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(1R,5E,7S,8R,9S,10S,11S,12S,16R,17S,18R,22S,26R,27S,28S)-8-[(1Z)-buta-1,3-dienyl]-22,27-dihydroxy-20-(hydroxymethyl)-16,24,28-trimethyl-10-[(1E,3E,5E)-nona-1,3,5-trienyl]-2,14-dioxaheptacyclo[14.13.0.01,17.07,12.09,11.018,27.022,26]nonacosa-5,19,24-triene-3,13,23-trione

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 d24056c9-3d7e-44a4-aad0-d0934aee4411
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name (1R,5E,7S,8R,9S,10S,11S,12S,16R,17S,18R,22S,26R,27S,28S)-8-[(1Z)-buta-1,3-dienyl]-22,27-dihydroxy-20-(hydroxymethyl)-16,24,28-trimethyl-10-[(1E,3E,5E)-nona-1,3,5-trienyl]-2,14-dioxaheptacyclo[14.13.0.01,17.07,12.09,11.018,27.022,26]nonacosa-5,19,24-triene-3,13,23-trione
SMILES (Canonical) CCCC=CC=CC=CC1C2C1C3C(C2C=CC=C)C=CCC(=O)OC45CC(C6(C(C4C5(COC3=O)C)C=C(CC7(C6C=C(C7=O)C)O)CO)O)C
SMILES (Isomeric) CCC/C=C/C=C/C=C/[C@H]1[C@@H]2[C@H]1[C@@H]3[C@H]([C@@H]2/C=C\C=C)/C=C/CC(=O)O[C@]45C[C@@H]([C@@]6([C@@H]([C@H]4[C@@]5(COC3=O)C)C=C(C[C@@]7([C@@H]6C=C(C7=O)C)O)CO)O)C
InChI InChI=1S/C44H54O8/c1-6-8-10-11-12-13-14-17-31-35-29(16-9-7-2)30-18-15-19-34(46)52-43-22-27(4)44(50)32(38(43)41(43,5)25-51-40(48)37(30)36(31)35)21-28(24-45)23-42(49)33(44)20-26(3)39(42)47/h7,9-18,20-21,27,29-33,35-38,45,49-50H,2,6,8,19,22-25H2,1,3-5H3/b11-10+,13-12+,16-9-,17-14+,18-15+/t27-,29-,30-,31-,32+,33-,35+,36-,37-,38-,41-,42-,43+,44-/m0/s1
InChI Key RTRLXYBQXKHELY-NIXOPUNSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C44H54O8
Molecular Weight 710.90 g/mol
Exact Mass 710.38186868 g/mol
Topological Polar Surface Area (TPSA) 130.00 Ų
XlogP 5.60
Atomic LogP (AlogP) 5.93
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,5E,7S,8R,9S,10S,11S,12S,16R,17S,18R,22S,26R,27S,28S)-8-[(1Z)-buta-1,3-dienyl]-22,27-dihydroxy-20-(hydroxymethyl)-16,24,28-trimethyl-10-[(1E,3E,5E)-nona-1,3,5-trienyl]-2,14-dioxaheptacyclo[14.13.0.01,17.07,12.09,11.018,27.022,26]nonacosa-5,19,24-triene-3,13,23-trione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9322 93.22%
Caco-2 - 0.8621 86.21%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.6101 61.01%
OATP2B1 inhibitior - 0.5769 57.69%
OATP1B1 inhibitior + 0.8120 81.20%
OATP1B3 inhibitior + 0.9375 93.75%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5526 55.26%
BSEP inhibitior + 0.9556 95.56%
P-glycoprotein inhibitior + 0.7608 76.08%
P-glycoprotein substrate + 0.7358 73.58%
CYP3A4 substrate + 0.7306 73.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9093 90.93%
CYP3A4 inhibition - 0.5804 58.04%
CYP2C9 inhibition - 0.7393 73.93%
CYP2C19 inhibition - 0.8734 87.34%
CYP2D6 inhibition - 0.9409 94.09%
CYP1A2 inhibition - 0.9137 91.37%
CYP2C8 inhibition + 0.7632 76.32%
CYP inhibitory promiscuity - 0.9184 91.84%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5465 54.65%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9173 91.73%
Skin irritation + 0.5435 54.35%
Skin corrosion - 0.9356 93.56%
Ames mutagenesis - 0.5237 52.37%
Human Ether-a-go-go-Related Gene inhibition + 0.8414 84.14%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.6108 61.08%
skin sensitisation - 0.9029 90.29%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity + 0.8216 82.16%
Acute Oral Toxicity (c) III 0.5272 52.72%
Estrogen receptor binding + 0.7944 79.44%
Androgen receptor binding + 0.7511 75.11%
Thyroid receptor binding + 0.6155 61.55%
Glucocorticoid receptor binding + 0.7262 72.62%
Aromatase binding + 0.5528 55.28%
PPAR gamma + 0.7349 73.49%
Honey bee toxicity - 0.6370 63.70%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9875 98.75%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.29% 97.25%
CHEMBL2581 P07339 Cathepsin D 94.84% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.90% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.44% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.16% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 91.88% 96.61%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.52% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.71% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.10% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.63% 99.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.64% 94.45%
CHEMBL1871 P10275 Androgen Receptor 84.39% 96.43%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 84.21% 96.90%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 81.74% 89.34%
CHEMBL3401 O75469 Pregnane X receptor 80.58% 94.73%

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.
Jatropha curcas

Cross-Links

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PubChem 162871515
LOTUS LTS0245574
wikiData Q105245356