Glabrol

Details

• Internal ID: f5c0a6d5-65a2-4b83-9af1-c53a6d89ada0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)C2CC(=O)C3=C(O2)C(=C(C=C3)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)[C@@H]2CC(=O)C3=C(O2)C(=C(C=C3)O)CC=C(C)C)O)C
• InChI: InChI=1S/C25H28O4/c1-15(2)5-7-17-13-18(8-11-21(17)26)24-14-23(28)20-10-12-22(27)19(25(20)29-24)9-6-16(3)4/h5-6,8,10-13,24,26-27H,7,9,14H2,1-4H3/t24-/m0/s1
• InChI Key: CUFAXDWQDQQKFF-DEOSSOPVSA-N
• Popularity: 20 references 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): 66.80 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.82
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 59870-65-4
• UNII-E4XEY076JN
• E4XEY076JN
• (S)-7-Hydroxy-2-(4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl)-8-(3-methylbut-2-en-1-yl)chroman-4-one
• MLS000697605
• (2S)-7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMR000470942
• 7-Hydroxy-2-(4-hydroxy-3-((E)-3-methyl-but-2-enyl)-phenyl)-8-(3-methyl-but-2-enyl)-1-benzopyran-4-one
• 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-7-HYDROXY-2-(4-HYDROXY-3-(3-METHYL-2-BUTEN-1-YL)PHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2S)-
• 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxy-3-(methyl-2-butenyl)phenyl)-8-(3-methyl-2-butenyl)-, (2S)-
• CHEMBL462721
• SCHEMBL15602627
• BDBM69609
• CHEBI:177851
• cid_11596309
• HMS2271C14
• HY-N4193
• NCGC00247523-01
• MS-26568
• CS-0032386
• Q27276872
• (2S)-7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)-3,4-dihydro-2H-1-benzopyran-4-one
• (2S)-7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-8-(3-methylbut-2-enyl)chroman-4-one
• (2S)-8-(3-methylbut-2-enyl)-2-[3-(3-methylbut-2-enyl)-4-oxidanyl-phenyl]-7-oxidanyl-2,3-dihydrochromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	+	0.6179	61.79%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8330	83.30%
OATP2B1 inhibitior	-	0.5835	58.35%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9239	92.39%
P-glycoprotein inhibitior	+	0.7841	78.41%
P-glycoprotein substrate	-	0.7519	75.19%
CYP3A4 substrate	+	0.5319	53.19%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.7235	72.35%
CYP3A4 inhibition	-	0.8183	81.83%
CYP2C9 inhibition	+	0.8873	88.73%
CYP2C19 inhibition	+	0.8995	89.95%
CYP2D6 inhibition	-	0.8065	80.65%
CYP1A2 inhibition	+	0.7807	78.07%
CYP2C8 inhibition	-	0.7864	78.64%
CYP inhibitory promiscuity	+	0.8661	86.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6706	67.06%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.6327	63.27%
Skin irritation	-	0.7571	75.71%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7022	70.22%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7310	73.10%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6401	64.01%
Estrogen receptor binding	+	0.9477	94.77%
Androgen receptor binding	+	0.7739	77.39%
Thyroid receptor binding	+	0.7536	75.36%
Glucocorticoid receptor binding	+	0.8291	82.91%
Aromatase binding	+	0.6389	63.89%
PPAR gamma	+	0.8906	89.06%
Honey bee toxicity	-	0.8136	81.36%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9913	99.13%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	37500 nM	IC50	PMID: 24047800

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.46%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.79%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.04%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.95%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.32%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.18%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.65%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.08%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.06%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.66%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.76%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.62%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.32%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.00%	96.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.74%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.08%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.66%	96.12%

Plants that contains it

• Euchresta formosana
• Euchresta horsfieldii
• Euchresta japonica
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Hovea parvicalyx
• Sophora alopecuroides
• Sophora prostrata
• Sophora tonkinensis

Cross-Links

• PubChem: 11596309
• NPASS: NPC150408
• ChEMBL: CHEMBL462721
• LOTUS: LTS0164961
• wikiData: Q27276872