(2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8S,9S,11R,12S,14S,15R,16R)-9,14-dihydroxy-7,7,12,16-tetramethyl-15-[(2R,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 22074c1d-e000-4f56-898a-aad335c5e27b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1S,3R,6S,8S,9S,11R,12S,14S,15R,16R)-9,14-dihydroxy-7,7,12,16-tetramethyl-15-[(2R,5S)-2-methyl-5-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]oxolan-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C(CCC23C1C(CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)OC7C(C(C(C(O7)CO)O)O)O)C)O)C)C)O)OC8C(C(C(C(O8)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@]34C[C@@]35CC[C@@H](C([C@H]5[C@H](C[C@@H]4[C@@]1(C[C@@H]([C@@H]2[C@]6(CC[C@H](O6)C(C)(C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)O)C)O)(C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• InChI: InChI=1S/C42H70O15/c1-36(2)24(55-34-30(51)28(49)26(47)21(16-43)53-34)9-11-42-18-41(42)13-12-38(5)33(20(46)15-39(38,6)23(41)14-19(45)32(36)42)40(7)10-8-25(56-40)37(3,4)57-35-31(52)29(50)27(48)22(17-44)54-35/h19-35,43-52H,8-18H2,1-7H3/t19-,20-,21+,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32+,33-,34-,35-,38+,39-,40+,41-,42+/m0/s1
• InChI Key: SJQZFBFRPIJBGH-XGIIQYFBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₅
• Molecular Weight: 815.00 g/mol
• Exact Mass: 814.47147152 g/mol
• Topological Polar Surface Area (TPSA): 248.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6581	65.81%
Caco-2	-	0.8798	87.98%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6782	67.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8338	83.38%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8108	81.08%
P-glycoprotein inhibitior	+	0.7513	75.13%
P-glycoprotein substrate	-	0.6240	62.40%
CYP3A4 substrate	+	0.7180	71.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8237	82.37%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.8009	80.09%
CYP2C19 inhibition	-	0.8368	83.68%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	+	0.6229	62.29%
CYP inhibitory promiscuity	-	0.9329	93.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6399	63.99%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9049	90.49%
Skin irritation	-	0.7237	72.37%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7926	79.26%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5124	51.24%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8551	85.51%
Acute Oral Toxicity (c)	I	0.6658	66.58%
Estrogen receptor binding	+	0.6794	67.94%
Androgen receptor binding	+	0.7604	76.04%
Thyroid receptor binding	-	0.5759	57.59%
Glucocorticoid receptor binding	+	0.6014	60.14%
Aromatase binding	+	0.6585	65.85%
PPAR gamma	+	0.7146	71.46%
Honey bee toxicity	-	0.6641	66.41%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8633	86.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.79%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.84%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.04%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.54%	96.09%
CHEMBL240	Q12809	HERG	93.47%	89.76%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.33%	96.21%
CHEMBL226	P30542	Adenosine A1 receptor	90.20%	95.93%
CHEMBL259	P32245	Melanocortin receptor 4	89.91%	95.38%
CHEMBL2996	Q05655	Protein kinase C delta	89.78%	97.79%
CHEMBL220	P22303	Acetylcholinesterase	88.13%	94.45%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.16%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.04%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.02%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.78%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.21%	96.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.90%	95.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.32%	91.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.21%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.43%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.10%	92.86%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	80.95%	97.31%
CHEMBL237	P41145	Kappa opioid receptor	80.56%	98.10%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.50%	92.62%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.38%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.37%	94.45%

Plants that contains it

• Astragalus amarus

Cross-Links

• PubChem: 163042170
• LOTUS: LTS0217376
• wikiData: Q105254491