(2S,3S)-2-(hydroxymethyl)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Details

• Internal ID: 3356392b-2484-4fc8-8159-1c2fa141b936
• Taxonomy: Lignans, neolignans and related compounds > Coumarinolignans
• IUPAC Name: (2S,3S)-2-(hydroxymethyl)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC4=C3OC(=O)C=C4)CO)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@@H](OC3=C(O2)C=CC4=C3OC(=O)C=C4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C25H26O12/c1-32-15-8-12(3-5-13(15)35-25-21(31)20(30)19(29)16(9-26)36-25)22-17(10-27)34-24-14(33-22)6-2-11-4-7-18(28)37-23(11)24/h2-8,16-17,19-22,25-27,29-31H,9-10H2,1H3/t16-,17+,19-,20+,21-,22+,25-/m1/s1
• InChI Key: YMHNZLAKKRLTCY-DCBGURTESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₁₂
• Molecular Weight: 518.50 g/mol
• Exact Mass: 518.14242626 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.8614	86.14%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.8522	85.22%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9278	92.78%
P-glycoprotein inhibitior	+	0.5929	59.29%
P-glycoprotein substrate	-	0.7721	77.21%
CYP3A4 substrate	+	0.5798	57.98%
CYP2C9 substrate	-	0.8306	83.06%
CYP2D6 substrate	-	0.8491	84.91%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.4709	47.09%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9389	93.89%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7744	77.44%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7658	76.58%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.7784	77.84%
Androgen receptor binding	+	0.6884	68.84%
Thyroid receptor binding	+	0.5352	53.52%
Glucocorticoid receptor binding	+	0.6259	62.59%
Aromatase binding	-	0.6172	61.72%
PPAR gamma	+	0.6722	67.22%
Honey bee toxicity	-	0.7554	75.54%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.6698	66.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.77%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.64%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.61%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.50%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.72%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.77%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.06%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	86.79%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.78%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.00%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.97%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.66%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.38%	97.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.68%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.27%	96.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.26%	94.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.24%	94.45%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.11%	92.38%

Plants that contains it

• Daphne feddei

Cross-Links

• PubChem: 45482322
• LOTUS: LTS0193270
• wikiData: Q105350537