Glycitein

Details

• Internal ID: 8d97addd-2e7a-449c-a16d-c5a28035680a
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones
• IUPAC Name: 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
• InChI Key: DXYUAIFZCFRPTH-UHFFFAOYSA-N
• Popularity: 1,094 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26 g/mol
• Exact Mass: 284.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.88
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 40957-83-3
• 7,4'-Dihydroxy-6-methoxyisoflavone
• 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-
• 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
• 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
• 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
• UNII-92M5F28TVF
• 92M5F28TVF
• CHEMBL513024
• CHEBI:34778
• 4',7-Dihydroxy-6-methoxyisoflavone
• MFCD00016679
• GLYCITEIN [USP-RS]
• SCHEMBL19720
• BIDD:ER0470
• Glycitein, analytical standard
• 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-chromen-4-one
• Glycitein, >=97% (HPLC)
• DTXSID40193960
• HMS3886N16
• BCP13270
• HY-N0016
• AC-998
• BDBM50241530
• LMPK12050104
• s9107
• AKOS015892762
• CCG-267294
• AS-71538
• LS-185206
• FT-0630616
• A825364
• Q-100465
• Q3109347
• 4-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-chromen-7-one
• 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4H-one
• GLYCITEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
• Glycitein, United States Pharmacopeia (USP) Reference Standard
• 7-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one; 7,4 inverted exclamation mark -Dihydroxy-6 methoxyisoflavone;Glycetein

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9779	97.79%
Caco-2	+	0.9346	93.46%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8113	81.13%
OATP2B1 inhibitior	+	0.5515	55.15%
OATP1B1 inhibitior	+	0.9561	95.61%
OATP1B3 inhibitior	+	0.9877	98.77%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7080	70.80%
P-glycoprotein inhibitior	-	0.6584	65.84%
P-glycoprotein substrate	-	0.9083	90.83%
CYP3A4 substrate	+	0.5600	56.00%
CYP2C9 substrate	-	0.8382	83.82%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.6447	64.47%
CYP2C9 inhibition	+	0.8876	88.76%
CYP2C19 inhibition	+	0.9315	93.15%
CYP2D6 inhibition	-	0.8064	80.64%
CYP1A2 inhibition	+	0.9264	92.64%
CYP2C8 inhibition	+	0.6925	69.25%
CYP inhibitory promiscuity	+	0.7815	78.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5580	55.80%
Eye corrosion	-	0.9749	97.49%
Eye irritation	+	0.8369	83.69%
Skin irritation	-	0.5737	57.37%
Skin corrosion	-	0.9616	96.16%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7149	71.49%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.9457	94.57%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.4825	48.25%
Acute Oral Toxicity (c)	III	0.7641	76.41%
Estrogen receptor binding	+	0.9272	92.72%
Androgen receptor binding	+	0.9147	91.47%
Thyroid receptor binding	+	0.7472	74.72%
Glucocorticoid receptor binding	+	0.8730	87.30%
Aromatase binding	+	0.8659	86.59%
PPAR gamma	+	0.7306	73.06%
Honey bee toxicity	-	0.8674	86.74%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.8637	86.37%

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	97.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.73%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.43%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.52%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.23%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.87%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.35%	99.15%
CHEMBL1937	Q92769	Histone deacetylase 2	87.21%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.03%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	85.93%	98.35%
CHEMBL3194	P02766	Transthyretin	85.08%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.63%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.00%	85.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.57%	95.53%
CHEMBL1907	P15144	Aminopeptidase N	82.45%	93.31%
CHEMBL2535	P11166	Glucose transporter	82.09%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.64%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.76%	96.09%

Plants that contains it

• Ammopiptanthus mongolicus
• Astragalus condensatus
• Bertya dimerostigma
• Dalbergia frutescens
• Delphinium barbeyi
• Glycine max
• Pueraria montana var. lobata
• Pueraria montana var. thomsonii
• Trifolium pratense
• Wisteria brachybotrys

Cross-Links

• PubChem: 5317750
• NPASS: NPC100971
• LOTUS: LTS0194715
• wikiData: Q3109347