Pedicularioside A

Details

• Internal ID: c3972004-867b-48cc-843c-48b8c52c3715
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OCCC3=CC(=C(C=C3)O)O)O)OC4C(C(CO4)(CO)O)O)OC(=O)C=CC5=CC(=C(C=C5)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OCCC3=CC(=C(C=C3)O)O)O)O[C@H]4[C@@H]([C@](CO4)(CO)O)O)OC(=O)/C=C/C5=CC(=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C34H44O19/c1-15-24(41)25(42)26(43)31(50-15)48-12-22-28(52-23(40)7-4-16-2-5-18(36)20(38)10-16)29(53-33-30(45)34(46,13-35)14-49-33)27(44)32(51-22)47-9-8-17-3-6-19(37)21(39)11-17/h2-7,10-11,15,22,24-33,35-39,41-46H,8-9,12-14H2,1H3/b7-4+/t15-,22+,24-,25+,26+,27+,28+,29+,30-,31+,32+,33-,34+/m0/s1
• InChI Key: DBGPKDZQZSWQHV-ZOOOYETHSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₁₉
• Molecular Weight: 756.70 g/mol
• Exact Mass: 756.24767917 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

• 135010-61-6
• 1-O-beta-(3,4-Dihydroxy-beta-phenyl)ethyl-4'-caffeoyl-beta-apiosyl(1-3')-alpha-rhamnosyl(1-6')glucopyranoside
• beta-D-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-D-apio-beta-D-furanosyl-(1-3)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-6))-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-
• [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5263	52.63%
Caco-2	-	0.9011	90.11%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.8122	81.22%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7568	75.68%
P-glycoprotein inhibitior	+	0.5770	57.70%
P-glycoprotein substrate	+	0.5708	57.08%
CYP3A4 substrate	+	0.7022	70.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8726	87.26%
CYP3A4 inhibition	-	0.8812	88.12%
CYP2C9 inhibition	-	0.8041	80.41%
CYP2C19 inhibition	-	0.8473	84.73%
CYP2D6 inhibition	-	0.8883	88.83%
CYP1A2 inhibition	-	0.8622	86.22%
CYP2C8 inhibition	+	0.7497	74.97%
CYP inhibitory promiscuity	-	0.7293	72.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5562	55.62%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.8045	80.45%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7107	71.07%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8197	81.97%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9292	92.92%
Acute Oral Toxicity (c)	III	0.7069	70.69%
Estrogen receptor binding	+	0.7860	78.60%
Androgen receptor binding	-	0.6079	60.79%
Thyroid receptor binding	+	0.5143	51.43%
Glucocorticoid receptor binding	+	0.5967	59.67%
Aromatase binding	+	0.5568	55.68%
PPAR gamma	+	0.7131	71.31%
Honey bee toxicity	-	0.6783	67.83%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.7829	78.29%

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	99.86%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.93%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.66%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.59%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	96.12%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.74%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.71%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.24%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.05%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.17%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.22%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.24%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.61%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.47%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.73%	96.95%
CHEMBL3194	P02766	Transthyretin	84.01%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.31%	80.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.73%	95.89%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.15%	96.37%
CHEMBL4581	P52732	Kinesin-like protein 1	80.90%	93.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.31%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.09%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.06%	94.33%

Plants that contains it

• Pedicularis muscicola
• Pedicularis spicata
• Pedicularis striata

Cross-Links

• PubChem: 6449948
• LOTUS: LTS0112739
• wikiData: Q105160772