(2R)-2beta-[3-Methoxy-4-(beta-D-glucopyranosyloxy)phenyl]-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-3alpha-methanol

Details

• Internal ID: d08074a8-0a16-4225-bbaa-99143e2364c5
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)CCCO
• SMILES (Isomeric): COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)CCCO
• InChI: InChI=1S/C26H34O11/c1-33-18-10-14(5-6-17(18)35-26-23(32)22(31)21(30)20(12-29)36-26)24-16(11-28)15-8-13(4-3-7-27)9-19(34-2)25(15)37-24/h5-6,8-10,16,20-24,26-32H,3-4,7,11-12H2,1-2H3/t16-,20-,21-,22+,23-,24+,26-/m1/s1
• InChI Key: NYAPVWGUAUDHRY-GAZXPUAESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₁
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.21011190 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5541	55.41%
Caco-2	-	0.8306	83.06%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6698	66.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8027	80.27%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7221	72.21%
P-glycoprotein inhibitior	-	0.4736	47.36%
P-glycoprotein substrate	-	0.5703	57.03%
CYP3A4 substrate	+	0.6487	64.87%
CYP2C9 substrate	-	0.8102	81.02%
CYP2D6 substrate	-	0.7408	74.08%
CYP3A4 inhibition	-	0.9089	90.89%
CYP2C9 inhibition	-	0.8423	84.23%
CYP2C19 inhibition	-	0.8431	84.31%
CYP2D6 inhibition	-	0.8690	86.90%
CYP1A2 inhibition	-	0.8081	80.81%
CYP2C8 inhibition	+	0.7765	77.65%
CYP inhibitory promiscuity	-	0.6844	68.44%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5855	58.55%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9412	94.12%
Skin irritation	-	0.8188	81.88%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7851	78.51%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8936	89.36%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7299	72.99%
Acute Oral Toxicity (c)	III	0.7425	74.25%
Estrogen receptor binding	+	0.8128	81.28%
Androgen receptor binding	+	0.5865	58.65%
Thyroid receptor binding	+	0.5586	55.86%
Glucocorticoid receptor binding	+	0.5615	56.15%
Aromatase binding	-	0.5055	50.55%
PPAR gamma	+	0.5584	55.84%
Honey bee toxicity	-	0.8097	80.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7455	74.55%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.29%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.75%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.95%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.25%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.77%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.69%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.03%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	88.51%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.89%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.33%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.31%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.92%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.76%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.40%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.05%	97.14%

Plants that contains it

• Acer carpinifolium
• Achlys triphylla
• Albizia procera
• Artemisia giraldii
• Berberis japonica
• Bobgunnia madagascariensis
• Bulbophyllum protractum
• Calodendrum capense
• Calystegia pubescens
• Cleistopholis staudtii
• Croton caudatus
• Cypripedium calceolus
• Diospyros japonica
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Elaeocarpus fuscoides
• Epimedium sagittatum
• Galium rubioides
• Helichrysum arenarium
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hortonia floribunda
• Hypericum revolutum
• Isodon nervosus
• Isodon xerophilus
• Jacobaea adonidifolia
• Juniperus communis var. depressa
• Lactuca sativa
• Lampranthus sociorum
• Leuzea centauroides
• Litsea salicifolia
• Lonicera macrantha
• Macaranga tanarius
• Meconopsis horridula
• Mesembryanthemum expansum
• Osmorhiza aristata
• Oxera splendida
• Pedicularis torta
• Perymenium mendezii
• Picea glauca
• Plocama calabrica
• Pongamia pinnata
• Protium tonkinense
• Psychotria serpens
• Pycnandra acuminata
• Seriphidium porrectum
• Stevia eupatoria
• Stipa robusta
• Succisa pratensis
• Tarchonanthus camphoratus
• Trachelospermum asiaticum
• Uncaria rhynchophylla
• Viburnum odoratissimum var. awabuki
• Vitex pinnata

Cross-Links

• PubChem: 10625848
• NPASS: NPC301377
• LOTUS: LTS0133507
• wikiData: Q105187415