[(2R,3S,4S,5R,6R)-6-[[(1S,3R,6S,8R,9S,11S,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]-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl acetate

Details

• Internal ID: aa2b325b-cc38-4306-98f0-0e16ede35ba5
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1S,3R,6S,8R,9S,11S,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]-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC45CC46CCC7(C(C(CC7(C6CC(C5C3(C)C)O)C)O)C8(CCC(O8)C(C)(C)O)C)C)COC(=O)C)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@H]3CC[C@]45C[C@]46CC[C@@]7([C@H]([C@H](C[C@]7([C@@H]6C[C@@H]([C@H]5C3(C)C)O)C)O)[C@]8(CC[C@H](O8)C(C)(C)O)C)C)COC(=O)C)O)O)O)O)O
• InChI: InChI=1S/C44H72O15/c1-20-28(48)30(50)32(52)36(55-20)58-33-31(51)29(49)24(18-54-21(2)45)56-37(33)57-26-11-13-44-19-43(44)15-14-40(7)35(42(9)12-10-27(59-42)39(5,6)53)23(47)17-41(40,8)25(43)16-22(46)34(44)38(26,3)4/h20,22-37,46-53H,10-19H2,1-9H3/t20-,22-,23-,24+,25-,26-,27-,28-,29+,30+,31-,32+,33+,34-,35-,36-,37-,40+,41-,42+,43-,44+/m0/s1
• InChI Key: LAUUTWHQIOJSKZ-VHSBJELASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₇₂O₁₅
• Molecular Weight: 841.00 g/mol
• Exact Mass: 840.48712159 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8323	83.23%
Caco-2	-	0.8859	88.59%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7951	79.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8187	81.87%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8037	80.37%
BSEP inhibitior	+	0.6091	60.91%
P-glycoprotein inhibitior	+	0.7659	76.59%
P-glycoprotein substrate	+	0.5490	54.90%
CYP3A4 substrate	+	0.7414	74.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.8168	81.68%
CYP2C9 inhibition	-	0.7746	77.46%
CYP2C19 inhibition	-	0.8622	86.22%
CYP2D6 inhibition	-	0.9448	94.48%
CYP1A2 inhibition	-	0.9001	90.01%
CYP2C8 inhibition	+	0.6959	69.59%
CYP inhibitory promiscuity	-	0.9296	92.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6625	66.25%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9076	90.76%
Skin irritation	-	0.6640	66.40%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3696	36.96%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6624	66.24%
skin sensitisation	-	0.9017	90.17%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9386	93.86%
Acute Oral Toxicity (c)	I	0.6144	61.44%
Estrogen receptor binding	+	0.7354	73.54%
Androgen receptor binding	+	0.7472	74.72%
Thyroid receptor binding	-	0.5892	58.92%
Glucocorticoid receptor binding	+	0.7281	72.81%
Aromatase binding	+	0.6890	68.90%
PPAR gamma	+	0.7568	75.68%
Honey bee toxicity	-	0.6240	62.40%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9541	95.41%

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	99.42%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.95%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.92%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	94.30%	97.31%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.59%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.49%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.37%	86.33%
CHEMBL1914	P06276	Butyrylcholinesterase	92.34%	95.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.29%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.57%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.89%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.79%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.78%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.28%	97.21%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.58%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.56%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	85.54%	95.93%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.12%	95.58%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.63%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.05%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.85%	91.19%
CHEMBL5255	O00206	Toll-like receptor 4	83.83%	92.50%
CHEMBL1871	P10275	Androgen Receptor	83.51%	96.43%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.45%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.61%	89.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.02%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.20%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.83%	85.31%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.29%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.00%	95.89%

Plants that contains it

• Astragalus amarus

Cross-Links

• PubChem: 21633211
• LOTUS: LTS0023698
• wikiData: Q105148982