methyl (E)-2-[(6'R)-6'-ethyl-4'-oxido-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizin-4-ium]-7'-yl]-3-methoxyprop-2-enoate

Details

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Internal ID cccef176-985d-49ca-8bb8-c2826d0abcdb
Taxonomy Organoheterocyclic compounds > Indolizidines
IUPAC Name methyl (E)-2-[(6'R)-6'-ethyl-4'-oxido-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizin-4-ium]-7'-yl]-3-methoxyprop-2-enoate
SMILES (Canonical) CCC1C[N+]2(CCC3(C2CC1C(=COC)C(=O)OC)C4=CC=CC=C4NC3=O)[O-]
SMILES (Isomeric) CC[C@H]1C[N+]2(CCC3(C2CC1/C(=C\OC)/C(=O)OC)C4=CC=CC=C4NC3=O)[O-]
InChI InChI=1S/C22H28N2O5/c1-4-14-12-24(27)10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-28-2)20(25)29-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15?,19?,22?,24?/m0/s1
InChI Key UQZWROIYWUBTCH-YGMNELGESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H28N2O5
Molecular Weight 400.50 g/mol
Exact Mass 400.19982200 g/mol
Topological Polar Surface Area (TPSA) 82.70 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.71
H-Bond Acceptor 5
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 methyl (E)-2-[(6'R)-6'-ethyl-4'-oxido-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizin-4-ium]-7'-yl]-3-methoxyprop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5935 59.35%
Caco-2 + 0.5000 50.00%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.4968 49.68%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8798 87.98%
OATP1B3 inhibitior + 0.9260 92.60%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.6480 64.80%
P-glycoprotein inhibitior + 0.5933 59.33%
P-glycoprotein substrate + 0.5910 59.10%
CYP3A4 substrate + 0.6554 65.54%
CYP2C9 substrate - 0.7970 79.70%
CYP2D6 substrate - 0.8727 87.27%
CYP3A4 inhibition - 0.7440 74.40%
CYP2C9 inhibition - 0.7290 72.90%
CYP2C19 inhibition - 0.7409 74.09%
CYP2D6 inhibition - 0.8522 85.22%
CYP1A2 inhibition - 0.7738 77.38%
CYP2C8 inhibition + 0.6559 65.59%
CYP inhibitory promiscuity - 0.8643 86.43%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8100 81.00%
Carcinogenicity (trinary) Non-required 0.5340 53.40%
Eye corrosion - 0.9825 98.25%
Eye irritation - 0.9857 98.57%
Skin irritation - 0.7665 76.65%
Skin corrosion - 0.9238 92.38%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7677 76.77%
Micronuclear + 0.7200 72.00%
Hepatotoxicity + 0.5875 58.75%
skin sensitisation - 0.8474 84.74%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.7654 76.54%
Acute Oral Toxicity (c) III 0.6058 60.58%
Estrogen receptor binding + 0.7849 78.49%
Androgen receptor binding + 0.7038 70.38%
Thyroid receptor binding + 0.5882 58.82%
Glucocorticoid receptor binding + 0.6383 63.83%
Aromatase binding - 0.6353 63.53%
PPAR gamma + 0.5660 56.60%
Honey bee toxicity - 0.8762 87.62%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.6500 65.00%
Fish aquatic toxicity + 0.9904 99.04%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.40% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.78% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.92% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.06% 97.09%
CHEMBL2581 P07339 Cathepsin D 89.68% 98.95%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 89.16% 93.03%
CHEMBL4072 P07858 Cathepsin B 88.24% 93.67%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.07% 97.25%
CHEMBL240 Q12809 HERG 88.06% 89.76%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.17% 99.23%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 85.86% 96.95%
CHEMBL4208 P20618 Proteasome component C5 85.48% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.89% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.47% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.30% 94.45%

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.
Uncaria macrophylla
Uncaria rhynchophylla
Uncaria sinensis

Cross-Links

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PubChem 5319410
NPASS NPC194130
LOTUS LTS0135054
wikiData Q105277577