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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] (2R)-2-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 3d4c653a-db55-4d04-86c0-eed7fe8aeccd
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] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1CC(C2(C1C(C(C3C(C2OC(=O)C)C(=C)C(=O)O3)OC(=O)C)C)C)O
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1[C@@H]([C@H]([C@H]3[C@H]([C@H]2OC(=O)C)C(=C)C(=O)O3)OC(=O)C)C)C)O
InChI InChI=1S/C24H34O9/c1-8-10(2)22(28)32-15-9-16(27)24(7)18(15)12(4)19(30-13(5)25)20-17(11(3)23(29)33-20)21(24)31-14(6)26/h10,12,15-21,27H,3,8-9H2,1-2,4-7H3/t10-,12+,15+,16-,17-,18-,19-,20-,21-,24-/m1/s1
InChI Key PHXYUQKASILPOW-KAXFTFLPSA-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 2.90
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] (2R)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9901 99.01%
Caco-2 - 0.6246 62.46%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.4041 40.41%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8484 84.84%
OATP1B3 inhibitior + 0.8792 87.92%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5679 56.79%
P-glycoprotein inhibitior + 0.6952 69.52%
P-glycoprotein substrate + 0.5050 50.50%
CYP3A4 substrate + 0.6449 64.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8873 88.73%
CYP3A4 inhibition + 0.5729 57.29%
CYP2C9 inhibition - 0.8237 82.37%
CYP2C19 inhibition - 0.7847 78.47%
CYP2D6 inhibition - 0.9512 95.12%
CYP1A2 inhibition - 0.7172 71.72%
CYP2C8 inhibition - 0.7150 71.50%
CYP inhibitory promiscuity - 0.9198 91.98%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.5310 53.10%
Eye corrosion - 0.9782 97.82%
Eye irritation - 0.8563 85.63%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.8878 88.78%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7156 71.56%
Micronuclear - 0.6700 67.00%
Hepatotoxicity + 0.7375 73.75%
skin sensitisation - 0.6590 65.90%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity + 0.8125 81.25%
Nephrotoxicity + 0.5640 56.40%
Acute Oral Toxicity (c) III 0.4364 43.64%
Estrogen receptor binding + 0.8310 83.10%
Androgen receptor binding + 0.6438 64.38%
Thyroid receptor binding + 0.6003 60.03%
Glucocorticoid receptor binding + 0.6476 64.76%
Aromatase binding + 0.6169 61.69%
PPAR gamma + 0.7074 70.74%
Honey bee toxicity - 0.6506 65.06%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9690 96.90%

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 97.93% 97.79%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.44% 97.25%
CHEMBL221 P23219 Cyclooxygenase-1 96.99% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.47% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.34% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.41% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.81% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.47% 85.14%
CHEMBL299 P17252 Protein kinase C alpha 89.72% 98.03%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 88.76% 96.47%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.29% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.16% 86.33%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.38% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.12% 97.09%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.79% 89.50%
CHEMBL340 P08684 Cytochrome P450 3A4 83.44% 91.19%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.08% 96.77%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 82.50% 98.75%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 82.18% 95.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.11% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.89% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.18% 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 163060378
LOTUS LTS0080065
wikiData Q105209294