22-O-Methyl-capsicoside D

Details

• Internal ID: a3d63618-61d4-4d6c-8650-14f5492ae662
• 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,16S,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,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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(CCC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)CO)O)OC8C(C(C(CO8)O)O)O)OC9C(C(C(C(O9)CO)O)OC2C(C(C(C(O2)CO)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(CC[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](CO8)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)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/C63H106O33/c1-23(21-84-55-47(79)43(75)39(71)32(16-64)87-55)8-13-63(83-5)24(2)37-31(96-63)15-29-27-7-6-25-14-26(9-11-61(25,3)28(27)10-12-62(29,37)4)86-57-49(81)45(77)51(36(20-68)91-57)92-60-54(53(42(74)35(19-67)90-60)94-56-46(78)38(70)30(69)22-85-56)95-59-50(82)52(41(73)34(18-66)89-59)93-58-48(80)44(76)40(72)33(17-65)88-58/h23-60,64-82H,6-22H2,1-5H3/t23-,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?/m1/s1
• InChI Key: BOGJTFPGODXYAG-UPIICVHQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₃H₁₀₆O₃₃
• Molecular Weight: 1391.50 g/mol
• Exact Mass: 1390.6616358 g/mol
• Topological Polar Surface Area (TPSA): 514.00 Ų
• XlogP: -4.00
• Atomic LogP (AlogP): -7.01
• H-Bond Acceptor: 33
• H-Bond Donor: 19
• Rotatable Bonds: 22

Synonyms

• 22-O-METHYL-CAPSICOSIDE D

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5474	54.74%
Caco-2	-	0.8713	87.13%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5940	59.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8815	88.15%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8468	84.68%
P-glycoprotein inhibitior	+	0.7430	74.30%
P-glycoprotein substrate	+	0.6634	66.34%
CYP3A4 substrate	+	0.7558	75.58%
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	+	0.7100	71.00%
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	-	0.8992	89.92%
Skin irritation	-	0.6918	69.18%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.7478	74.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8428	84.28%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.9260	92.60%
skin sensitisation	-	0.9353	93.53%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9577	95.77%
Acute Oral Toxicity (c)	I	0.6939	69.39%
Estrogen receptor binding	+	0.8529	85.29%
Androgen receptor binding	+	0.7018	70.18%
Thyroid receptor binding	+	0.5558	55.58%
Glucocorticoid receptor binding	+	0.6632	66.32%
Aromatase binding	+	0.6543	65.43%
PPAR gamma	+	0.7929	79.29%
Honey bee toxicity	-	0.5707	57.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	98.65%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.58%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.96%	97.09%
CHEMBL237	P41145	Kappa opioid receptor	94.53%	98.10%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.01%	96.61%
CHEMBL233	P35372	Mu opioid receptor	93.47%	97.93%
CHEMBL226	P30542	Adenosine A1 receptor	93.16%	95.93%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	92.51%	92.86%
CHEMBL4302	P08183	P-glycoprotein 1	92.16%	92.98%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.97%	97.29%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.77%	97.25%
CHEMBL204	P00734	Thrombin	90.62%	96.01%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.24%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.64%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	89.43%	93.18%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	89.40%	95.36%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	88.46%	95.58%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.77%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.68%	89.05%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.00%	98.05%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.62%	92.88%
CHEMBL206	P03372	Estrogen receptor alpha	86.52%	97.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.48%	92.94%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.04%	97.86%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	84.64%	92.38%
CHEMBL2996	Q05655	Protein kinase C delta	84.50%	97.79%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.32%	91.24%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.21%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.52%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.31%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.12%	92.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.91%	95.89%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.36%	97.50%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.10%	92.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.86%	97.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.58%	96.47%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.11%	98.46%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.74%	91.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.54%	93.56%
CHEMBL2360	P00492	Hypoxanthine-guanine phosphoribosyltransferase	80.45%	87.38%
CHEMBL1871	P10275	Androgen Receptor	80.38%	96.43%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	80.12%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.03%	100.00%

Plants that contains it

• Capsicum annuum

Cross-Links

• PubChem: 76316014
• LOTUS: LTS0093363
• wikiData: Q104939217