Glyasperin C

Details

• Internal ID: 499d6fff-175d-49d6-a7ef-d32fa831d44d
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 5-O-methylated isoflavonoids
• IUPAC Name: 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OCC(C2)C3=C(C=C(C=C3)O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC[C@H](C2)C3=C(C=C(C=C3)O)O)OC)C
• InChI: InChI=1S/C21H24O5/c1-12(2)4-6-16-19(24)10-20-17(21(16)25-3)8-13(11-26-20)15-7-5-14(22)9-18(15)23/h4-5,7,9-10,13,22-24H,6,8,11H2,1-3H3/t13-/m0/s1
• InChI Key: RCZMWVKBVFOCEE-ZDUSSCGKSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.16237386 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 142474-53-1
• CHEBI:69089
• 85CR4734XV
• Glyasperin C - Glycyrrhiza uralensis (liquorice)
• (R)-4-(7-Hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)chroman-3-yl)benzene-1,3-diol
• 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]benzene-1,3-diol
• 4-((R)-7-Hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl)-benzene-1,3-diol
• 1,3-Benzenediol,4-[(3R)-3,4-dihydro-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-3-yl]-
• 4-[(3r)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-chromen-3-yl]benzene-1,3-diol
• 1,3-BENZENEDIOL, 4-((3R)-3,4-DIHYDRO-7-HYDROXY-5-METHOXY-6-(3-METHYL-2-BUTEN-1-YL)-2H-1-BENZOPYRAN-3-YL)-
• 1,3-BENZENEDIOL, 4-(3,4-DIHYDRO-7-HYDROXY-5-METHOXY-6-(3-METHYL-2-BUTENYL)-2H-1-BENZOPYRAN-3-YL)-, (R)-
• 4-((3R)-3,4-DIHYDRO-7-HYDROXY-5-METHOXY-6-(3-METHYL-2-BUTEN-1-YL)-2H-1-BENZOPYRAN-3-YL)-1,3-BENZENEDIOL
• 4-[(R)-7-Hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl]-benzene-1,3-diol
• 4-((3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-3-yl)benzene-1,3-diol
• UNII-85CR4734XV
• CHEMBL1630857
• DTXSID40162055
• HY-N9919
• BDBM50172096
• MS-25583
• XG170491
• CS-0213814
• E80558
• Q27137430
• 4-[(3R)-7-hydroxy-5-methoxy-6-(3-methylbut-2-enyl)chroman-3-yl]benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9657	96.57%
Caco-2	+	0.7677	76.77%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7468	74.68%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8951	89.51%
OATP1B3 inhibitior	+	0.9224	92.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8149	81.49%
P-glycoprotein inhibitior	-	0.4755	47.55%
P-glycoprotein substrate	+	0.5995	59.95%
CYP3A4 substrate	+	0.6134	61.34%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.4888	48.88%
CYP3A4 inhibition	-	0.7310	73.10%
CYP2C9 inhibition	+	0.7765	77.65%
CYP2C19 inhibition	+	0.8637	86.37%
CYP2D6 inhibition	-	0.5398	53.98%
CYP1A2 inhibition	+	0.8762	87.62%
CYP2C8 inhibition	+	0.6377	63.77%
CYP inhibitory promiscuity	+	0.9195	91.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7717	77.17%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.6036	60.36%
Skin irritation	-	0.8179	81.79%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7147	71.47%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8377	83.77%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7823	78.23%
Acute Oral Toxicity (c)	III	0.5623	56.23%
Estrogen receptor binding	+	0.8490	84.90%
Androgen receptor binding	+	0.7396	73.96%
Thyroid receptor binding	+	0.7020	70.20%
Glucocorticoid receptor binding	+	0.7988	79.88%
Aromatase binding	-	0.5271	52.71%
PPAR gamma	+	0.7700	77.00%
Honey bee toxicity	-	0.8172	81.72%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1973	P14679	Tyrosinase	177 nM; 177 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	99.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.32%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.12%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.53%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.25%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.03%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.57%	99.17%
CHEMBL2535	P11166	Glucose transporter	88.00%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.03%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.24%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	82.98%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.82%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	82.63%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.47%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.32%	89.00%
CHEMBL240	Q12809	HERG	81.61%	89.76%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.54%	85.00%

Plants that contains it

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

Cross-Links

• PubChem: 480859
• NPASS: NPC53986
• ChEMBL: CHEMBL1630857
• LOTUS: LTS0120599
• wikiData: Q27137430