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

Details

• Internal ID: d204e85e-4526-4461-b58c-91e03bfff38f
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18+,19-,20+,21+/m0/s1
• InChI Key: ZCOLJUOHXJRHDI-FZHKGVQDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.10564683 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9370	93.70%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5888	58.88%
OATP1B1 inhibitior	+	0.9521	95.21%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5394	53.94%
P-glycoprotein inhibitior	-	0.8277	82.77%
P-glycoprotein substrate	-	0.9175	91.75%
CYP3A4 substrate	+	0.5951	59.51%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.6652	66.52%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8281	82.81%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5316	53.16%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6946	69.46%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.4741	47.41%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7238	72.38%
Androgen receptor binding	+	0.7130	71.30%
Thyroid receptor binding	+	0.6096	60.96%
Glucocorticoid receptor binding	+	0.6300	63.00%
Aromatase binding	+	0.6456	64.56%
PPAR gamma	+	0.8322	83.22%
Honey bee toxicity	-	0.7440	74.40%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.8218	82.18%

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%
CHEMBL2581	P07339	Cathepsin D	97.10%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.38%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.51%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.25%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.75%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.01%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.86%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	88.57%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.49%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.85%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.34%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.04%	99.17%
CHEMBL3194	P02766	Transthyretin	85.31%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.58%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.09%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.45%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.95%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.32%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.87%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.63%	95.83%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.12%	90.71%

Plants that contains it

• Baptisia nuttalliana
• Ficus septica
• Genista ephedroides
• Lupinus albus
• Lupinus mexicanus
• Retama sphaerocarpa
• Styphnolobium japonicum
• Thermopsis lanceolata
• Thermopsis rhombifolia
• Trifolium pratense

Cross-Links

• PubChem: 154496625
• LOTUS: LTS0115026
• wikiData: Q105371326