Glyasperin D

Details

• Internal ID: c1ca24c0-7bc4-447a-88bb-72f33976169d
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 7-O-methylated isoflavonoids
• IUPAC Name: 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=C2C(=C1OC)CC(CO2)C3=C(C=C(C=C3)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=C2C(=C1OC)C[C@@H](CO2)C3=C(C=C(C=C3)O)O)OC)C
• InChI: InChI=1S/C22H26O5/c1-13(2)5-7-17-20(25-3)11-21-18(22(17)26-4)9-14(12-27-21)16-8-6-15(23)10-19(16)24/h5-6,8,10-11,14,23-24H,7,9,12H2,1-4H3/t14-/m0/s1
• InChI Key: DDMAUIOCNQXFHL-AWEZNQCLSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.17802393 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.34
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 142561-10-2
• CHEBI:69084
• T6ZF2ZY8CW
• 4-((R)-5,7-Dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl)-benzene-1,3-diol
• 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]benzene-1,3-diol
• 4-[(3r)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-chromen-3-yl]benzene-1,3-diol
• GlyasperinD
• 1,3-BENZENEDIOL, 4-((3R)-3,4-DIHYDRO-5,7-DIMETHOXY-6-(3-METHYL-2-BUTEN-1-YL)-2H-1-BENZOPYRAN-3-YL)-
• 1,3-BENZENEDIOL, 4-(3,4-DIHYDRO-5,7-DIMETHOXY-6-(3-METHYL-2-BUTENYL)-2H-1-BENZOPYRAN-3-YL)-, (R)-
• 4-((3R)-3,4-DIHYDRO-5,7-DIMETHOXY-6-(3-METHYL-2-BUTEN-1-YL)-2H-1-BENZOPYRAN-3-YL)-1,3-BENZENEDIOL
• 4-[(R)-5,7-Dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl]-benzene-1,3-diol
• 4-((3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-3-yl)benzene-1,3-diol
• UNII-T6ZF2ZY8CW
• MLS000697603
• CHEMBL1563332
• DTXSID80931525
• HMS2270J03
• HY-N6975
• BDBM50172095
• AKOS040760428
• NCGC00247521-01
• NCGC00247521-02
• SMR000470940
• CS-0101416
• Q27137423
• 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)chroman-3-yl]benzene-1,3-diol
• 4-[5,7-Dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]benzene-1,3-diol
• NCGC00247521-02_C22H26O5_4-[(3R)-5,7-Dimethoxy-6-(3-methyl-2-buten-1-yl)-3,4-dihydro-2H-chromen-3-yl]-1,3-benzenediol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9587	95.87%
Caco-2	+	0.8545	85.45%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7518	75.18%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9108	91.08%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8506	85.06%
P-glycoprotein inhibitior	+	0.6021	60.21%
P-glycoprotein substrate	+	0.6075	60.75%
CYP3A4 substrate	+	0.6091	60.91%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.4888	48.88%
CYP3A4 inhibition	-	0.6063	60.63%
CYP2C9 inhibition	+	0.7865	78.65%
CYP2C19 inhibition	+	0.8838	88.38%
CYP2D6 inhibition	-	0.5544	55.44%
CYP1A2 inhibition	+	0.8800	88.00%
CYP2C8 inhibition	+	0.6717	67.17%
CYP inhibitory promiscuity	+	0.9468	94.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7644	76.44%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.7747	77.47%
Skin irritation	-	0.8098	80.98%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4570	45.70%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8318	83.18%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8165	81.65%
Acute Oral Toxicity (c)	III	0.5817	58.17%
Estrogen receptor binding	+	0.8623	86.23%
Androgen receptor binding	+	0.7345	73.45%
Thyroid receptor binding	+	0.6694	66.94%
Glucocorticoid receptor binding	+	0.7425	74.25%
Aromatase binding	-	0.6571	65.71%
PPAR gamma	+	0.7439	74.39%
Honey bee toxicity	-	0.7936	79.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1973	P14679	Tyrosinase	154 nM; 154 nM	IC50; IC50	via Super-PRED; PMID: 26841168

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.84%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.68%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.10%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.97%	94.45%
CHEMBL2535	P11166	Glucose transporter	90.60%	98.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.04%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.70%	95.89%
CHEMBL240	Q12809	HERG	87.90%	89.76%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.82%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.59%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.96%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.58%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.47%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.36%	92.62%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.22%	89.50%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.13%	94.03%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.97%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.62%	97.09%

Plants that contains it

• Glycyrrhiza aspera
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 480860
• NPASS: NPC38664
• ChEMBL: CHEMBL1563332
• LOTUS: LTS0164224
• wikiData: Q27137423