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

Details

• Internal ID: 61cc1e40-6792-4b3b-8587-22b429498ca8
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-12-5-8(23)4-11-14(12)16(27)18(29)20(31-11)7-1-2-9(24)10(25)3-7/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
• InChI Key: QJTYCCFDQWFJHU-HMGRVEAOSA-N
• Popularity: 3 references 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: -0.20
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• CHEMBL1255591
• 34199-21-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9460	94.60%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5980	59.80%
OATP1B1 inhibitior	+	0.9203	92.03%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5486	54.86%
P-glycoprotein inhibitior	-	0.6824	68.24%
P-glycoprotein substrate	-	0.7608	76.08%
CYP3A4 substrate	+	0.6206	62.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8440	84.40%
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	+	0.8993	89.93%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.7981	79.81%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4656	46.56%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6071	60.71%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8472	84.72%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7416	74.16%
Androgen receptor binding	+	0.7000	70.00%
Thyroid receptor binding	+	0.5484	54.84%
Glucocorticoid receptor binding	+	0.6704	67.04%
Aromatase binding	+	0.5604	56.04%
PPAR gamma	+	0.7620	76.20%
Honey bee toxicity	-	0.7120	71.20%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5849	58.49%
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	99.73%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.55%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.80%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.33%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.32%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.56%	99.15%
CHEMBL3194	P02766	Transthyretin	92.49%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	89.98%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.92%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.73%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.22%	95.64%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.07%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.76%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.41%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.49%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.33%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.63%	90.71%
CHEMBL2424	Q04760	Glyoxalase I	82.16%	91.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.42%	97.09%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.73%	80.78%

Plants that contains it

• Artemisia capillaris
• Artemisia monosperma
• Lactuca indica
• Saxifraga stolonifera
• Styphnolobium japonicum

Cross-Links

• PubChem: 52946987
• NPASS: NPC172075
• LOTUS: LTS0079602
• wikiData: Q105222875