O-Methylcapsicoside A

Details

• Internal ID: 1dab8d3d-7c9e-40ec-958e-00c819cdd661
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(2R)-4-[(1R,2S,4S,7S,8R,9S,12S,13S,15R,16R,18S)-16-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-hydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CCC5C4(CC(C(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)O)OC9C(C(C(C(O9)CO)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O)C)C)OC1(CCC(C)COC1C(C(C(C(O1)CO)O)O)O)OC
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC[C@@H]5[C@@]4(C[C@H]([C@@H](C5)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)O)C)C)OC1(CC[C@@H](C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)OC
• InChI: InChI=1S/C64H108O35/c1-22(21-87-56-47(81)43(77)38(72)31(15-65)89-56)8-11-64(86-5)23(2)37-30(99-64)13-27-25-7-6-24-12-29(28(71)14-63(24,4)26(25)9-10-62(27,37)3)88-57-50(84)46(80)52(36(20-70)94-57)95-61-55(54(42(76)35(19-69)93-61)97-59-49(83)45(79)40(74)33(17-67)91-59)98-60-51(85)53(41(75)34(18-68)92-60)96-58-48(82)44(78)39(73)32(16-66)90-58/h22-61,65-85H,6-21H2,1-5H3/t22-,23+,24+,25-,26+,27+,28-,29-,30+,31-,32-,33-,34-,35-,36-,37+,38-,39-,40-,41-,42-,43+,44+,45+,46-,47-,48-,49-,50-,51-,52+,53+,54+,55-,56-,57-,58+,59+,60+,61+,62+,63+,64?/m1/s1
• InChI Key: QKQPATPXWFRSQO-VYIDYXGMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₄H₁₀₈O₃₅
• Molecular Weight: 1437.50 g/mol
• Exact Mass: 1436.6671151 g/mol
• Topological Polar Surface Area (TPSA): 554.00 Ų
• XlogP: -5.10
• Atomic LogP (AlogP): -8.68
• H-Bond Acceptor: 35
• H-Bond Donor: 21
• Rotatable Bonds: 23

Synonyms

• CHEMBL2271371

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5474	54.74%
Caco-2	-	0.8727	87.27%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5940	59.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8674	86.74%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8630	86.30%
P-glycoprotein inhibitior	+	0.7432	74.32%
P-glycoprotein substrate	+	0.5701	57.01%
CYP3A4 substrate	+	0.7537	75.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8203	82.03%
CYP3A4 inhibition	-	0.9587	95.87%
CYP2C9 inhibition	-	0.9121	91.21%
CYP2C19 inhibition	-	0.8946	89.46%
CYP2D6 inhibition	-	0.9538	95.38%
CYP1A2 inhibition	-	0.9208	92.08%
CYP2C8 inhibition	+	0.6911	69.11%
CYP inhibitory promiscuity	-	0.9656	96.56%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6210	62.10%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.6918	69.18%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.9078	90.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8368	83.68%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8635	86.35%
skin sensitisation	-	0.9353	93.53%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9257	92.57%
Acute Oral Toxicity (c)	I	0.6939	69.39%
Estrogen receptor binding	+	0.8602	86.02%
Androgen receptor binding	+	0.7212	72.12%
Thyroid receptor binding	+	0.5591	55.91%
Glucocorticoid receptor binding	+	0.6615	66.15%
Aromatase binding	+	0.6582	65.82%
PPAR gamma	+	0.7971	79.71%
Honey bee toxicity	-	0.5658	56.58%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.3911	39.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.77%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.17%	96.61%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.33%	96.21%
CHEMBL220	P22303	Acetylcholinesterase	94.06%	94.45%
CHEMBL237	P41145	Kappa opioid receptor	93.84%	98.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.69%	97.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	93.24%	92.86%
CHEMBL4302	P08183	P-glycoprotein 1	92.67%	92.98%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.50%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	91.51%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.76%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	90.61%	93.18%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	90.05%	92.38%
CHEMBL204	P00734	Thrombin	89.59%	96.01%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.45%	97.29%
CHEMBL233	P35372	Mu opioid receptor	89.02%	97.93%
CHEMBL2094135	Q96BI3	Gamma-secretase	88.83%	98.05%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	88.27%	95.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.14%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	86.84%	95.58%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.71%	95.89%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.67%	89.05%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.61%	97.86%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.85%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.77%	95.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.59%	91.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.48%	93.56%
CHEMBL2996	Q05655	Protein kinase C delta	84.27%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.20%	97.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.06%	96.38%
CHEMBL5255	O00206	Toll-like receptor 4	83.77%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.26%	97.25%
CHEMBL1871	P10275	Androgen Receptor	83.21%	96.43%
CHEMBL259	P32245	Melanocortin receptor 4	82.85%	95.38%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.59%	100.00%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	81.97%	92.78%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.93%	94.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.32%	86.33%

Plants that contains it

• Capsicum annuum

Cross-Links

• PubChem: 76334189
• LOTUS: LTS0176386
• wikiData: Q105223272