[(1S,4R,4aR,8aS)-4-acetyloxy-5,5,8a-trimethyl-1-[(E)-3-oxobut-1-enyl]-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]methyl acetate

Details

Top
Internal ID 5b32f036-31be-4636-b26b-e5eb5fc354c0
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name [(1S,4R,4aR,8aS)-4-acetyloxy-5,5,8a-trimethyl-1-[(E)-3-oxobut-1-enyl]-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]methyl acetate
SMILES (Canonical) CC(=O)C=CC1C(=CC(C2C1(CCCC2(C)C)C)OC(=O)C)COC(=O)C
SMILES (Isomeric) CC(=O)/C=C/[C@@H]1C(=C[C@H]([C@H]2[C@]1(CCCC2(C)C)C)OC(=O)C)COC(=O)C
InChI InChI=1S/C22H32O5/c1-14(23)8-9-18-17(13-26-15(2)24)12-19(27-16(3)25)20-21(4,5)10-7-11-22(18,20)6/h8-9,12,18-20H,7,10-11,13H2,1-6H3/b9-8+/t18-,19-,20-,22+/m1/s1
InChI Key VWSIRBHDCATCTC-SDMLLVAWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C22H32O5
Molecular Weight 376.50 g/mol
Exact Mass 376.22497412 g/mol
Topological Polar Surface Area (TPSA) 69.70 Ų
XlogP 3.50
Atomic LogP (AlogP) 4.02
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(1S,4R,4aR,8aS)-4-acetyloxy-5,5,8a-trimethyl-1-[(E)-3-oxobut-1-enyl]-1,4,4a,6,7,8-hexahydronaphthalen-2-yl]methyl acetate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9952 99.52%
Caco-2 + 0.6732 67.32%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8341 83.41%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8488 84.88%
OATP1B3 inhibitior + 0.8168 81.68%
MATE1 inhibitior - 0.6400 64.00%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.7220 72.20%
P-glycoprotein inhibitior + 0.7114 71.14%
P-glycoprotein substrate - 0.7562 75.62%
CYP3A4 substrate + 0.6454 64.54%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9127 91.27%
CYP3A4 inhibition - 0.8592 85.92%
CYP2C9 inhibition - 0.6241 62.41%
CYP2C19 inhibition - 0.7232 72.32%
CYP2D6 inhibition - 0.8839 88.39%
CYP1A2 inhibition - 0.7024 70.24%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.6425 64.25%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8900 89.00%
Carcinogenicity (trinary) Non-required 0.5514 55.14%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9414 94.14%
Skin irritation - 0.6136 61.36%
Skin corrosion - 0.9768 97.68%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4664 46.64%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.6851 68.51%
skin sensitisation - 0.5600 56.00%
Respiratory toxicity - 0.6778 67.78%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity + 0.5080 50.80%
Acute Oral Toxicity (c) III 0.7835 78.35%
Estrogen receptor binding - 0.4924 49.24%
Androgen receptor binding - 0.5225 52.25%
Thyroid receptor binding + 0.6293 62.93%
Glucocorticoid receptor binding + 0.7936 79.36%
Aromatase binding - 0.6401 64.01%
PPAR gamma + 0.6364 63.64%
Honey bee toxicity - 0.7903 79.03%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

Top

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.89% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.53% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.14% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.80% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.24% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.88% 97.09%
CHEMBL340 P08684 Cytochrome P450 3A4 81.49% 91.19%
CHEMBL2581 P07339 Cathepsin D 81.08% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.87% 100.00%
CHEMBL4040 P28482 MAP kinase ERK2 80.06% 83.82%

Plants that contains it

Top
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.
Rutidosis murchisonii

Cross-Links

Top
PubChem 162955309
LOTUS LTS0063331
wikiData Q105298251