Oroxindin

Details

• Internal ID: 00c097b7-d9ae-491d-bedb-8275d4ee1281
• 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-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)OC4C(C(C(C(O4)C(=O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O
• InChI: InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1
• InChI Key: LNOHXHDWGCMVCO-NTKSAMNMSA-N
• Popularity: 8 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

• Oroxindin
• 51059-44-0
• Wogonin 7-O-glucuronide
• Glychionide B
• UNII-ETX4944Z3R
• ETX4944Z3R
• CHEBI:61282
• 5,7-dihydroxy-8-methoxyflavone 7-O-beta-D-glucuronide
• wogonin 7-O-beta-glucuronine methyl ester
• CHEMBL464732
• (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
• wogonin 7-O-beta-D-glucuronide
• DTXSID80199062
• Wogonin 7-glucuronide
• 5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acid
• MFCD08704808
• MEGxp0_000537
• ACon1_000851
• DTXCID10121553
• WOGONIN 7-beta-D-GLUCURONIDE
• HY-N0399
• BDBM50478452
• s9115
• AKOS015897144
• CCG-269333
• Wogonoside, >=95% (LC/MS-ELSD)
• WOGONIN 7-.BETA.-D-GLUCURONIDE
• NCGC00169296-01
• WOGONIN 7-O-.BETA.-D-GLUCURONIDE
• CS-0008934
• W0012
• WOGONIN 7-O-beta-D-GLUCURONOPYRANOSIDE
• WOGONIN 7-O-.BETA.-D-GLUCURONOPYRANOSIDE
• A854472
• Q3356626
• W-202920
• BRD-K72010518-001-01-0
• (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
• .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 5-HYDROXY-8-METHOXY-4-OXO-2-PHENYL-4H-1-BENZOPYRAN-7-YL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7483	74.83%
Caco-2	-	0.8411	84.11%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6619	66.19%
OATP2B1 inhibitior	-	0.5068	50.68%
OATP1B1 inhibitior	+	0.9128	91.28%
OATP1B3 inhibitior	+	0.9857	98.57%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8078	80.78%
P-glycoprotein inhibitior	-	0.6771	67.71%
P-glycoprotein substrate	-	0.8420	84.20%
CYP3A4 substrate	+	0.5827	58.27%
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	+	0.7586	75.86%
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	-	0.9155	91.55%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.4671	46.71%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9291	92.91%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8081	80.81%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.8093	80.93%
Androgen receptor binding	+	0.7171	71.71%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7600	76.00%
Aromatase binding	-	0.4897	48.97%
PPAR gamma	+	0.6531	65.31%
Honey bee toxicity	-	0.7954	79.54%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	99.02%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.57%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.76%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.91%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.85%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	91.62%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.03%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.00%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.49%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.34%	99.23%
CHEMBL3194	P02766	Transthyretin	84.26%	90.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	83.44%	89.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.34%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.12%	85.14%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.07%	83.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.33%	97.14%

Plants that contains it

• Andrographis paniculata
• Atractylodes lancea
• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum scorzonerifolium
• Lawrencella rosea
• Parinari campestris
• Prunus persica
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Scutellaria alpina
• Scutellaria altissima
• Scutellaria baicalensis
• Scutellaria comosa
• Scutellaria discolor
• Scutellaria galericulata
• Scutellaria grossa
• Scutellaria indica
• Scutellaria iskanderi
• Scutellaria orientalis
• Scutellaria pekinensis var. pekinensis
• Scutellaria phyllostachya
• Scutellaria prostrata
• Scutellaria scandens
• Stizophyllum riparium
• Utricularia vulgaris
• Vincetoxicum amplexicaule

Cross-Links

• PubChem: 3084961
• NPASS: NPC264735
• LOTUS: LTS0114948
• wikiData: Q3356626