Gentamicin C1a

Details

• Internal ID: 2dc28ba1-f4c0-46b7-bf12-3e80ccebf2d8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides > Aminocyclitol glycosides
• IUPAC Name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• SMILES (Canonical): CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CN)N)N)N)O
• SMILES (Isomeric): C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC[C@H](O3)CN)N)N)N)O
• InChI: InChI=1S/C19H39N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1
• InChI Key: VEGXETMJINRLTH-BOZYPMBZSA-N
• Popularity: 171 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₉N₅O₇
• Molecular Weight: 449.50 g/mol
• Exact Mass: 449.28494860 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -5.00
• Atomic LogP (AlogP): -3.98
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 26098-04-4
• Gentamycin C1A
• Gentamycin C12
• AV4A72IATD
• (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• DTXSID4023092
• CHEBI:27784
• (1R,2S,3S,4R,6S)-4,6-diamino-3-[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyloxy]-2-hydroxycyclohexyl 2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranoside
• (1R,2S,3S,4R,6S)-4,6-diamino-3-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyloxy)-2-hydroxycyclohexyl 2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranoside
• (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-4,6-diamino-3-((2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl)oxy-2-hydroxycyclohexyl)oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• RefChem:142890
• DTXCID803092
• Gentamicin Cla
• Gentamicin C1A Deuterated Pentaacetate Salt
• (1R,2S,3S,4R,6S)-4,6-diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranoside
• (2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-4,6-Diamino-3-(((2R,3R,6S)-3-Amino-6-(Aminomethyl)Tetrahydro-2H-Pyran-2-Yl)Oxy)-2-Hydroxycyclohexyl)Oxy)-5-Methyl-4-(Methylamino)Tetrahydro-2H-Pyran-3,5-Diol
• (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]-5-methyl-4-(methylamino)tetrahydropyran-3,5-diol
• O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-2-deoxy-D-streptamine
• C19H39N5O7
• UNII-AV4A72IATD
• BRN 1356351
• Septocin
• (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-4,6-DIAMINO-3-((2R,3R,6S)-3-AMINO-6-(AMINOMETHYL)-TETRAHYDRO-2H-PYRAN-2-YLOXY)-2-HYDR OXYCYCLOHEXYLOXY)-5-METHYL-4-(METHYLAMINO)-TETRAHYDRO-2H-PYRAN-3,5-DIOL
• O-3-Deoxy-4-C-methyl-3-(methylamino)-?-L-arabinopyranosyl-(1-6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-?-D-erythro-hexopyranosyl-(1-4)]-2-deoxy-D-streptamine Pentaacetate Salt Deuterated; Gentamicin D Acetate Deuterated ; Gentamycin C1a Acetate Deuterated; Gentamicin C3 Acetate Deuterated
• Liposomal Gentamicin
• Gentocin (*sulfate*)
• Garamycin (*sulfate*)
• Gentamicin C1a pentaacetate
• SCHEMBL66939
• GENTAMICIN C1A [MI]
• CHEMBL194126
• orb1982733
• TLC G-65
• D-STREPTAMINE, O-3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-ERYTHRO-HEXOPYRANOSYL-(1->4))-2-DEOXY-
• MSK160235
• MSK160235-100MW
• AG16458
• DB04729
• MSK160235-1000MW
• AG170748
• D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl-(1-4))-2-deoxy-
• DA-63737
• HY-148286
• CS-0618278
• NS00011538
• C00908
• G78435
• Gentamicin C1a Deuterated Pentaacetate (>90%)
• Gentamicin C1a Solution in Methanol/Water, 100ug/mL
• Q27095468
• Gentamicin C1a Solution in Methanol/Water, 1000ug/mL
• OXYCYCLOHEXYLOXY)-5-METHYL-4-(METHYLAMINO)-TETRAHYDRO-2H-PYRAN-3,5-DIOL
• (2R,3R,4R,5R)-2-((1S,2S,3R,4S,6R)-4,6-DIAMINO-3-((2R,3R,6S)-3-AMINO-6-(AMINOMETHYL)-TETRAHYDRO-2H-PYRAN-2-YLOXY)-2-HYDR

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9893	98.93%
Caco-2	-	0.8327	83.27%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Lysosomes	0.6214	62.14%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9141	91.41%
P-glycoprotein inhibitior	-	0.8517	85.17%
P-glycoprotein substrate	-	0.9363	93.63%
CYP3A4 substrate	+	0.6548	65.48%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.6940	69.40%
CYP3A4 inhibition	-	0.9756	97.56%
CYP2C9 inhibition	-	0.9187	91.87%
CYP2C19 inhibition	-	0.8876	88.76%
CYP2D6 inhibition	-	0.9049	90.49%
CYP1A2 inhibition	-	0.9169	91.69%
CYP2C8 inhibition	+	0.5306	53.06%
CYP inhibitory promiscuity	-	0.9421	94.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6056	60.56%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9676	96.76%
Skin irritation	-	0.7608	76.08%
Skin corrosion	-	0.9175	91.75%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4520	45.20%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6102	61.02%
skin sensitisation	-	0.8463	84.63%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.7388	73.88%
Acute Oral Toxicity (c)	III	0.4984	49.84%
Estrogen receptor binding	-	0.6838	68.38%
Androgen receptor binding	+	0.5483	54.83%
Thyroid receptor binding	-	0.7375	73.75%
Glucocorticoid receptor binding	+	0.7037	70.37%
Aromatase binding	+	0.6900	69.00%
PPAR gamma	+	0.6148	61.48%
Honey bee toxicity	-	0.9636	96.36%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.9336	93.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.58%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.27%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.96%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.84%	95.93%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	91.48%	95.58%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	91.28%	97.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.75%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	86.95%	93.18%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	86.74%	82.86%
CHEMBL204	P00734	Thrombin	86.46%	96.01%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.17%	91.03%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.17%	96.77%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.58%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.13%	94.33%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	83.32%	87.16%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.84%	97.14%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.43%	97.53%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.38%	95.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.67%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.53%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.25%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.21%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.97%	96.21%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.36%	82.69%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 72396
• LOTUS: LTS0189712
• wikiData: Q27095468