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1405-89-6 molecular structure
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zinc(2+) ion (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-5-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-(carboxylatomethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoate

ChemBase ID: 130851
Molecular Formular: C66H101N17O16SZn
Molecular Mass: 1486.05744
Monoisotopic Mass: 1483.66243324
SMILES and InChIs

SMILES:
CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)[O-])NC(=O)[C@H](CC(C)C)NC(=O)C1CN=C(S1)C(C(C)CC)N)CC(=O)N)CC(=O)[O-])Cc1cnc[nH]1)Cc1ccccc1.[Zn+2]
Canonical SMILES:
NCCC[C@H]1NC(=O)[C@H](CCCCNC(=O)[C@H](CC(=O)N)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)[C@H](CC)C)Cc1ccccc1)Cc1[nH]cnc1)CC(=O)[O-])NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)C1CN=C(S1)C(C(CC)C)N)CC(C)C)CCC(=O)[O-].[Zn+2]
InChI:
InChI=1S/C66H103N17O16S.Zn/c1-9-35(6)52(69)66-72-32-48(100-66)63(97)80-43(26-34(4)5)59(93)75-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)76-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-73-39)77-60(94)44(27-38-18-13-12-14-19-38)81-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)74-56(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,70,73)(H,71,89)(H,74,90)(H,75,93)(H,76,98)(H,77,94)(H,78,96)(H,79,95)(H,80,97)(H,81,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88);/q;+2/p-2/t35?,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48?,52?,53-,54-;/m0./s1
InChIKey:
NKULICGUDKGGRL-FCHFGNCGSA-L

Cite this record

CBID:130851 http://www.chembase.cn/molecule-130851.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
zinc(2+) ion (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-5-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-(carboxylatomethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}-2-methylbutyl]carbamoyl}butanoate
IUPAC Traditional name
zinc(2+) ion (4R)-4-[(2S)-2-{[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazol-5-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-(carboxylatomethyl)-9-(3H-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}butanoate
Synonyms
Bacitracin zinc salt
Zinc bacitracin
杆菌肽锌
杆菌肽 锌盐
CAS Number
1405-89-6
EC Number
215-787-8
MDL Number
MFCD00130598
PubChem SID
24891810
162225129
24892095
PubChem CID
57402735

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 57402735 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.4586437  H Acceptors 20 
H Donor 15  LogD (pH = 5.5) -7.635476 
LogD (pH = 7.4) -7.1978397  Log P -7.2495475 
Molar Refractivity 385.3236 cm3 Polarizability 142.77258 Å3
Polar Surface Area 536.53 Å2 Rotatable Bonds 31 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble50 mg/mL, clear, yellow expand Show data source
Melting Point
250 °C (dec.)(lit.) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Suitability
meets USP testing specifications expand Show data source
Biological Source
from Bacillus licheniformis expand Show data source
Loss on Drying
≤5% loss on drying expand Show data source
Empirical Formula (Hill Notation)
C66H101N17O16SZn expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B5150 external link
Application
Bacitracin zinc salt is a peptide antibiotic used to study dysruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism. It is used to study the biosynthesis of sterols and squalene.
Biochem/physiol Actions
Bacitracin is a protease inhibitor. Antimicrobial spectrum: Gram-positive bacteria. Mode of Action: Inhibits bacterial cell wall synthesis by inhibiting dephosphorylation of lipid pyrophosphate.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Sigma Aldrich - B8800 external link
Application
Bacitracin is used to study the disruption of bacterial cell wall synthesis at the level of peptidoglycan biosynthesis and isoprenyl metabolism. Used to study the biosynthesis of sterols and squalene.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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