5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: 683d2a09-b8a5-4f3d-9bdc-6e2f0a7dece7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17-,18-,21+,22+,23-,24-,26-,27-/m1/s1
• InChI Key: FIAAVMJLAGNUKW-IGIFRGNCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -2.39
• H-Bond Acceptor: 15
• H-Bond Donor: 11
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6251	62.51%
Caco-2	-	0.9152	91.52%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5454	54.54%
OATP2B1 inhibitior	-	0.5548	55.48%
OATP1B1 inhibitior	+	0.7711	77.11%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6705	67.05%
P-glycoprotein inhibitior	-	0.5691	56.91%
P-glycoprotein substrate	-	0.8398	83.98%
CYP3A4 substrate	+	0.5621	56.21%
CYP2C9 substrate	-	0.6194	61.94%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	-	0.8760	87.60%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9102	91.02%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	-	0.8801	88.01%
CYP2C8 inhibition	+	0.6604	66.04%
CYP inhibitory promiscuity	-	0.7721	77.21%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6914	69.14%
Eye corrosion	-	0.9937	99.37%
Eye irritation	-	0.8867	88.67%
Skin irritation	-	0.7949	79.49%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.6329	63.29%
Human Ether-a-go-go-Related Gene inhibition	+	0.7423	74.23%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7446	74.46%
skin sensitisation	-	0.8739	87.39%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6787	67.87%
Acute Oral Toxicity (c)	IV	0.4242	42.42%
Estrogen receptor binding	+	0.7148	71.48%
Androgen receptor binding	+	0.7374	73.74%
Thyroid receptor binding	-	0.5169	51.69%
Glucocorticoid receptor binding	-	0.5206	52.06%
Aromatase binding	+	0.6474	64.74%
PPAR gamma	+	0.7165	71.65%
Honey bee toxicity	-	0.7665	76.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.6549	65.49%

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	99.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.05%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.61%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.73%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.61%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.95%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.89%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.20%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.69%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.08%	97.09%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.75%	89.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.70%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.26%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.97%	91.71%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.76%	93.10%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.13%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	80.62%	98.35%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.51%	85.11%

Plants that contains it

• Artemisia monosperma
• Crataegus monogyna
• Gutierrezia microcephala
• Justicia buchii
• Teucridium parvifolium

Cross-Links

• PubChem: 162845817
• LOTUS: LTS0097973
• wikiData: Q104995547