[(1R,3R,4R,5R,6S,10S,12S,13S,16R,18S,21R)-4,6,12,17,17-pentamethyl-8-(2-methylpropanoyl)-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-7-en-3-yl] acetate

Details

• Internal ID: cc92756a-c9fa-4a01-92d7-85c36f1b474f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(1R,3R,4R,5R,6S,10S,12S,13S,16R,18S,21R)-4,6,12,17,17-pentamethyl-8-(2-methylpropanoyl)-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docos-7-en-3-yl] acetate
• SMILES (Canonical): CC1C=C(OC2C1C3(C(CC45CC46CCC(C(C6CCC5C3(C2)C)(C)C)OC7C(C(C(CO7)O)O)O)OC(=O)C)C)C(=O)C(C)C
• SMILES (Isomeric): C[C@@H]1C=C(O[C@@H]2[C@H]1[C@]3([C@@H](C[C@@]45C[C@@]46CC[C@@H](C([C@@H]6CC[C@H]5[C@@]3(C2)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)OC(=O)C)C)C(=O)C(C)C
• InChI: InChI=1S/C37H56O9/c1-18(2)29(40)22-13-19(3)28-23(45-22)14-34(7)25-10-9-24-33(5,6)26(46-32-31(42)30(41)21(39)16-43-32)11-12-36(24)17-37(25,36)15-27(35(28,34)8)44-20(4)38/h13,18-19,21,23-28,30-32,39,41-42H,9-12,14-17H2,1-8H3/t19-,21-,23+,24+,25+,26+,27-,28+,30+,31-,32+,34+,35-,36-,37+/m1/s1
• InChI Key: QCYLIQBVLZBPNK-WRRJDLEGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₆O₉
• Molecular Weight: 644.80 g/mol
• Exact Mass: 644.39243336 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.55
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8440	84.40%
Caco-2	-	0.8522	85.22%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7958	79.58%
OATP2B1 inhibitior	-	0.8652	86.52%
OATP1B1 inhibitior	+	0.8088	80.88%
OATP1B3 inhibitior	+	0.9167	91.67%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.7783	77.83%
P-glycoprotein substrate	+	0.5462	54.62%
CYP3A4 substrate	+	0.7215	72.15%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8871	88.71%
CYP3A4 inhibition	-	0.8700	87.00%
CYP2C9 inhibition	-	0.7471	74.71%
CYP2C19 inhibition	-	0.8968	89.68%
CYP2D6 inhibition	-	0.9465	94.65%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.6440	64.40%
CYP inhibitory promiscuity	-	0.9652	96.52%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6540	65.40%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9236	92.36%
Skin irritation	-	0.5817	58.17%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7685	76.85%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6574	65.74%
skin sensitisation	-	0.8760	87.60%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6808	68.08%
Acute Oral Toxicity (c)	I	0.3738	37.38%
Estrogen receptor binding	+	0.7077	70.77%
Androgen receptor binding	+	0.7180	71.80%
Thyroid receptor binding	-	0.5517	55.17%
Glucocorticoid receptor binding	+	0.7054	70.54%
Aromatase binding	+	0.7256	72.56%
PPAR gamma	+	0.6958	69.58%
Honey bee toxicity	-	0.6314	63.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9808	98.08%

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	98.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.64%	96.77%
CHEMBL2581	P07339	Cathepsin D	92.09%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.75%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.55%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	88.70%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.19%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.46%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.51%	97.25%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.01%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.20%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.11%	92.62%
CHEMBL204	P00734	Thrombin	83.99%	96.01%
CHEMBL1937	Q92769	Histone deacetylase 2	83.86%	94.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.70%	92.88%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.69%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.31%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.10%	80.96%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.45%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.97%	96.61%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.93%	89.50%
CHEMBL2535	P11166	Glucose transporter	81.54%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.99%	96.47%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.47%	94.80%

Plants that contains it

• Actaea asiatica
• Centella asiatica

Cross-Links

• PubChem: 16091661
• NPASS: NPC170814
• ChEMBL: CHEMBL501327
• LOTUS: LTS0276469
• wikiData: Q105218659