[(1S,2S,4R,5S,6S,10S,11R,12R,13R,14S,15R)-13-acetyloxy-5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-trideca-2,4-dienoate

Details

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Internal ID e5f827f6-aff5-47a3-a562-5020d63395a3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
IUPAC Name [(1S,2S,4R,5S,6S,10S,11R,12R,13R,14S,15R)-13-acetyloxy-5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-trideca-2,4-dienoate
SMILES (Canonical) CCCCCCCCC=CC=CC(=O)OC1C2C3C(O3)(C(C4(C(C2(C(C(C1(C(=C)C)O)OC(=O)C)C)O)C=C(C4=O)C)O)O)CO
SMILES (Isomeric) CCCCCCCC/C=C/C=C/C(=O)O[C@@H]1[C@@H]2[C@H]3[C@](O3)([C@H]([C@]4([C@H]([C@]2([C@@H]([C@H]([C@]1(C(=C)C)O)OC(=O)C)C)O)C=C(C4=O)C)O)O)CO
InChI InChI=1S/C35H50O11/c1-7-8-9-10-11-12-13-14-15-16-17-25(38)45-30-26-29-32(19-36,46-29)31(40)35(43)24(18-21(4)27(35)39)34(26,42)22(5)28(44-23(6)37)33(30,41)20(2)3/h14-18,22,24,26,28-31,36,40-43H,2,7-13,19H2,1,3-6H3/b15-14+,17-16+/t22-,24+,26+,28-,29+,30-,31-,32+,33+,34+,35-/m1/s1
InChI Key CEEFNBYRKPOUJV-GBSKIJSSSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C35H50O11
Molecular Weight 646.80 g/mol
Exact Mass 646.33531241 g/mol
Topological Polar Surface Area (TPSA) 183.00 Ų
XlogP 4.10
Atomic LogP (AlogP) 2.38
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 13

Synonyms

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[acetoxy-tetrahydroxy-(hydroxymethyl)-isopropenyl-dimethyl-oxo-[?]yl] (2E,4E)-trideca-2,4-dienoate

2D Structure

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2D Structure of [(1S,2S,4R,5S,6S,10S,11R,12R,13R,14S,15R)-13-acetyloxy-5,6,11,14-tetrahydroxy-4-(hydroxymethyl)-8,12-dimethyl-7-oxo-14-prop-1-en-2-yl-3-oxatetracyclo[9.4.0.02,4.06,10]pentadec-8-en-15-yl] (2E,4E)-trideca-2,4-dienoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9006 90.06%
Caco-2 - 0.8378 83.78%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.7094 70.94%
OATP2B1 inhibitior - 0.8587 85.87%
OATP1B1 inhibitior + 0.7965 79.65%
OATP1B3 inhibitior + 0.9351 93.51%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5526 55.26%
BSEP inhibitior + 0.7861 78.61%
P-glycoprotein inhibitior + 0.7556 75.56%
P-glycoprotein substrate + 0.5901 59.01%
CYP3A4 substrate + 0.7124 71.24%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8984 89.84%
CYP3A4 inhibition - 0.5477 54.77%
CYP2C9 inhibition + 0.5474 54.74%
CYP2C19 inhibition - 0.7515 75.15%
CYP2D6 inhibition - 0.9236 92.36%
CYP1A2 inhibition - 0.7128 71.28%
CYP2C8 inhibition + 0.7040 70.40%
CYP inhibitory promiscuity - 0.8708 87.08%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7011 70.11%
Eye corrosion - 0.9870 98.70%
Eye irritation - 0.9100 91.00%
Skin irritation - 0.5708 57.08%
Skin corrosion - 0.9372 93.72%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7236 72.36%
Micronuclear - 0.7000 70.00%
Hepatotoxicity - 0.5157 51.57%
skin sensitisation - 0.8835 88.35%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.6403 64.03%
Acute Oral Toxicity (c) III 0.4650 46.50%
Estrogen receptor binding + 0.7575 75.75%
Androgen receptor binding + 0.7200 72.00%
Thyroid receptor binding + 0.5431 54.31%
Glucocorticoid receptor binding + 0.6766 67.66%
Aromatase binding + 0.6218 62.18%
PPAR gamma + 0.6466 64.66%
Honey bee toxicity - 0.7853 78.53%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6570 65.70%
Fish aquatic toxicity + 0.9920 99.20%

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 96.19% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.06% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.46% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 92.96% 94.73%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.81% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.53% 99.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.14% 96.09%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 91.94% 94.80%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.42% 95.56%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 90.88% 96.90%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 89.64% 96.95%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 89.62% 92.32%
CHEMBL4040 P28482 MAP kinase ERK2 87.75% 83.82%
CHEMBL2996 Q05655 Protein kinase C delta 87.16% 97.79%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 86.40% 89.34%
CHEMBL4769 O95749 Geranylgeranyl pyrophosphate synthetase 85.47% 92.08%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.17% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.62% 89.00%
CHEMBL299 P17252 Protein kinase C alpha 81.89% 98.03%
CHEMBL5043 Q6P179 Endoplasmic reticulum aminopeptidase 2 80.99% 91.81%
CHEMBL340 P08684 Cytochrome P450 3A4 80.94% 91.19%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.63% 100.00%

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.
Stellera chamaejasme

Cross-Links

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PubChem 118705845
LOTUS LTS0243794
wikiData Q104955578