[2-(Hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 3-hydroxy-4-methoxybenzoate

Details

• Internal ID: 17fcff25-474b-477b-956f-f93050684247
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [2-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] 3-hydroxy-4-methoxybenzoate
• SMILES (Canonical): COC1=C(C=C(C=C1)C(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C(=O)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O
• InChI: InChI=1S/C23H28O13/c1-31-12-3-2-9(6-11(12)26)20(30)34-18-10-4-5-32-21(14(10)23(8-25)19(18)36-23)35-22-17(29)16(28)15(27)13(7-24)33-22/h2-6,10,13-19,21-22,24-29H,7-8H2,1H3
• InChI Key: DSVKJARKMOAAKJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₃
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.15299094 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.01
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 6-Isovanillylcatalpol
• [1a-(hydroxymethyl)-2-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2,5a,6,6a-tetrahydro-1bH-oxireno[[?]:[?]]cyclopenta[[?]]pyran-6-yl] 3-hydroxy-4-methoxy-benzoate
• 2-(Hexopyranosyloxy)-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-6-yl 3-hydroxy-4-methoxybenzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6435	64.35%
Caco-2	-	0.8940	89.40%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5653	56.53%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.7993	79.93%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7743	77.43%
P-glycoprotein inhibitior	-	0.6211	62.11%
P-glycoprotein substrate	-	0.5367	53.67%
CYP3A4 substrate	+	0.6796	67.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.8901	89.01%
CYP2C9 inhibition	-	0.8604	86.04%
CYP2C19 inhibition	-	0.7030	70.30%
CYP2D6 inhibition	-	0.8722	87.22%
CYP1A2 inhibition	-	0.8509	85.09%
CYP2C8 inhibition	+	0.6795	67.95%
CYP inhibitory promiscuity	-	0.7046	70.46%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5543	55.43%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9372	93.72%
Skin irritation	-	0.7812	78.12%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5408	54.08%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.5852	58.52%
Acute Oral Toxicity (c)	III	0.5594	55.94%
Estrogen receptor binding	+	0.6951	69.51%
Androgen receptor binding	-	0.5460	54.60%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4649	46.49%
Aromatase binding	+	0.5827	58.27%
PPAR gamma	+	0.7007	70.07%
Honey bee toxicity	-	0.7858	78.58%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7049	70.49%
Fish aquatic toxicity	+	0.6878	68.78%

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	97.88%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.60%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.50%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.80%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	93.09%	91.49%
CHEMBL4208	P20618	Proteasome component C5	91.78%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.67%	99.17%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL3194	P02766	Transthyretin	89.04%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.02%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.99%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.34%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.60%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.58%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.41%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.24%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.20%	86.92%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.45%	96.90%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.74%	91.07%
CHEMBL5255	O00206	Toll-like receptor 4	82.03%	92.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.70%	95.83%

Plants that contains it

• Veronica turrilliana

Cross-Links

• PubChem: 495171
• LOTUS: LTS0097860
• wikiData: Q104988051