(3b,16a,20R)-3,16,20,22,25-Pentahydroxy-5-cucurbiten-11-one 3-[rhamnosyl-(1->4)-[glucosyl-(1->6)]-glucoside]

Details

• Internal ID: 1ac7828b-4dd7-4d36-814a-8b69a1a7ab06
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: 3-[3,4-dihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-17-(2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CC(C6C(C)(C(CCC(C)(C)O)O)O)O)C)C)C)C3(C)C)COC7C(C(C(C(O7)CO)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CC(C6C(C)(C(CCC(C)(C)O)O)O)O)C)C)C)C3(C)C)COC7C(C(C(C(O7)CO)O)O)O)O)O)O
• InChI: InChI=1S/C48H80O20/c1-20-30(53)32(55)36(59)41(64-20)68-38-25(19-63-40-35(58)33(56)31(54)24(18-49)65-40)66-42(37(60)34(38)57)67-29-13-11-22-21(44(29,4)5)10-12-26-45(6)16-23(50)39(46(45,7)17-28(52)47(22,26)8)48(9,62)27(51)14-15-43(2,3)61/h10,20,22-27,29-42,49-51,53-62H,11-19H2,1-9H3
• InChI Key: SDJJKTYFMLJFRO-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₂₀
• Molecular Weight: 977.10 g/mol
• Exact Mass: 976.52429494 g/mol
• Topological Polar Surface Area (TPSA): 335.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.73
• H-Bond Acceptor: 20
• H-Bond Donor: 13
• Rotatable Bonds: 13

Synonyms

• CHEBI:190719
• 3-[3,4-dihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-17-(2,3,6-trihydroxy-6-methylheptan-2-yl)-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8258	82.58%
Caco-2	-	0.8867	88.67%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8432	84.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8489	84.89%
OATP1B3 inhibitior	-	0.3515	35.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.9239	92.39%
P-glycoprotein inhibitior	+	0.7460	74.60%
P-glycoprotein substrate	+	0.6070	60.70%
CYP3A4 substrate	+	0.7262	72.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8687	86.87%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.8769	87.69%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9147	91.47%
CYP2C8 inhibition	+	0.6588	65.88%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.5396	53.96%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.7778	77.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7148	71.48%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6751	67.51%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8310	83.10%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.8212	82.12%
Androgen receptor binding	+	0.7437	74.37%
Thyroid receptor binding	-	0.5107	51.07%
Glucocorticoid receptor binding	+	0.7271	72.71%
Aromatase binding	+	0.6262	62.62%
PPAR gamma	+	0.8004	80.04%
Honey bee toxicity	-	0.6417	64.17%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9477	94.77%

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	99.27%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.12%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.27%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.01%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.73%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.83%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.43%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.21%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.40%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	86.19%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.12%	94.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.86%	93.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.51%	86.92%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.41%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.96%	100.00%
CHEMBL4581	P52732	Kinesin-like protein 1	84.91%	93.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.10%	95.89%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.11%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.03%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	83.03%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.94%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.80%	97.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.19%	85.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.89%	97.36%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	81.77%	95.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.67%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.62%	95.89%

Plants that contains it

• Cyclanthera pedata

Cross-Links

• PubChem: 131751715
• LOTUS: LTS0217909
• wikiData: Q105250679