1,3-Benzodioxol-5-ol, 6-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl)-, (S)-

Details

• Internal ID: 92696bfb-edfc-4446-a40c-896c4922bcc8
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Pyranoisoflavonoids
• IUPAC Name: 6-[(3S)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]-1,3-benzodioxol-5-ol
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OCC(C3)C4=CC5=C(C=C4O)OCO5)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC[C@@H](C3)C4=CC5=C(C=C4O)OCO5)C
• InChI: InChI=1S/C21H20O5/c1-21(2)6-5-14-17(26-21)4-3-12-7-13(10-23-20(12)14)15-8-18-19(9-16(15)22)25-11-24-18/h3-6,8-9,13,22H,7,10-11H2,1-2H3/t13-/m1/s1
• InChI Key: ADVVUFYZTDQZLS-CYBMUJFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.40 g/mol
• Exact Mass: 352.13107373 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 1,3-Benzodioxol-5-ol, 6-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl)-, (S)-
• 6-(8,8-Dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl)-1,3-benzodioxol-5-ol-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9592	95.92%
Caco-2	+	0.7989	79.89%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7989	79.89%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.9016	90.16%
OATP1B3 inhibitior	+	0.9614	96.14%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8808	88.08%
P-glycoprotein inhibitior	+	0.6086	60.86%
P-glycoprotein substrate	-	0.5599	55.99%
CYP3A4 substrate	+	0.6144	61.44%
CYP2C9 substrate	-	0.6229	62.29%
CYP2D6 substrate	-	0.7023	70.23%
CYP3A4 inhibition	+	0.6368	63.68%
CYP2C9 inhibition	+	0.6861	68.61%
CYP2C19 inhibition	+	0.7121	71.21%
CYP2D6 inhibition	-	0.6168	61.68%
CYP1A2 inhibition	-	0.6788	67.88%
CYP2C8 inhibition	-	0.6416	64.16%
CYP inhibitory promiscuity	+	0.7972	79.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4585	45.85%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.5483	54.83%
Skin irritation	-	0.7719	77.19%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3969	39.69%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7418	74.18%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7186	71.86%
Acute Oral Toxicity (c)	III	0.4939	49.39%
Estrogen receptor binding	+	0.9532	95.32%
Androgen receptor binding	+	0.6339	63.39%
Thyroid receptor binding	+	0.7113	71.13%
Glucocorticoid receptor binding	+	0.6993	69.93%
Aromatase binding	+	0.6048	60.48%
PPAR gamma	+	0.8674	86.74%
Honey bee toxicity	-	0.8308	83.08%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9879	98.79%

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	98.95%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.05%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.24%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	95.90%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.22%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.20%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.89%	96.77%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	89.91%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.97%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	88.63%	80.96%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.38%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.25%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.27%	100.00%
CHEMBL236	P41143	Delta opioid receptor	86.16%	99.35%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.98%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.63%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.74%	99.15%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	82.16%	82.67%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	81.37%	99.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.15%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.93%	97.09%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	80.69%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.61%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.37%	93.10%

Plants that contains it

• Berchemia discolor
• Dalbergia hupeana
• Dalbergia nitidula

Cross-Links

• PubChem: 22296339
• LOTUS: LTS0040237
• wikiData: Q104909841