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[(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-4,9-diacetyloxy-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 3-methylbutanoate

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 fafb2966-d0b0-4572-abb1-e35f30012403
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
IUPAC Name [(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-4,9-diacetyloxy-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 3-methylbutanoate
SMILES (Canonical) CC1C2C(CC(C2(C(C3C(C1OC(=O)C)OC(=O)C3=C)OC(=O)C)C)O)OC(=O)CC(C)C
SMILES (Isomeric) C[C@H]1[C@@H]2[C@H](C[C@H]([C@]2([C@@H]([C@H]3[C@H]([C@@H]1OC(=O)C)OC(=O)C3=C)OC(=O)C)C)O)OC(=O)CC(C)C
InChI InChI=1S/C24H34O9/c1-10(2)8-17(28)32-15-9-16(27)24(7)19(15)12(4)20(30-13(5)25)21-18(11(3)23(29)33-21)22(24)31-14(6)26/h10,12,15-16,18-22,27H,3,8-9H2,1-2,4-7H3/t12-,15-,16+,18+,19+,20+,21+,22+,24+/m0/s1
InChI Key ARCBDBQHANOQNW-LYGMSERTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H34O9
Molecular Weight 466.50 g/mol
Exact Mass 466.22028266 g/mol
Topological Polar Surface Area (TPSA) 125.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 1.94
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-4,9-diacetyloxy-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 3-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9857 98.57%
Caco-2 - 0.6306 63.06%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.5476 54.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8380 83.80%
OATP1B3 inhibitior - 0.2314 23.14%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.6288 62.88%
P-glycoprotein inhibitior + 0.7001 70.01%
P-glycoprotein substrate + 0.5656 56.56%
CYP3A4 substrate + 0.6518 65.18%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8873 88.73%
CYP3A4 inhibition - 0.5744 57.44%
CYP2C9 inhibition - 0.7795 77.95%
CYP2C19 inhibition - 0.7784 77.84%
CYP2D6 inhibition - 0.9474 94.74%
CYP1A2 inhibition - 0.7200 72.00%
CYP2C8 inhibition - 0.7809 78.09%
CYP inhibitory promiscuity - 0.9455 94.55%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8600 86.00%
Carcinogenicity (trinary) Non-required 0.5806 58.06%
Eye corrosion - 0.9796 97.96%
Eye irritation - 0.8368 83.68%
Skin irritation - 0.5371 53.71%
Skin corrosion - 0.9113 91.13%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6076 60.76%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.6625 66.25%
skin sensitisation - 0.6319 63.19%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.6444 64.44%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.7934 79.34%
Acute Oral Toxicity (c) III 0.3687 36.87%
Estrogen receptor binding + 0.7747 77.47%
Androgen receptor binding + 0.6199 61.99%
Thyroid receptor binding + 0.5795 57.95%
Glucocorticoid receptor binding + 0.6058 60.58%
Aromatase binding + 0.6189 61.89%
PPAR gamma + 0.6420 64.20%
Honey bee toxicity - 0.6410 64.10%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9831 98.31%

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
CHEMBL2996 Q05655 Protein kinase C delta 97.49% 97.79%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.39% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 96.31% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.11% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.76% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.11% 96.09%
CHEMBL2581 P07339 Cathepsin D 89.34% 98.95%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 89.24% 96.47%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.34% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.10% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.19% 99.23%
CHEMBL299 P17252 Protein kinase C alpha 87.08% 98.03%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.83% 91.07%
CHEMBL340 P08684 Cytochrome P450 3A4 84.19% 91.19%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.19% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.25% 95.56%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.15% 89.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.98% 97.09%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.63% 95.71%
CHEMBL5028 O14672 ADAM10 81.18% 97.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.51% 89.00%

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.
Gaillardia pulchella

Cross-Links

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PubChem 162904820
LOTUS LTS0179267
wikiData Q104917215