Dihydromyricetin

Details

• Internal ID: 5e18658f-0f8b-4db8-ae5d-f6e59811b490
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins > Epigallocatechins
• IUPAC Name: (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=C(C=C(C(=C1O)O)O)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O
• SMILES (Isomeric): C1=C(C=C(C(=C1O)O)O)[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O
• InChI: InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m0/s1
• InChI Key: KJXSIXMJHKAJOD-LSDHHAIUSA-N
• Popularity: 106 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₈
• Molecular Weight: 320.25 g/mol
• Exact Mass: 320.05321734 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.89
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 1

Synonyms

• Ampelopsin
• 27200-12-0
• Ampeloptin
• (+)-Dihydromyricetin
• (+)-Ampelopsin
• (2r,3r)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-one
• Ampelopsin (flavanol)
• Telocapil
• Myriceline spe
• C15H12O8
• Flavanone, 3,3',4',5,5',7-hexahydroxy-
• 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R-trans)-
• UNII-KD8QND6427
• (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
• KD8QND6427
• CHEBI:28429
• 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R,3R)-
• 3,3',4',5,5',7-Hexahydroxy-2,3-dihydroflavanonol
• (2R,3R)-2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
• (2R-trans)-2,3-Dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
• (2R,3R)-3,5,7,3',4',5'-hexahydroxyflavanone
• (2R,3R)-3,3',4',5,5',7-hexahydroxy-2,3-dihydroflavanonol
• dihydro-myricetin
• Ampelopsin;Ampeloptin
• (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
• AMPELOPSIN [MI]
• (2r,3r)-dihydromyricetin
• Dihydromyricetin (diH-Myr)
• Dihydromyricetin (Ampeloptin)
• Dihydromyricetin - Ampeloptin
• SCHEMBL723736
• DIHYDROMYRICETIN [INCI]
• CHEMBL3348861
• DTXSID50181676
• BDBM212434
• HMS3884B17
• Dihydromyricetin, >=98% (HPLC)
• HY-N0112
• Dihydromyricetin, analytical standard
• MFCD00189451
• s2399
• AKOS022168215
• AC-8004
• CCG-267699
• CS-3809
• NCGC00346604-01
• AS-71702
• LS-39586
• D5464
• SW219328-1
• C02906
• A818952
• Q422305
• 2B89FBAC-4DD1-44C9-BE2A-9D0C173BDFD8
• Q-100341
• (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9071	90.71%
Caco-2	-	0.9553	95.53%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5892	58.92%
OATP2B1 inhibitior	-	0.5536	55.36%
OATP1B1 inhibitior	+	0.9298	92.98%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8964	89.64%
P-glycoprotein inhibitior	-	0.8898	88.98%
P-glycoprotein substrate	-	0.9609	96.09%
CYP3A4 substrate	-	0.5462	54.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7991	79.91%
CYP3A4 inhibition	+	0.6951	69.51%
CYP2C9 inhibition	-	0.5823	58.23%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9287	92.87%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.6369	63.69%
CYP inhibitory promiscuity	+	0.5822	58.22%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6750	67.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9696	96.96%
Skin irritation	+	0.5835	58.35%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6789	67.89%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5177	51.77%
Acute Oral Toxicity (c)	II	0.7348	73.48%
Estrogen receptor binding	+	0.6761	67.61%
Androgen receptor binding	+	0.6805	68.05%
Thyroid receptor binding	+	0.6998	69.98%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	+	0.7033	70.33%
Honey bee toxicity	-	0.8969	89.69%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9124	91.24%

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	98.94%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.40%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.81%	99.23%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.68%	96.12%
CHEMBL3194	P02766	Transthyretin	87.58%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.24%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	86.84%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.27%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.17%	86.33%
CHEMBL2581	P07339	Cathepsin D	81.07%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.45%	94.45%

Plants that contains it

• Alangium grisolleoides
• Ampelopsis cantoniensis
• Ampelopsis japonica
• Artemisia afra
• Brassica carinata
• Burkea africana
• Catha edulis
• Catharanthus roseus
• Cedrus deodara
• Cercidiphyllum japonicum
• Cistus × incanus
• Cryptocarya alba
• Cyphostemma digitatum
• Epipactis palustris
• Goniothalamus amuyon
• Hovenia dulcis
• Intsia bijuga
• Manilkara zapota
• Nekemias grossedentata
• Onobrychis viciifolia
• Pimenta dioica
• Pinus contorta
• Rhododendron dauricum
• Rumex obtusifolius
• Stachyurus himalaicus
• Uvaria griffithii
• Xanthoceras sorbifolium
• Zephyranthes citrina

Cross-Links

• PubChem: 161557
• NPASS: NPC19721
• LOTUS: LTS0061492
• wikiData: Q422305