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1-[(12S,13R,18R)-7-[[(12S,13R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-6-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 2bed04a3-20a4-4745-a35e-111ed7c2e56e
Taxonomy Alkaloids and derivatives > Macroline alkaloids
IUPAC Name 1-[(12S,13R,18R)-7-[[(12S,13R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-6-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone
SMILES (Canonical) CC(=O)C1=COCC2C1CC3C4=C(CC2N3C)C5=C(N4C)C=C(C(=C5)CC6C7CC8C9=C(CC(C7COC6(C)O)N8C)C1=CC=CC=C1N9C)OC
SMILES (Isomeric) CC(=O)C1=COC[C@@H]2[C@H]1CC3C4=C(C[C@@H]2N3C)C5=C(N4C)C=C(C(=C5)CC6[C@@H]7CC8C9=C(C[C@@H]([C@@H]7COC6(C)O)N8C)C1=CC=CC=C1N9C)OC
InChI InChI=1S/C43H52N4O5/c1-22(48)30-19-51-20-31-25(30)14-38-42-29(17-35(31)44(38)3)27-12-23(40(50-7)18-37(27)47(42)6)13-33-26-15-39-41-28(24-10-8-9-11-34(24)46(41)5)16-36(45(39)4)32(26)21-52-43(33,2)49/h8-12,18-19,25-26,31-33,35-36,38-39,49H,13-17,20-21H2,1-7H3/t25-,26+,31+,32+,33?,35-,36-,38?,39?,43?/m0/s1
InChI Key JGXFRVOHTXTCCH-BKNHQHATSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C43H52N4O5
Molecular Weight 704.90 g/mol
Exact Mass 704.39377077 g/mol
Topological Polar Surface Area (TPSA) 81.30 Ų
XlogP 4.40
Atomic LogP (AlogP) 5.85
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 1-[(12S,13R,18R)-7-[[(12S,13R,18R)-16-hydroxy-3,16,20-trimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8-tetraen-17-yl]methyl]-6-methoxy-3,20-dimethyl-15-oxa-3,20-diazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4(9),5,7,16-pentaen-17-yl]ethanone

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9092 90.92%
Caco-2 - 0.8040 80.40%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.4747 47.47%
OATP2B1 inhibitior + 0.5792 57.92%
OATP1B1 inhibitior + 0.8595 85.95%
OATP1B3 inhibitior + 0.9157 91.57%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior + 0.9809 98.09%
P-glycoprotein inhibitior + 0.8114 81.14%
P-glycoprotein substrate + 0.8281 82.81%
CYP3A4 substrate + 0.7484 74.84%
CYP2C9 substrate - 0.8080 80.80%
CYP2D6 substrate - 0.7442 74.42%
CYP3A4 inhibition + 0.5323 53.23%
CYP2C9 inhibition - 0.7336 73.36%
CYP2C19 inhibition - 0.6376 63.76%
CYP2D6 inhibition - 0.7246 72.46%
CYP1A2 inhibition - 0.6142 61.42%
CYP2C8 inhibition + 0.7771 77.71%
CYP inhibitory promiscuity + 0.6797 67.97%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5497 54.97%
Eye corrosion - 0.9879 98.79%
Eye irritation - 0.9227 92.27%
Skin irritation - 0.7980 79.80%
Skin corrosion - 0.9464 94.64%
Ames mutagenesis + 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7623 76.23%
Micronuclear + 0.6700 67.00%
Hepatotoxicity - 0.5234 52.34%
skin sensitisation - 0.8690 86.90%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.7632 76.32%
Acute Oral Toxicity (c) III 0.6255 62.55%
Estrogen receptor binding + 0.8492 84.92%
Androgen receptor binding + 0.7710 77.10%
Thyroid receptor binding + 0.6160 61.60%
Glucocorticoid receptor binding + 0.7964 79.64%
Aromatase binding + 0.6666 66.66%
PPAR gamma + 0.7758 77.58%
Honey bee toxicity - 0.6710 67.10%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5355 53.55%
Fish aquatic toxicity + 0.9864 98.64%

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 99.27% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.61% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.54% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.91% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.34% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.93% 97.25%
CHEMBL2581 P07339 Cathepsin D 95.45% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.84% 94.45%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 94.40% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.35% 86.33%
CHEMBL2535 P11166 Glucose transporter 93.07% 98.75%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 93.00% 96.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.22% 97.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.03% 99.17%
CHEMBL1951 P21397 Monoamine oxidase A 88.89% 91.49%
CHEMBL255 P29275 Adenosine A2b receptor 87.13% 98.59%
CHEMBL340 P08684 Cytochrome P450 3A4 86.93% 91.19%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.71% 95.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.77% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.67% 94.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.03% 89.50%
CHEMBL2378 P30307 Dual specificity phosphatase Cdc25C 82.58% 96.67%
CHEMBL1914 P06276 Butyrylcholinesterase 80.88% 95.00%

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.
Alstonia angustifolia
Alstonia macrophylla

Cross-Links

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PubChem 102069292
LOTUS LTS0225687
wikiData Q104402076