Trichosanthoside A

Details

• Internal ID: 1568cb49-3393-4088-9197-71ce51e9654b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides
• IUPAC Name: [(2R,3R,4R,5R,6R)-4-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-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)O)O)OC5C(C(C(CO5)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)O)O[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O
• InChI: InChI=1S/C34H44O19/c1-14-29(52-32-26(44)24(42)21(40)13-48-32)25(43)27(45)34(49-14)53-31-28(46)33(47-9-8-16-3-6-18(37)20(39)11-16)50-22(12-35)30(31)51-23(41)7-4-15-2-5-17(36)19(38)10-15/h2-7,10-11,14,21-22,24-40,42-46H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25-,26+,27+,28+,29-,30+,31+,32-,33+,34-/m0/s1
• InChI Key: LBVGAYBWQMMXPM-AEFXDUGHSA-N
• Popularity: 5 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: -2.00
• Atomic LogP (AlogP): -2.55
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

• ((2R,3R,4R,5R,6R)-4-((2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-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
• [(2R,3R,4R,5R,6R)-4-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-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
• RefChem:191283
• 244207-07-6
• CHEMBL506843

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7025	70.25%
Caco-2	-	0.8937	89.37%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7309	73.09%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.8703	87.03%
OATP1B3 inhibitior	+	0.9547	95.47%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7816	78.16%
P-glycoprotein inhibitior	+	0.5915	59.15%
P-glycoprotein substrate	+	0.5226	52.26%
CYP3A4 substrate	+	0.6859	68.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9168	91.68%
CYP2C9 inhibition	-	0.8684	86.84%
CYP2C19 inhibition	-	0.9206	92.06%
CYP2D6 inhibition	-	0.9026	90.26%
CYP1A2 inhibition	-	0.8912	89.12%
CYP2C8 inhibition	+	0.6887	68.87%
CYP inhibitory promiscuity	-	0.8468	84.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6875	68.75%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9085	90.85%
Skin irritation	-	0.8244	82.44%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7614	76.14%
Micronuclear	-	0.6567	65.67%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8397	83.97%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9761	97.61%
Acute Oral Toxicity (c)	III	0.7951	79.51%
Estrogen receptor binding	+	0.7597	75.97%
Androgen receptor binding	-	0.7445	74.45%
Thyroid receptor binding	+	0.5311	53.11%
Glucocorticoid receptor binding	+	0.5573	55.73%
Aromatase binding	-	0.5082	50.82%
PPAR gamma	+	0.7028	70.28%
Honey bee toxicity	-	0.6648	66.48%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.7225	72.25%

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	99.85%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.13%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.89%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.70%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.55%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.82%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.16%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	90.35%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.17%	99.17%
CHEMBL3194	P02766	Transthyretin	90.12%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	87.64%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.20%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.00%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.88%	97.36%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	84.27%	96.37%
CHEMBL4208	P20618	Proteasome component C5	84.13%	90.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.68%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.39%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.28%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.94%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.60%	90.71%

Plants that contains it

• Globularia bisnagarica
• Globularia trichosantha

Cross-Links

• PubChem: 10652682
• LOTUS: LTS0036707
• wikiData: Q105149658