Chrysin 8-C-beta-D-glucopyranoside

Details

• Internal ID: 7e62eb72-2b8c-41da-89e5-bd106e2b6696
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-phenyl-8-[(2S,4R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4C([C@H]([C@@H](C(O4)CO)O)O)O
• InChI: InChI=1S/C21H20O9/c22-8-14-17(26)18(27)19(28)21(30-14)16-11(24)6-10(23)15-12(25)7-13(29-20(15)16)9-4-2-1-3-5-9/h1-7,14,17-19,21-24,26-28H,8H2/t14?,17-,18+,19?,21+/m1/s1
• InChI Key: PFJBHVURUOQVHW-SZSUEBNWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₉
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.11073221 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• LMPK12110141

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9331	93.31%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	-	0.5425	54.25%
OATP1B1 inhibitior	+	0.8732	87.32%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6571	65.71%
P-glycoprotein inhibitior	-	0.6863	68.63%
P-glycoprotein substrate	-	0.8754	87.54%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6194	61.94%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.4487	44.87%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7894	78.94%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5565	55.65%
Human Ether-a-go-go-Related Gene inhibition	-	0.4738	47.38%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7036	70.36%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.7405	74.05%
Androgen receptor binding	+	0.7629	76.29%
Thyroid receptor binding	+	0.5181	51.81%
Glucocorticoid receptor binding	+	0.6586	65.86%
Aromatase binding	+	0.7540	75.40%
PPAR gamma	+	0.7621	76.21%
Honey bee toxicity	-	0.7952	79.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.6921	69.21%

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	99.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.91%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.92%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.37%	89.00%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	89.81%	89.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.76%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.55%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.82%	94.00%
CHEMBL308	P06493	Cyclin-dependent kinase 1	84.83%	91.73%
CHEMBL3401	O75469	Pregnane X receptor	83.83%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.43%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.26%	99.23%

Plants that contains it

• Scutellaria amoena

Cross-Links

• PubChem: 44257620
• LOTUS: LTS0022660
• wikiData: Q105207782