(2S,3S)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Details

• Internal ID: 86469b26-67b8-416b-aa84-4f95af567ad1
• Taxonomy: Lignans, neolignans and related compounds > Coumarinolignans
• IUPAC Name: (2S,3S)-3-(3,4-dihydroxy-5-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• InChI: InChI=1S/C20H18O9/c1-25-12-7-10(5-11(22)16(12)24)17-14(8-21)27-20-18-9(3-4-15(23)28-18)6-13(26-2)19(20)29-17/h3-7,14,17,21-22,24H,8H2,1-2H3/t14-,17-/m0/s1
• InChI Key: ATBGMZCSYDMJJM-YOEHRIQHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₉
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.09508215 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8398	83.98%
Caco-2	-	0.6969	69.69%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7952	79.52%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	+	0.8324	83.24%
OATP1B3 inhibitior	+	0.8603	86.03%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5787	57.87%
P-glycoprotein inhibitior	+	0.5771	57.71%
P-glycoprotein substrate	-	0.8045	80.45%
CYP3A4 substrate	+	0.5059	50.59%
CYP2C9 substrate	-	0.8204	82.04%
CYP2D6 substrate	-	0.8209	82.09%
CYP3A4 inhibition	-	0.8695	86.95%
CYP2C9 inhibition	-	0.8137	81.37%
CYP2C19 inhibition	-	0.8360	83.60%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.8928	89.28%
CYP2C8 inhibition	+	0.4943	49.43%
CYP inhibitory promiscuity	-	0.6499	64.99%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7085	70.85%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.8623	86.23%
Skin irritation	-	0.8347	83.47%
Skin corrosion	-	0.9689	96.89%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6611	66.11%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.9126	91.26%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7693	76.93%
Acute Oral Toxicity (c)	III	0.6727	67.27%
Estrogen receptor binding	+	0.8766	87.66%
Androgen receptor binding	+	0.7435	74.35%
Thyroid receptor binding	-	0.5075	50.75%
Glucocorticoid receptor binding	+	0.8506	85.06%
Aromatase binding	+	0.5490	54.90%
PPAR gamma	+	0.6480	64.80%
Honey bee toxicity	-	0.8489	84.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7619	76.19%

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	99.13%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.02%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.44%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.97%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.82%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.79%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.13%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.80%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.72%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.74%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.69%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.72%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.52%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.04%	97.09%
CHEMBL1255126	O15151	Protein Mdm4	80.41%	90.20%

Plants that contains it

• Mallotus apelta

Cross-Links

• PubChem: 133561782
• LOTUS: LTS0048392
• wikiData: Q104918259