Pimentol

Details

• Internal ID: f14e3f16-6873-44f6-8dfb-f21631ac46dd
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxy-3-methoxy-5-prop-2-enylphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• SMILES (Canonical): COC1=C(C(=CC(=C1)CC=C)OC2C(C(C(C(O2)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C(=CC(=C1)CC=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C3=CC(=C(C(=C3)O)O)O)O)O)O)O
• InChI: InChI=1S/C23H26O12/c1-3-4-10-5-14(32-2)18(27)15(6-10)34-23-21(30)20(29)19(28)16(35-23)9-33-22(31)11-7-12(24)17(26)13(25)8-11/h3,5-8,16,19-21,23-30H,1,4,9H2,2H3/t16-,19-,20+,21-,23-/m1/s1
• InChI Key: LFQREKVEOMIWQF-JTLUYSSBSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₁₂
• Molecular Weight: 494.40 g/mol
• Exact Mass: 494.14242626 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.29
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• Ericifolin
• 141913-95-3
• UNII-3U53LNA6A3
• 3U53LNA6A3
• [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-hydroxy-3-methoxy-5-prop-2-enylphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
• beta-D-Glucopyranoside, 2-hydroxy-3-methoxy-5-(2-propenyl)phenyl, 6-(3,4,5-trihydroxybenzoate)
• CHEMBL498040
• DTXSID50161857
• CHEBI:175810
• AKOS040735861
• Q27258035
• .BETA.-D-GLUCOPYRANOSIDE, 2-HYDROXY-3-METHOXY-5-(2-PROPENYL)PHENYL, 6-(3,4,5-TRIHYDROXYBENZOATE)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5835	58.35%
Caco-2	-	0.8831	88.31%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6537	65.37%
OATP2B1 inhibitior	-	0.8461	84.61%
OATP1B1 inhibitior	-	0.3416	34.16%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8442	84.42%
P-glycoprotein inhibitior	-	0.5206	52.06%
P-glycoprotein substrate	-	0.7542	75.42%
CYP3A4 substrate	+	0.6187	61.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8316	83.16%
CYP3A4 inhibition	-	0.5440	54.40%
CYP2C9 inhibition	-	0.7858	78.58%
CYP2C19 inhibition	-	0.7739	77.39%
CYP2D6 inhibition	-	0.8872	88.72%
CYP1A2 inhibition	-	0.8126	81.26%
CYP2C8 inhibition	+	0.7799	77.99%
CYP inhibitory promiscuity	-	0.5903	59.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7304	73.04%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7557	75.57%
Micronuclear	+	0.6866	68.66%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8166	81.66%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.9265	92.65%
Acute Oral Toxicity (c)	III	0.7569	75.69%
Estrogen receptor binding	+	0.7626	76.26%
Androgen receptor binding	-	0.5452	54.52%
Thyroid receptor binding	+	0.5144	51.44%
Glucocorticoid receptor binding	+	0.6898	68.98%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5932	59.32%
Honey bee toxicity	-	0.8089	80.89%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9517	95.17%

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	98.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.59%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.13%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.14%	95.17%
CHEMBL3401	O75469	Pregnane X receptor	89.70%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.55%	95.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.20%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.84%	92.62%
CHEMBL3194	P02766	Transthyretin	86.79%	90.71%
CHEMBL2581	P07339	Cathepsin D	85.52%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.34%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.70%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.67%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.32%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.15%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.76%	96.00%
CHEMBL4208	P20618	Proteasome component C5	81.74%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.55%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.50%	96.90%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.92%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	80.46%	91.19%

Plants that contains it

• Albertisia papuana
• Artemisia biennis
• Astragalus asper
• Aulacomnium androgynum
• Cosmos pringlei
• Dahlstedtia araripensis
• Daphnopsis macrophylla
• Derris trifoliata
• Dioscorea althaeoides
• Drimia maritima
• Erythrina sacleuxii
• Ficus salicifolia
• Gardneria nutans
• Glycyrrhiza lepidota
• Lafoensia glyptocarpa
• Lonchocarpus parviflorus
• Magnolia sprengeri
• Melaleuca ericifolia
• Osteophloeum platyspermum
• Pimenta dioica
• Taraxacum bicorne
• Valeriana fedtschenkoi

Cross-Links

• PubChem: 9917512
• NPASS: NPC239966
• LOTUS: LTS0274998
• wikiData: Q27258035