Colistin

ID: ALA1255711

Chembl Id: CHEMBL1255711

PubChem CID: 71457946

Max Phase: Preclinical

Molecular Formula: C53H102N16O12

Molecular Weight: 1155.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H](CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O)[C@@H](C)O

Standard InChI:  InChI=1S/C53H102N16O12/c1-9-31(6)12-10-11-13-43(72)61-35(15-21-55)46(74)68-42(32(7)70)28-60-34(14-20-54)45(73)65-39-19-25-59-53(81)44(33(8)71)69-50(78)38(18-24-58)63-47(75)36(16-22-56)64-51(79)40(26-29(2)3)67-52(80)41(27-30(4)5)66-48(76)37(17-23-57)62-49(39)77/h29-42,44,60,70-71H,9-28,54-58H2,1-8H3,(H,59,81)(H,61,72)(H,62,77)(H,63,75)(H,64,79)(H,65,73)(H,66,76)(H,67,80)(H,68,74)(H,69,78)/t31?,32-,33-,34+,35+,36+,37+,38+,39+,40+,41-,42+,44+/m1/s1

Standard InChI Key:  ZAVVEJFNDKHVPT-JPOBDFTKSA-N

Alternative Forms

1. Parent:

   

   ALA1255711

   N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1155.50

Molecular Weight (Monoisotopic): 1154.7863

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. Bai PY,Qin SS,Chu WC,Yang Y,Cui DY,Hua YG,Yang QQ,Zhang E.  (2018)  Synthesis and antibacterial bioactivities of cationic deacetyl linezolid amphiphiles.,  155  [PMID:29966917] [10.1016/j.ejmech.2018.06.054]

2. Idowu T,Arthur G,Zhanel GG,Schweizer F.  (2019)  Heterodimeric Rifampicin-Tobramycin conjugates break intrinsic resistance of Pseudomonas aeruginosa to doxycycline and chloramphenicol in vitro and in a Galleria mellonella in vivo model.,  174  [PMID:31022550] [10.1016/j.ejmech.2019.04.034]

3. Mazzotta S,Cebrero-Cangueiro T,Frattaruolo L,Vega-Holm M,Carretero-Ledesma M,Sánchez-Céspedes J,Cappello AR,Aiello F,Pachón J,Vega-Pérez JM,Iglesias-Guerra F,Pachón-Ibáñez ME.  (2020)  Exploration of piperazine-derived thioureas as antibacterial and anti-inflammatory agents. In vitro evaluation against clinical isolates of colistin-resistant Acinetobacter baumannii.,  30  (18): [PMID:32717617] [10.1016/j.bmcl.2020.127411]

4. Demchenko S,Lesyk R,Zuegg J,Elliott AG,Fedchenkova Y,Suvorova Z,Demchenko A.  (2020)  Synthesis, antibacterial and antifungal activity of new 3-biphenyl-3H-Imidazo[1,2-a]azepin-1-ium bromides.,  201  [PMID:32619924] [10.1016/j.ejmech.2020.112477]

5. Pearce AN, Chen D, Edmeades LR, Cadelis MM, Troudi A, Brunel JM, Bourguet-Kondracki ML, Copp BR..  (2021)  Repurposing primaquine as a polyamine conjugate to become an antibiotic adjuvant.,  38  [PMID:33831695] [10.1016/j.bmc.2021.116110]

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8. Lopes AP, de Oliveira Castelo Branco RR, de Alcântara Oliveira FA, Campos MAS, de Carvalho Sousa B, Agostinho ÍRC, Gonzalez AGM, Rocha JA, Pinheiro REE, Araújo AR, Dos Santos Soares MJ..  (2021)  Antimicrobial, modulatory, and antibiofilm activity of tt-farnesol on bacterial and fungal strains of importance to human health.,  47  [PMID:34118413] [10.1016/j.bmcl.2021.128192]

9. Wang Z, Li Q, Li J, Shang L, Li J, Chou S, Lyu Y, Shan A..  (2022)  pH-Responsive Antimicrobial Peptide with Selective Killing Activity for Bacterial Abscess Therapy.,  65  (7.0): [PMID:35294199] [10.1021/acs.jmedchem.1c01485]

10. Li SA, Cadelis MM, Deed RC, Douafer H, Bourguet-Kondracki ML, Michel Brunel J, Copp BR..  (2022)  Valorisation of the diterpene podocarpic acid - Antibiotic and antibiotic enhancing activities of polyamine conjugates.,  64  [PMID:35477062] [10.1016/j.bmc.2022.116762]

11. D'Agostino I, Ardino C, Poli G, Sannio F, Lucidi M, Poggialini F, Visaggio D, Rango E, Filippi S, Petricci E, Visca P, Botta L, Docquier JD, Dreassi E..  (2022)  Antibacterial alkylguanidino ureas: Molecular simplification approach, searching for membrane-based MoA.,  231  [PMID:35168113] [10.1016/j.ejmech.2022.114158]

12. Dai XJ, Liu Y, Xue LP, Xiong XP, Zhou Y, Zheng YC, Liu HM..  (2021)  Reversible Lysine Specific Demethylase 1 (LSD1) Inhibitors: A Promising Wrench to Impair LSD1.,  64  (5.0): [PMID:33619958] [10.1021/acs.jmedchem.0c02176]

13. Li H, Mattingly AE, Smith RD, Melander RJ, Ernst RK, Melander C..  (2023)  6-Bromoindirubin-3'-oxime derivatives are highly active colistin adjuvants against Klebsiella pneumoniae.,  14  (2.0): [PMID:36846374] [10.1039/d2md00370h]

14. Durcik M, Cotman AE, Toplak Ž, Možina Š, Skok Ž, Szili PE, Czikkely M, Maharramov E, Vu TH, Piras MV, Zidar N, Ilaš J, Zega A, Trontelj J, Pardo LA, Hughes D, Huseby D, Berruga-Fernández T, Cao S, Simoff I, Svensson R, Korol SV, Jin Z, Vicente F, Ramos MC, Mundy JEA, Maxwell A, Stevenson CEM, Lawson DM, Glinghammar B, Sjöström E, Bohlin M, Oreskär J, Alvér S, Janssen GV, Sterk GJ, Kikelj D, Pal C, Tomašič T, Peterlin Mašič L..  (2023)  New Dual Inhibitors of Bacterial Topoisomerases with Broad-Spectrum Antibacterial Activity and In Vivo Efficacy against Vancomycin-Intermediate Staphylococcus aureus.,  66  (6): [PMID:36877255] [10.1021/acs.jmedchem.2c01905]

Source

Source(1):

• Scientific Literature