Leonloside D

Details

• Internal ID: 5a4259b7-973c-4bfd-a1f2-8ce884625fa0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• InChI: InChI=1S/C59H96O27/c1-24-34(63)38(67)43(72)50(79-24)85-47-28(20-61)81-48(46(75)41(47)70)77-21-29-36(65)40(69)45(74)52(83-29)86-53(76)59-16-14-54(2,3)18-26(59)25-8-9-32-55(4)12-11-33(56(5,23-62)31(55)10-13-58(32,7)57(25,6)15-17-59)84-49-42(71)37(66)30(22-78-49)82-51-44(73)39(68)35(64)27(19-60)80-51/h8,24,26-52,60-75H,9-23H2,1-7H3/t24-,26-,27+,28+,29+,30-,31+,32+,33-,34-,35+,36+,37-,38+,39-,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1
• InChI Key: VQYKWDTZZCEBNL-HVDQNFNGSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₆O₂₇
• Molecular Weight: 1237.40 g/mol
• Exact Mass: 1236.61389778 g/mol
• Topological Polar Surface Area (TPSA): 433.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -3.57
• H-Bond Acceptor: 27
• H-Bond Donor: 16
• Rotatable Bonds: 14

Synonyms

• 20830-84-6
• LeonlosideD
• Leontoside D
• orb1684467
• SCHEMBL30341000
• DTXSID001317894
• HY-N8116
• AKOS040760515
• FS-7219
• DA-64917
• CS-0140162
• E88754
• 6-Deoxy-alpha-L-mannopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->6)-1-O-{3beta-[(4-O-beta-D-glucopyranosyl-alpha-L-arabinopyranosyl)oxy]-23-hydroxy-28-oxoolean-12-en-28-yl}-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9023	90.23%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.8946	89.46%
P-glycoprotein inhibitior	+	0.7445	74.45%
P-glycoprotein substrate	+	0.5119	51.19%
CYP3A4 substrate	+	0.7412	74.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.7677	76.77%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7747	77.47%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8959	89.59%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.7886	78.86%
Androgen receptor binding	+	0.7469	74.69%
Thyroid receptor binding	+	0.5794	57.94%
Glucocorticoid receptor binding	+	0.7679	76.79%
Aromatase binding	+	0.6827	68.27%
PPAR gamma	+	0.8262	82.62%
Honey bee toxicity	-	0.6326	63.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.9603	96.03%

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	99.05%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.10%	95.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.16%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.80%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.86%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.85%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.60%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.90%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.89%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.24%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.59%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.65%	90.17%
CHEMBL2581	P07339	Cathepsin D	84.52%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.35%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.93%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.44%	94.00%
CHEMBL4302	P08183	P-glycoprotein 1	83.43%	92.98%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.16%	96.90%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.62%	97.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.43%	95.89%
CHEMBL5028	O14672	ADAM10	81.42%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.70%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	80.45%	92.50%

Plants that contains it

• Anemone coronaria
• Bongardia chrysogonum
• Pulsatilla cernua

Cross-Links

• PubChem: 21633190
• LOTUS: LTS0186326
• wikiData: Q104888324