Dentatin

Details

• Internal ID: 2ee8732a-895a-4c17-bcfb-f4ce5e66f0c1
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: 5-methoxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
• SMILES (Canonical): CC1(C=CC2=C(C3=C(C(=C2O1)C(C)(C)C=C)OC(=O)C=C3)OC)C
• SMILES (Isomeric): CC1(C=CC2=C(C3=C(C(=C2O1)C(C)(C)C=C)OC(=O)C=C3)OC)C
• InChI: InChI=1S/C20H22O4/c1-7-19(2,3)15-17-12(8-9-14(21)23-17)16(22-6)13-10-11-20(4,5)24-18(13)15/h7-11H,1H2,2-6H3
• InChI Key: QBFYQVZGIDUNIY-UHFFFAOYSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.15180918 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.45
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Poncitrin
• 22980-57-0
• NSC 380684
• CHEBI:69939
• NSC380684
• NSC-380684
• 5-methoxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
• 10-(1,1-Dimethyl-allyl)-5-methoxy-8,8-dimethyl-8H-pyrano(3,2-g)chromen-2-one
• 2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 10-(1,1-dimethyl-2-propen-1-yl)-5-methoxy-8,8-dimethyl-
• 10-(1,1-Dimethyl-allyl)-5-methoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one
• QS6H8T54ZE
• CHEMBL552132
• DTXSID80177527
• QBFYQVZGIDUNIY-UHFFFAOYSA-N
• AKOS040735267
• Q27138282
• 10-(1,1-dimethylallyl)-5-methoxy-2,2-dimethyl-pyrano[3,2-g]chromen-8-one
• 2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 10-(1,1-dimethylallyl)-5-methoxy-8,8-dimethyl-
• 10-(1,1-Dimethyl-2-propen-1-yl)-5-methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one
• 2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 5-methoxy-8,8-dimethyl-10-(1,1-dimethyl-2-propenyl)
• 5-METHOXY-8,8-DIMETHYL-10-(2-METHYLBUT-3-EN-2-YL)-2H,8H-PYRANO[3,2-G]CHROMEN-2-ONE
• 8,8-dimethyl-10-(1,1-dimethyl-2-propenyl)-5-methoxy-2h,8h-benzo[1,2-b:5,4-b']dipyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.6443	64.43%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6646	66.46%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.8984	89.84%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7704	77.04%
P-glycoprotein inhibitior	-	0.4911	49.11%
P-glycoprotein substrate	-	0.7133	71.33%
CYP3A4 substrate	+	0.6062	60.62%
CYP2C9 substrate	-	0.6661	66.61%
CYP2D6 substrate	-	0.8419	84.19%
CYP3A4 inhibition	+	0.7685	76.85%
CYP2C9 inhibition	-	0.7802	78.02%
CYP2C19 inhibition	+	0.6540	65.40%
CYP2D6 inhibition	-	0.7786	77.86%
CYP1A2 inhibition	+	0.6154	61.54%
CYP2C8 inhibition	+	0.4515	45.15%
CYP inhibitory promiscuity	+	0.5672	56.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9213	92.13%
Carcinogenicity (trinary)	Danger	0.4379	43.79%
Eye corrosion	-	0.9666	96.66%
Eye irritation	+	0.6040	60.40%
Skin irritation	-	0.7864	78.64%
Skin corrosion	-	0.9726	97.26%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6588	65.88%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.7824	78.24%
skin sensitisation	-	0.7552	75.52%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6677	66.77%
Acute Oral Toxicity (c)	II	0.4611	46.11%
Estrogen receptor binding	+	0.8587	85.87%
Androgen receptor binding	+	0.5837	58.37%
Thyroid receptor binding	+	0.7159	71.59%
Glucocorticoid receptor binding	+	0.7493	74.93%
Aromatase binding	+	0.8778	87.78%
PPAR gamma	+	0.7961	79.61%
Honey bee toxicity	-	0.6664	66.64%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9882	98.82%

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	96.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.91%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.84%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.04%	99.23%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.74%	85.30%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.68%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.04%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.71%	97.14%
CHEMBL1907	P15144	Aminopeptidase N	82.42%	93.31%
CHEMBL3401	O75469	Pregnane X receptor	81.51%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.19%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.00%	85.94%
CHEMBL1937	Q92769	Histone deacetylase 2	80.54%	94.75%

Plants that contains it

• Asterolasia squamuligera
• Catharanthus roseus
• Cinnamomum chekiangense
• Citrus trifoliata
• Clausena excavata
• Clausena harmandiana
• Clausena wallichii
• Moringa oleifera
• Paramignya monophylla
• Pluchea dioscoridis
• Pyrola rotundifolia
• Stevia alpina

Cross-Links

• PubChem: 342801
• NPASS: NPC289316
• ChEMBL: CHEMBL552132
• LOTUS: LTS0166691
• wikiData: Q27138282