ID: ALA1200558

Max Phase: Approved

First Approval: 1948

Molecular Formula: C66H103N17O16S

Molecular Weight: 1422.72

Molecule Type: Protein

Representations

Synonyms (12): Bacilliquin | Bacitracin | Bacitracin(non-injectable) | Bacitracin, sterile | Bacitracinum | Fortracin | Parentracin | Penitracin | Topitracin | Tropitracin | Zutracin | NSC-755905
Synonyms from Alternative Forms(12):

Trade Names(6): Albac 50 | Baci-rx | Baciferm 50 | Baciguent | Baciim | Bacitracin

Canonical SMILES:  CC[C@H](C)[C@H](N)C1=N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](Cc3cnc[nH]3)NC(=O)[C@@H](Cc3ccccc3)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCCN)NC2=O)[C@@H](C)CC)CS1

Standard InChI:  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

Standard InChI Key:  CLKOFPXJLQSYAH-ABRJDSQDSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Protein

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 1422.72

Molecular Weight (Monoisotopic): 1421.7489

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Wächter GA, Matooq G, Hoffmann JJ, Maiese WM, Singh MP, Montenegro G, Timmermann BN..  (1999)  Antibacterial diterpenoid acids from Azorella compacta.,  62  (9): [PMID:10514324] [10.1021/np990134u]

2. Sieradzki K, Chung M, Tomasz A..  (2008)  Role of a sodium-dependent symporter homologue in the thermosensitivity of beta-lactam antibiotic resistance and cell wall composition in Staphylococcus aureus.,  52  (2): [PMID:18056270] [10.1128/aac.00504-07]

3. Steidl R, Pearson S, Stephenson RE, Ledala N, Sitthisak S, Wilkinson BJ, Jayaswal RK..  (2008)  Staphylococcus aureus cell wall stress stimulon gene-lacZ fusion strains: potential for use in screening for cell wall-active antimicrobials.,  52  (8): [PMID:18541730] [10.1128/aac.00273-08]

4. Cui L, Neoh HM, Shoji M, Hiramatsu K..  (2009)  Contribution of vraSR and graSR point mutations to vancomycin resistance in vancomycin-intermediate Staphylococcus aureus.,  53  (3): [PMID:19124662] [10.1128/aac.01173-08]

5. Ramón-García S, Martín C, Thompson CJ, Aínsa JA..  (2009)  Role of the Mycobacterium tuberculosis P55 efflux pump in intrinsic drug resistance, oxidative stress responses, and growth.,  53  (9): [PMID:19564371] [10.1128/aac.00550-09]

6. Becker P, Hakenbeck R, Henrich B..  (2009)  An ABC transporter of Streptococcus pneumoniae involved in susceptibility to vancoresmycin and bacitracin.,  53  (5): [PMID:19273682] [10.1128/aac.01485-08]

7. Katayama Y, Murakami-Kuroda H, Cui L, Hiramatsu K..  (2009)  Selection of heterogeneous vancomycin-intermediate Staphylococcus aureus by imipenem.,  53  (8): [PMID:19451283] [10.1128/aac.00834-08]

8. Collins B, Curtis N, Cotter PD, Hill C, Ross RP..  (2010)  The ABC transporter AnrAB contributes to the innate resistance of Listeria monocytogenes to nisin, bacitracin, and various beta-lactam antibiotics.,  54  (10): [PMID:20643901] [10.1128/aac.00503-10]

9. Collins B, Joyce S, Hill C, Cotter PD, Ross RP..  (2010)  TelA contributes to the innate resistance of Listeria monocytogenes to nisin and other cell wall-acting antibiotics.,  54  (11): [PMID:20713661] [10.1128/aac.00290-10]

10. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

11. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

12. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

13. Unpublished dataset, 

14. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

15. Chen M, Vijay V, Shi Q, Liu Z, Fang H, Tong W..  (2011)  FDA-approved drug labeling for the study of drug-induced liver injury.,  16  (15-16): [PMID:21624500] [10.1016/j.drudis.2011.05.007]

16. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

17. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

18. Cieslik W, Musiol R, Nycz JE, Jampilek J, Vejsova M, Wolff M, Machura B, Polanski J..  (2012)  Contribution to investigation of antimicrobial activity of styrylquinolines.,  20  (24): [PMID:23159041] [10.1016/j.bmc.2012.10.027]

19. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

20. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

21. Krátký M, Bősze S, Baranyai Z, Szabó I, Stolaříková J, Paraskevopoulos G, Vinšová J..  (2015)  Synthesis and in vitro biological evaluation of 2-(phenylcarbamoyl)phenyl 4-substituted benzoates.,  23  (4): [PMID:25593095] [10.1016/j.bmc.2014.12.019]

22. WHO Anatomical Therapeutic Chemical Classification, 

23. DrugMatrix,  [10.6019/CHEMBL3885881]

24. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

25. Mokhlesi A, Stuhldreier F, Wex KW, Berscheid A, Hartmann R, Rehberg N, Sureechatchaiyan P, Chaidir C, Kassack MU, Kalscheuer R, Brötz-Oesterhelt H, Wesselborg S, Stork B, Daletos G, Proksch P..  (2017)  Cyclic Cystine-Bridged Peptides from the Marine Sponge Clathria basilana Induce Apoptosis in Tumor Cells and Depolarize the Bacterial Cytoplasmic Membrane.,  80  (11): [PMID:29094598] [10.1021/acs.jnatprod.7b00477]

26. Elsebaei MM, Mohammad H, Abouf M, Abutaleb NS, Hegazy YA, Ghiaty A, Chen L, Zhang J, Malwal SR, Oldfield E, Seleem MN, Mayhoub AS..  (2018)  Alkynyl-containing phenylthiazoles: Systemically active antibacterial agents effective against methicillin-resistant Staphylococcus aureus (MRSA).,  148  [PMID:29459278] [10.1016/j.ejmech.2018.02.031]

27. Yang D, Qin W, Shi X, Zhu B, Xie M, Zhao H, Teng B, Wu Y, Zhao R, Yin F, Ren P, Liu L, Li Z..  (2018)  Stabilized β-Hairpin Peptide Inhibits Insulin Degrading Enzyme.,  61  (18): [PMID:30148634] [10.1021/acs.jmedchem.8b00418]

28. Unpublished dataset, 

29. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

30. Gou S, Li B, Ouyang X, Ba Z, Zhong C, Zhang T, Chang L, Zhu Y, Zhang J, Zhu N, Zhang Y, Liu H, Ni J..  (2021)  Novel Broad-Spectrum Antimicrobial Peptide Derived from Anoplin and Its Activity on Bacterial Pneumonia in Mice.,  64  (15.0): [PMID:34180670] [10.1021/acs.jmedchem.1c00614]

Source

Source(8):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• AstraZeneca Deposited Data
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data