Molecular Details

DICL_CP_0422226 - (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol

Basic Molecular Information

Basic Information

DICL ID

DICL_CP_0422226

PubChem CID

6032

Molecular Formula

C₁₈H₃₆N₄O₁₁

Molecular Weight

484.503 g/mol

Synonyms/Alias

['kanamycin'; 'KANAMYCIN A'; '59-01-8'; 'Kanamicina'; 'Kanamycine'; 'Kanamycinum'; 'KanamycinA'; 'KM (the Antibiotic)'; ...['kanamycin'; 'KANAMYCIN A'; '59-01-8'; 'Kanamicina'; 'Kanamycine'; 'Kanamycinum'; 'KanamycinA'; 'KM (the Antibiotic)'; 'CHEBI:17630'; 'HSDB 3107'; '8063-07-8'; 'EINECS 200-411-7'; 'UNII-EQK9Q303C5'; 'BRN 0061647'; 'EQK9Q303C5'; 'Kanamycin Base'; "4;6-Diamino-2-hydroxy-1;3-cyclohexane 3;6'diamino-3;6'-dideoxydi-alpha-D-glucoside"; 'Kanamycin A monosulfate'; '(2R;3S;4S;5R;6R)-2-(aminomethyl)-6-[(1R;2R;3S;4R;6S)-4;6-diamino-3-[(2S;3R;4S;5S;6R)-4-amino-3;5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3;4;5-triol'; 'KAN'; 'DTXSID3023184'; "Glucopyranoside; 4;6-diamino-2-hydroxy-1;3-cyclohexylene 3;6'-diamino-3;6'-dideoxydi-; D-"; 'D-Streptamine; O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1;4))-2-deoxy-'; 'D-Streptamine; O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy-'; 'Kanamycin A Deuterated'; "4;6-diamino-2-hydroxy-1;3-cyclohexylene 3;6'-diamino-3;6'-dideoxydi-D-glucopyranoside"; 'Kanamicina [Italian]'; 'Kanamycin [INN:BAN]'; 'Kanamycine [INN-French]'; 'Kanamycinum [INN-Latin]'; '(1S;2R;3R;4S;6R)-4;6-diamino-3-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside'; '(1S;2R;3R;4S;6R)-4;6-diamino-3-[(6-amino-6-deoxy-alpha-D-glucopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside'; '(2R;3S;4S;5R;6R)-2-(aminomethyl)-6-{[(1R;2R;3S;4R;6S)-4;6-diamino-3-{[(2S;3R;4S;5S;6R)-4-amino-3;5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3;4;5-triol'; '2-(aminomethyl)-6-[4;6-diamino-3-[4-amino-3;5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3;4;5-triol'; 'D-Streptamine; O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-'; 'O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-D-streptamine'; 'UNII-RUC37XUP2P'; 'Kanamycins'; 'Kanamycin Complex'; 'Kanamycin;(S)'; 'Liposomal Kanamycin'; '(2R;3S;4S;5R;6R)-2-(aminomethyl)-6-[(1R;2R;3S;4R;6S)-4;6-diamino-3-[(2S;3R;4S;5S;6R)-4-amino-3;5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3;4;5-triol'; '1174286-24-8'; 'Kanamycinum (Latin)'; 'Prestwick3_000394'; 'Kantrex (1:1 sulfate)'; 'Klebcil (1:1 sulfate)'; 'KANAMYCIN A [MI]'; 'RUC37XUP2P'; 'KANAMYCIN A [HSDB]'; 'SCHEMBL2735'; 'CHEMBL1384'; 'BSPBio_000607'; 'DivK1c_000024'; 'KANAMYCIN A [WHO-IP]'; 'BPBio1_000669'; 'CHEBI:6104'; 'DTXCID503184'; 'DTXSID2041171'; 'GTPL12132'; 'KBio1_000024'; 'A07AA08'; 'J01GB04'; 'S01AA24'; 'NINDS_000024'; 'EINECS 232-512-7'; 'BDBM50031282'; 'AKOS025293505'; 'DB01172'; 'IDI1_000024'; 'SMP2_000007'; 'NCGC00179506-01'; 'NCGC00179506-05'; 'AS-14003'; 'D-Streptamine; O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.4)]-2-deoxy-'; 'HY-16566'; 'AB00513827'; 'CS-0006792'; 'NS00098990'; 'C01822'; 'K-0250'; 'EN300-19735925'; 'BRD-K08327065-065-01-9'; 'BRD-K08327065-065-04-3'; 'Q27094615'; 'Kanamycin sulfate; Antibiotic for Culture Media Use Only'; '(2R;3S;4S;5R;6R)-2-(aminomethyl)-6-((1R;2R;3S;4R;6S)-4;6-diamino-3-((2S;3R;4S;5S;6R)-4-amino-3;5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-3;4;5-triol'; 'ANTIBIOTIC COMPLEX FROM STREPTOMYCES KANAMYCETICUS CONTAINING KANAMYCIN A (MAJOR); KANAMYCIN B AND KANAMYCIN C'; 'D-STREPTAMINE; O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXY-'; 'D-Streptamine; O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.4))-2-deoxy-'; 'O-3-Amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-2-deoxy-D-streptamine']

InChI Key

SBUJHOSQTJFQJX-NOAMYHISSA-N

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(2...

IUPAC Name

(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol

CAS Number

59-01-8

Structure Information

Chemical Structure Visualization

SMILES Notation

2D Molecular Drawing

Carbon (C)

Hydrogen (H)

Oxygen (O)

Nitrogen (N)

Sulfur (S)

SDF

69 71 0 0 0 0 0 0 0 0999 V2000
-0.4012 -1.5493 -2.1821 C 0 0 0 0 0 0 0 0 0 0 0 0
0.9180 -0.7524 -2.1579 C 0 0 2 0 0 0 0 0 0 0 0 0
1.2385 -0.205...

Download SDF File (5830 bytes)

Experimental Data

Activity Data

Target Ion Channel

Gap junction beta-2 protein (connexin 26)

Uniprot Accession Number

P29033

Function

Inhibitor

Species

Homo sapiens (Human)

IC₅₀

IC₅₀: 9400 nM

EC₅₀

N/A (Not available)

K_i

N/A (Not available)

K_d

N/A (Not available)

Inhibition

N/A (Not available)

Experimental Conditions

pH 7.0

Holding Potential

Not specified

Temperature

room temperature

Test Method

Fluorometric Imaging Plate Reader (FLIPR) Membrane Potential Assay

Test Species

E. coli

Binding Information

Binding Site

Not specified

Binding Site Residue

Not specified

Disease Information

Related Disease

Not specified

References

DOI

10.1021/acsmedchemlett.8b00158

URL

N/A (Not available)

PMID

30034603

Patent

N/A (Not available)

Computed Properties

Heavy Atom Count

Rotatable Bonds

logP

-7.2914

Complexity

107.7922

TPSA (Å²)

282.61

H-Bond Donors

H-Bond Acceptors

Ring Count

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