Daidzin

Details

• Internal ID: f7288219-31ef-4f48-980e-58b6af3d64ba
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
• InChI Key: KYQZWONCHDNPDP-QNDFHXLGSA-N
• Popularity: 1,005 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₉
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.11073221 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.34
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 552-66-9
• Daidzoside
• Daidzein 7-O-glucoside
• Daidzein 7-glucoside
• Daidzein-7-glucoside
• daidzein 7-O-beta-D-glucoside
• 7-(beta-D-Glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• UNII-4R2X91A5M5
• BRN 0059741
• NPI 031D
• CHEBI:42202
• 4R2X91A5M5
• 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 4-18-00-01808 (Beilstein Handbook Reference)
• 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
• DAIDZIN (USP-RS)
• DAIDZIN [USP-RS]
• 3-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• DZN
• daidzein-7-o-glucoside
• Dadzin
• 2vle
• 7-O-glucosyl-4'-hydroxyisoflavone
• MFCD00017466
• DAIDZEIN DAIDZIN
• 7-O-beta-D-glucopyranoside
• Daidzin, analytical standard
• MLS006010640
• BIDD:ER0154
• DAIDZEIN DAIDZIN [MI]
• SCHEMBL315373
• CHEMBL486422
• MEGxp0_000530
• NPI-031D
• ACon1_002092
• DTXSID00862180
• 4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-
• KYQZWONCHDNPDP-QNDFHXLGSA-N
• Daidzin, >=95.0% (HPLC)
• 3-(4-hydroxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
• Daidzein 7-O-|A-D-glucopyranoside
• HY-N0018
• Daidzein 7-O-beta-D-glucopyranoside
• BDBM50409029
• STL565871
• 7,4'-Dihydroxyisoflavone 7-glucoside
• CCG-208383
• CS-4237
• DB02115
• DAIDZEIN 7-O-.BETA.-D-GLUCOSIDE
• NCGC00163532-02
• NCGC00163532-03
• NCGC00179839-01
• AS-35078
• LS-39679
• SMR001833087
• DAIDZIN (CONSTITUENT OF ASTRAGALUS)
• DAIDZIN (CONSTITUENT OF SOY ISOFLAVONES)
• 4',7-Dihydroxyisoflavone 7-O-b-D-glucopyranoside
• A830561
• DAIDZIN (CONSTITUENT OF ASTRAGALUS) [DSC]
• Daidzin, primary pharmaceutical reference standard
• Q-100628
• Q3814656
• DAIDZIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
• 4',7-DIHYDROXYISOFLAVONE; 7-O-B-D-GLUCOPYRANOSIDE
• Daidzin, United States Pharmacopeia (USP) Reference Standard
• 3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
• 3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside
• 3-(4-hydroxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-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	-	0.9373	93.73%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.5522	55.22%
OATP1B1 inhibitior	+	0.9448	94.48%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5966	59.66%
P-glycoprotein inhibitior	-	0.7649	76.49%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.6224	62.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8415	84.15%
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	+	0.6553	65.53%
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	-	0.8843	88.43%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5807	58.07%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5509	55.09%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.6731	67.31%
Androgen receptor binding	+	0.7560	75.60%
Thyroid receptor binding	+	0.5685	56.85%
Glucocorticoid receptor binding	+	0.6801	68.01%
Aromatase binding	+	0.6221	62.21%
PPAR gamma	+	0.8090	80.90%
Honey bee toxicity	-	0.7453	74.53%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.8218	82.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1935	P05091	Aldehyde dehydrogenase	80 nM; 40 nM	IC50; IC50	PMID: 11563931; PMID: 11063613
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3162.3 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	5623.4 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	25118.9 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	99.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.43%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.21%	89.00%
CHEMBL242	Q92731	Estrogen receptor beta	93.36%	98.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.20%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.48%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.07%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.97%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.28%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.93%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.81%	91.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.97%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.18%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.87%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.80%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.33%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	83.29%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.72%	96.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.76%	97.28%
CHEMBL3401	O75469	Pregnane X receptor	80.69%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	80.27%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.02%	96.00%

Plants that contains it

• Adenocarpus artemisiifolius
• Astragalus condensatus
• Astragalus multiceps
• Baptisia bracteata
• Baptisia lecontei
• Begonia nantoensis
• Bertya dimerostigma
• Cicer arietinum
• Cicer flexuosum
• Cullen corylifolium
• Cullen drupaceum
• Cullen plicatum
• Delphinium barbeyi
• Ducrosia ismaelis
• Erythrina latissima
• Flemingia macrophylla
• Froelichia floridana
• Genista sessilifolia
• Glycine max
• Hibiscus schizopetalus
• Hyoscyamus pusillus
• Justicia adhatoda
• Maackia amurensis
• Murraya exotica
• Murraya paniculata
• Ormosia henryi
• Phyllolobium chinense
• Platymiscium floribundum
• Pterocarpus indicus
• Pueraria montana var. lobata
• Pueraria montana var. thomsonii
• Pueraria tuberosa
• Punica granatum
• Retama sphaerocarpa
• Rubia cordifolia
• Styrax agrestis
• Teucrium marum
• Thermopsis rhombifolia
• Trifolium pratense
• Urceola laevigata
• Vigna angularis
• Vigna radiata
• Ziziphus jujuba var. spinosa

Cross-Links

• PubChem: 107971
• NPASS: NPC161749
• ChEMBL: CHEMBL486422
• LOTUS: LTS0223055
• wikiData: Q3814656