Acicerone

Details

• Internal ID: 7b478d8c-5f70-4cbc-bf01-ebee8b9d1882
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 7-O-methylated isoflavonoids > 7-O-methylisoflavones
• IUPAC Name: 3-(1,3-benzodioxol-5-yl)-6-hydroxy-7-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)OC=C(C2=O)C3=CC4=C(C=C3)OCO4)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)OC=C(C2=O)C3=CC4=C(C=C3)OCO4)O
• InChI: InChI=1S/C17H12O6/c1-20-15-6-14-10(5-12(15)18)17(19)11(7-21-14)9-2-3-13-16(4-9)23-8-22-13/h2-7,18H,8H2,1H3
• InChI Key: WKFSLLANSCHECV-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₆
• Molecular Weight: 312.27 g/mol
• Exact Mass: 312.06338810 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 2746-86-3
• 6-Hydroxy-7-methoxy-3',4'-methylenedioxyisoflavone
• 3-(Benzo[d][1,3]dioxol-5-yl)-6-hydroxy-7-methoxy-4H-chromen-4-one
• SCHEMBL29365787
• FA65457
• 3-(1,3-benzodioxol-5-yl)-6-hydroxy-7-methoxy-chromen-4-one
• 3-(1,3-benzodioxol-5-yl)-6-hydroxy-7-methoxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9849	98.49%
Caco-2	+	0.8192	81.92%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8138	81.38%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.9459	94.59%
OATP1B3 inhibitior	+	0.9711	97.11%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6496	64.96%
P-glycoprotein inhibitior	-	0.4407	44.07%
P-glycoprotein substrate	-	0.8556	85.56%
CYP3A4 substrate	+	0.5730	57.30%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.8058	80.58%
CYP3A4 inhibition	+	0.8527	85.27%
CYP2C9 inhibition	+	0.8760	87.60%
CYP2C19 inhibition	+	0.8680	86.80%
CYP2D6 inhibition	+	0.6119	61.19%
CYP1A2 inhibition	-	0.5473	54.73%
CYP2C8 inhibition	-	0.6151	61.51%
CYP inhibitory promiscuity	+	0.8201	82.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4163	41.63%
Eye corrosion	-	0.9811	98.11%
Eye irritation	-	0.6155	61.55%
Skin irritation	-	0.7070	70.70%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7771	77.71%
Micronuclear	+	0.8674	86.74%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8283	82.83%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4883	48.83%
Acute Oral Toxicity (c)	III	0.6682	66.82%
Estrogen receptor binding	+	0.9307	93.07%
Androgen receptor binding	+	0.8391	83.91%
Thyroid receptor binding	+	0.5511	55.11%
Glucocorticoid receptor binding	+	0.8376	83.76%
Aromatase binding	+	0.7659	76.59%
PPAR gamma	+	0.8224	82.24%
Honey bee toxicity	-	0.8336	83.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	+	0.9082	90.82%

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	99.03%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.27%	96.77%
CHEMBL2581	P07339	Cathepsin D	97.62%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.96%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.42%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.99%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL3438	Q05513	Protein kinase C zeta	89.26%	88.48%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	88.68%	82.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.94%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	87.69%	94.75%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.65%	80.96%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.30%	92.62%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.92%	80.78%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.85%	95.78%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.66%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.48%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.85%	96.09%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	83.22%	93.24%
CHEMBL2535	P11166	Glucose transporter	82.85%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.12%	96.00%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.02%	85.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.89%	99.17%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.65%	95.53%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.46%	90.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.46%	94.80%

Plants that contains it

• Ageratina petiolaris
• Artemisia carvifolia
• Astragalus cicer

Cross-Links

• PubChem: 24721438
• NPASS: NPC48971
• LOTUS: LTS0163083
• wikiData: Q105307301