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Fissinolide

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 3061cf89-408f-4b9b-9fb6-6098b9ad7c91
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name methyl 2-[(2S,5R,6R,13S,14R,16S)-14-acetyloxy-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]acetate
SMILES (Canonical) CC(=O)OC1C2CC3=C4CC(=O)OC(C4(CCC3C(C2=O)(C(C1(C)C)CC(=O)OC)C)C)C5=COC=C5
SMILES (Isomeric) CC(=O)O[C@@H]1[C@@H]2CC3=C4CC(=O)O[C@H]([C@@]4(CC[C@@H]3C(C2=O)([C@H](C1(C)C)CC(=O)OC)C)C)C5=COC=C5
InChI InChI=1S/C29H36O8/c1-15(30)36-26-18-11-17-19(29(5,24(18)33)21(27(26,2)3)13-22(31)34-6)7-9-28(4)20(17)12-23(32)37-25(28)16-8-10-35-14-16/h8,10,14,18-19,21,25-26H,7,9,11-13H2,1-6H3/t18-,19+,21+,25+,26-,28-,29?/m1/s1
InChI Key YOTCKRFNSMJTGD-ZFZOQYKTSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C29H36O8
Molecular Weight 512.60 g/mol
Exact Mass 512.24101810 g/mol
Topological Polar Surface Area (TPSA) 109.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 4.73
H-Bond Acceptor 8
H-Bond Donor 0
Rotatable Bonds 4

Synonyms

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1915-69-1
(-)-Fissinolide
methyl 2-[(2S,5R,6R,13S,14R,16S)-14-acetyloxy-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]acetate
DTXSID50911692
CHEBI:168378
7,11-Methano-2H-cycloocta(f)(2)benzopyran-8-acetic acid, 10-(acetyloxy)-4-(3-furanyl)-1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-4a,7,9,9-tetramethyl-2,13-dioxo-, methyl ester, (4alpha,4aalpha,6aalpha,7alpha,8alpha,10beta,11alpha)-
Methyl 10-(acetyloxy)-4-(3-furanyl)-1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-4a,7,9,9-tetramethyl-2,13-dioxo-7,11-methano-2H-cycloocta(f)(2)benzopyran-8-acetate (4alpha,4aalpha,6aalpha,7alpha,8alpha,10beta,11alpha)-
11046-11-0
Methyl [10-(acetyloxy)-4-(furan-3-yl)-4a,7,9,9-tetramethyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-2H-7,11-methanocycloocta[3,4]benzo[1,2-c]pyran-8-yl]acetate
methyl 2-[(2S,5R,6R,13S,14R,16S)-14-acetyloxy-6-(uran-3-yl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]acetate

2D Structure

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2D Structure of Fissinolide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9932 99.32%
Caco-2 - 0.6557 65.57%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8326 83.26%
OATP2B1 inhibitior - 0.7188 71.88%
OATP1B1 inhibitior - 0.7739 77.39%
OATP1B3 inhibitior + 0.9479 94.79%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.9643 96.43%
P-glycoprotein inhibitior + 0.8357 83.57%
P-glycoprotein substrate + 0.5243 52.43%
CYP3A4 substrate + 0.6872 68.72%
CYP2C9 substrate - 0.5962 59.62%
CYP2D6 substrate - 0.8407 84.07%
CYP3A4 inhibition + 0.7960 79.60%
CYP2C9 inhibition - 0.7754 77.54%
CYP2C19 inhibition - 0.8086 80.86%
CYP2D6 inhibition - 0.9266 92.66%
CYP1A2 inhibition - 0.8292 82.92%
CYP2C8 inhibition + 0.7086 70.86%
CYP inhibitory promiscuity - 0.5901 59.01%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5245 52.45%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.8747 87.47%
Skin irritation - 0.6856 68.56%
Skin corrosion - 0.9275 92.75%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7792 77.92%
Micronuclear - 0.6400 64.00%
Hepatotoxicity + 0.6160 61.60%
skin sensitisation - 0.8388 83.88%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) I 0.5641 56.41%
Estrogen receptor binding + 0.8784 87.84%
Androgen receptor binding + 0.7060 70.60%
Thyroid receptor binding + 0.6243 62.43%
Glucocorticoid receptor binding + 0.8570 85.70%
Aromatase binding + 0.7327 73.27%
PPAR gamma + 0.7756 77.56%
Honey bee toxicity - 0.7518 75.18%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9969 99.69%

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 98.48% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.24% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.19% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.90% 94.45%
CHEMBL4040 P28482 MAP kinase ERK2 96.32% 83.82%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 89.28% 94.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.06% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.85% 86.33%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 87.42% 91.24%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.65% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.98% 99.23%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 84.59% 94.80%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.27% 92.62%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.24% 100.00%
CHEMBL255 P29275 Adenosine A2b receptor 83.03% 98.59%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 82.95% 95.71%
CHEMBL340 P08684 Cytochrome P450 3A4 82.49% 91.19%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.37% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.27% 89.00%
CHEMBL5028 O14672 ADAM10 81.51% 97.50%

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.
Khaya grandifoliola
Khaya senegalensis
Swietenia mahagoni

Cross-Links

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PubChem 6451333
LOTUS LTS0144115
wikiData Q82881868