Kanamycin A

ID: ALA223520

Chembl Id: CHEMBL223520

PubChem CID: 11274101

Max Phase: Phase

Molecular Formula: C18H36N4O11

Molecular Weight: 484.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Kanamycin a | CHEMBL223520|SBUJHOSQTJFQJX-KSACQAOKSA-N

Canonical SMILES:  NC[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)C[C@@H]2N)[C@@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6+,7-,8+,9-,10+,11-,12-,13+,14-,15+,16-,17-,18+/m1/s1

Standard InChI Key:  SBUJHOSQTJFQJX-KSACQAOKSA-N

Alternative Forms

1. Parent:

   

   ALA223520

   KANAMYCIN A

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 484.50

Molecular Weight (Monoisotopic): 484.2381

AlogP: -7.29

#Rotatable Bonds: 6

Polar Surface Area: 282.61

Molecular Species: BASE

HBA: 15

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 15

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.05

CX Basic pKa: 9.34

CX LogP: -7.06

CX LogD: -12.20

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.17

Np Likeness Score: 1.56

References

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2. Cashman DJ, Rife JP, Kellogg GE..  (2001)  Which aminoglycoside ring is most important for binding? A hydropathic analysis of gentamicin, paromomycin, and analogues.,  11  (2): [PMID:11206440] [10.1016/s0960-894x(00)00615-6]

3. Leclerc F, Cedergren R..  (1998)  Modeling RNA-ligand interactions: the Rev-binding element RNA-aminoglycoside complex.,  41  (2): [PMID:9457241] [10.1021/jm970372r]

4. Wang H, Tor Y.  (1997)  Dimeric aminoglycosides: Design, synthesis and RNA binding,  7  (14): [10.1016/S0960-894X(97)00339-9]

5. Allen NE, Alborn WE, Kirst HA, Toth JE..  (1987)  Comparison of aminoglycoside antibiotics with respect to uptake and lethal activity in Escherichia coli.,  30  (2): [PMID:3543366] [10.1021/jm00385a015]

6. Evans JM, Turner BA, Bowen S, Ho AM, Sarver RW, Benson E, Parker CN..  (2003)  Inhibition of bacterial IF2 binding to fMet-tRNA((fMet)) by aminoglycosides.,  13  (6): [PMID:12643896] [10.1016/s0960-894x(03)00085-4]

7. Means JA, Hines JV..  (2005)  Fluorescence resonance energy transfer studies of aminoglycoside binding to a T box antiterminator RNA.,  15  (8): [PMID:15808490] [10.1016/j.bmcl.2005.02.007]

8. Hainrichson M, Yaniv O, Cherniavsky M, Nudelman I, Shallom-Shezifi D, Yaron S, Baasov T..  (2007)  Overexpression and initial characterization of the chromosomal aminoglycoside 3'-O-phosphotransferase APH(3')-IIb from Pseudomonas aeruginosa.,  51  (2): [PMID:17088479] [10.1128/aac.01034-06]

9. Bodoor K, Boyapati V, Gopu V, Boisdore M, Allam K, Miller J, Treleaven WD, Weldeghiorghis T, Aboul-ela F..  (2009)  Design and implementation of an ribonucleic acid (RNA) directed fragment library.,  52  (12): [PMID:19445516] [10.1021/jm9000659]

10. Zhang J, Chiang FI, Wu L, Czyryca PG, Li D, Chang CW..  (2008)  Surprising alteration of antibacterial activity of 5"-modified neomycin against resistant bacteria.,  51  (23): [PMID:19012394] [10.1021/jm800997s]

11. Bera S, Zhanel GG, Schweizer F..  (2010)  Antibacterial activities of aminoglycoside antibiotics-derived cationic amphiphiles. Polyol-modified neomycin B-, kanamycin A-, amikacin-, and neamine-based amphiphiles with potent broad spectrum antibacterial activity.,  53  (9): [PMID:20373816] [10.1021/jm1000437]

12. Feldman MB, Terry DS, Altman RB, Blanchard SC..  (2010)  Aminoglycoside activity observed on single pre-translocation ribosome complexes.,  6  (1): [PMID:19946275] [10.1038/nchembio.274]

13. Toth M, Frase H, Chow JW, Smith C, Vakulenko SB..  (2010)  Mutant APH(2'')-IIa enzymes with increased activity against amikacin and isepamicin.,  54  (4): [PMID:20145089] [10.1128/aac.01444-09]

14. Khalil H, Chen T, Riffon R, Wang R, Wang Z..  (2008)  Synergy between polyethylenimine and different families of antibiotics against a resistant clinical isolate of Pseudomonas aeruginosa.,  52  (5): [PMID:18285485] [10.1128/aac.01071-07]

15. Yan RB, Yuan M, Wu Y, You X, Ye XS..  (2011)  Rational design and synthesis of potent aminoglycoside antibiotics against resistant bacterial strains.,  19  (1): [PMID:21177112] [10.1016/j.bmc.2010.11.065]

16. Kruhlak NL, Choi SS, Contrera JF, Weaver JL, Willard JM, Hastings KL, Sancilio LF..  (2008)  Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.,  18  (2): [PMID:20020916] [10.1080/15376510701857262]

17. Maiti M, Nauwelaerts K, Herdewijn P..  (2012)  Pre-microRNA binding aminoglycosides and antitumor drugs as inhibitors of Dicer catalyzed microRNA processing.,  22  (4): [PMID:22257890] [10.1016/j.bmcl.2011.12.103]

18. Vong K, Auclair K..  (2012)  Understanding and overcoming aminoglycoside resistance caused by N-6'-acetyltransferase.,  3  (4): [PMID:28018574] [10.1039/c2md00253a]

19. Kumar V, Remers WA..  (1979)  Aminoglycoside antibiotics. 2. N,N-Dialkylkanamycins.,  22  (4): [PMID:107311] [10.1021/jm00190a015]

20. Goodreid JD, Wong K, Leung E, McCaw SE, Gray-Owen SD, Lough A, Houry WA, Batey RA..  (2014)  Total synthesis and antibacterial testing of the A54556 cyclic acyldepsipeptides isolated from Streptomyces hawaiiensis.,  77  (10): [PMID:25255326] [10.1021/np500158q]

21. Chang CW, Takemoto JY..  (2014)  Antifungal Amphiphilic Aminoglycosides.,  5  (8): [PMID:25110571] [10.1039/c4md00078a]

22. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates