17-Ethenyl-18-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-19-oxa-2,12-diazapentacyclo[14.3.1.02,14.05,13.06,11]icosa-3,5,7,9,11,13-hexaene-20-carboxylic acid

Details

Top
Internal ID e4521ea5-bc58-4046-91ce-b474003d133c
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
IUPAC Name 17-ethenyl-18-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-19-oxa-2,12-diazapentacyclo[14.3.1.02,14.05,13.06,11]icosa-3,5,7,9,11,13-hexaene-20-carboxylic acid
SMILES (Canonical) C=CC1C2CC3=C4C(=C5C=CC=CC5=N4)C=CN3C(C2C(=O)O)OC1OC6C(C(C(C(O6)CO)O)O)O
SMILES (Isomeric) C=CC1C2CC3=C4C(=C5C=CC=CC5=N4)C=CN3C(C2C(=O)O)OC1OC6C(C(C(C(O6)CO)O)O)O
InChI InChI=1S/C26H28N2O9/c1-2-11-14-9-16-19-13(12-5-3-4-6-15(12)27-19)7-8-28(16)23(18(14)24(33)34)36-25(11)37-26-22(32)21(31)20(30)17(10-29)35-26/h2-8,11,14,17-18,20-23,25-26,29-32H,1,9-10H2,(H,33,34)
InChI Key MYJKHRHLAAMOED-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C26H28N2O9
Molecular Weight 512.50 g/mol
Exact Mass 512.17948047 g/mol
Topological Polar Surface Area (TPSA) 164.00 Ų
XlogP 0.30
Atomic LogP (AlogP) 0.49
H-Bond Acceptor 10
H-Bond Donor 5
Rotatable Bonds 5

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 17-Ethenyl-18-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-19-oxa-2,12-diazapentacyclo[14.3.1.02,14.05,13.06,11]icosa-3,5,7,9,11,13-hexaene-20-carboxylic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7012 70.12%
Caco-2 - 0.8811 88.11%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.4207 42.07%
OATP2B1 inhibitior - 0.7081 70.81%
OATP1B1 inhibitior + 0.8700 87.00%
OATP1B3 inhibitior + 0.9424 94.24%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8316 83.16%
BSEP inhibitior + 0.7536 75.36%
P-glycoprotein inhibitior - 0.6103 61.03%
P-glycoprotein substrate - 0.7236 72.36%
CYP3A4 substrate + 0.6715 67.15%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8715 87.15%
CYP3A4 inhibition - 0.7441 74.41%
CYP2C9 inhibition - 0.8929 89.29%
CYP2C19 inhibition - 0.8864 88.64%
CYP2D6 inhibition - 0.8927 89.27%
CYP1A2 inhibition - 0.6891 68.91%
CYP2C8 inhibition + 0.6519 65.19%
CYP inhibitory promiscuity - 0.6452 64.52%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5853 58.53%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9642 96.42%
Skin irritation - 0.7901 79.01%
Skin corrosion - 0.9422 94.22%
Ames mutagenesis - 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4095 40.95%
Micronuclear + 0.8900 89.00%
Hepatotoxicity - 0.5841 58.41%
skin sensitisation - 0.8710 87.10%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.7039 70.39%
Acute Oral Toxicity (c) III 0.5501 55.01%
Estrogen receptor binding + 0.8041 80.41%
Androgen receptor binding + 0.7122 71.22%
Thyroid receptor binding + 0.5851 58.51%
Glucocorticoid receptor binding + 0.5934 59.34%
Aromatase binding + 0.6452 64.52%
PPAR gamma + 0.7569 75.69%
Honey bee toxicity - 0.7358 73.58%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity - 0.4530 45.30%

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
CHEMBL220 P22303 Acetylcholinesterase 96.42% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.13% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.56% 91.11%
CHEMBL2581 P07339 Cathepsin D 93.41% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.02% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.31% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.41% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.07% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.26% 95.56%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.62% 95.83%
CHEMBL3891 P07384 Calpain 1 84.38% 93.04%
CHEMBL1868 P17948 Vascular endothelial growth factor receptor 1 83.20% 96.47%
CHEMBL5028 O14672 ADAM10 82.78% 97.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.03% 99.17%
CHEMBL5805 Q9NR97 Toll-like receptor 8 81.48% 96.25%

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.
Ophiorrhiza japonica
Ophiorrhiza kuroiwai
Simira rubescens
Simira williamsii

Cross-Links

Top
PubChem 163192292
LOTUS LTS0080790
wikiData Q104399114