acacetin-8-C-neohesperidoside

Details

• Internal ID: bbf99165-f6ce-473e-a964-8ad3bab5c8b1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• InChI: InChI=1S/C28H32O14/c1-10-20(33)22(35)24(37)28(39-10)42-27-23(36)21(34)17(9-29)41-26(27)19-14(31)7-13(30)18-15(32)8-16(40-25(18)19)11-3-5-12(38-2)6-4-11/h3-8,10,17,20-24,26-31,33-37H,9H2,1-2H3/t10-,17+,20-,21+,22+,23-,24+,26-,27+,28-/m0/s1
• InChI Key: AOXGLIJSZLOQNZ-WBXLRLGPSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₄
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.17920569 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.75
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• CHEBI:70626
• 2''-O-alpha-rhamnosyl-4'-O-methylvitexin
• (1S)-1,5-anhydro-2-O-(6-deoxy-alpha-L-mannopyranosyl)-1-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-yl]-D-glucitol
• Acacetin-8-C-alpha-rhamnosyl-(1->2)-beta-glucopyranoside
• (1S)-1,5-anhydro-2-O-(6-deoxy-alpha-L-mannopyranosyl)-1-(5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-yl)-D-glucitol
• 8-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
• RefChem:108649
• 2''-O-a-Rhamnosyl-4'-O-methylvitexin
• Acacetin-8-C-a-rhamnosyl-(1->2)-b-glucopyranoside
• Acacetin-8-C-I+--rhamnosyl-(1->2)-I2-glucopyranoside
• Margaritene
• 64271-10-9
• 4H-1-Benzopyran-4-one, 8-[2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-
• orb1680344
• DTXSID001318266
• AKOS040763441
• FS-8387
• Q27138959
• 8-[2-O-(6-Deoxy-|A-L-mannopyranosyl)-|A-D-glucopyranosyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8978	89.78%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.7055	70.55%
OATP1B1 inhibitior	+	0.8238	82.38%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7738	77.38%
P-glycoprotein inhibitior	-	0.6233	62.33%
P-glycoprotein substrate	-	0.5744	57.44%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	0.8555	85.55%
CYP2D6 substrate	-	0.8543	85.43%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.6006	60.06%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5135	51.35%
Human Ether-a-go-go-Related Gene inhibition	+	0.6707	67.07%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8758	87.58%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8459	84.59%
Androgen receptor binding	+	0.7504	75.04%
Thyroid receptor binding	+	0.5670	56.70%
Glucocorticoid receptor binding	+	0.6773	67.73%
Aromatase binding	+	0.6145	61.45%
PPAR gamma	+	0.7410	74.10%
Honey bee toxicity	-	0.7402	74.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.60%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.37%	94.00%
CHEMBL2581	P07339	Cathepsin D	97.00%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.51%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.74%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.07%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.06%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.42%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.76%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.78%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	88.76%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.09%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.89%	85.14%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.17%	81.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.12%	97.09%
CHEMBL1907	P15144	Aminopeptidase N	84.05%	93.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.15%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.06%	90.00%
CHEMBL308	P06493	Cyclin-dependent kinase 1	81.35%	91.73%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.98%	89.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.88%	95.89%

Plants that contains it

• Citrus japonica
• Piper aduncum

Cross-Links

• PubChem: 70698254
• LOTUS: LTS0271872
• wikiData: Q27138959