Oroxylin A glucoronide

Details

• Internal ID: e64960b6-322d-4577-98e0-f13935f549f1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-6-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC=CC=C3)OC4C(C(C(C(O4)C(=O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1O)C(=O)C=C(O2)C3=CC=CC=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O
• InChI: InChI=1S/C22H20O11/c1-30-19-13(32-22-18(27)16(25)17(26)20(33-22)21(28)29)8-12-14(15(19)24)10(23)7-11(31-12)9-5-3-2-4-6-9/h2-8,16-18,20,22,24-27H,1H3,(H,28,29)/t16-,17-,18+,20-,22+/m0/s1
• InChI Key: QXIPXNZUEQYPLZ-QSUZLTIMSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₁₁
• Molecular Weight: 460.40 g/mol
• Exact Mass: 460.10056145 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.45
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• Oroxylin A glucoronide
• Oroxyloside
• Oroxylin A 7-O-beta-D-glucuronide
• Oroxylin A 7-o-glucuronide
• Oroxylin A-7-O-glucuronide
• Oroxylin 7-glucuronide
• 6-Methoxybaicalein 7-glucuronide
• Oroxylin a-7-glucoronide
• UNII-O84RM2NAEQ
• O84RM2NAEQ
• oroxylin 7-O-beta-D-glucuronide
• (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-6-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
• 5,7-dihydroxy-6-methoxyflavone 7-O-beta-D-glucuronide
• 5-hydroxy-6-methoxy-flavone-7-yl beta-D-glucopyranosiduronic acid
• 5-hydroxy-6-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acid
• beta-D-Glucopyranosiduronic acid, 5-hydroxy-6-methoxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl
• Oroxylin A 7-glucuronide
• MEGxp0_000536
• CHEMBL4171934
• SCHEMBL21695683
• ACon1_001096
• CHEBI:61670
• DTXSID201310901
• HY-N2481
• MFCD23379930
• AKOS027326569
• Oroxyloside; Oroxylin A 7-glucuronide
• NCGC00169680-01
• AC-34588
• AS-82761
• Oroxyloside;Oroxylin A-7-O--D-glucuronide
• CS-0022752
• OROXYLIN A-7-O-.BETA.-D-GLUCURONIDE
• BRD-K83886129-001-01-1
• Q27131267
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 5-HYDROXY-6-METHOXY-4-OXO-2-PHENYL-4H-1-BENZOPYRAN-7-YL
• NCGC00169680-02!(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-6-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7483	74.83%
Caco-2	-	0.8787	87.87%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	+	0.6319	63.19%
OATP1B1 inhibitior	+	0.8459	84.59%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7840	78.40%
P-glycoprotein inhibitior	-	0.6448	64.48%
P-glycoprotein substrate	-	0.8329	83.29%
CYP3A4 substrate	+	0.5897	58.97%
CYP2C9 substrate	-	0.8245	82.45%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.7674	76.74%
CYP2C9 inhibition	-	0.8642	86.42%
CYP2C19 inhibition	-	0.8511	85.11%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.6411	64.11%
CYP2C8 inhibition	+	0.7926	79.26%
CYP inhibitory promiscuity	-	0.7677	76.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5903	59.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8971	89.71%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6164	61.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5222	52.22%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9143	91.43%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.8342	83.42%
Androgen receptor binding	+	0.7123	71.23%
Thyroid receptor binding	+	0.5308	53.08%
Glucocorticoid receptor binding	+	0.7834	78.34%
Aromatase binding	+	0.5384	53.84%
PPAR gamma	+	0.6756	67.56%
Honey bee toxicity	-	0.8076	80.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9235	92.35%

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%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.74%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.27%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.97%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.88%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.08%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.80%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.37%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.61%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.76%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	83.22%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	83.08%	95.64%
CHEMBL3194	P02766	Transthyretin	80.08%	90.71%

Plants that contains it

• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Scutellaria alpina
• Scutellaria altissima
• Scutellaria baicalensis
• Scutellaria comosa
• Scutellaria galericulata
• Scutellaria grossa
• Scutellaria immaculata
• Scutellaria iskanderi
• Scutellaria lateriflora
• Scutellaria phyllostachya
• Scutellaria prostrata
• Scutellaria racemosa
• Scutellaria squarrosa

Cross-Links

• PubChem: 14655552
• NPASS: NPC284498
• LOTUS: LTS0224895
• wikiData: Q27131267