Laricitrin

Details

• Internal ID: a305182c-66fe-4a81-bd30-a4176a68a3b5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
• InChI: InChI=1S/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3
• InChI Key: CFYMYCCYMJIYAB-UHFFFAOYSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₈
• Molecular Weight: 332.26 g/mol
• Exact Mass: 332.05321734 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• 53472-37-0
• 3'-O-Methylmyricetin
• JQZ2DUC4C9
• 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxychromen-4-one
• CHEBI:31763
• DTXSID40415210
• RefChem:924531
• DTXCID90366061
• Larycitrin
• 3'-Methylmyricetin
• Myricetin 3'-methyl ether
• UNII-JQZ2DUC4C9
• 2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-
• LARICYTRIN
• orb1682231
• CHEMBL2260151
• SCHEMBL19213534
• SCHEMBL29929477
• HY-N8840
• 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
• LMPK12112482
• MSK159720
• AKOS040761971
• FL45941
• 4',5,5',7-tetrahydroxy-3'-methoxyflavonol
• CS-0149154
• 3,4',5,5',7-Pentahydroxy-3'-methoxyflavone
• Q3217922
• 3'-O-Methylmyricetin; 4',5,5',7-Tetrahydroxy-3'-methoxyflavonol
• 2-(3,4-dihydroxy-5-methoxy-phenyl)-3,5,7-trihydroxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9095	90.95%
Caco-2	-	0.5549	55.49%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6297	62.97%
OATP2B1 inhibitior	-	0.5161	51.61%
OATP1B1 inhibitior	+	0.8396	83.96%
OATP1B3 inhibitior	+	0.9904	99.04%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7793	77.93%
P-glycoprotein inhibitior	-	0.7373	73.73%
P-glycoprotein substrate	-	0.6125	61.25%
CYP3A4 substrate	+	0.5630	56.30%
CYP2C9 substrate	-	0.6887	68.87%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	+	0.6330	63.30%
CYP2C9 inhibition	-	0.7982	79.82%
CYP2C19 inhibition	-	0.6361	63.61%
CYP2D6 inhibition	-	0.8687	86.87%
CYP1A2 inhibition	+	0.9091	90.91%
CYP2C8 inhibition	+	0.9280	92.80%
CYP inhibitory promiscuity	+	0.7089	70.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6208	62.08%
Eye corrosion	-	0.9790	97.90%
Eye irritation	+	0.7485	74.85%
Skin irritation	-	0.6006	60.06%
Skin corrosion	-	0.9153	91.53%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6893	68.93%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9054	90.54%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6600	66.00%
Acute Oral Toxicity (c)	III	0.6309	63.09%
Estrogen receptor binding	+	0.8835	88.35%
Androgen receptor binding	+	0.7303	73.03%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8770	87.70%
Aromatase binding	+	0.7748	77.48%
PPAR gamma	+	0.8469	84.69%
Honey bee toxicity	-	0.8785	87.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.8562	85.62%

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	98.55%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.41%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.96%	89.00%
CHEMBL3194	P02766	Transthyretin	92.58%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.39%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.39%	95.56%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	90.80%	98.11%
CHEMBL2581	P07339	Cathepsin D	90.28%	98.95%
CHEMBL2424	Q04760	Glyoxalase I	89.82%	91.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.48%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.21%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.49%	96.09%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	85.21%	98.21%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.44%	96.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.26%	99.23%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.84%	95.64%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.96%	94.42%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.41%	99.15%
CHEMBL1255126	O15151	Protein Mdm4	81.46%	90.20%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.61%	90.71%

Plants that contains it

• Cedrus atlantica
• Medicago arborea
• Medicago lupulina
• Medicago orbicularis
• Rhodomyrtus tomentosa

Cross-Links

• PubChem: 5282154
• NPASS: NPC133953
• LOTUS: LTS0209105
• wikiData: Q3217922