Isofraxoside

Details

• Internal ID: e66fee7e-46ed-4620-9e47-52e1d86e3d6f
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Coumarin glycosides
• IUPAC Name: 8-hydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H18O10/c1-23-7-4-6-2-3-9(18)25-14(6)13(22)15(7)26-16-12(21)11(20)10(19)8(5-17)24-16/h2-4,8,10-12,16-17,19-22H,5H2,1H3/t8-,10-,11+,12-,16+/m1/s1
• InChI Key: RVWWDDKOKZXKCJ-ZOLYHUHESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₁₀
• Molecular Weight: 370.31 g/mol
• Exact Mass: 370.08999677 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.31
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 24778-11-8
• DTXSID101347440
• AKOS040735214
• XI163791
• 8-hydroxy-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5647	56.47%
Caco-2	-	0.9095	90.95%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5367	53.67%
OATP2B1 inhibitior	-	0.5613	56.13%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.9769	97.69%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7183	71.83%
P-glycoprotein inhibitior	-	0.8636	86.36%
P-glycoprotein substrate	-	0.8770	87.70%
CYP3A4 substrate	+	0.5113	51.13%
CYP2C9 substrate	-	0.8239	82.39%
CYP2D6 substrate	-	0.8498	84.98%
CYP3A4 inhibition	-	0.9107	91.07%
CYP2C9 inhibition	-	0.9346	93.46%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.8772	87.72%
CYP2C8 inhibition	+	0.4439	44.39%
CYP inhibitory promiscuity	-	0.8094	80.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6881	68.81%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9196	91.96%
Skin irritation	-	0.8111	81.11%
Skin corrosion	-	0.9624	96.24%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6583	65.83%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9164	91.64%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8904	89.04%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.6871	68.71%
Androgen receptor binding	+	0.5277	52.77%
Thyroid receptor binding	-	0.5462	54.62%
Glucocorticoid receptor binding	+	0.7654	76.54%
Aromatase binding	+	0.6859	68.59%
PPAR gamma	+	0.6608	66.08%
Honey bee toxicity	-	0.8702	87.02%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6949	69.49%
Fish aquatic toxicity	+	0.6492	64.92%

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	98.67%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.01%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.13%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	91.98%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.81%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.58%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.50%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.48%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.09%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.52%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.14%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.08%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.55%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.31%	94.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.44%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.08%	99.23%

Plants that contains it

• Aframomum daniellii
• Alchornea cordifolia
• Atalantia wightii
• Balanophora japonica
• Campanula alliariifolia subsp. letschchumensis
• Corydalis persica
• Corynanthe pachyceras
• Cota tinctoria
• Cynoglossum amabile
• Glycosmis pseudoracemosa
• Haplophyllum obtusifolium
• Iphiona grantioides
• Juniperus horizontalis
• Lathyrus tingitanus
• Plectranthus caninus
• Rauvolfia salicifolia
• Strychnos spinosa
• Tetradium glabrifolium

Cross-Links

• PubChem: 11508953
• NPASS: NPC47474
• LOTUS: LTS0004262
• wikiData: Q104387531