O-Acetylretuline

Details

Top
Internal ID c82698b7-960f-46a5-ab40-9e99f2132c14
Taxonomy Alkaloids and derivatives > Strychnos alkaloids
IUPAC Name [(9S,10S,11R,17S)-8-acetyl-12-ethylidene-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6-trien-10-yl]methyl acetate
SMILES (Canonical) CC=C1CN2CCC34C2CC1C(C3N(C5=CC=CC=C45)C(=O)C)COC(=O)C
SMILES (Isomeric) CC=C1CN2CCC34[C@@H]2C[C@@H]1[C@@H]([C@@H]3N(C5=CC=CC=C45)C(=O)C)COC(=O)C
InChI InChI=1S/C23H28N2O3/c1-4-16-12-24-10-9-23-19-7-5-6-8-20(19)25(14(2)26)22(23)18(13-28-15(3)27)17(16)11-21(23)24/h4-8,17-18,21-22H,9-13H2,1-3H3/t17-,18-,21-,22-,23?/m0/s1
InChI Key PTRWORWVJKGZCI-IDASFKSMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C23H28N2O3
Molecular Weight 380.50 g/mol
Exact Mass 380.20999276 g/mol
Topological Polar Surface Area (TPSA) 49.80 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.89
H-Bond Acceptor 4
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

Top
O-Acetylretuline
DTXSID90939779
1-Acetylcur-19-en-17-yl acetate
Curan-17-ol, 1-acetyl-19,20-didehydro-, acetate (ester), (16a,19E)-

2D Structure

Top
2D Structure of O-Acetylretuline

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9539 95.39%
Caco-2 + 0.7735 77.35%
Blood Brain Barrier + 0.9500 95.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7860 78.60%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9038 90.38%
OATP1B3 inhibitior + 0.9365 93.65%
MATE1 inhibitior - 0.7431 74.31%
OCT2 inhibitior + 0.5250 52.50%
BSEP inhibitior + 0.7383 73.83%
P-glycoprotein inhibitior + 0.6761 67.61%
P-glycoprotein substrate + 0.5153 51.53%
CYP3A4 substrate + 0.6297 62.97%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7095 70.95%
CYP3A4 inhibition + 0.6370 63.70%
CYP2C9 inhibition - 0.5866 58.66%
CYP2C19 inhibition + 0.5793 57.93%
CYP2D6 inhibition - 0.7709 77.09%
CYP1A2 inhibition - 0.6365 63.65%
CYP2C8 inhibition + 0.4716 47.16%
CYP inhibitory promiscuity + 0.6361 63.61%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8800 88.00%
Carcinogenicity (trinary) Non-required 0.6598 65.98%
Eye corrosion - 0.9882 98.82%
Eye irritation - 0.9785 97.85%
Skin irritation - 0.8015 80.15%
Skin corrosion - 0.9341 93.41%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7966 79.66%
Micronuclear + 0.5600 56.00%
Hepatotoxicity - 0.5197 51.97%
skin sensitisation - 0.8391 83.91%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.6441 64.41%
Acute Oral Toxicity (c) III 0.6459 64.59%
Estrogen receptor binding + 0.6687 66.87%
Androgen receptor binding + 0.6666 66.66%
Thyroid receptor binding - 0.5479 54.79%
Glucocorticoid receptor binding - 0.5375 53.75%
Aromatase binding - 0.6999 69.99%
PPAR gamma - 0.5107 51.07%
Honey bee toxicity - 0.8357 83.57%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9898 98.98%

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 99.33% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.58% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.58% 97.25%
CHEMBL2581 P07339 Cathepsin D 92.24% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.19% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.48% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.78% 91.11%
CHEMBL5028 O14672 ADAM10 87.40% 97.50%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 87.12% 94.62%
CHEMBL340 P08684 Cytochrome P450 3A4 86.11% 91.19%
CHEMBL4208 P20618 Proteasome component C5 84.51% 90.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 83.43% 82.69%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.12% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.75% 86.33%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.20% 100.00%

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.
Strychnos kasengaensis
Strychnos pungens

Cross-Links

Top
PubChem 176986
LOTUS LTS0192668
wikiData Q82916341