gamma-L-Glutamyl-butirosin B

Details

• Internal ID: 0524fbb4-8449-4f78-acb0-e3e35fca3138
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > 2-deoxystreptamine aminoglycosides > 4,5-disubstituted 2-deoxystreptamines
• IUPAC Name: (2S)-2-amino-5-[[(3S)-4-[[(1R,2S,3R,4R,5S)-5-amino-4-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-hydroxycyclohexyl]amino]-3-hydroxy-4-oxobutyl]amino]-5-oxopentanoic acid
• SMILES (Canonical): C1C(C(C(C(C1NC(=O)C(CCNC(=O)CCC(C(=O)O)N)O)O)OC2C(C(C(O2)CO)O)O)OC3C(C(C(C(O3)CN)O)O)N)N
• SMILES (Isomeric): C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1NC(=O)[C@H](CCNC(=O)CC[C@@H](C(=O)O)N)O)O)O[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
• InChI: InChI=1S/C26H48N6O15/c27-6-12-17(37)19(39)15(30)25(44-12)46-21-9(29)5-10(16(36)22(21)47-26-20(40)18(38)13(7-33)45-26)32-23(41)11(34)3-4-31-14(35)2-1-8(28)24(42)43/h8-13,15-22,25-26,33-34,36-40H,1-7,27-30H2,(H,31,35)(H,32,41)(H,42,43)/t8-,9-,10+,11-,12+,13+,15+,16-,17+,18+,19+,20+,21+,22+,25+,26-/m0/s1
• InChI Key: YGLNWHGPOZHVMV-BHZFYAMWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₈N₆O₁₅
• Molecular Weight: 684.70 g/mol
• Exact Mass: 684.31776485 g/mol
• Topological Polar Surface Area (TPSA): 378.00 Ų
• XlogP: -10.30
• Atomic LogP (AlogP): -8.44
• H-Bond Acceptor: 18
• H-Bond Donor: 14
• Rotatable Bonds: 15

Synonyms

• gamma-L-Glutamyl-butirosin B
• CHEBI:65108
• (1R,2R,3S,4R,6S)-6-amino-4-{[(2S)-4-(L-gamma-glutamylamino)-2-hydroxybutanoyl]amino}-3-hydroxy-2-(beta-D-ribofuranosyloxy)cyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside
• (1R,2R,3S,4R,6S)-6-amino-4-(((2S)-4-(L-gamma-glutamylamino)-2-hydroxybutanoyl)amino)-3-hydroxy-2-(beta-D-ribofuranosyloxy)cyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside
• (2S)-2-amino-5-(((3S)-4-(((1R,2S,3R,4R,5S)-5-amino-4-((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl)oxy-3-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)oxy-2-hydroxycyclohexyl)amino)-3-hydroxy-4-oxobutyl)amino)-5-oxopentanoic acid
• (2S)-2-amino-5-[[(3S)-4-[[(1R,2S,3R,4R,5S)-5-amino-4-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-2-hydroxycyclohexyl]amino]-3-hydroxy-4-oxobutyl]amino]-5-oxopentanoic acid
• RefChem:142345
• 4-glutamyl-(S)-2-hydroxy-4-aminobutanoyl-ribostamycin
• C18005
• Q27133657

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9550	95.50%
Caco-2	-	0.8790	87.90%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.4584	45.84%
OATP2B1 inhibitior	-	0.5810	58.10%
OATP1B1 inhibitior	+	0.8944	89.44%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7925	79.25%
P-glycoprotein inhibitior	+	0.5937	59.37%
P-glycoprotein substrate	-	0.5406	54.06%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.9391	93.91%
CYP2C9 inhibition	-	0.9493	94.93%
CYP2C19 inhibition	-	0.9247	92.47%
CYP2D6 inhibition	-	0.9311	93.11%
CYP1A2 inhibition	-	0.9412	94.12%
CYP2C8 inhibition	+	0.5297	52.97%
CYP inhibitory promiscuity	-	0.9190	91.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6794	67.94%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9213	92.13%
Skin irritation	-	0.7878	78.78%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4165	41.65%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.5162	51.62%
skin sensitisation	-	0.9099	90.99%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7458	74.58%
Acute Oral Toxicity (c)	III	0.4717	47.17%
Estrogen receptor binding	+	0.6783	67.83%
Androgen receptor binding	+	0.5425	54.25%
Thyroid receptor binding	-	0.5356	53.56%
Glucocorticoid receptor binding	+	0.6011	60.11%
Aromatase binding	+	0.6763	67.63%
PPAR gamma	+	0.6460	64.60%
Honey bee toxicity	-	0.6954	69.54%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	-	0.8319	83.19%

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	98.44%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	97.87%	95.58%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.46%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.85%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.56%	97.09%
CHEMBL2094135	Q96BI3	Gamma-secretase	95.54%	98.05%
CHEMBL2581	P07339	Cathepsin D	94.10%	98.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	92.35%	92.29%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	90.41%	82.86%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.66%	96.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.57%	96.61%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.00%	93.10%
CHEMBL2514	O95665	Neurotensin receptor 2	87.84%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.11%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	87.10%	91.19%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.98%	96.21%
CHEMBL221	P23219	Cyclooxygenase-1	86.50%	90.17%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	86.32%	96.28%
CHEMBL226	P30542	Adenosine A1 receptor	86.29%	95.93%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	85.71%	91.83%
CHEMBL5255	O00206	Toll-like receptor 4	85.50%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.23%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.62%	91.24%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.39%	94.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.63%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.58%	96.47%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	83.51%	97.29%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.30%	92.32%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.11%	94.45%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	82.95%	88.42%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.88%	90.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.67%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.44%	89.50%
CHEMBL233	P35372	Mu opioid receptor	81.61%	97.93%
CHEMBL220	P22303	Acetylcholinesterase	80.64%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.24%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 46174033
• LOTUS: LTS0098160
• wikiData: Q27133657