Glabranin

Details

• Internal ID: 1a5cb341-bbb7-42bc-875b-3160866d69a5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC=CC=C3)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC=CC=C3)C
• InChI: InChI=1S/C20H20O4/c1-12(2)8-9-14-15(21)10-16(22)19-17(23)11-18(24-20(14)19)13-6-4-3-5-7-13/h3-8,10,18,21-22H,9,11H2,1-2H3/t18-/m0/s1
• InChI Key: DAWSYIQAGQMLFS-SFHVURJKSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.31
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 41983-91-9
• Glabranine
• 8-Prenylpinocembrin
• CHEBI:5368
• TNP00074
• (2S)-5,7-dihydroxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• (S)-2,3-Dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-, (S)-
• (2s)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenyl-2,3-dihydro-4h-chromen-4-one
• 8-dimethylallylpinocembrin
• TimTec1_002029
• SCHEMBL320136
• CHEMBL253998
• BDBM26663
• DTXSID00194796
• HMS1539M05
• HY-N3942
• LMPK12140164
• STL564423
• AKOS001737904
• NCGC00017206-01
• NCGC00017206-02
• NCGC00142379-01
• LS-39551
• MS-24833
• XP161632
• CS-0024491
• C09752
• SR-01000530493
• SR-01000530493-1
• BRD-K83252656-001-01-7
• Q27106734
• (2S)-5,7-dihydroxy-8-(3-methylbut-2-enyl)-2-phenyl-chroman-4-one
• (2S)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
• (2S)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-2-phenyl-, (2S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	+	0.8450	84.50%
Blood Brain Barrier	-	0.5629	56.29%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7746	77.46%
OATP2B1 inhibitior	-	0.7307	73.07%
OATP1B1 inhibitior	+	0.8946	89.46%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6214	62.14%
P-glycoprotein inhibitior	-	0.5050	50.50%
P-glycoprotein substrate	-	0.8660	86.60%
CYP3A4 substrate	-	0.5201	52.01%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	+	0.6075	60.75%
CYP2C9 inhibition	+	0.9007	90.07%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.5927	59.27%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6627	66.27%
CYP inhibitory promiscuity	+	0.9271	92.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6821	68.21%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.5453	54.53%
Skin irritation	-	0.7351	73.51%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6413	64.13%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7491	74.91%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.5561	55.61%
Acute Oral Toxicity (c)	III	0.4391	43.91%
Estrogen receptor binding	+	0.7552	75.52%
Androgen receptor binding	+	0.6652	66.52%
Thyroid receptor binding	+	0.5732	57.32%
Glucocorticoid receptor binding	+	0.6397	63.97%
Aromatase binding	-	0.5565	55.65%
PPAR gamma	+	0.8621	86.21%
Honey bee toxicity	-	0.8886	88.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3622	P33261	Cytochrome P450 2C19	1000 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3162.3 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.75%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	92.94%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.88%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.59%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.60%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.19%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.97%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.31%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.74%	97.09%

Plants that contains it

• Acritopappus longifolius
• Adenocarpus hispanicus
• Annona glabra
• Annona glauca
• Annona squamosa
• Bicuiba oleifera
• Campylopus clavatus
• Eysenhardtia platycarpa
• Glycyrrhiza
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza lepidota
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Helichrysum forskahlii
• Mitracarpus hirtus
• Parthenocissus tricuspidata
• Piscidia piscipula
• Plumbago indica
• Rhododendron maximum
• Sarracenia flava
• Sophora tomentosa
• Tasmannia lanceolata
• Tephrosia major
• Viola odorata

Cross-Links

• PubChem: 124049
• NPASS: NPC37496
• ChEMBL: CHEMBL253998
• LOTUS: LTS0250433
• wikiData: Q27106734