4'-O-Methylglabridin

Details

• Internal ID: ec8de2a4-2bf4-4890-8eef-79955018fd00
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Pyranoisoflavonoids
• IUPAC Name: 2-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]-5-methoxyphenol
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OCC(C3)C4=C(C=C(C=C4)OC)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC[C@H](C3)C4=C(C=C(C=C4)OC)O)C
• InChI: InChI=1S/C21H22O4/c1-21(2)9-8-17-19(25-21)7-4-13-10-14(12-24-20(13)17)16-6-5-15(23-3)11-18(16)22/h4-9,11,14,22H,10,12H2,1-3H3/t14-/m0/s1
• InChI Key: ZZAIPFIGEGQNHP-AWEZNQCLSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.15180918 g/mol
• Topological Polar Surface Area (TPSA): 47.90 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.30
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 4'-O-Methylglabridin
• EL27NKY4TA
• UNII-EL27NKY4TA
• 68978-09-6
• 2-((3R)-3,4-Dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-5-methoxyphenol
• Phenol, 2-((3R)-3,4-dihydro-8,8-dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-5-methoxy-
• CHEMBL511536
• SCHEMBL13794191
• DTXSID001315155

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9739	97.39%
Caco-2	+	0.9118	91.18%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8262	82.62%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.9062	90.62%
OATP1B3 inhibitior	+	0.9780	97.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8601	86.01%
P-glycoprotein inhibitior	-	0.4794	47.94%
P-glycoprotein substrate	+	0.6380	63.80%
CYP3A4 substrate	+	0.6690	66.90%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	+	0.3827	38.27%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.6000	60.00%
CYP2C19 inhibition	+	0.9012	90.12%
CYP2D6 inhibition	-	0.7460	74.60%
CYP1A2 inhibition	+	0.6118	61.18%
CYP2C8 inhibition	+	0.5912	59.12%
CYP inhibitory promiscuity	+	0.7648	76.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.6190	61.90%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.6291	62.91%
Skin irritation	-	0.8244	82.44%
Skin corrosion	-	0.9634	96.34%
Ames mutagenesis	+	0.5463	54.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6477	64.77%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8706	87.06%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7529	75.29%
Acute Oral Toxicity (c)	III	0.4262	42.62%
Estrogen receptor binding	+	0.9570	95.70%
Androgen receptor binding	+	0.6592	65.92%
Thyroid receptor binding	+	0.7995	79.95%
Glucocorticoid receptor binding	+	0.5720	57.20%
Aromatase binding	+	0.5321	53.21%
PPAR gamma	+	0.8360	83.60%
Honey bee toxicity	-	0.7992	79.92%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9733	97.33%

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	99.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.07%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.86%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.96%	93.40%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.08%	99.15%
CHEMBL2581	P07339	Cathepsin D	93.82%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	93.61%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.97%	95.89%
CHEMBL4208	P20618	Proteasome component C5	92.29%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.76%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.54%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.14%	97.09%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	89.42%	100.00%
CHEMBL1907	P15144	Aminopeptidase N	89.33%	93.31%
CHEMBL233	P35372	Mu opioid receptor	89.23%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.69%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.13%	94.00%
CHEMBL236	P41143	Delta opioid receptor	88.09%	99.35%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.67%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.04%	93.99%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.03%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.38%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.20%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.28%	95.89%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.96%	96.69%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	82.21%	94.67%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.12%	89.05%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.10%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.81%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	80.86%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.54%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.14%	95.71%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza uralensis
• Mitracarpus hirtus
• Zingiber officinale

Cross-Links

• PubChem: 9927807
• NPASS: NPC68205
• LOTUS: LTS0211997
• wikiData: Q105386615