(6R)-6-[(1R,3R,6S,8R,11S,12S,14S,15R,16R,18R)-14,18-dihydroxy-7,7,12,16-tetramethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylheptan-3-one

Details

• Internal ID: 6d3c8cc7-d1ee-4a71-944d-cec521adc50b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (6R)-6-[(1R,3R,6S,8R,11S,12S,14S,15R,16R,18R)-14,18-dihydroxy-7,7,12,16-tetramethyl-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methylheptan-3-one
• SMILES (Canonical): CC(C)C(=O)CCC(C)C1C(CC2(C1(CC(C34C2CCC5C3(C4)CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)O)C)C)O
• SMILES (Isomeric): C[C@H](CCC(=O)C(C)C)[C@H]1[C@H](C[C@@]2([C@@]1(C[C@H]([C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)C)O
• InChI: InChI=1S/C36H60O9/c1-18(2)20(38)9-8-19(3)27-21(39)14-33(6)24-11-10-23-32(4,5)26(45-31-30(43)29(42)28(41)22(16-37)44-31)12-13-35(23)17-36(24,35)25(40)15-34(27,33)7/h18-19,21-31,37,39-43H,8-17H2,1-7H3/t19-,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31+,33+,34-,35-,36+/m1/s1
• InChI Key: APNOBRRKGDSVMK-HCQLUDASSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₆₀O₉
• Molecular Weight: 636.90 g/mol
• Exact Mass: 636.42373349 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7501	75.01%
Caco-2	-	0.8506	85.06%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	0.7213	72.13%
OATP1B1 inhibitior	+	0.8207	82.07%
OATP1B3 inhibitior	+	0.9083	90.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7542	75.42%
BSEP inhibitior	-	0.5330	53.30%
P-glycoprotein inhibitior	+	0.7342	73.42%
P-glycoprotein substrate	-	0.6310	63.10%
CYP3A4 substrate	+	0.7124	71.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8483	84.83%
CYP3A4 inhibition	-	0.8358	83.58%
CYP2C9 inhibition	-	0.6864	68.64%
CYP2C19 inhibition	-	0.8410	84.10%
CYP2D6 inhibition	-	0.9527	95.27%
CYP1A2 inhibition	-	0.8117	81.17%
CYP2C8 inhibition	+	0.5151	51.51%
CYP inhibitory promiscuity	-	0.9532	95.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7500	75.00%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.6526	65.26%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.7785	77.85%
Human Ether-a-go-go-Related Gene inhibition	+	0.7931	79.31%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.9039	90.39%
skin sensitisation	-	0.9082	90.82%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7192	71.92%
Acute Oral Toxicity (c)	I	0.3723	37.23%
Estrogen receptor binding	+	0.6251	62.51%
Androgen receptor binding	+	0.7531	75.31%
Thyroid receptor binding	-	0.5660	56.60%
Glucocorticoid receptor binding	+	0.6001	60.01%
Aromatase binding	+	0.6594	65.94%
PPAR gamma	+	0.6248	62.48%
Honey bee toxicity	-	0.6643	66.43%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8992	89.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.35%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.95%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	98.79%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.45%	91.11%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	96.10%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.52%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	94.04%	91.24%
CHEMBL2581	P07339	Cathepsin D	92.29%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.55%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.90%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.89%	92.62%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.20%	96.47%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.70%	99.17%
CHEMBL237	P41145	Kappa opioid receptor	85.70%	98.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.68%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.49%	96.95%
CHEMBL5255	O00206	Toll-like receptor 4	84.43%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.84%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.53%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.31%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.24%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.62%	100.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.42%	82.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.82%	94.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.78%	92.88%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.43%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.28%	89.00%
CHEMBL1075317	P61964	WD repeat-containing protein 5	81.13%	96.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.96%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.89%	91.19%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.56%	89.05%
CHEMBL2094135	Q96BI3	Gamma-secretase	80.26%	98.05%
CHEMBL2514	O95665	Neurotensin receptor 2	80.26%	100.00%

Plants that contains it

• Curculigo orchioides

Cross-Links

• PubChem: 101618894
• NPASS: NPC42310
• LOTUS: LTS0063383
• wikiData: Q104916429