Dihydrodaidzin

Details

• Internal ID: 4542439f-ebb9-4365-8a5b-5111250c6871
• 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]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(C(=O)C2=C(O1)C=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O
• SMILES (Isomeric): C1C(C(=O)C2=C(O1)C=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=C(C=C4)O
• InChI: InChI=1S/C21H22O9/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/h1-7,14,16,18-23,25-27H,8-9H2/t14?,16-,18-,19+,20-,21-/m1/s1
• InChI Key: KKJXSJGKUZBVIH-RGHIGTIISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₉
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 121927-96-6
• 3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SCHEMBL571768
• CHEMBL464455
• CHEBI:191478
• AKOS040760080
• 7,4'-Dihydroxyisoflavanone 7-O-glucoside
• 3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9277	92.77%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	-	0.5704	57.04%
OATP1B1 inhibitior	+	0.8963	89.63%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5685	56.85%
P-glycoprotein inhibitior	-	0.7918	79.18%
P-glycoprotein substrate	-	0.8548	85.48%
CYP3A4 substrate	+	0.5944	59.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8353	83.53%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	-	0.5916	59.16%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8871	88.71%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5379	53.79%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6431	64.31%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.6729	67.29%
Androgen receptor binding	+	0.6548	65.48%
Thyroid receptor binding	+	0.5856	58.56%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5125	51.25%
PPAR gamma	+	0.7619	76.19%
Honey bee toxicity	-	0.7917	79.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.84%	97.09%
CHEMBL2581	P07339	Cathepsin D	96.19%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	92.70%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.41%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.88%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.84%	96.09%
CHEMBL4208	P20618	Proteasome component C5	89.80%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.62%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.07%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.47%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.53%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	85.58%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.43%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.45%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.58%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.15%	96.21%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.13%	85.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.67%	95.78%

Plants that contains it

• Glycine max

Cross-Links

• PubChem: 10341941
• NPASS: NPC271479
• LOTUS: LTS0257140
• wikiData: Q105142223