Isoxanthohumol(Sophora)

Details

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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

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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

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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
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Isoxanthohumol(Sophora)

3D Structure

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ADMET Properties (via admetSAR 2)

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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

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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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Humulus lupulus
Sophora flavescens

Cross-Links

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PubChem 513197
NPASS NPC76338
ChEMBL CHEMBL492828
LOTUS LTS0254582
wikiData Q6086616