[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl] (1S,3R,6S,7S,12S,14R,15R,16R)-14-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-[(2R,4S,5R)-4,5-dihydroxy-6-methyl-3-[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate

Details

• Internal ID: beba954c-7e0d-4117-8801-3efdde395e48
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl] (1S,3R,6S,7S,12S,14R,15R,16R)-14-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-[(2R,4S,5R)-4,5-dihydroxy-6-methyl-3-[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-7,12,16-trimethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC(=O)C2(C3CCC4C5(CC(C(C5(CCC46C3(C6)CCC2OC7C(C(C(C(O7)C)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C(C)CCC=C(C)C)OC9C(C(C(O9)CO)O)O)C)C)O)O)O
• SMILES (Isomeric): CC1[C@@H]([C@@H](C([C@@H](O1)OC(=O)[C@@]2([C@H](CC[C@@]34C2CCC5[C@@]3(C4)CC[C@]6([C@]5(C[C@H]([C@@H]6[C@H](C)CCC=C(C)C)O[C@H]7C([C@H]([C@H](O7)CO)O)O)C)C)O[C@H]8C([C@H]([C@H](C(O8)C)O)O)O[C@H]9[C@H](C([C@@H](C(O9)CO)O)O)O)C)O)O)O
• InChI: InChI=1S/C53H86O21/c1-22(2)10-9-11-23(3)32-26(69-45-40(63)36(59)28(20-55)70-45)18-50(7)29-12-13-30-51(8,48(66)74-44-41(64)37(60)33(56)24(4)67-44)31(14-15-52(30)21-53(29,52)17-16-49(32,50)6)72-47-43(39(62)34(57)25(5)68-47)73-46-42(65)38(61)35(58)27(19-54)71-46/h10,23-47,54-65H,9,11-21H2,1-8H3/t23-,24?,25?,26-,27?,28-,29?,30?,31+,32+,33+,34+,35-,36+,37+,38?,39+,40?,41?,42+,43?,44+,45-,46+,47+,49-,50+,51+,52-,53+/m1/s1
• InChI Key: DTVJERQJXPAODQ-QBGDHTETSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₁
• Molecular Weight: 1059.20 g/mol
• Exact Mass: 1058.56615975 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 21
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7858	78.58%
Caco-2	-	0.8868	88.68%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8138	81.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8269	82.69%
OATP1B3 inhibitior	+	0.8678	86.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8917	89.17%
P-glycoprotein inhibitior	+	0.7528	75.28%
P-glycoprotein substrate	+	0.5088	50.88%
CYP3A4 substrate	+	0.7249	72.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8541	85.41%
CYP3A4 inhibition	-	0.9395	93.95%
CYP2C9 inhibition	-	0.7289	72.89%
CYP2C19 inhibition	-	0.8433	84.33%
CYP2D6 inhibition	-	0.9250	92.50%
CYP1A2 inhibition	-	0.8420	84.20%
CYP2C8 inhibition	+	0.6240	62.40%
CYP inhibitory promiscuity	-	0.8748	87.48%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6206	62.06%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.6279	62.79%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.7878	78.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7729	77.29%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8290	82.90%
skin sensitisation	-	0.8813	88.13%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8949	89.49%
Acute Oral Toxicity (c)	I	0.4458	44.58%
Estrogen receptor binding	+	0.8154	81.54%
Androgen receptor binding	+	0.7580	75.80%
Thyroid receptor binding	-	0.4882	48.82%
Glucocorticoid receptor binding	+	0.7527	75.27%
Aromatase binding	+	0.6470	64.70%
PPAR gamma	+	0.8095	80.95%
Honey bee toxicity	-	0.6185	61.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9709	97.09%

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	99.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.74%	94.45%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	96.02%	95.58%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.41%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.92%	98.95%
CHEMBL3837	P07711	Cathepsin L	92.09%	96.61%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.00%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.89%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.73%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.61%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	89.53%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.46%	97.09%
CHEMBL284	P27487	Dipeptidyl peptidase IV	88.43%	95.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.30%	98.75%
CHEMBL4683	Q12884	Fibroblast activation protein alpha	88.19%	93.07%
CHEMBL1951	P21397	Monoamine oxidase A	88.10%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	88.08%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.50%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.38%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.27%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.10%	95.89%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	87.09%	97.47%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	86.98%	96.03%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	86.19%	92.88%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.13%	93.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.06%	96.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.05%	96.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.00%	89.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.37%	92.94%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	85.18%	92.78%
CHEMBL237	P41145	Kappa opioid receptor	84.95%	98.10%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.66%	97.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.36%	100.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.24%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.70%	95.36%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.56%	92.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.15%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.70%	97.36%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.55%	94.33%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	82.40%	99.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.36%	95.50%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	82.19%	92.86%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.86%	96.47%
CHEMBL5255	O00206	Toll-like receptor 4	81.70%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.25%	82.50%
CHEMBL233	P35372	Mu opioid receptor	80.20%	97.93%

Plants that contains it

• Amphilophium paniculatum

Cross-Links

• PubChem: 162867142
• LOTUS: LTS0263078
• wikiData: Q104989042