[(1S,12S,14R)-4-acetyl-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] acetate

Details

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Internal ID e6727c6d-8371-47af-821f-53c37bc4126c
Taxonomy Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthamine-type amaryllidaceae alkaloids
IUPAC Name [(1S,12S,14R)-4-acetyl-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] acetate
SMILES (Canonical) CC(=O)N1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)OC(=O)C
SMILES (Isomeric) CC(=O)N1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)OC(=O)C
InChI InChI=1S/C20H23NO5/c1-12(22)21-9-8-20-7-6-15(25-13(2)23)10-17(20)26-19-16(24-3)5-4-14(11-21)18(19)20/h4-7,15,17H,8-11H2,1-3H3/t15-,17-,20-/m0/s1
InChI Key ISSJWVMTALZOHY-KNBMTAEXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H23NO5
Molecular Weight 357.40 g/mol
Exact Mass 357.15762283 g/mol
Topological Polar Surface Area (TPSA) 65.10 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.34
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,12S,14R)-4-acetyl-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9741 97.41%
Caco-2 + 0.7314 73.14%
Blood Brain Barrier + 0.9250 92.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Lysosomes 0.4057 40.57%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9299 92.99%
OATP1B3 inhibitior + 0.9306 93.06%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.8123 81.23%
P-glycoprotein inhibitior - 0.6112 61.12%
P-glycoprotein substrate + 0.6471 64.71%
CYP3A4 substrate + 0.7132 71.32%
CYP2C9 substrate - 0.8003 80.03%
CYP2D6 substrate - 0.8046 80.46%
CYP3A4 inhibition - 0.5815 58.15%
CYP2C9 inhibition - 0.7003 70.03%
CYP2C19 inhibition - 0.6707 67.07%
CYP2D6 inhibition - 0.9221 92.21%
CYP1A2 inhibition - 0.8771 87.71%
CYP2C8 inhibition - 0.6371 63.71%
CYP inhibitory promiscuity - 0.8782 87.82%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5020 50.20%
Eye corrosion - 0.9889 98.89%
Eye irritation - 0.9835 98.35%
Skin irritation - 0.8293 82.93%
Skin corrosion - 0.9438 94.38%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7187 71.87%
Micronuclear + 0.5500 55.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.8602 86.02%
Respiratory toxicity + 0.9111 91.11%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.6445 64.45%
Acute Oral Toxicity (c) III 0.7002 70.02%
Estrogen receptor binding + 0.7593 75.93%
Androgen receptor binding - 0.6492 64.92%
Thyroid receptor binding + 0.5563 55.63%
Glucocorticoid receptor binding + 0.5774 57.74%
Aromatase binding - 0.6435 64.35%
PPAR gamma + 0.5438 54.38%
Honey bee toxicity - 0.7741 77.41%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6155 61.55%
Fish aquatic toxicity + 0.9367 93.67%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.46% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.23% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.88% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.31% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 90.04% 91.19%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.24% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.47% 95.89%
CHEMBL5028 O14672 ADAM10 86.44% 97.50%
CHEMBL2413 P32246 C-C chemokine receptor type 1 86.01% 89.50%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 85.70% 89.05%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.16% 99.23%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 84.99% 90.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.47% 97.14%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.31% 94.00%
CHEMBL1744525 P43490 Nicotinamide phosphoribosyltransferase 82.36% 96.25%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.55% 96.00%

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.
Atriplex muricata
Chromolaena laevigata
Crinum asiaticum
Crotalaria crispata
Haplopappus deserticola
Hesperocyparis arizonica
Seriphidium junceum
Viburnum lantana

Cross-Links

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PubChem 21826143
NPASS NPC25499
LOTUS LTS0217556
wikiData Q105119775