[(1S,15R,17S,18S,19R)-18-acetyloxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9-trien-17-yl] acetate

Details

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Internal ID 706d5933-d5d0-4dde-bbf9-c25370a11c56
Taxonomy Alkaloids and derivatives > Amaryllidaceae alkaloids > Lycorine-type amaryllidaceae alkaloids
IUPAC Name [(1S,15R,17S,18S,19R)-18-acetyloxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9-trien-17-yl] acetate
SMILES (Canonical) CC(=O)OC1CC2CCN3C2C(C1OC(=O)C)C4=CC5=C(C=C4C3)OCO5
SMILES (Isomeric) CC(=O)O[C@H]1C[C@H]2CCN3[C@H]2[C@@H]([C@@H]1OC(=O)C)C4=CC5=C(C=C4C3)OCO5
InChI InChI=1S/C20H23NO6/c1-10(22)26-17-5-12-3-4-21-8-13-6-15-16(25-9-24-15)7-14(13)18(19(12)21)20(17)27-11(2)23/h6-7,12,17-20H,3-5,8-9H2,1-2H3/t12-,17+,18+,19-,20-/m1/s1
InChI Key IUKYXZADSGGCJJ-OHNCIUIWSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H23NO6
Molecular Weight 373.40 g/mol
Exact Mass 373.15253745 g/mol
Topological Polar Surface Area (TPSA) 74.30 Ų
XlogP 1.90
Atomic LogP (AlogP) 1.97
H-Bond Acceptor 7
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,15R,17S,18S,19R)-18-acetyloxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2,4(8),9-trien-17-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 + 0.9559 95.59%
Caco-2 + 0.6521 65.21%
Blood Brain Barrier + 0.9000 90.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6429 64.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9155 91.55%
OATP1B3 inhibitior + 0.9151 91.51%
MATE1 inhibitior - 0.7200 72.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.8798 87.98%
P-glycoprotein inhibitior - 0.4943 49.43%
P-glycoprotein substrate - 0.6111 61.11%
CYP3A4 substrate + 0.6275 62.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.6573 65.73%
CYP3A4 inhibition + 0.8609 86.09%
CYP2C9 inhibition - 0.8788 87.88%
CYP2C19 inhibition + 0.8060 80.60%
CYP2D6 inhibition + 0.5399 53.99%
CYP1A2 inhibition + 0.8233 82.33%
CYP2C8 inhibition - 0.8191 81.91%
CYP inhibitory promiscuity + 0.6196 61.96%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5437 54.37%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9363 93.63%
Skin irritation - 0.8282 82.82%
Skin corrosion - 0.9506 95.06%
Ames mutagenesis - 0.6154 61.54%
Human Ether-a-go-go-Related Gene inhibition - 0.3662 36.62%
Micronuclear + 0.5100 51.00%
Hepatotoxicity + 0.6750 67.50%
skin sensitisation - 0.8457 84.57%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity + 0.6438 64.38%
Acute Oral Toxicity (c) III 0.6739 67.39%
Estrogen receptor binding + 0.6447 64.47%
Androgen receptor binding + 0.5774 57.74%
Thyroid receptor binding - 0.5422 54.22%
Glucocorticoid receptor binding + 0.7151 71.51%
Aromatase binding - 0.5527 55.27%
PPAR gamma + 0.6212 62.12%
Honey bee toxicity - 0.7598 75.98%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.8139 81.39%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.93% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.57% 96.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 94.98% 96.77%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.30% 95.89%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.24% 95.89%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 90.67% 83.57%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.98% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.69% 86.33%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 89.48% 90.24%
CHEMBL340 P08684 Cytochrome P450 3A4 89.28% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.53% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.48% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.34% 94.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.21% 95.56%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 83.15% 90.95%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.81% 93.04%
CHEMBL5028 O14672 ADAM10 82.50% 97.50%
CHEMBL2581 P07339 Cathepsin D 81.31% 98.95%

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.
Narcissus tazetta

Cross-Links

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PubChem 45483145
LOTUS LTS0144699
wikiData Q105120682