(R)-Hispaglabridin A

Details

• Internal ID: db95a325-e9fa-46fe-9028-8f2c6e54be19
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Pyranoisoflavonoids
• IUPAC Name: 4-(8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl)-2-(3-methylbut-2-enyl)benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)C2CC3=C(C4=C(C=C3)OC(C=C4)(C)C)OC2)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)C2CC3=C(C4=C(C=C3)OC(C=C4)(C)C)OC2)O)C
• InChI: InChI=1S/C25H28O4/c1-15(2)5-7-19-21(26)9-8-18(23(19)27)17-13-16-6-10-22-20(24(16)28-14-17)11-12-25(3,4)29-22/h5-6,8-12,17,26-27H,7,13-14H2,1-4H3
• InChI Key: HZHXMXSXYQCAIG-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₄
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.19875937 g/mol
• Topological Polar Surface Area (TPSA): 58.90 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.51
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• CHEBI:175139
• HZHXMXSXYQCAIG-UHFFFAOYSA-N
• (R)-4-(8,8-Dimethyl-2,3,4,8-tetrahydropyrano[2,3-f]chromen-3-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
• 1,3-Benzenediol, 4-(3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl)-2-(3-methyl-2-butenyl)-, (R)-
• 1,3-Benzenediol, 4-[(3R)-3,4-dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-3-yl]-2-(3-methyl-2-butenyl)-
• 4-(3,4-dihydro-8 ,8-dimethyl-2h,8h-benzo[1,2-b:3,4-b'] dipyran-3-yl)-2-(3-methyl-2-butenyl)-1,3-benzenediol
• 4-(8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-]chromen-3-yl)-2-(3-methylbut-2-enyl)benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9712	97.12%
Caco-2	+	0.6693	66.93%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7709	77.09%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.8648	86.48%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9704	97.04%
P-glycoprotein inhibitior	+	0.6694	66.94%
P-glycoprotein substrate	+	0.6163	61.63%
CYP3A4 substrate	+	0.6448	64.48%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	+	0.3827	38.27%
CYP3A4 inhibition	-	0.8709	87.09%
CYP2C9 inhibition	+	0.7230	72.30%
CYP2C19 inhibition	+	0.8285	82.85%
CYP2D6 inhibition	-	0.8388	83.88%
CYP1A2 inhibition	+	0.5894	58.94%
CYP2C8 inhibition	+	0.5719	57.19%
CYP inhibitory promiscuity	+	0.8361	83.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7434	74.34%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.7339	73.39%
Skin irritation	-	0.7912	79.12%
Skin corrosion	-	0.9345	93.45%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7559	75.59%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8087	80.87%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7767	77.67%
Acute Oral Toxicity (c)	III	0.5079	50.79%
Estrogen receptor binding	+	0.9453	94.53%
Androgen receptor binding	+	0.7453	74.53%
Thyroid receptor binding	+	0.7207	72.07%
Glucocorticoid receptor binding	+	0.7713	77.13%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.8927	89.27%
Honey bee toxicity	-	0.7836	78.36%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	99.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.85%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	97.21%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.66%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.68%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.45%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.05%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.88%	100.00%
CHEMBL236	P41143	Delta opioid receptor	90.48%	99.35%
CHEMBL233	P35372	Mu opioid receptor	89.56%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.13%	97.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	87.70%	85.30%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.75%	91.38%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.62%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.74%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.34%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.74%	94.73%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.12%	85.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.25%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.58%	99.17%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.51%	83.10%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.36%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.35%	93.56%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.27%	97.50%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.80%	97.50%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	80.28%	96.39%

Plants that contains it

• Chimonanthus praecox
• Eumachia forsteriana
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis

Cross-Links

• PubChem: 4484221
• NPASS: NPC78634
• LOTUS: LTS0256698
• wikiData: Q104910893