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

Details

• Internal ID: 67a0cdfe-0035-4219-afbf-b67484b54531
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O[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
• InChI: InChI=1S/C27H30O17/c28-6-12-15(33)18(36)20(38)26(40-12)43-23-11(32)5-10(31)14-17(35)25(22(42-24(14)23)8-1-3-9(30)4-2-8)44-27-21(39)19(37)16(34)13(7-29)41-27/h1-5,12-13,15-16,18-21,26-34,36-39H,6-7H2/t12-,13-,15-,16-,18+,19+,20-,21-,26+,27+/m1/s1
• InChI Key: VMOKZQAQPBUNRW-PXJYGDGDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₇
• Molecular Weight: 626.50 g/mol
• Exact Mass: 626.14829948 g/mol
• Topological Polar Surface Area (TPSA): 286.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -3.07
• H-Bond Acceptor: 17
• H-Bond Donor: 11
• Rotatable Bonds: 7

Synonyms

• 99224-12-1
• HERBACETIN-3,8-DIGLUCOPYRANOSIDE
• Herbacetin 3,8-O-diglucoside
• CHEMBL596219
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• Herbacetin 3,8-diglucoside
• DTXSID70912828
• CHEBI:191048
• BDBM50304345
• 4H-1-Benzopyran-4-one, 3,8-bis(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-
• 8-(Hexopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9183	91.83%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5553	55.53%
OATP1B1 inhibitior	+	0.9116	91.16%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6094	60.94%
P-glycoprotein inhibitior	-	0.4679	46.79%
P-glycoprotein substrate	-	0.8171	81.71%
CYP3A4 substrate	+	0.5694	56.94%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.6860	68.60%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8673	86.73%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6914	69.14%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6196	61.96%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6435	64.35%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.7676	76.76%
Androgen receptor binding	+	0.6752	67.52%
Thyroid receptor binding	-	0.5421	54.21%
Glucocorticoid receptor binding	-	0.5545	55.45%
Aromatase binding	+	0.5531	55.31%
PPAR gamma	+	0.6915	69.15%
Honey bee toxicity	-	0.7520	75.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.80%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.57%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.45%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.37%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.90%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	88.67%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.10%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.18%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.71%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.59%	86.92%
CHEMBL3194	P02766	Transthyretin	83.89%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.56%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	82.15%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.80%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.02%	95.56%

Plants that contains it

• Rhodiola rosea

Cross-Links

• PubChem: 5491604
• NPASS: NPC8573
• ChEMBL: CHEMBL596219
• LOTUS: LTS0226544
• wikiData: Q82883243