Teupolioside

Details

• Internal ID: 869ffbe1-1d74-4711-b997-067716ad232a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C35H46O20/c1-14-24(43)27(46)32(55-34-28(47)26(45)25(44)21(12-36)51-34)35(50-14)54-31-29(48)33(49-9-8-16-3-6-18(39)20(41)11-16)52-22(13-37)30(31)53-23(42)7-4-15-2-5-17(38)19(40)10-15/h2-7,10-11,14,21-22,24-41,43-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25-,26-,27+,28+,29+,30+,31+,32+,33+,34-,35-/m0/s1
• InChI Key: SDRRSTAVRUERNC-GUTOYVNHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₆O₂₀
• Molecular Weight: 786.70 g/mol
• Exact Mass: 786.25824385 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -3.19
• H-Bond Acceptor: 20
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

• Lamiuside A
• 143617-02-1
• trans-Lamalboside
• Teupolioside HTN
• Teupolioside, (-)-
• 88458S9198
• (2R,3R,4R,5R,6R)-4-(((2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl (E)-3-(3,4-dihydroxyphenyl)acrylate
• UNII-88458S9198
• TEUPOLIOSIDE [INCI]
• DTXSID50162480
• AKOS040754176
• beta-d-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-beta-d-galactopyranosyl-(1-2)-O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-, 4-((2E)-3-(3,4-dihydroxyphenyl)-2-propenoate)
• beta-d-Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-beta-d-galactopyranosyl-(1-2)-O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (E)-
• XT178243
• Q27269886
• .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL O-.BETA.-D-GALACTOPYRANOSYL-(1-2)-O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-3)-, 4-((2E)-3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE)
• .BETA.-D-GLUCOPYRANOSIDE, 2-(3,4-DIHYDROXYPHENYL)ETHYL O-.BETA.-D-GALACTOPYRANOSYL-(1-2)-O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1-3)-, 4-(3-(3,4-DIHYDROXYPHENYL)-2-PROPENOATE), (E)-
• [(2R,3R,4R,5R,6R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)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	-	0.7512	75.12%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7836	78.36%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8682	86.82%
OATP1B3 inhibitior	+	0.9632	96.32%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8593	85.93%
P-glycoprotein inhibitior	-	0.4531	45.31%
P-glycoprotein substrate	-	0.5840	58.40%
CYP3A4 substrate	+	0.6676	66.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.7548	75.48%
CYP2C19 inhibition	-	0.8660	86.60%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8666	86.66%
CYP2C8 inhibition	+	0.7166	71.66%
CYP inhibitory promiscuity	-	0.7002	70.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6737	67.37%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9110	91.10%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7739	77.39%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.8442	84.42%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.9678	96.78%
Acute Oral Toxicity (c)	III	0.7702	77.02%
Estrogen receptor binding	+	0.7902	79.02%
Androgen receptor binding	-	0.7047	70.47%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	+	0.5637	56.37%
Aromatase binding	+	0.5374	53.74%
PPAR gamma	+	0.7110	71.10%
Honey bee toxicity	-	0.6521	65.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7970	79.70%

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	99.72%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.41%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	96.44%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.58%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.38%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.31%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.45%	99.17%
CHEMBL3194	P02766	Transthyretin	93.43%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	93.40%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.83%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.78%	86.92%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.57%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.36%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.61%	96.37%
CHEMBL4208	P20618	Proteasome component C5	80.48%	90.00%

Plants that contains it

• Lamium album
• Lamium purpureum
• Teucrium polium

Cross-Links

• PubChem: 16062094
• LOTUS: LTS0181210
• wikiData: Q27269886