Herbacin

Details

• Internal ID: 2ea97440-2166-4f21-b3a0-9f05624ceec9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-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)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)O
• InChI: InChI=1S/C21H20O12/c22-6-11-13(26)15(28)17(30)21(31-11)33-19-10(25)5-9(24)12-14(27)16(29)18(32-20(12)19)7-1-3-8(23)4-2-7/h1-5,11,13,15,17,21-26,28-30H,6H2/t11-,13-,15+,17-,21+/m0/s1
• InChI Key: WWEKCPWUOZWBRI-USXYKIIOSA-N
• Popularity: 0 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: 0.40
• Atomic LogP (AlogP): -0.54
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• 11021-22-0
• Herbacetin-8-glucoside
• Herbacetin 8-O-glucoside
• 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 4H-1-Benzopyran-4-one, 8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-
• 8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• DTXSID80911544
• XH161784
• 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-8-yl hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9383	93.83%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.7227	72.27%
OATP1B1 inhibitior	+	0.8790	87.90%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.4674	46.74%
P-glycoprotein inhibitior	-	0.6055	60.55%
P-glycoprotein substrate	-	0.7583	75.83%
CYP3A4 substrate	+	0.5911	59.11%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
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	+	0.7582	75.82%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.7761	77.61%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4506	45.06%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6196	61.96%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8129	81.29%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7460	74.60%
Androgen receptor binding	+	0.7202	72.02%
Thyroid receptor binding	+	0.5313	53.13%
Glucocorticoid receptor binding	+	0.6170	61.70%
Aromatase binding	+	0.6255	62.55%
PPAR gamma	+	0.7276	72.76%
Honey bee toxicity	-	0.7519	75.19%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
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	99.66%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.47%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.46%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.90%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.05%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.90%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.81%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.09%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.10%	99.17%
CHEMBL3194	P02766	Transthyretin	86.79%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.40%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.99%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	84.95%	91.49%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.40%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.28%	91.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.56%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	80.75%	98.35%

Plants that contains it

• Alcea rosea
• Calluna vulgaris
• Equisetum hyemale

Cross-Links

• PubChem: 5748571
• NPASS: NPC68286
• LOTUS: LTS0099462
• wikiData: Q82881691