lactam
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point221 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.024 g/LNot Available
LogP-0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP-2.9ALOGPS
logP-6.8ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)9.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area530.87 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity363.14 m³·mol⁻¹ChemAxon
Polarizability147.15 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0f79-1228910011-797a0ade3d94224122c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-4944200011-d12f20c9baa9394318f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9632100000-f2bc96584ade64ddae6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0wb9-1228900000-f1be165ec00c831482aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgm-6249600021-e9dab8ea8d4bc2a73519Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o3-9766400021-36bafa1e5409665b9d8aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00626 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00626 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00626
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9084687
KEGG Compound IDC15482
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBacitracin
METLIN IDNot Available
PubChem Compound10909430
PDB IDNot Available
ChEBI ID35862
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tay WM, Epperson JD, da Silva GF, Ming LJ: 1H NMR, mechanism, and mononuclear oxidative activity of the antibiotic metallopeptide bacitracin: the role of D-Glu-4, interaction with pyrophosphate moiety, DNA binding and cleavage, and bioactivity. J Am Chem Soc. 2010 Apr 28;132(16):5652-61. doi: 10.1021/ja910504t. [PubMed:20359222 ]
  2. Karala AR, Ruddock LW: Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010 Jun;277(11):2454-62. doi: 10.1111/j.1742-4658.2010.07660.x. Epub 2010 Apr 30. [PubMed:20477872 ]

Enzymes

General function:
Involved in protein binding
Specific function:
Is able to inhibit all four classes of proteinases by a unique 'trapping' mechanism. This protein has a peptide stretch, called the 'bait region' which contains specific cleavage sites for different proteinases. When a proteinase cleaves the bait region, a conformational change is induced in the protein which traps the proteinase. The entrapped enzyme remains active against low molecular weight substrates (activity against high molecular weight substrates is greatly reduced). Following cleavage in the bait region a thioester bond is hydrolyzed and mediates the covalent binding of the protein to the proteinase
Gene Name:
A2M
Uniprot ID:
P01023
Molecular weight:
163289.9
References
  1. Maxfield FR, Davies PJ, Klempner L, Willingham MC, Pastan I: Epidermal growth factor stimulation of DNA synthesis is potentiated by compounds that inhibit its clustering in coated pits. Proc Natl Acad Sci U S A. 1979 Nov;76(11):5731-5. [PubMed:42903 ]
  2. Dickson RB, Willingham MC, Pastan I: Binding and internalization of 125I-alpha 2-macroglobulin by cultured fibroblasts. J Biol Chem. 1981 Apr 10;256(7):3454-9. [PubMed:6162847 ]
  3. Dickson RB, Willingham MC, Gallo M, Pastan I: Inhibition by bacitracin of high affinity binding of 125I-alpha 2M to plasma membranes. FEBS Lett. 1981 Apr 20;126(2):265-8. [PubMed:6165617 ]
  4. Hanover JA, Cheng S, Willingham MC, Pastan IH: alpha 2-Macroglobulin binding to cultured fibroblasts. Solubilization and partial purification of binding sites. J Biol Chem. 1983 Jan 10;258(1):370-7. [PubMed:6184373 ]
  5. Gliemann J, Larsen TR, Sottrup-Jensen L: Cell association and degradation of alpha 2-macroglobulin-trypsin complexes in hepatocytes and adipocytes. Biochim Biophys Acta. 1983 Mar 31;756(2):230-7. [PubMed:6187372 ]
General function:
Involved in catalytic activity
Specific function:
Plays a role in the cellular breakdown of insulin, IAPP, glucagon, bradykinin, kallidin and other peptides, and thereby plays a role in intercellular peptide signaling. Degrades amyloid formed by APP and IAPP. May play a role in the degradation and clearance of naturally secreted amyloid beta-protein by neurons and microglia
Gene Name:
IDE
Uniprot ID:
P14735
Molecular weight:
117967.5
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Medina V, Kesner L, Stracher A: Purification of nonantibiotic insulinase inhibitors from bacitracin. Biochem Med Metab Biol. 1993 Apr;49(2):255-64. [PubMed:8484964 ]