(1S,3R,6S,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecan-9-one

Details

• Internal ID: c99b1162-ca13-4174-929f-b5b9c9c78609
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (1S,3R,6S,8R,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecan-9-one
• SMILES (Canonical): CC1(C(CCC23C1C(=O)CC4C2(C3)CCC5(C4(CC(C5C6(CCC(O6)C(C)(C)O)C)O)C)C)OC7C(C(C(C(O7)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@]34C[C@@]35CC[C@@H](C([C@@H]5C(=O)C[C@H]4[C@@]1(C[C@@H]([C@@H]2[C@]6(CC[C@H](O6)C(C)(C)O)C)O)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C36H58O10/c1-30(2)22(45-29-26(42)25(41)24(40)20(16-37)44-29)9-11-36-17-35(36)13-12-32(5)28(34(7)10-8-23(46-34)31(3,4)43)19(39)15-33(32,6)21(35)14-18(38)27(30)36/h19-29,37,39-43H,8-17H2,1-7H3/t19-,20+,21-,22-,23-,24+,25-,26+,27-,28-,29-,32+,33-,34+,35-,36+/m0/s1
• InChI Key: WLZFXKYSYQRZFH-LCOJSZFRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₈O₁₀
• Molecular Weight: 650.80 g/mol
• Exact Mass: 650.40299804 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7975	79.75%
Caco-2	-	0.8463	84.63%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.8151	81.51%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	-	0.7373	73.73%
P-glycoprotein inhibitior	+	0.7222	72.22%
P-glycoprotein substrate	-	0.6123	61.23%
CYP3A4 substrate	+	0.7208	72.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8640	86.40%
CYP3A4 inhibition	-	0.7581	75.81%
CYP2C9 inhibition	-	0.7687	76.87%
CYP2C19 inhibition	-	0.8741	87.41%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.8914	89.14%
CYP2C8 inhibition	+	0.5852	58.52%
CYP inhibitory promiscuity	-	0.9309	93.09%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6640	66.40%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9190	91.90%
Skin irritation	-	0.6681	66.81%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.6804	68.04%
Human Ether-a-go-go-Related Gene inhibition	+	0.6639	66.39%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6783	67.83%
skin sensitisation	-	0.9090	90.90%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7463	74.63%
Acute Oral Toxicity (c)	I	0.5727	57.27%
Estrogen receptor binding	+	0.5792	57.92%
Androgen receptor binding	+	0.7612	76.12%
Thyroid receptor binding	-	0.5721	57.21%
Glucocorticoid receptor binding	+	0.6249	62.49%
Aromatase binding	+	0.6730	67.30%
PPAR gamma	+	0.6203	62.03%
Honey bee toxicity	-	0.6973	69.73%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9205	92.05%

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	98.68%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.38%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	95.63%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.59%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.48%	97.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.13%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.99%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.24%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.64%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.45%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.41%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.48%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.66%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.44%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.37%	96.61%
CHEMBL1977	P11473	Vitamin D receptor	87.30%	99.43%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.09%	83.57%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.28%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.07%	95.89%
CHEMBL1871	P10275	Androgen Receptor	83.87%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.23%	97.14%
CHEMBL3401	O75469	Pregnane X receptor	81.27%	94.73%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.75%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.40%	92.62%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.24%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.04%	94.00%

Plants that contains it

• Astragalus trimestris

Cross-Links

• PubChem: 10508453
• LOTUS: LTS0234568
• wikiData: Q105308372