(3E)-5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 873ef465-2d5e-4d74-be65-33c6723ee974
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids
• IUPAC Name: (3E)-5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1C(=CC2=CC=C(C=C2)O)C(=O)C3=C(C=C(C=C3O1)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1/C(=C\C2=CC=C(C=C2)O)/C(=O)C3=C(C=C(C=C3O1)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H22O10/c23-8-16-19(27)20(28)21(29)22(32-16)31-13-6-14(25)17-15(7-13)30-9-11(18(17)26)5-10-1-3-12(24)4-2-10/h1-7,16,19-25,27-29H,8-9H2/b11-5+/t16-,19-,20+,21-,22-/m1/s1
• InChI Key: LXFPGLZWBWQSME-VSVBYZELSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.06
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 2,3-Dihydro-3-(4-hydroxybenzylidene)-5-hydroxy-7-(beta-D-glucopyranosyloxy)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5712	57.12%
Caco-2	-	0.9104	91.04%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5340	53.40%
OATP2B1 inhibitior	-	0.5560	55.60%
OATP1B1 inhibitior	+	0.9345	93.45%
OATP1B3 inhibitior	+	0.9622	96.22%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6476	64.76%
P-glycoprotein inhibitior	-	0.7089	70.89%
P-glycoprotein substrate	-	0.8924	89.24%
CYP3A4 substrate	+	0.5763	57.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.8558	85.58%
CYP2C19 inhibition	-	0.7238	72.38%
CYP2D6 inhibition	-	0.8463	84.63%
CYP1A2 inhibition	-	0.8395	83.95%
CYP2C8 inhibition	-	0.5996	59.96%
CYP inhibitory promiscuity	-	0.6037	60.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8642	86.42%
Skin irritation	-	0.8046	80.46%
Skin corrosion	-	0.9617	96.17%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5773	57.73%
Micronuclear	+	0.5733	57.33%
Hepatotoxicity	-	0.7425	74.25%
skin sensitisation	-	0.7986	79.86%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4104	41.04%
Estrogen receptor binding	+	0.7482	74.82%
Androgen receptor binding	+	0.6877	68.77%
Thyroid receptor binding	+	0.5382	53.82%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5813	58.13%
PPAR gamma	+	0.8217	82.17%
Honey bee toxicity	-	0.7402	74.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9164	91.64%

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	99.35%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.32%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.29%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	93.91%	95.93%
CHEMBL2581	P07339	Cathepsin D	93.07%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.44%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.21%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.01%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.04%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	88.84%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.97%	96.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.33%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.78%	86.33%
CHEMBL4208	P20618	Proteasome component C5	85.93%	90.00%
CHEMBL3194	P02766	Transthyretin	83.60%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.74%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.21%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.80%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.70%	86.92%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.70%	85.00%

Plants that contains it

• Polygonatum odoratum

Cross-Links

• PubChem: 46211619
• NPASS: NPC10863
• LOTUS: LTS0026965
• wikiData: Q105158819