Gentamicin

Details

• Internal ID: 17088971-3954-4418-a544-296f7f43f6c3
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides > Aminocyclitol glycosides
• IUPAC Name: 2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• SMILES (Canonical): CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
• SMILES (Isomeric): CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
• InChI: InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3
• InChI Key: CEAZRRDELHUEMR-UHFFFAOYSA-N
• Popularity: 19,674 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₄₃N₅O₇
• Molecular Weight: 477.60 g/mol
• Exact Mass: 477.31624873 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -3.33
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• Garamycin
• Gentacycol
• Gentavet
• Uromycine
• Cidomycin
• Gentamicinum
• Gentamycinum
• Refobacin TM
• Gentamicina
• Gentamicine
• Gentamicins
• Garasol
• Refobacin
• Gentamycin-creme
• GENTAMYCIN
• Gentamycins
• Gentocin
• 1403-66-3
• Oksitselanim
• Centicin
• Lyramycin
• Septigen
• Gentamicin sulphate sterile
• Gentamicine [INN-French]
• Gentamicinum [INN-Latin]
• Gentamycin-creme [German]
• Gentamicina [INN-Spanish]
• Genoptic S.O.P.
• HSDB 3087
• UNII-T6Z9V48IKG
• Gentamicin (TN)
• EINECS 215-765-8
• Gentamicin (BAN)
• Gentamicin [INN]
• Gentamycin C1
• Gentamicin [INN:BAN]
• 2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• T6Z9V48IKG
• C21H43N5O7
• 4,6-diamino-3-{[3-deoxy-4-c-methyl-3-(methylamino)pentopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)heptopyranoside
• G-Myticin
• Gentacidin
• Alcomicin
• Bristagen
• Gentafair
• Gentamar
• Jenamicin
• Apogen
• Gentak
• Spectro-Genta
• Ocu-Mycin
• Gentamcin Sulfate
• U-Gencin
• G-Mycin
• Genoptic Liquifilm
• Garamicin
• C21-H43-N5-O7
• Gentamycin Complex
• Garamycin (TN)
• Gentamicinum (Latin)
• D0L9UU
• SCHEMBL537630
• CHEMBL329592
• GTPL2427
• DTXSID5034642
• SCHEMBL19996168
• CHEBI:17833
• (1R,2S,3S,4R,6S)-4,6-diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl (6x)-2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-alpha-D-erythro-heptopyranoside
• STL454325
• AKOS015961211
• DB00798
• J4.074F
• 2-[4,6-diamino-3-[3-amino-6-(1-methylaminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol
• AC-13386
• LS-71146
• FT-0626646
• FT-0668965
• D08013
• EN300-19875459
• Q422482
• (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• 1294497-75-8
• 2-{[4,6-diamino-3-({3-amino-6-[1-(methylamino)ethyl]oxan-2-yl}oxy)-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• 4,6-diamino-3-(3-deoxy-4-C-methyl-3-(methylamino)pentopyranosyloxy)-2-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)heptopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9658	96.58%
Caco-2	-	0.8366	83.66%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Lysosomes	0.6360	63.60%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.9438	94.38%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.7560	75.60%
P-glycoprotein substrate	-	0.8075	80.75%
CYP3A4 substrate	+	0.6723	67.23%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.6940	69.40%
CYP3A4 inhibition	-	0.9517	95.17%
CYP2C9 inhibition	-	0.8910	89.10%
CYP2C19 inhibition	-	0.9043	90.43%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.9034	90.34%
CYP2C8 inhibition	-	0.6097	60.97%
CYP inhibitory promiscuity	-	0.9294	92.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5967	59.67%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9716	97.16%
Skin irritation	-	0.7653	76.53%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.6665	66.65%
Human Ether-a-go-go-Related Gene inhibition	+	0.6520	65.20%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5270	52.70%
skin sensitisation	-	0.8362	83.62%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7839	78.39%
Acute Oral Toxicity (c)	III	0.5659	56.59%
Estrogen receptor binding	-	0.5635	56.35%
Androgen receptor binding	+	0.5833	58.33%
Thyroid receptor binding	-	0.7153	71.53%
Glucocorticoid receptor binding	+	0.6935	69.35%
Aromatase binding	+	0.6939	69.39%
PPAR gamma	+	0.6129	61.29%
Honey bee toxicity	-	0.8406	84.06%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.8684	86.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.52%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.20%	95.93%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.08%	96.38%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	92.76%	91.03%
CHEMBL284	P27487	Dipeptidyl peptidase IV	92.22%	95.69%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.13%	96.77%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	91.68%	95.58%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.79%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.19%	94.45%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	89.81%	95.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.32%	96.21%
CHEMBL4040	P28482	MAP kinase ERK2	89.29%	83.82%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.35%	97.14%
CHEMBL204	P00734	Thrombin	86.07%	96.01%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.73%	89.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.72%	94.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.46%	96.47%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.95%	85.31%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	84.81%	97.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.07%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.97%	97.25%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.93%	97.47%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.71%	82.69%
CHEMBL237	P41145	Kappa opioid receptor	82.06%	98.10%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.02%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.72%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.26%	98.75%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	80.11%	87.16%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.01%	92.88%

Plants that contains it

• Citrus × aurantium
• Citrus deliciosa

Cross-Links

• PubChem: 3467
• NPASS: NPC56298
• LOTUS: LTS0182202
• wikiData: Q422482