methyl (Z)-2-[(3S,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)spiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Details

Top
Internal ID 2a722ead-732b-4812-b4f1-36ef18e82896
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
IUPAC Name methyl (Z)-2-[(3S,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)spiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
SMILES (Canonical) CCC1C(CC2C3(CCN2C1CC(=O)C)C4=CC=CC=C4NC3=O)C(=COC)C(=O)OC
SMILES (Isomeric) CC[C@@H]1[C@H](C[C@H]2[C@]3(CCN2[C@H]1CC(=O)C)C4=CC=CC=C4NC3=O)/C(=C/OC)/C(=O)OC
InChI InChI=1S/C25H32N2O5/c1-5-16-17(18(14-31-3)23(29)32-4)13-22-25(10-11-27(22)21(16)12-15(2)28)19-8-6-7-9-20(19)26-24(25)30/h6-9,14,16-17,21-22H,5,10-13H2,1-4H3,(H,26,30)/b18-14-/t16-,17+,21+,22+,25+/m1/s1
InChI Key VWNYHBABHBBFQC-ISZZZUSESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C25H32N2O5
Molecular Weight 440.50 g/mol
Exact Mass 440.23112213 g/mol
Topological Polar Surface Area (TPSA) 84.90 Ų
XlogP 2.00
Atomic LogP (AlogP) 3.05
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of methyl (Z)-2-[(3S,5'S,6'R,7'S,8'aS)-6'-ethyl-2-oxo-5'-(2-oxopropyl)spiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9685 96.85%
Caco-2 + 0.6708 67.08%
Blood Brain Barrier + 0.9000 90.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8116 81.16%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8690 86.90%
OATP1B3 inhibitior + 0.9164 91.64%
MATE1 inhibitior - 0.6600 66.00%
OCT2 inhibitior - 0.7322 73.22%
BSEP inhibitior + 0.9473 94.73%
P-glycoprotein inhibitior + 0.8699 86.99%
P-glycoprotein substrate + 0.7194 71.94%
CYP3A4 substrate + 0.6724 67.24%
CYP2C9 substrate - 0.8116 81.16%
CYP2D6 substrate - 0.7654 76.54%
CYP3A4 inhibition - 0.7170 71.70%
CYP2C9 inhibition - 0.7130 71.30%
CYP2C19 inhibition - 0.6999 69.99%
CYP2D6 inhibition - 0.8869 88.69%
CYP1A2 inhibition - 0.6709 67.09%
CYP2C8 inhibition + 0.6143 61.43%
CYP inhibitory promiscuity - 0.5066 50.66%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5619 56.19%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.9845 98.45%
Skin irritation - 0.7920 79.20%
Skin corrosion - 0.9331 93.31%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9439 94.39%
Micronuclear + 0.7600 76.00%
Hepatotoxicity + 0.5625 56.25%
skin sensitisation - 0.8843 88.43%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.5518 55.18%
Acute Oral Toxicity (c) III 0.6317 63.17%
Estrogen receptor binding + 0.8156 81.56%
Androgen receptor binding + 0.6992 69.92%
Thyroid receptor binding + 0.5466 54.66%
Glucocorticoid receptor binding + 0.6295 62.95%
Aromatase binding - 0.5677 56.77%
PPAR gamma + 0.6567 65.67%
Honey bee toxicity - 0.7988 79.88%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9857 98.57%

Targets

Top

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 99.13% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.53% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.28% 85.14%
CHEMBL2581 P07339 Cathepsin D 95.68% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.17% 95.56%
CHEMBL4208 P20618 Proteasome component C5 91.22% 90.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.44% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.32% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.45% 97.25%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.70% 99.23%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 84.73% 93.03%
CHEMBL4072 P07858 Cathepsin B 83.66% 93.67%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.08% 97.09%
CHEMBL255 P29275 Adenosine A2b receptor 81.10% 98.59%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.49% 93.00%
CHEMBL5028 O14672 ADAM10 80.44% 97.50%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.17% 90.71%

Plants that contains it

Top
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

Cross-Links

Top
PubChem 53326135
LOTUS LTS0032631
wikiData Q105298191