4-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)methoxy]-5-methylchromen-2-one

Details

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Internal ID a9851620-c216-4824-ab74-7a03ebccc729
Taxonomy Phenylpropanoids and polyketides > Coumarins and derivatives
IUPAC Name 4-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)methoxy]-5-methylchromen-2-one
SMILES (Canonical) CC1=C2C(=CC=C1)OC(=O)C=C2OCC3C(=C)CCC4C3(CCC(C4(C)C)O)C
SMILES (Isomeric) CC1=C2C(=CC=C1)OC(=O)C=C2OCC3C(=C)CCC4C3(CCC(C4(C)C)O)C
InChI InChI=1S/C25H32O4/c1-15-9-10-20-24(3,4)21(26)11-12-25(20,5)17(15)14-28-19-13-22(27)29-18-8-6-7-16(2)23(18)19/h6-8,13,17,20-21,26H,1,9-12,14H2,2-5H3
InChI Key QKWGJTUEZOQNLJ-UHFFFAOYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C25H32O4
Molecular Weight 396.50 g/mol
Exact Mass 396.23005950 g/mol
Topological Polar Surface Area (TPSA) 55.80 Ų
XlogP 5.00
Atomic LogP (AlogP) 5.25
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)methoxy]-5-methylchromen-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9837 98.37%
Caco-2 + 0.5561 55.61%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.8289 82.89%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8958 89.58%
OATP1B3 inhibitior + 0.8368 83.68%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8026 80.26%
BSEP inhibitior + 0.9722 97.22%
P-glycoprotein inhibitior - 0.4292 42.92%
P-glycoprotein substrate - 0.6642 66.42%
CYP3A4 substrate + 0.7076 70.76%
CYP2C9 substrate - 0.7957 79.57%
CYP2D6 substrate - 0.8165 81.65%
CYP3A4 inhibition + 0.6047 60.47%
CYP2C9 inhibition + 0.8053 80.53%
CYP2C19 inhibition + 0.8994 89.94%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition + 0.9106 91.06%
CYP2C8 inhibition + 0.5913 59.13%
CYP inhibitory promiscuity - 0.7788 77.88%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.6945 69.45%
Eye corrosion - 0.9923 99.23%
Eye irritation - 0.8928 89.28%
Skin irritation - 0.6894 68.94%
Skin corrosion - 0.9544 95.44%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9251 92.51%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.6174 61.74%
skin sensitisation - 0.8138 81.38%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity - 0.9102 91.02%
Acute Oral Toxicity (c) III 0.4826 48.26%
Estrogen receptor binding + 0.7824 78.24%
Androgen receptor binding + 0.7720 77.20%
Thyroid receptor binding + 0.6411 64.11%
Glucocorticoid receptor binding + 0.8191 81.91%
Aromatase binding + 0.7173 71.73%
PPAR gamma + 0.7337 73.37%
Honey bee toxicity - 0.8302 83.02%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 1.0000 100.00%

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 98.63% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.83% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.37% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.17% 95.56%
CHEMBL2581 P07339 Cathepsin D 93.48% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.17% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.69% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.09% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 90.96% 94.75%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 88.90% 96.21%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.23% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.54% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.25% 99.23%
CHEMBL3401 O75469 Pregnane X receptor 86.48% 94.73%
CHEMBL3192 Q9BY41 Histone deacetylase 8 86.46% 93.99%
CHEMBL240 Q12809 HERG 83.36% 89.76%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.90% 92.62%
CHEMBL1871 P10275 Androgen Receptor 81.41% 96.43%
CHEMBL4040 P28482 MAP kinase ERK2 81.34% 83.82%
CHEMBL325 Q13547 Histone deacetylase 1 81.31% 95.92%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 81.17% 95.78%
CHEMBL5028 O14672 ADAM10 80.55% 97.50%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.33% 90.24%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 80.03% 85.49%

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.
Nassauvia argentea
Nassauvia revoluta

Cross-Links

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PubChem 14186841
LOTUS LTS0267533
wikiData Q105223369