Auriculatin

Details

• Internal ID: 152922e8-614b-4ca4-85d6-0467b2ee26fd
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 7-(2,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=C(C=C(C=C4)O)O)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=C(C=C(C=C4)O)O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C25H24O6/c1-13(2)5-7-17-23-16(9-10-25(3,4)31-23)21(28)20-22(29)18(12-30-24(17)20)15-8-6-14(26)11-19(15)27/h5-6,8-12,26-28H,7H2,1-4H3
• InChI Key: IEKQCBVQJGWJRO-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₆
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.15728848 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.27
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 20387-73-9
• 7-(2,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
• NSC285657
• S9EN4D8F6C
• NSC 285657
• NSC-285657
• 7-(2,4-Dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methyl-2-butenyl)-2H,6H-benzo[1,2-b
• UNII-S9EN4D8F6C
• SCHEMBL3130630
• CHEMBL4217183
• DTXSID10174322
• CHEBI:178567
• LMPK12050315
• XA161660
• 2H,6H-BENZO(1,2-B:5,4-B')DIPYRAN-6-ONE, 7-(2,4-DIHYDROXYPHENYL)-5-HYDROXY-2,2-DIMETHYL-10-(3-METHYL-2-BUTENYL)-
• 7-(2,4-DIHYDROXYPHENYL)-5-HYDROXY-2,2-DIMETHYL-10-(3-METHYL-2-BUTENYL)-2H,6H-BENZO(1,2-B:5,4-B')DIPYRAN-6-ONE
• 7-(2,4-Dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-2H,6H-pyrano[3,2-g]chromen-6-one
• NCGC00384972-01!7-(2,4-dihydroxyphenyl)-5-hydroxy-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	-	0.5921	59.21%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7533	75.33%
OATP2B1 inhibitior	-	0.5666	56.66%
OATP1B1 inhibitior	+	0.8550	85.50%
OATP1B3 inhibitior	+	0.9068	90.68%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8594	85.94%
P-glycoprotein inhibitior	+	0.6857	68.57%
P-glycoprotein substrate	-	0.5113	51.13%
CYP3A4 substrate	+	0.6343	63.43%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.6518	65.18%
CYP2C9 inhibition	+	0.8955	89.55%
CYP2C19 inhibition	+	0.8886	88.86%
CYP2D6 inhibition	-	0.8828	88.28%
CYP1A2 inhibition	+	0.5462	54.62%
CYP2C8 inhibition	+	0.6463	64.63%
CYP inhibitory promiscuity	+	0.9135	91.35%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6150	61.50%
Eye corrosion	-	0.9911	99.11%
Eye irritation	+	0.6158	61.58%
Skin irritation	-	0.7131	71.31%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	+	0.5563	55.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7217	72.17%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5301	53.01%
skin sensitisation	-	0.7288	72.88%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6664	66.64%
Acute Oral Toxicity (c)	III	0.7045	70.45%
Estrogen receptor binding	+	0.9410	94.10%
Androgen receptor binding	+	0.8205	82.05%
Thyroid receptor binding	+	0.7008	70.08%
Glucocorticoid receptor binding	+	0.8500	85.00%
Aromatase binding	+	0.7329	73.29%
PPAR gamma	+	0.8756	87.56%
Honey bee toxicity	-	0.7932	79.32%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9921	99.21%

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	99.85%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.79%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.64%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.57%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.03%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.99%	94.73%
CHEMBL4208	P20618	Proteasome component C5	89.84%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.16%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	88.69%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.37%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.64%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.76%	99.17%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.99%	80.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.95%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.68%	99.15%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.77%	91.38%
CHEMBL221	P23219	Cyclooxygenase-1	80.44%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.35%	95.89%

Plants that contains it

• Anthotroche myoporoides
• Astragalus flexus
• Erythrina bidwillii
• Erythrina senegalensis
• Erythrina sigmoidea
• Erythrina variegata
• Erythrina vogelii
• Helenium virginicum
• Heliotropium digynum
• Hypericum caprifoliatum
• Millettia extensa
• Nannoglottis ravida
• Ormosia monosperma

Cross-Links

• PubChem: 5358847
• NPASS: NPC200625
• LOTUS: LTS0152052
• wikiData: Q83044398