Auriculin

Details

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Internal ID 878db71c-48a4-40c7-9ffa-37252c52aca7
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
IUPAC Name 5-hydroxy-7-(2-hydroxy-4-methoxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
SMILES (Canonical) CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=C(C=C(C=C4)OC)O)O)C=CC(O2)(C)C)C
SMILES (Isomeric) CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=C(C=C(C=C4)OC)O)O)C=CC(O2)(C)C)C
InChI InChI=1S/C26H26O6/c1-14(2)6-8-18-24-17(10-11-26(3,4)32-24)22(28)21-23(29)19(13-31-25(18)21)16-9-7-15(30-5)12-20(16)27/h6-7,9-13,27-28H,8H2,1-5H3
InChI Key VQGWUEFARIAFPF-UHFFFAOYSA-N
Popularity 15,476 references in papers

Physical and Chemical Properties

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Molecular Formula C26H26O6
Molecular Weight 434.50 g/mol
Exact Mass 434.17293854 g/mol
Topological Polar Surface Area (TPSA) 85.20 Ų
XlogP 5.80
Atomic LogP (AlogP) 5.57
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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30431-68-6
Auriculatin 4'-methyl ether
5-Hydroxy-3-(2-hydroxy-4-methoxyphenyl)-8,8-dimethyl-10-(3-methyl-2-butenyl)-4H,8H-benzo[1,2-b
Auriculin (ketone)
SCHEMBL669210
DTXSID00184516
LMPK12050316

2D Structure

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2D Structure of Auriculin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9926 99.26%
Caco-2 - 0.5221 52.21%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.8253 82.53%
OATP2B1 inhibitior - 0.7161 71.61%
OATP1B1 inhibitior + 0.8740 87.40%
OATP1B3 inhibitior - 0.2715 27.15%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9285 92.85%
P-glycoprotein inhibitior + 0.8087 80.87%
P-glycoprotein substrate - 0.5862 58.62%
CYP3A4 substrate + 0.6541 65.41%
CYP2C9 substrate - 0.5948 59.48%
CYP2D6 substrate - 0.8144 81.44%
CYP3A4 inhibition - 0.7314 73.14%
CYP2C9 inhibition + 0.8308 83.08%
CYP2C19 inhibition + 0.9399 93.99%
CYP2D6 inhibition - 0.7995 79.95%
CYP1A2 inhibition - 0.5996 59.96%
CYP2C8 inhibition + 0.6648 66.48%
CYP inhibitory promiscuity + 0.9008 90.08%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9513 95.13%
Carcinogenicity (trinary) Non-required 0.5849 58.49%
Eye corrosion - 0.9900 99.00%
Eye irritation + 0.5246 52.46%
Skin irritation - 0.7681 76.81%
Skin corrosion - 0.9573 95.73%
Ames mutagenesis + 0.5963 59.63%
Human Ether-a-go-go-Related Gene inhibition + 0.7236 72.36%
Micronuclear - 0.5000 50.00%
Hepatotoxicity - 0.5448 54.48%
skin sensitisation - 0.8174 81.74%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.6596 65.96%
Acute Oral Toxicity (c) III 0.7473 74.73%
Estrogen receptor binding + 0.9471 94.71%
Androgen receptor binding + 0.8097 80.97%
Thyroid receptor binding + 0.7226 72.26%
Glucocorticoid receptor binding + 0.8557 85.57%
Aromatase binding + 0.6809 68.09%
PPAR gamma + 0.8630 86.30%
Honey bee toxicity - 0.7597 75.97%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9894 98.94%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.94% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 97.81% 91.49%
CHEMBL2581 P07339 Cathepsin D 97.72% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.83% 86.33%
CHEMBL4208 P20618 Proteasome component C5 94.49% 90.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 93.43% 99.15%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.92% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.28% 94.00%
CHEMBL221 P23219 Cyclooxygenase-1 91.86% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.10% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.48% 99.17%
CHEMBL3401 O75469 Pregnane X receptor 90.28% 94.73%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.40% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.82% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.25% 95.89%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.15% 96.09%
CHEMBL2535 P11166 Glucose transporter 81.27% 98.75%
CHEMBL3492 P49721 Proteasome Macropain subunit 80.95% 90.24%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 80.25% 95.71%
CHEMBL1907 P15144 Aminopeptidase N 80.00% 93.31%

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.
Millettia extensa

Cross-Links

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PubChem 5491651
LOTUS LTS0088037
wikiData Q83055427