ContaminantDB: Bacitracin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:21:42 UTC

Update Date

2016-11-09 01:17:26 UTC

Accession Number

CHEM022149

Identification

Common Name

Bacitracin

Class

Small Molecule

Description

Bacitracin is a combination of at least 9 bacitracins. 60-80% of commercially prepared bacitracin is bacitracin A. The bacillus that produces bacitracin was first isolated from a knee scrape in 1945 from the knee wound of a child named Margaret Tracy. Bacitracin was granted FDA approval on 29 July 1948.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Bacitracin a2a	ChEBI
A.L. labs brand OF bacitracin zinc salt	HMDB
Ak tracin	HMDB
Akorn brand OF bacitracin	HMDB
Lee brand OF bacitracin	HMDB
Pharmascience brand OF bacitracin	HMDB
Reed and carnrick brand OF bacitracin	HMDB
Topitracin	HMDB
Zinc bacitracin	HMDB
Bacitracin a	HMDB
Baci-RX	HMDB
Bacitracin pharmascience brand	HMDB
Bacitracin zinc complex	HMDB
Bacitracine martinet	HMDB
McNeil brand OF bacitracin	HMDB
OcuTracin	HMDB
Baci RX	HMDB
Bacitracin akorn brand	HMDB
Bacitracin mcneil brand	HMDB
Bacitracin zinc	HMDB
Martinet, bacitracine	HMDB
Ocu tracin	HMDB
Ocu-tracin	HMDB
Ocumed brand OF bacitracin	HMDB
Zeba RX	HMDB
Zeba-RX	HMDB
Zinc, bacitracin	HMDB
Ak-tracin	HMDB
Altracin	HMDB
Baci im	HMDB
Baci-im	HMDB
Bacitin	HMDB
Bacitracin dioptic brand	HMDB
Bacitracin lee brand	HMDB
Bacitracin, zinc	HMDB
Ciba vision brand OF bacitracin	HMDB
Dioptic brand OF bacitracin	HMDB
Pharma tek brand OF bacitracin	HMDB

Chemical Formula

C₆₆H₁₀₃N₁₇O₁₆S

Average Molecular Mass

1422.693 g/mol

Monoisotopic Mass

1421.749 g/mol

CAS Registry Number

1405-87-4

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 Name

baciguent

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 Key

CLKOFPXJLQSYAH-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.

Kingdom

Organic compounds

Super Class

Organic Polymers

Class

Polypeptides

Sub Class

Not Available

Direct Parent

Polypeptides

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

homodetic cyclic peptide (CHEBI:35862 )
polypeptide (CHEBI:35862 )
Non-ribosomal peptides (C15482 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-6.8	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	9.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	530.87 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	363.14 m³·mol⁻¹	ChemAxon
Polarizability	147.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-1228910011-797a0ade3d94224122c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-4944200011-d12f20c9baa9394318f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9632100000-f2bc96584ade64ddae6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0wb9-1228900000-f1be165ec00c831482ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgm-6249600021-e9dab8ea8d4bc2a73519	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05o3-9766400021-36bafa1e5409665b9d8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0003920000-17ed06ed1358f2553f33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0nmi-0109400002-a4e62e7e2b6f20ebb356	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fsl-9743300001-ee63bf15f5f7e08b0d0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0001900000-898dbfd2300b1dfad2bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a7i-1019110000-9b9ef93049647047beb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mn-6966100000-81bb35604ad0986abff2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00626

HMDB ID

HMDB0014764

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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.

Bacitracin (CHEM022149)

Structure for CHEM022149: Bacitracin