(2R,3R)-2-Methyl-3-(3,5-dimethoxy-4-hydroxyphenyl)-5-methoxy-2,3-dihydro-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one

Details

• Internal ID: 7e259855-3fa2-499a-810b-03046ed4b552
• Taxonomy: Lignans, neolignans and related compounds > Coumarinolignans
• IUPAC Name: (2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-5-methoxy-2-methyl-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• SMILES (Canonical): CC1C(OC2=C(C=C3C=CC(=O)OC3=C2O1)OC)C4=CC(=C(C(=C4)OC)O)OC
• SMILES (Isomeric): C[C@@H]1[C@H](OC2=C(C=C3C=CC(=O)OC3=C2O1)OC)C4=CC(=C(C(=C4)OC)O)OC
• InChI: InChI=1S/C21H20O8/c1-10-18(12-8-13(24-2)17(23)14(9-12)25-3)29-20-15(26-4)7-11-5-6-16(22)28-19(11)21(20)27-10/h5-10,18,23H,1-4H3/t10-,18+/m1/s1
• InChI Key: FVBTTWTYDYBUNY-MGNBDDOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₈
• Molecular Weight: 400.40 g/mol
• Exact Mass: 400.11581759 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (2R,3R)-2-Methyl-3-(3,5-dimethoxy-4-hydroxyphenyl)-5-methoxy-2,3-dihydro-9H-pyrano[2,3-f]-1,4-benzodioxin-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9640	96.40%
Caco-2	+	0.7147	71.47%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7609	76.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8554	85.54%
OATP1B3 inhibitior	+	0.9093	90.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8537	85.37%
P-glycoprotein inhibitior	+	0.8232	82.32%
P-glycoprotein substrate	-	0.7838	78.38%
CYP3A4 substrate	+	0.5066	50.66%
CYP2C9 substrate	-	0.6765	67.65%
CYP2D6 substrate	-	0.8294	82.94%
CYP3A4 inhibition	-	0.7913	79.13%
CYP2C9 inhibition	-	0.9510	95.10%
CYP2C19 inhibition	-	0.8243	82.43%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.7115	71.15%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.5995	59.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4416	44.16%
Eye corrosion	-	0.9827	98.27%
Eye irritation	-	0.8164	81.64%
Skin irritation	-	0.7255	72.55%
Skin corrosion	-	0.9833	98.33%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5467	54.67%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9477	94.77%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8670	86.70%
Acute Oral Toxicity (c)	II	0.6121	61.21%
Estrogen receptor binding	+	0.8776	87.76%
Androgen receptor binding	+	0.6992	69.92%
Thyroid receptor binding	+	0.6415	64.15%
Glucocorticoid receptor binding	+	0.8642	86.42%
Aromatase binding	+	0.5838	58.38%
PPAR gamma	+	0.7435	74.35%
Honey bee toxicity	-	0.8586	85.86%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9217	92.17%

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	98.27%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.66%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.23%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.66%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.28%	99.23%
CHEMBL2581	P07339	Cathepsin D	89.06%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.08%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.44%	99.15%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.19%	94.03%

Plants that contains it

• Hibiscus syriacus
• Mondia whitei

Cross-Links

• PubChem: 11732116
• NPASS: NPC176903
• LOTUS: LTS0240730
• wikiData: Q105002245