Jamaicin

Details

• Internal ID: 39904cb7-6d3c-432c-b2c2-70912ee55291
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Pyranoisoflavonoids
• IUPAC Name: 3-(6-methoxy-1,3-benzodioxol-5-yl)-8,8-dimethylpyrano[2,3-f]chromen-4-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OC=C(C3=O)C4=CC5=C(C=C4OC)OCO5)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC=C(C3=O)C4=CC5=C(C=C4OC)OCO5)C
• InChI: InChI=1S/C22H18O6/c1-22(2)7-6-12-16(28-22)5-4-13-20(23)15(10-25-21(12)13)14-8-18-19(27-11-26-18)9-17(14)24-3/h4-10H,11H2,1-3H3
• InChI Key: WITLAWYGGVAFLU-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₆
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.11033829 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.38
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• AnCoA4
• 24211-36-7
• 3-(6-Methoxy-1,3-benzodioxol-5-yl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
• 3-(6-Methoxy-1,3-benzodioxol-5-yl)-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b]dipyran-4-one
• 3-(6-Methoxybenzo[d][1,3]dioxol-5-yl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one
• AnCoA-4
• starbld0000871
• An Co A4
• An-Co-A4
• MEGxp0_001337
• SCHEMBL9924622
• CHEMBL3758966
• ACon1_001789
• BCP17379
• LMPK12050075
• AKOS040745562
• NCGC00180139-01
• AC-36956
• An-Co-A4; An Co A4; AnCoA-4; Jamaicin
• J-015401
• BRD-K76773944-001-01-3
• 3-(6-methoxy-1,3-benzodioxol-5-yl)-8,8-dimethylpyrano[2,3-f]chromen-4-one
• 3-[2-Methoxy-4,5-(methylenedioxy)phenyl]-8,8-dimethyl-4H,8H-Benzo[1,2-b:3,4-b']dipyran-4-one
• NCGC00180139-02!3-(6-methoxy-1,3-benzodioxol-5-yl)-8,8-dimethylpyrano[2,3-f]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.6939	69.39%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7730	77.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9298	92.98%
OATP1B3 inhibitior	+	0.9564	95.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8783	87.83%
P-glycoprotein inhibitior	+	0.9269	92.69%
P-glycoprotein substrate	-	0.7226	72.26%
CYP3A4 substrate	+	0.6376	63.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8223	82.23%
CYP3A4 inhibition	+	0.9676	96.76%
CYP2C9 inhibition	+	0.6848	68.48%
CYP2C19 inhibition	+	0.9288	92.88%
CYP2D6 inhibition	+	0.5597	55.97%
CYP1A2 inhibition	-	0.6490	64.90%
CYP2C8 inhibition	-	0.6108	61.08%
CYP inhibitory promiscuity	+	0.9229	92.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4045	40.45%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.6966	69.66%
Skin irritation	-	0.8041	80.41%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7693	76.93%
Micronuclear	+	0.6774	67.74%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7215	72.15%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.6874	68.74%
Acute Oral Toxicity (c)	III	0.5168	51.68%
Estrogen receptor binding	+	0.9524	95.24%
Androgen receptor binding	+	0.7769	77.69%
Thyroid receptor binding	+	0.7593	75.93%
Glucocorticoid receptor binding	+	0.8859	88.59%
Aromatase binding	+	0.5688	56.88%
PPAR gamma	+	0.8163	81.63%
Honey bee toxicity	-	0.7928	79.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9858	98.58%

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	99.11%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.80%	96.77%
CHEMBL2581	P07339	Cathepsin D	97.54%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.24%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.59%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.08%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.34%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.47%	86.33%
CHEMBL2535	P11166	Glucose transporter	89.84%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.11%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.52%	97.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.60%	94.80%
CHEMBL4208	P20618	Proteasome component C5	85.97%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.03%	95.89%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	84.63%	80.96%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.65%	89.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.64%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	83.54%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.20%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.87%	93.99%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.67%	82.67%

Plants that contains it

• Isodon rubescens
• Millettia dura
• Millettia ferruginea
• Millettia griffoniana
• Millettia ichthyochtona
• Millettia pachyloba
• Millettia usaramensis
• Piscidia piscipula

Cross-Links

• PubChem: 12304682
• NPASS: NPC273021
• LOTUS: LTS0192104
• wikiData: Q104395449