Arzanol

Details

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Internal ID 86c4fb1b-f0ce-4c99-b418-583025202939
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
IUPAC Name 3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methylpyran-2-one
SMILES (Canonical) CCC1=C(C(=C(C(=O)O1)CC2=C(C(=C(C(=C2O)CC=C(C)C)O)C(=O)C)O)O)C
SMILES (Isomeric) CCC1=C(C(=C(C(=O)O1)CC2=C(C(=C(C(=C2O)CC=C(C)C)O)C(=O)C)O)O)C
InChI InChI=1S/C22H26O7/c1-6-16-11(4)18(24)15(22(28)29-16)9-14-19(25)13(8-7-10(2)3)20(26)17(12(5)23)21(14)27/h7,24-27H,6,8-9H2,1-5H3
InChI Key ZOIAPLVBZQQHCG-UHFFFAOYSA-N
Popularity 13 references in papers

Physical and Chemical Properties

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Molecular Formula C22H26O7
Molecular Weight 402.40 g/mol
Exact Mass 402.16785316 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 3.90
Atomic LogP (AlogP) 3.64
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 6

Synonyms

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32274-52-5
3-[4-Acetyl-2,3,6-trihydroxy-5-(3-methyl-2-butenyl)benzyl]-6-ethyl-4-hydroxy-5-methyl-2H-pyran-2-one
CHEMBL225421
BDBM50109833
Arzanol, from Helichrysum italicum, >=98%
2H-Pyran-2-one, 3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methyl-2-butenyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methyl-
3-[[3-acetyl-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]methyl]-6-ethyl-4-hydroxy-5-methyl-pyran-2-one

2D Structure

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2D Structure of Arzanol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9434 94.34%
Caco-2 - 0.5211 52.11%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7971 79.71%
OATP2B1 inhibitior - 0.5577 55.77%
OATP1B1 inhibitior - 0.3583 35.83%
OATP1B3 inhibitior + 0.9035 90.35%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.5594 55.94%
P-glycoprotein inhibitior - 0.6788 67.88%
P-glycoprotein substrate - 0.8066 80.66%
CYP3A4 substrate + 0.5425 54.25%
CYP2C9 substrate + 0.8398 83.98%
CYP2D6 substrate - 0.8737 87.37%
CYP3A4 inhibition - 0.5480 54.80%
CYP2C9 inhibition + 0.6823 68.23%
CYP2C19 inhibition + 0.7271 72.71%
CYP2D6 inhibition - 0.8055 80.55%
CYP1A2 inhibition - 0.5887 58.87%
CYP2C8 inhibition - 0.7202 72.02%
CYP inhibitory promiscuity + 0.5865 58.65%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8900 89.00%
Carcinogenicity (trinary) Non-required 0.7118 71.18%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.5876 58.76%
Skin irritation - 0.7707 77.07%
Skin corrosion - 0.9302 93.02%
Ames mutagenesis - 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4014 40.14%
Micronuclear - 0.6100 61.00%
Hepatotoxicity + 0.7301 73.01%
skin sensitisation - 0.7359 73.59%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.7195 71.95%
Acute Oral Toxicity (c) III 0.4989 49.89%
Estrogen receptor binding + 0.8167 81.67%
Androgen receptor binding + 0.5992 59.92%
Thyroid receptor binding - 0.5564 55.64%
Glucocorticoid receptor binding + 0.7596 75.96%
Aromatase binding + 0.5948 59.48%
PPAR gamma + 0.8311 83.11%
Honey bee toxicity - 0.8973 89.73%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6951 69.51%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL5658 O14684 Prostaglandin E synthase 400 nM
IC50
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 98.64% 89.34%
CHEMBL3401 O75469 Pregnane X receptor 93.88% 94.73%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.46% 91.11%
CHEMBL2581 P07339 Cathepsin D 92.80% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.28% 94.45%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 88.93% 96.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.40% 89.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 86.21% 97.21%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 83.47% 93.65%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 80.19% 83.57%

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.
Helichrysum italicum

Cross-Links

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PubChem 54682566
LOTUS LTS0143220
wikiData Q104401634