Bacitracin (CED0002340)

Record Information
Version1.0
Creation Date2016-05-25 18:21:42 UTC
Update Date2026-09-01 08:36:29 UTC
Accession NumberCHEM022149
Identification
Common NameBacitracin
ClassSmall Molecule
Description
Bacitracin is a compound with the chemical formula C66H103N17O16S. Bacitracin belongs to the polypeptides, a class of organic polymers within the organic compounds. With an average molecular weight of 1,423 g/mol, Bacitracin is a heavy molecule. This compound is found in or released from five recorded sources, including antennas in electrical and electronic equipment, as well as healthcare, pharmaceuticals and veterinary products such as antibacterials, antibiotics, antiinfectives, and throat preparations. Recorded exposure routes for the substance include oral, respiratory, topical, cutaneous, intramuscular, irrigation, and ophthalmic, as well as electro-osmosis. In terms of biological activity, Bacitracin has two recorded protein targets, acting as an inhibitor of the insulin-degrading enzyme (IDE) and Alpha-2-macroglobulin ().
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass1422.693 g/mol
Monoisotopic Mass1421.749 g/mol
CAS Registry Number1405-87-4
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
SMILESCC[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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-1228910011-797a0ade3d94224122c6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dr-4944200011-d12f20c9baa9394318f5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9632100000-f2bc96584ade64ddae6fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0wb9-1228900000-f1be165ec00c831482aeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zgm-6249600021-e9dab8ea8d4bc2a73519Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05o3-9766400021-36bafa1e5409665b9d8aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-0003920000-17ed06ed1358f2553f33Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0nmi-0109400002-a4e62e7e2b6f20ebb356Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fsl-9743300001-ee63bf15f5f7e08b0d0dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0001900000-898dbfd2300b1dfad2bcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a7i-1019110000-9b9ef93049647047beb0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mn-6966100000-81bb35604ad0986abff2Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
347AntibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
390Throat preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Bacitracin Drug Metabolism Action Pathway
Bacitracin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureUndecaprenyl-diphosphataseP60932Escherichia coli (strain K12)Predicted (SEA)0.155698
Click to view 3D structureEndothelin receptor type BQ9N0W7Oryctolagus cuniculusPredicted (SEA)7.31783
Beclin-1 structureClick to view 3D structureBeclin-1Q14457HumansPredicted (SEA)21.3307
Click to view 3D structureCalcitonin receptorP32214Rattus norvegicusPredicted (SEA)39.5474
Click to view 3D structureVoltage-dependent calcium channel alpha-1 subunitO18323Blattella germanicaPredicted (SEA)35.4214
Click to view 3D structureEndothelin receptor type BP28088Bos taurusPredicted (SEA)16.3483
Sodium channel protein type 9 subunit alpha structureClick to view 3D structureSodium channel protein type 9 subunit alphaQ15858HumansPredicted (SEA)92.7963
Sodium channel protein type 4 subunit alpha structureClick to view 3D structureSodium channel protein type 4 subunit alphaP35499HumansPredicted (SEA)46.8652
Tumor necrosis factor receptor superfamily member 10B structureClick to view 3D structureTumor necrosis factor receptor superfamily member 10BO14763HumansPredicted (SEA)33.6309
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)67.2617
Melanocortin receptor 4 structureClick to view 3D structureMelanocortin receptor 4P32245HumansPredicted (SEA)130.865
Melanocyte-stimulating hormone receptor structureClick to view 3D structureMelanocyte-stimulating hormone receptorQ01726HumansPredicted (SEA)118.097
Click to view 3D structureOxytocin-like receptorQ5D7U5Gallus gallusPredicted (SEA)7.78492
Vasopressin V1a receptor structureClick to view 3D structureVasopressin V1a receptorP37288HumansPredicted (SEA)28.2593
Oxytocin receptor structureClick to view 3D structureOxytocin receptorP30559HumansPredicted (SEA)25.6124
Click to view 3D structureMelanocyte-stimulating hormone receptorQ01727Mus musculusPredicted (SEA)120.666
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)126.038
Click to view 3D structureGlucagon-1O42143Xenopus laevisPredicted (SEA)78.1606
Sodium channel protein type 8 subunit alpha structureClick to view 3D structureSodium channel protein type 8 subunit alphaQ9UQD0HumansPredicted (SEA)73.8011
Click to view 3D structureMelanocortin receptor 5P41149Mus musculusPredicted (SEA)126.116
Click to view 3D structureEndothelin receptor type BP21451Rattus norvegicusPredicted (SEA)44.919
Plasminogen structureClick to view 3D structurePlasminogenP00747HumansPredicted (SEA)111.247
Click to view 3D structureVasopressin V1b receptorP47901HumansPredicted (SEA)27.0137
Melanocortin receptor 3 structureClick to view 3D structureMelanocortin receptor 3P41968HumansPredicted (SEA)121.211
Plasma kallikrein structureClick to view 3D structurePlasma kallikreinP03952HumansPredicted (SEA)83.3765
Concentrations
Not Available
External Links
DrugBank IDDB00626
HMDB IDHMDB0014764
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBacitracin
Chemspider ID9084687
ChEBI ID35862
PubChem Compound ID10909430
Kegg Compound IDC15482
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
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.
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.