[6,7-dihydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxybenzoate

Details

• Internal ID: 4dfac85f-d556-4e5c-a44b-5d7e46fe6c60
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [6,7-dihydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxybenzoate
• SMILES (Canonical): C1=COC(C2C1C(C(C2(CO)O)O)OC(=O)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C(C2(CO)O)O)OC(=O)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
• InChI: InChI=1S/C22H28O13/c23-7-12-14(26)15(27)16(28)21(33-12)35-20-13-11(5-6-32-20)17(18(29)22(13,31)8-24)34-19(30)9-1-3-10(25)4-2-9/h1-6,11-18,20-21,23-29,31H,7-8H2
• InChI Key: LUGJLRPURFUBRI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₃
• Molecular Weight: 500.40 g/mol
• Exact Mass: 500.15299094 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -3.07
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5822	58.22%
Caco-2	-	0.9224	92.24%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5469	54.69%
OATP2B1 inhibitior	-	0.7162	71.62%
OATP1B1 inhibitior	+	0.7713	77.13%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7365	73.65%
P-glycoprotein inhibitior	-	0.6813	68.13%
P-glycoprotein substrate	-	0.7362	73.62%
CYP3A4 substrate	+	0.6368	63.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8546	85.46%
CYP3A4 inhibition	-	0.9197	91.97%
CYP2C9 inhibition	-	0.9482	94.82%
CYP2C19 inhibition	-	0.8346	83.46%
CYP2D6 inhibition	-	0.8656	86.56%
CYP1A2 inhibition	-	0.9075	90.75%
CYP2C8 inhibition	+	0.6960	69.60%
CYP inhibitory promiscuity	-	0.8525	85.25%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9367	93.67%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6025	60.25%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8181	81.81%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5590	55.90%
Acute Oral Toxicity (c)	III	0.5135	51.35%
Estrogen receptor binding	+	0.6726	67.26%
Androgen receptor binding	-	0.4834	48.34%
Thyroid receptor binding	+	0.5646	56.46%
Glucocorticoid receptor binding	-	0.5334	53.34%
Aromatase binding	+	0.6929	69.29%
PPAR gamma	+	0.7070	70.70%
Honey bee toxicity	-	0.7580	75.80%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.6642	66.42%

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	95.82%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.77%	86.33%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	90.68%	94.97%
CHEMBL4208	P20618	Proteasome component C5	90.40%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.91%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	88.07%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.58%	99.17%
CHEMBL3194	P02766	Transthyretin	87.41%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.78%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.38%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.13%	89.00%
CHEMBL2581	P07339	Cathepsin D	84.67%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.54%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	83.68%	91.49%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.14%	95.83%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.11%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.04%	97.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.82%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.75%	94.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.95%	94.23%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	80.13%	93.00%

Plants that contains it

• Catalpa bignonioides

Cross-Links

• PubChem: 51136432
• LOTUS: LTS0010728
• wikiData: Q105157407