[(1S,4aS,5aR,6S,10aS)-6'-methoxy-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-yl] acetate

Details

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Internal ID 97d8da1d-60d4-4c8c-96ca-a1358c775d88
Taxonomy Organoheterocyclic compounds > Indolizidines
IUPAC Name [(1S,4aS,5aR,6S,10aS)-6'-methoxy-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-yl] acetate
SMILES (Canonical) CC1C2CN3CCC4(C3CC2C(=CO1)OC(=O)C)C5=C(C=C(C=C5)OC)NC4=O
SMILES (Isomeric) C[C@H]1[C@@H]2CN3CC[C@@]4([C@H]3C[C@@H]2C(=CO1)OC(=O)C)C5=C(C=C(C=C5)OC)NC4=O
InChI InChI=1S/C22H26N2O5/c1-12-16-10-24-7-6-22(17-5-4-14(27-3)8-18(17)23-21(22)26)20(24)9-15(16)19(11-28-12)29-13(2)25/h4-5,8,11-12,15-16,20H,6-7,9-10H2,1-3H3,(H,23,26)/t12-,15-,16-,20+,22-/m0/s1
InChI Key GFBRPLWLNZPYAL-LVSKTSOBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H26N2O5
Molecular Weight 398.50 g/mol
Exact Mass 398.18417193 g/mol
Topological Polar Surface Area (TPSA) 77.10 Ų
XlogP 1.50
Atomic LogP (AlogP) 2.42
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,4aS,5aR,6S,10aS)-6'-methoxy-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-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 + 0.9405 94.05%
Caco-2 + 0.5683 56.83%
Blood Brain Barrier + 0.9250 92.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.4929 49.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8804 88.04%
OATP1B3 inhibitior + 0.9131 91.31%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.7835 78.35%
P-glycoprotein inhibitior + 0.8070 80.70%
P-glycoprotein substrate + 0.6400 64.00%
CYP3A4 substrate + 0.7016 70.16%
CYP2C9 substrate - 0.6054 60.54%
CYP2D6 substrate - 0.6571 65.71%
CYP3A4 inhibition - 0.5946 59.46%
CYP2C9 inhibition - 0.7122 71.22%
CYP2C19 inhibition - 0.7698 76.98%
CYP2D6 inhibition - 0.8253 82.53%
CYP1A2 inhibition - 0.7693 76.93%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.7919 79.19%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5760 57.60%
Eye corrosion - 0.9881 98.81%
Eye irritation - 0.9917 99.17%
Skin irritation - 0.7760 77.60%
Skin corrosion - 0.9381 93.81%
Ames mutagenesis - 0.6244 62.44%
Human Ether-a-go-go-Related Gene inhibition + 0.8974 89.74%
Micronuclear + 0.6400 64.00%
Hepatotoxicity - 0.5750 57.50%
skin sensitisation - 0.8639 86.39%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.6765 67.65%
Acute Oral Toxicity (c) III 0.6519 65.19%
Estrogen receptor binding + 0.7446 74.46%
Androgen receptor binding + 0.7980 79.80%
Thyroid receptor binding + 0.5623 56.23%
Glucocorticoid receptor binding + 0.6845 68.45%
Aromatase binding + 0.6159 61.59%
PPAR gamma + 0.5420 54.20%
Honey bee toxicity - 0.7360 73.60%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9767 97.67%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.49% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.43% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.06% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.96% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.84% 86.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 93.48% 92.94%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.30% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.39% 94.00%
CHEMBL4208 P20618 Proteasome component C5 90.35% 90.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.17% 97.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 89.37% 91.07%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 87.67% 90.71%
CHEMBL340 P08684 Cytochrome P450 3A4 86.67% 91.19%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.53% 99.23%
CHEMBL2581 P07339 Cathepsin D 86.06% 98.95%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 85.45% 91.03%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 85.33% 89.05%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 85.28% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.61% 95.89%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 84.59% 94.08%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.04% 92.62%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.43% 96.77%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.90% 89.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.68% 97.14%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.23% 93.00%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 80.89% 94.78%

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.
Catharanthus roseus

Cross-Links

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PubChem 5315230
NPASS NPC180059
LOTUS LTS0179697
wikiData Q105106461