5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: f3910519-4ddb-42f4-803d-4c044433fdcd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C(=C(C(=C3C2=O)O)O)O)O)C4=CC=C(C=C4)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C(=C(C(=C3C2=O)O)O)O)O)C4=CC=C(C=C4)O)O)O)O
• InChI: InChI=1S/C21H20O12/c1-6-10(23)13(26)17(30)21(31-6)33-20-12(25)9-11(24)14(27)15(28)16(29)19(9)32-18(20)7-2-4-8(22)5-3-7/h2-6,10,13,17,21-24,26-30H,1H3/t6-,10-,13+,17+,21-/m0/s1
• InChI Key: XSSVMGXVGVASHY-AMWZKJLXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8357	83.57%
Caco-2	-	0.8360	83.60%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	+	0.5877	58.77%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7155	71.55%
P-glycoprotein inhibitior	-	0.6020	60.20%
P-glycoprotein substrate	-	0.6831	68.31%
CYP3A4 substrate	+	0.5969	59.69%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5306	53.06%
CYP2C8 inhibition	+	0.7036	70.36%
CYP inhibitory promiscuity	-	0.5648	56.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7833	78.33%
Skin irritation	-	0.6220	62.20%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.5326	53.26%
Human Ether-a-go-go-Related Gene inhibition	-	0.5695	56.95%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6324	63.24%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6582	65.82%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.6466	64.66%
Androgen receptor binding	+	0.6838	68.38%
Thyroid receptor binding	+	0.5474	54.74%
Glucocorticoid receptor binding	+	0.7547	75.47%
Aromatase binding	-	0.4825	48.25%
PPAR gamma	+	0.7057	70.57%
Honey bee toxicity	-	0.7750	77.50%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5250	52.50%
Fish aquatic toxicity	+	0.9457	94.57%

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	98.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.56%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.57%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.54%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.52%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.11%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	90.86%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	88.72%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.98%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.95%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.90%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.93%	90.71%
CHEMBL1944	P08473	Neprilysin	81.13%	92.63%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.94%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.45%	99.15%

Plants that contains it

• Ajuga genevensis
• Boronia pinnata
• Cleistanthus indochinensis
• Cleome spinosa
• Cyrtomium falcatum
• Ekebergia capensis
• Elymus repens
• Glochidion sphaerogynum
• Melaleuca quinquenervia
• Pinguicula vulgaris
• Pongamiopsis pervilleana
• Semialarium mexicanum

Cross-Links

• PubChem: 10961589
• NPASS: NPC101426
• LOTUS: LTS0034624
• wikiData: Q105341233