[(3R,4S,5R,6S)-4-acetyloxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] acetate

Details

• Internal ID: fb99426e-6957-4b47-b7ed-d19b5907c4a0
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(3R,4S,5R,6S)-4-acetyloxy-6-[[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC45CC46CCC7(C(C(CC7(C6CC(C5C3(C)C)OC8C(C(C(CO8)O)O)O)C)O)C9(CCC(O9)C(C)(C)O)C)C)OC(=O)C)OC(=O)C)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](CO[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@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O)[C@]9(CC[C@H](O9)C(C)(C)O)C)C)OC(=O)C)OC(=O)C)O)O)O
• InChI: InChI=1S/C50H80O19/c1-22-32(55)34(57)36(59)42(63-22)68-38-37(65-24(3)52)28(64-23(2)51)20-62-43(38)67-30-12-14-50-21-49(50)16-15-46(8)39(48(10)13-11-31(69-48)45(6,7)60)25(53)18-47(46,9)29(49)17-27(40(50)44(30,4)5)66-41-35(58)33(56)26(54)19-61-41/h22,25-43,53-60H,11-21H2,1-10H3/t22-,25-,26+,27-,28+,29-,30-,31-,32-,33-,34+,35+,36+,37-,38+,39-,40-,41-,42-,43-,46+,47-,48+,49-,50+/m0/s1
• InChI Key: OMSRQZAODQUOIO-RQOMYHKRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₈₀O₁₉
• Molecular Weight: 985.20 g/mol
• Exact Mass: 984.52938032 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7649	76.49%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7856	78.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8271	82.71%
OATP1B3 inhibitior	+	0.9463	94.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8037	80.37%
BSEP inhibitior	+	0.8909	89.09%
P-glycoprotein inhibitior	+	0.7645	76.45%
P-glycoprotein substrate	+	0.6536	65.36%
CYP3A4 substrate	+	0.7491	74.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.8018	80.18%
CYP2C9 inhibition	-	0.8092	80.92%
CYP2C19 inhibition	-	0.8481	84.81%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.7383	73.83%
CYP inhibitory promiscuity	-	0.9730	97.30%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9030	90.30%
Skin irritation	-	0.7112	71.12%
Skin corrosion	-	0.9289	92.89%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7344	73.44%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6591	65.91%
skin sensitisation	-	0.9025	90.25%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9442	94.42%
Acute Oral Toxicity (c)	I	0.5987	59.87%
Estrogen receptor binding	+	0.7910	79.10%
Androgen receptor binding	+	0.7407	74.07%
Thyroid receptor binding	-	0.5061	50.61%
Glucocorticoid receptor binding	+	0.7761	77.61%
Aromatase binding	+	0.6561	65.61%
PPAR gamma	+	0.8125	81.25%
Honey bee toxicity	-	0.5805	58.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9565	95.65%

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	98.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.99%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.43%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.84%	89.00%
CHEMBL1914	P06276	Butyrylcholinesterase	92.83%	95.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.65%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.47%	83.57%
CHEMBL340	P08684	Cytochrome P450 3A4	90.72%	91.19%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	90.13%	95.58%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.29%	96.95%
CHEMBL204	P00734	Thrombin	88.72%	96.01%
CHEMBL259	P32245	Melanocortin receptor 4	88.42%	95.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.09%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.76%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.74%	97.36%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.55%	91.07%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.45%	95.71%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	86.22%	97.31%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.96%	100.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	85.82%	95.69%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.32%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.92%	97.14%
CHEMBL2581	P07339	Cathepsin D	83.78%	98.95%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.72%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.32%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.83%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.81%	100.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.55%	98.75%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	81.52%	98.99%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.20%	85.31%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.62%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.56%	97.09%

Plants that contains it

• Astragalus thracicus

Cross-Links

• PubChem: 101129085
• NPASS: NPC19335