4-Hydroxy-3-prenylbenzoic acid glucoside

Details

• Internal ID: edb1c5af-3274-4e23-907a-0beed782937d
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 3-(3-methylbut-2-enyl)-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)C(=O)O)OC2C(C(C(C(O2)CO)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)C(=O)O)OC2C(C(C(C(O2)CO)O)O)O)C
• InChI: InChI=1S/C18H24O8/c1-9(2)3-4-10-7-11(17(23)24)5-6-12(10)25-18-16(22)15(21)14(20)13(8-19)26-18/h3,5-7,13-16,18-22H,4,8H2,1-2H3,(H,23,24)
• InChI Key: ZTHSABILDCCHJR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₈
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.14711772 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• CHEBI:175737
• 3-(3-methylbut-2-enyl)-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7442	74.42%
Caco-2	-	0.8076	80.76%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	0.7183	71.83%
OATP1B1 inhibitior	+	0.9245	92.45%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6405	64.05%
P-glycoprotein inhibitior	-	0.8660	86.60%
P-glycoprotein substrate	-	0.9097	90.97%
CYP3A4 substrate	-	0.5354	53.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.8706	87.06%
CYP2C9 inhibition	-	0.6264	62.64%
CYP2C19 inhibition	-	0.5808	58.08%
CYP2D6 inhibition	-	0.7378	73.78%
CYP1A2 inhibition	+	0.5238	52.38%
CYP2C8 inhibition	+	0.4751	47.51%
CYP inhibitory promiscuity	+	0.5627	56.27%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7918	79.18%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9011	90.11%
Skin irritation	-	0.8000	80.00%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.7323	73.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.7469	74.69%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.6610	66.10%
skin sensitisation	-	0.7551	75.51%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.4893	48.93%
Acute Oral Toxicity (c)	III	0.6687	66.87%
Estrogen receptor binding	+	0.6083	60.83%
Androgen receptor binding	-	0.6764	67.64%
Thyroid receptor binding	-	0.6125	61.25%
Glucocorticoid receptor binding	+	0.5400	54.00%
Aromatase binding	+	0.5765	57.65%
PPAR gamma	+	0.5982	59.82%
Honey bee toxicity	-	0.8683	86.83%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8800	88.00%
Fish aquatic toxicity	+	0.9591	95.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	94.06%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.49%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.67%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.54%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.89%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.95%	96.09%
CHEMBL3194	P02766	Transthyretin	88.63%	90.71%
CHEMBL2581	P07339	Cathepsin D	86.85%	98.95%
CHEMBL4208	P20618	Proteasome component C5	82.58%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.60%	95.56%

Plants that contains it

• Prunus dulcis

Cross-Links

• PubChem: 12312707
• LOTUS: LTS0237706
• wikiData: Q105382928