Isoxanthohumol(Sophora)

Details

• Internal ID: c05fc1c3-9ef2-415b-8781-f327251cb592
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=CC=C(C=C3)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=CC=C(C=C3)O)C
• InChI: InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3
• InChI Key: YKGCBLWILMDSAV-UHFFFAOYSA-N
• Popularity: 82 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.32
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 521-48-2
• Isoxanthohumol(Sophora)
• (2S)-Isoxanthohumol
• 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• CHEMBL492828
• 7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one
• (+/-)-Isoxanthohumol
• UNII-B3BXQ4EZD6
• 5-Methylsophoraflavanone B
• Isoxanthohumol, HPLC Grade
• SCHEMBL904557
• HY-N2584A
• CHEBI:171798
• Isoxanthohumol, >=99% (HPLC)
• Isoxanthohumol, analytical standard
• BCP23864
• BDBM50252521
• LMPK12140553
• MFCD00238718
• SMP2_000215
• NCGC00390429-01
• MS-25527
• 4',7-dihydroxy-5-methoxy-8-prenylflavanone
• CS-0064440
• 4',7-dihydroxy-5-methoxy-8-c-prenylflavanone
• Q6086616
• Isoxanthohumol, primary pharmaceutical reference standard
• 7-hydroxy-2-(4-hydroxy-phenyl)-5-methoxy-8-(3-methyl-but-2-enyl)-chroman-4-one
• 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chroman-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-
• 7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-2,3-dihydro-4H-chromen-4-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.8888	88.88%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8193	81.93%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8759	87.59%
OATP1B3 inhibitior	+	0.8676	86.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7040	70.40%
P-glycoprotein inhibitior	+	0.6152	61.52%
P-glycoprotein substrate	-	0.7641	76.41%
CYP3A4 substrate	+	0.5904	59.04%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.7235	72.35%
CYP3A4 inhibition	-	0.8156	81.56%
CYP2C9 inhibition	+	0.8217	82.17%
CYP2C19 inhibition	+	0.9318	93.18%
CYP2D6 inhibition	-	0.6465	64.65%
CYP1A2 inhibition	+	0.7807	78.07%
CYP2C8 inhibition	+	0.5533	55.33%
CYP inhibitory promiscuity	+	0.8924	89.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6868	68.68%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.6660	66.60%
Skin irritation	-	0.8018	80.18%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4230	42.30%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.8307	83.07%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5311	53.11%
Acute Oral Toxicity (c)	III	0.6532	65.32%
Estrogen receptor binding	+	0.8560	85.60%
Androgen receptor binding	+	0.7107	71.07%
Thyroid receptor binding	+	0.6662	66.62%
Glucocorticoid receptor binding	+	0.7632	76.32%
Aromatase binding	-	0.5486	54.86%
PPAR gamma	+	0.7939	79.39%
Honey bee toxicity	-	0.7510	75.10%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9846	98.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	27700 nM	IC50	PMID: 18565755
CHEMBL299	P17252	Protein kinase C alpha	45300 nM	IC50	PMID: 22537682
CHEMBL3920	Q04759	Protein kinase C theta	31600 nM	IC50	PMID: 22537682

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.97%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.44%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.54%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.57%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.22%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.67%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.49%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.41%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.25%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.23%	94.73%
CHEMBL2535	P11166	Glucose transporter	86.13%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.87%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.57%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.12%	89.00%
CHEMBL4208	P20618	Proteasome component C5	83.52%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.16%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.68%	95.89%

Plants that contains it

• Humulus lupulus
• Sophora flavescens

Cross-Links

• PubChem: 513197
• NPASS: NPC76338
• ChEMBL: CHEMBL492828
• LOTUS: LTS0254582
• wikiData: Q6086616