Sisomicin

Details

• Internal ID: e6e5768b-6cd2-4734-bbca-000d0aea756a
• 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-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-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(CC=C(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(O3)CN)N)N)N)O
• InChI: InChI=1S/C19H37N5O7/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/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1
• InChI Key: URWAJWIAIPFPJE-YFMIWBNJSA-N
• Popularity: 1,420 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₇N₅O₇
• Molecular Weight: 447.50 g/mol
• Exact Mass: 447.26929854 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -5.10
• Atomic LogP (AlogP): -3.85
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• Rickamicin
• Sisomycin
• 32385-11-8
• Sissomicin
• Siseptin
• Antibiotic 6640
• Antibiotic 66-40
• Sch 13475
• Dehydrogentamicin Cla
• Sch-13475
• X55XSL74YQ
• CHEBI:9169
• Sisomin
• 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-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-
• Sisomicinum
• Sisomicina
• Sisomicine
• (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• Sisomicine [INN-French]
• Sisomicinum [INN-Latin]
• Salvamina
• Sisomicina [INN-Spanish]
• Siseptin sulfate
• (1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yloxy]-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside
• (1s,2s,3r,4s,6r)-4,6-Diamino-3-{[(2s,3r)-3-Amino-6-(Aminomethyl)-3,4-Dihydro-2h-Pyran-2-Yl]oxy}-2-Hydroxycyclohexyl 3-Deoxy-4-C-Methyl-3-(Methylamino)-Beta-L-Arabinopyranoside
• (2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-4,6-diamino-3-(((2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol
• O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine
• EINECS 251-018-2
• UNII-X55XSL74YQ
• BRN 1357913
• Sisomicin [USAN:INN:BAN]
• Sch13475
• sisomicin-sulfate
• SiS
• SISO
• SISOMICIN [INN]
• SISOMICIN [MI]
• Sisomicin (USAN/INN)
• SISOMICIN [USAN]
• SISOMICIN [WHO-DD]
• SCHEMBL49395
• O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-2-deoxy-D-streptamine
• O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-L-streptamine
• CHEMBL221886
• GTPL10858
• HY-B1222A
• URWAJWIAIPFPJE-YFMIWBNJSA-N
• (2S-CIS)-4-O-(3-AMINO-6-(AMINOMETHYL)-3,4-DIHYDRO-2H-PYRAN-2-YL)-2-DEOXY-6-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL)-D-STREPTAMINE
• AKOS015895179
• DB12604
• (2S-cis)-4-O-(3-Amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)-2-deoxy-6-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl)-D-streptamine
• CS-0013807
• C00494
• D02544
• GENTAMICIN SULFATE IMPURITY A [EP IMPURITY]
• NETILMICIN SULFATE IMPURITY A [EP IMPURITY]
• Q3962119
• (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxy-cyclohexoxy]-5-methyl-4-(methylamino)tetrahydropyran-3,5-diol
• (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• 2-DEOXY-4-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL)-6-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-GLYCERO-HEX-4-ENOPYRANOSYL)-L-STREPTAMINE
• O-3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA-L-ARABINOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-GLYCERO-HEX-4-ENOPYRANOSYL-(1->6))-2-DEOXY-L-STREPTAMINE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9808	98.08%
Caco-2	-	0.8521	85.21%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Lysosomes	0.6850	68.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9333	93.33%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8043	80.43%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.7223	72.23%
CYP3A4 substrate	+	0.6361	63.61%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7168	71.68%
CYP3A4 inhibition	-	0.9853	98.53%
CYP2C9 inhibition	-	0.9209	92.09%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9115	91.15%
CYP2C8 inhibition	+	0.5200	52.00%
CYP inhibitory promiscuity	-	0.9204	92.04%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5513	55.13%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9776	97.76%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.9167	91.67%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4289	42.89%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.7551	75.51%
skin sensitisation	-	0.8259	82.59%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6783	67.83%
Acute Oral Toxicity (c)	III	0.7999	79.99%
Estrogen receptor binding	-	0.8683	86.83%
Androgen receptor binding	+	0.5580	55.80%
Thyroid receptor binding	-	0.7227	72.27%
Glucocorticoid receptor binding	+	0.6517	65.17%
Aromatase binding	+	0.6949	69.49%
PPAR gamma	+	0.6457	64.57%
Honey bee toxicity	-	0.8340	83.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.7780	77.80%

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	98.37%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.41%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.53%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.73%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	86.38%	97.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.99%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.85%	90.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.29%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.08%	96.95%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	83.98%	82.86%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.76%	97.28%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.13%	92.88%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.88%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.74%	82.69%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 36119
• LOTUS: LTS0006195
• wikiData: Q3962119