Ligustroflavone

Details

• Internal ID: 47cfd129-550f-4a5b-9265-6f59629042c7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)OC6C(C(C(C(O6)C)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O18/c1-11-22(37)25(40)28(43)31(46-11)45-10-20-24(39)27(42)30(51-32-29(44)26(41)23(38)12(2)47-32)33(50-20)48-15-7-16(35)21-17(36)9-18(49-19(21)8-15)13-3-5-14(34)6-4-13/h3-9,11-12,20,22-35,37-44H,10H2,1-2H3/t11-,12-,20+,22-,23-,24+,25+,26+,27-,28+,29+,30+,31+,32-,33+/m0/s1
• InChI Key: NULBHTHMVOCGOE-ZBCCAYPVSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₈
• Molecular Weight: 724.70 g/mol
• Exact Mass: 724.22146442 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.25
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

• 260413-62-5
• Nuezhenoside
• Ligustroflavone(Nuezhenoside)
• 7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• SCHEMBL14964152
• HY-N0546
• s9096
• AKOS026674258
• CCG-270411
• AC-34537
• AS-82735
• CS-0009074
• 2-(4-Hydroxyphenyl)-5-hydroxy-7-[(2-O,6-O-di-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)oxy]-4H-1-benzopyran-4-one
• 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-deoxy--L-mannopyranosyl-(1->2)-[6-deoxy--L-mannopyranosyl-(1->6)]--D-glucopyranoside
• 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8945	89.45%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.7138	71.38%
OATP1B1 inhibitior	+	0.9346	93.46%
OATP1B3 inhibitior	+	0.9191	91.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6625	66.25%
P-glycoprotein inhibitior	-	0.6306	63.06%
P-glycoprotein substrate	+	0.6155	61.55%
CYP3A4 substrate	+	0.6129	61.29%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.8866	88.66%
CYP2C9 inhibition	-	0.9354	93.54%
CYP2C19 inhibition	-	0.9441	94.41%
CYP2D6 inhibition	-	0.9486	94.86%
CYP1A2 inhibition	-	0.9149	91.49%
CYP2C8 inhibition	+	0.7148	71.48%
CYP inhibitory promiscuity	-	0.6833	68.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6581	65.81%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9147	91.47%
Skin irritation	-	0.8285	82.85%
Skin corrosion	-	0.9647	96.47%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3610	36.10%
Micronuclear	+	0.6992	69.92%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9410	94.10%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.9296	92.96%
Acute Oral Toxicity (c)	III	0.6694	66.94%
Estrogen receptor binding	+	0.7788	77.88%
Androgen receptor binding	+	0.6083	60.83%
Thyroid receptor binding	+	0.5364	53.64%
Glucocorticoid receptor binding	+	0.5563	55.63%
Aromatase binding	+	0.5539	55.39%
PPAR gamma	+	0.7455	74.55%
Honey bee toxicity	-	0.6872	68.72%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.8930	89.30%

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	99.47%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.20%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.29%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.83%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.80%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.07%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.48%	94.73%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.92%	83.57%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.45%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.31%	97.36%
CHEMBL3194	P02766	Transthyretin	89.07%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	88.69%	98.35%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.43%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.13%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.75%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.70%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.12%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.36%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.75%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.55%	97.09%

Plants that contains it

• Ligustrum lucidum
• Ligustrum vulgare
• Staphylea arguta

Cross-Links

• PubChem: 10417462
• NPASS: NPC226003
• LOTUS: LTS0059446
• wikiData: Q105185924