Gancaonin I

Details

• Internal ID: 6af5e572-13e4-4526-b8ac-b4f51e1b6cd7
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[4,6-dimethoxy-5-(3-methylbut-2-enyl)-1-benzofuran-2-yl]benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=C2C(=C1OC)C=C(O2)C3=C(C=C(C=C3)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=C2C(=C1OC)C=C(O2)C3=C(C=C(C=C3)O)O)OC)C
• InChI: InChI=1S/C21H22O5/c1-12(2)5-7-15-18(24-3)11-20-16(21(15)25-4)10-19(26-20)14-8-6-13(22)9-17(14)23/h5-6,8-11,22-23H,7H2,1-4H3
• InChI Key: DKVBYQAVNNRVNN-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.10 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.04
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 126716-36-7
• 6XTP69UV3S
• 4-(4,6-Dimethoxy-5-(3-methyl-but-2-enyl)-benzofuran-2-yl)-benzene-1,3-diol
• UNII-6XTP69UV3S
• 4-[4,6-dimethoxy-5-(3-methylbut-2-enyl)-1-benzofuran-2-yl]benzene-1,3-diol
• CHEMBL3808735
• CHEBI:69099
• DTXSID90155275
• 1,3-BENZENEDIOL, 4-(4,6-DIMETHOXY-5-(3-METHYL-2-BUTEN-1-YL)-2-BENZOFURANYL)-
• 4-(4,6-DIMETHOXY-5-(3-METHYL-2-BUTEN-1-YL)-2-BENZOFURANYL)-1,3-BENZENEDIOL
• 4-(4,6-dimethoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl)benzene-1,3-diol
• 4-[4,6-Dimethoxy-5-(3-methyl-but-2-enyl)-benzofuran-2-yl]-benzene-1,3-diol
• 4-[4,6-dimethoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol
• DTXCID6077766
• SCHEMBL22704765
• BDBM50539739
• LMPK12160046
• AKOS032949097
• NCGC00385808-01
• Q27137440
• 2-(3,4-Dihydroxyphenyl)-4,6-dimethoxy-5-prenylbenzofuran
• 4-[4,6-dimethoxy-5-(3-methylbut-2-enyl)benzofuran-2-yl]benzene-1,3-diol
• 4-[4,6-Dimethoxy-5-(3-methyl-2-butenyl)-2-benzofuranyl]-1,3-benzenediol, 9CI
• NCGC00385808-01_C21H22O5_4-[4,6-Dimethoxy-5-(3-methyl-2-buten-1-yl)-1-benzofuran-2-yl]-1,3-benzenediol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.8212	82.12%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6263	62.63%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.8510	85.10%
OATP1B3 inhibitior	+	0.8827	88.27%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7895	78.95%
P-glycoprotein inhibitior	+	0.6487	64.87%
P-glycoprotein substrate	+	0.6419	64.19%
CYP3A4 substrate	+	0.5603	56.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4182	41.82%
CYP3A4 inhibition	+	0.5738	57.38%
CYP2C9 inhibition	+	0.8857	88.57%
CYP2C19 inhibition	+	0.8953	89.53%
CYP2D6 inhibition	-	0.6585	65.85%
CYP1A2 inhibition	+	0.8882	88.82%
CYP2C8 inhibition	+	0.7722	77.22%
CYP inhibitory promiscuity	+	0.9873	98.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4477	44.77%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.5627	56.27%
Skin irritation	-	0.7937	79.37%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3968	39.68%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.7788	77.88%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8956	89.56%
Acute Oral Toxicity (c)	III	0.6102	61.02%
Estrogen receptor binding	+	0.9541	95.41%
Androgen receptor binding	+	0.8236	82.36%
Thyroid receptor binding	+	0.7736	77.36%
Glucocorticoid receptor binding	+	0.8979	89.79%
Aromatase binding	+	0.7223	72.23%
PPAR gamma	+	0.9380	93.80%
Honey bee toxicity	-	0.7855	78.55%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9945	99.45%

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%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.83%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.79%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.78%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.97%	94.00%
CHEMBL3194	P02766	Transthyretin	89.55%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	89.35%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.52%	89.00%
CHEMBL2535	P11166	Glucose transporter	87.57%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.54%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	85.25%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.85%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.62%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.71%	99.15%
CHEMBL5747	Q92793	CREB-binding protein	81.82%	95.12%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.33%	96.09%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 480777
• NPASS: NPC37226
• LOTUS: LTS0174681
• wikiData: Q27137440