4-[(2S,3S,4R,5S)-4-[(2R,3R,4R,5R)-4-[(2S,3R,4R,5R,6S)-5-[(2R,3R,4S,5R,6R)-5-amino-3-[[(2R)-2-aminopropanoyl]amino]-4-hydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-methylideneoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-N-[3-(4-aminobutylamino)propyl]benzamide

Details

• Internal ID: d54bf598-cc1e-4cc5-887b-9524b9469c8b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• IUPAC Name: 4-[(2S,3S,4R,5S)-4-[(2R,3R,4R,5R)-4-[(2S,3R,4R,5R,6S)-5-[(2R,3R,4S,5R,6R)-5-amino-3-[[(2R)-2-aminopropanoyl]amino]-4-hydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-methylideneoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-N-[3-(4-aminobutylamino)propyl]benzamide
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(C(OC(=C)C3O)OC4C(OC(C4O)OC5=CC=C(C=C5)C(=O)NCCCNCCCCN)CO)O)CO)NC(=O)C(C)N)O)N
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H](O[C@H]([C@@H]([C@H]2O)O)O[C@H]3[C@H]([C@@H](OC(=C)[C@@H]3O)O[C@H]4[C@@H](O[C@H]([C@H]4O)OC5=CC=C(C=C5)C(=O)NCCCNCCCCN)CO)O)CO)NC(=O)[C@@H](C)N)O)N
• InChI: InChI=1S/C40H66N6O18/c1-17(42)35(55)46-25-27(50)24(43)18(2)57-37(25)62-32-22(15-47)60-38(29(52)28(32)51)64-34-26(49)19(3)58-39(31(34)54)63-33-23(16-48)61-40(30(33)53)59-21-9-7-20(8-10-21)36(56)45-14-6-13-44-12-5-4-11-41/h7-10,17-18,22-34,37-40,44,47-54H,3-6,11-16,41-43H2,1-2H3,(H,45,56)(H,46,55)/t17-,18-,22+,23+,24+,25-,26+,27+,28-,29-,30+,31-,32+,33+,34-,37-,38+,39+,40-/m1/s1
• InChI Key: PGEKDAOSVRPCSY-AMGOUKICSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₆N₆O₁₈
• Molecular Weight: 919.00 g/mol
• Exact Mass: 918.44335928 g/mol
• Topological Polar Surface Area (TPSA): 384.00 Ų
• XlogP: -6.20
• Atomic LogP (AlogP): -5.96
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 21

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6399	63.99%
Caco-2	-	0.8672	86.72%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.4588	45.88%
OATP2B1 inhibitior	-	0.8655	86.55%
OATP1B1 inhibitior	+	0.8576	85.76%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9015	90.15%
P-glycoprotein inhibitior	+	0.7263	72.63%
P-glycoprotein substrate	+	0.8074	80.74%
CYP3A4 substrate	+	0.7021	70.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8162	81.62%
CYP3A4 inhibition	-	0.8070	80.70%
CYP2C9 inhibition	-	0.8895	88.95%
CYP2C19 inhibition	-	0.8444	84.44%
CYP2D6 inhibition	-	0.8568	85.68%
CYP1A2 inhibition	-	0.8939	89.39%
CYP2C8 inhibition	+	0.7225	72.25%
CYP inhibitory promiscuity	-	0.8998	89.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6184	61.84%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.7606	76.06%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7839	78.39%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.8554	85.54%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7662	76.62%
Acute Oral Toxicity (c)	III	0.6349	63.49%
Estrogen receptor binding	+	0.8146	81.46%
Androgen receptor binding	+	0.6769	67.69%
Thyroid receptor binding	+	0.5316	53.16%
Glucocorticoid receptor binding	+	0.6800	68.00%
Aromatase binding	+	0.6188	61.88%
PPAR gamma	+	0.7876	78.76%
Honey bee toxicity	-	0.7074	70.74%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7935	79.35%

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	98.39%	91.11%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	97.81%	87.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.74%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.95%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.79%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	95.64%	81.11%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	94.08%	97.29%
CHEMBL3401	O75469	Pregnane X receptor	92.46%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	92.36%	90.24%
CHEMBL4208	P20618	Proteasome component C5	91.80%	90.00%
CHEMBL4581	P52732	Kinesin-like protein 1	91.27%	93.18%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.88%	95.58%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.33%	90.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.32%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.00%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	87.84%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.11%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.35%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.33%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.06%	93.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.80%	92.86%
CHEMBL2514	O95665	Neurotensin receptor 2	84.09%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.84%	95.83%
CHEMBL3891	P07384	Calpain 1	83.13%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.06%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.79%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.76%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.52%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.00%	94.80%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139589104
• LOTUS: LTS0101432
• wikiData: Q105208350