Semduramicin

Details

• Internal ID: f964f14d-be4e-4ceb-83b0-dc3e10bf018a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > C-glycosyl compounds
• IUPAC Name: 2-[(2R,3S,4S,5R,6S)-2,4-dihydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-3-methyloxan-2-yl]acetic acid
• SMILES (Canonical): CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C6C(C(C(C(O6)(CC(=O)O)O)C)O)OC)C)O)C)C)OC7CCC(C(O7)C)OC)(C)O)C
• SMILES (Isomeric): C[C@H]1C[C@H]([C@@](O[C@@H]1[C@H]2C[C@@H]([C@@H](O2)[C@@]3(CC[C@@H](O3)[C@@]4(CC[C@@]5(O4)C[C@@H]([C@H]([C@H](O5)[C@@H](C)[C@H]6[C@@H]([C@H]([C@@H]([C@](O6)(CC(=O)O)O)C)O)OC)C)O)C)C)O[C@H]7CC[C@@H]([C@H](O7)C)OC)(C)O)C
• InChI: InChI=1S/C45H76O16/c1-22-18-23(2)43(9,50)58-36(22)30-19-31(55-34-13-12-29(52-10)27(6)54-34)40(56-30)42(8)15-14-32(57-42)41(7)16-17-44(61-41)20-28(46)24(3)37(59-44)25(4)38-39(53-11)35(49)26(5)45(51,60-38)21-33(47)48/h22-32,34-40,46,49-51H,12-21H2,1-11H3,(H,47,48)/t22-,23+,24+,25+,26-,27+,28-,29-,30+,31-,32+,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+/m0/s1
• InChI Key: WINSLRIENGBHSH-ASZYJFLUSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₆O₁₆
• Molecular Weight: 873.10 g/mol
• Exact Mass: 872.51333633 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 15
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

• 113378-31-7
• Semduramicina
• Semduramicine
• Semduramicinum
• UNII-P6VXL377WL
• P6VXL377WL
• UK-61,689
• Semduramicine [INN-French]
• Semduramicinum [INN-Latin]
• Semduramicina [INN-Spanish]
• UK-61689
• UK 61,689
• DTXSID801016181
• Semduramicine (INN-French)
• Semduramicinum (INN-Latin)
• Semduramicina (INN-Spanish)
• SEMDURAMICIN (MART.)
• SEMDURAMICIN [MART.]
• (3R,4S,5S,6R,7S,22S)-23,27-Didemethoxy-2,6,22-tridemethyl-5,11-di-O-demethyl-6-methoxy-22-(((2S,5S,6R)-tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)oxy)lonomycin A
• Lonomycin A, 23,27-didemethoxy-2,6,22-tridemethyl-5,11-di-O-demethyl-6-methoxy-22-((tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl)oxy)-, (3R,4S,5S,6R,7S,22S(2S,5S,6R))-
• 2-[(2R,3S,4S,5R,6S)-2,4-dihydroxy-6-[(1R)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxyoxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-methoxy-3-methyloxan-2-yl]acetic acid
• Semduramicin [USAN:INN:BAN]
• (3R,4S,5S,6R,7S,22S)-23,27-Didemethoxy-2,6,22-tridemethyl-5,11-di-O-demethyl-6-methoxy-22-[[(2S,5S,6R)-tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl]oxy]lonomycin A
• SEMDURAMICIN [MI]
• SEMDURAMICIN 150
• Semduramicin (USAN/INN)
• SEMDURAMICIN [INN]
• SEMDURAMICIN MYCELIA
• SEMDURAMICIN [USAN]
• CHEMBL1207444
• DTXCID301474318
• AKOS040754006
• DB11545
• D05820
• Q27286294

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7993	79.93%
Caco-2	-	0.8756	87.56%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7334	73.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8625	86.25%
OATP1B3 inhibitior	+	0.8136	81.36%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7067	70.67%
P-glycoprotein inhibitior	+	0.7715	77.15%
P-glycoprotein substrate	+	0.8049	80.49%
CYP3A4 substrate	+	0.7368	73.68%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8807	88.07%
CYP3A4 inhibition	-	0.8595	85.95%
CYP2C9 inhibition	-	0.8561	85.61%
CYP2C19 inhibition	-	0.8986	89.86%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	-	0.9383	93.83%
CYP2C8 inhibition	+	0.6824	68.24%
CYP inhibitory promiscuity	-	0.9304	93.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6269	62.69%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9057	90.57%
Skin irritation	-	0.6007	60.07%
Skin corrosion	-	0.9239	92.39%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6559	65.59%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5926	59.26%
skin sensitisation	-	0.9119	91.19%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.9150	91.50%
Acute Oral Toxicity (c)	I	0.6882	68.82%
Estrogen receptor binding	+	0.7385	73.85%
Androgen receptor binding	+	0.7246	72.46%
Thyroid receptor binding	-	0.5063	50.63%
Glucocorticoid receptor binding	+	0.8565	85.65%
Aromatase binding	+	0.6282	62.82%
PPAR gamma	+	0.7627	76.27%
Honey bee toxicity	-	0.6620	66.20%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.8561	85.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	99.84%	96.01%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.57%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.07%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	98.26%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.01%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.52%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	93.36%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.23%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.70%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.39%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.76%	96.61%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.35%	97.28%
CHEMBL340	P08684	Cytochrome P450 3A4	90.10%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.87%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.28%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.01%	95.89%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	86.98%	97.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.83%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.34%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	85.56%	92.50%
CHEMBL226	P30542	Adenosine A1 receptor	84.72%	95.93%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.60%	89.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.50%	91.03%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.95%	99.15%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.78%	100.00%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	82.71%	97.43%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.62%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.62%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.29%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.64%	86.33%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.14%	85.31%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 71327
• LOTUS: LTS0276055
• wikiData: Q27286294