[(2R,3R,4S,5R,6R)-2-[[(1S,3R,6S,8S,9S,11R,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] acetate

Details

• Internal ID: 7fbfd144-84d2-497a-b155-7d69892c825f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2R,3R,4S,5R,6R)-2-[[(1S,3R,6S,8S,9S,11R,12S,14S,15R,16R)-9,14-dihydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(OC(C1O)OC2CCC34CC35CCC6(C(C(CC6(C5CC(C4C2(C)C)O)C)O)C7(CCC(O7)C(C)(C)O)C)C)CO)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1O)O[C@H]2CC[C@]34C[C@]35CC[C@@]6([C@H]([C@H](C[C@]6([C@H]5C[C@@H]([C@@H]4C2(C)C)O)C)O)[C@]7(CC[C@H](O7)C(C)(C)O)C)C)CO)O
• InChI: InChI=1S/C38H62O11/c1-19(40)46-28-26(43)22(17-39)47-31(27(28)44)48-24-10-12-38-18-37(38)14-13-34(6)30(36(8)11-9-25(49-36)33(4,5)45)21(42)16-35(34,7)23(37)15-20(41)29(38)32(24,2)3/h20-31,39,41-45H,9-18H2,1-8H3/t20-,21-,22+,23+,24-,25-,26+,27+,28-,29+,30-,31-,34+,35-,36+,37-,38+/m0/s1
• InChI Key: NIPOOHDDUAPIFF-DSLFZHOISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₂O₁₁
• Molecular Weight: 694.90 g/mol
• Exact Mass: 694.42921279 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.83
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8885	88.85%
Caco-2	-	0.8693	86.93%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7617	76.17%
OATP2B1 inhibitior	-	0.8651	86.51%
OATP1B1 inhibitior	+	0.8092	80.92%
OATP1B3 inhibitior	+	0.9286	92.86%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7537	75.37%
BSEP inhibitior	-	0.9076	90.76%
P-glycoprotein inhibitior	+	0.7667	76.67%
P-glycoprotein substrate	-	0.5352	53.52%
CYP3A4 substrate	+	0.7371	73.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8810	88.10%
CYP3A4 inhibition	-	0.6999	69.99%
CYP2C9 inhibition	-	0.7265	72.65%
CYP2C19 inhibition	-	0.8681	86.81%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.8983	89.83%
CYP2C8 inhibition	+	0.6112	61.12%
CYP inhibitory promiscuity	-	0.8791	87.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6537	65.37%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9126	91.26%
Skin irritation	-	0.6723	67.23%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6731	67.31%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6249	62.49%
skin sensitisation	-	0.9127	91.27%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7703	77.03%
Acute Oral Toxicity (c)	I	0.6298	62.98%
Estrogen receptor binding	+	0.6018	60.18%
Androgen receptor binding	+	0.7513	75.13%
Thyroid receptor binding	-	0.5842	58.42%
Glucocorticoid receptor binding	+	0.6250	62.50%
Aromatase binding	+	0.6719	67.19%
PPAR gamma	+	0.6546	65.46%
Honey bee toxicity	-	0.6375	63.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9111	91.11%

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	98.98%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.02%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.25%	96.09%
CHEMBL204	P00734	Thrombin	96.16%	96.01%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.34%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.76%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.68%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.27%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.08%	96.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.59%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.37%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.63%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	87.28%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	85.70%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.01%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.99%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.88%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.81%	95.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.44%	89.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.40%	86.33%
CHEMBL259	P32245	Melanocortin receptor 4	84.20%	95.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.03%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	83.88%	92.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.96%	82.50%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	82.60%	95.36%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.53%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.34%	89.34%
CHEMBL226	P30542	Adenosine A1 receptor	81.83%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.85%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.80%	91.07%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.69%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.62%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.46%	95.56%

Plants that contains it

• Astragalus verrucosus

Cross-Links

• PubChem: 163079421
• LOTUS: LTS0251426
• wikiData: Q105179943