Oroxin A

Details

• Internal ID: e5e60548-27c1-480a-b033-68553e8b102c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,6-dihydroxy-2-phenyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-8-14-17(25)19(27)20(28)21(31-14)30-13-7-12-15(18(26)16(13)24)10(23)6-11(29-12)9-4-2-1-3-5-9/h1-7,14,17,19-22,24-28H,8H2/t14-,17-,19+,20-,21-/m1/s1
• InChI Key: IPQKDIRUZHOIOM-IAAKTDFRSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.10564683 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 57396-78-8
• baicalein-7-o-glucoside
• baicalein 7-O-glucoside
• 5,6-dihydroxy-2-phenyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5,6-dihydroxy-2-phenyl-
• OroxinA
• Oroxin A; Baicalein-7-O-glucoside; Baikalin
• Baicalein 7-O-glucopyranoside
• CHEMBL516858
• SCHEMBL6238244
• baicalein 7-O-beta-D-glucoside
• DTXSID70904521
• IPQKDIRUZHOIOM-IAAKTDFRSA-N
• HY-N2025
• MFCD22125001
• s9189
• AKOS030573618
• CCG-269033
• NCGC00017393-02
• NCGC00142466-01
• MS-27709
• CS-0018488
• BAICALEIN 7-O-B-D-GLUCOPYRANOSIDE (BAICALIN)
• 5,6-Dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl -D-glucopyranoside
• 5,6-Dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl hexopyranoside #
• 5,6-Dihydroxy-2-phenyl-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9459	94.59%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.6198	61.98%
OATP1B1 inhibitior	+	0.8521	85.21%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5875	58.75%
P-glycoprotein inhibitior	-	0.8334	83.34%
P-glycoprotein substrate	-	0.8694	86.94%
CYP3A4 substrate	+	0.5532	55.32%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.6569	65.69%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8174	81.74%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5064	50.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5777	57.77%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8760	87.60%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7639	76.39%
Androgen receptor binding	+	0.7528	75.28%
Thyroid receptor binding	+	0.5529	55.29%
Glucocorticoid receptor binding	+	0.6998	69.98%
Aromatase binding	+	0.7569	75.69%
PPAR gamma	+	0.7903	79.03%
Honey bee toxicity	-	0.6778	67.78%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.8218	82.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	11220.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 794.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	12589.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	17782.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.90%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.00%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.92%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.68%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.23%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.21%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.47%	99.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.54%	94.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.54%	95.50%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.15%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	83.93%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	83.14%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.53%	96.21%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.23%	94.62%

Plants that contains it

• Oroxylum indicum
• Scutellaria baicalensis
• Scutellaria comosa
• Scutellaria glabrata
• Scutellaria immaculata
• Scutellaria pekinensis var. pekinensis
• Scutellaria phyllostachya

Cross-Links

• PubChem: 5320313
• NPASS: NPC45618
• ChEMBL: CHEMBL516858
• LOTUS: LTS0136774
• wikiData: Q72497982