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

Details

• Internal ID: f0d9e85a-9c02-459e-8195-49f5be3c091a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C29H34O18/c1-41-13-3-9(4-14(42-2)18(13)33)26-27(21(36)17-11(32)5-10(31)6-12(17)44-26)47-29-25(40)23(38)20(35)16(46-29)8-43-28-24(39)22(37)19(34)15(7-30)45-28/h3-6,15-16,19-20,22-25,28-35,37-40H,7-8H2,1-2H3/t15-,16-,19-,20-,22+,23+,24-,25-,28-,29+/m1/s1
• InChI Key: XQNUUVURUCLCRZ-CJCKZRPTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₈
• Molecular Weight: 670.60 g/mol
• Exact Mass: 670.17451423 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.40
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5623	56.23%
Caco-2	-	0.9103	91.03%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	-	0.5854	58.54%
OATP1B1 inhibitior	+	0.8542	85.42%
OATP1B3 inhibitior	+	0.9748	97.48%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5542	55.42%
P-glycoprotein inhibitior	-	0.4782	47.82%
P-glycoprotein substrate	+	0.5093	50.93%
CYP3A4 substrate	+	0.6389	63.89%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.9208	92.08%
CYP2C19 inhibition	-	0.9124	91.24%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.7924	79.24%
CYP inhibitory promiscuity	-	0.7113	71.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9080	90.80%
Skin irritation	-	0.8442	84.42%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4227	42.27%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7386	73.86%
Acute Oral Toxicity (c)	III	0.7041	70.41%
Estrogen receptor binding	+	0.8438	84.38%
Androgen receptor binding	+	0.5618	56.18%
Thyroid receptor binding	+	0.5312	53.12%
Glucocorticoid receptor binding	+	0.6087	60.87%
Aromatase binding	+	0.6032	60.32%
PPAR gamma	+	0.7516	75.16%
Honey bee toxicity	-	0.7667	76.67%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.7167	71.67%

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	99.34%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.71%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.88%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.42%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.20%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.98%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.34%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.25%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.12%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.38%	95.56%
CHEMBL3194	P02766	Transthyretin	86.20%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.43%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.83%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.14%	92.62%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	82.04%	98.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.59%	99.15%

Plants that contains it

• Afrocarpus gracilior
• Agave xylonacantha
• Anthemis cretica
• Antiphiona pinnatisecta
• Calophyllum inophyllum
• Lycopodium japonicum
• Maackia tashiroi
• Monoon cupulare
• Thelypteris esquirolii
• Turnera diffusa

Cross-Links

• PubChem: 16109838
• NPASS: NPC157699
• LOTUS: LTS0007084
• wikiData: Q105339915