[(3aR,4S,6aR,8S,9R,9aS,9bR)-8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl] 2-methylprop-2-enoate

Details

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Internal ID bc60b8e8-2350-4e0f-a25e-3ad59c407264
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4S,6aR,8S,9R,9aS,9bR)-8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl] 2-methylprop-2-enoate
SMILES (Canonical) CC(=C)C(=O)OC1CC(=C)C2CC(C3(C2C4C1C(=C)C(=O)O4)CO3)O
SMILES (Isomeric) CC(=C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H]([C@@]3([C@@H]2[C@H]4[C@@H]1C(=C)C(=O)O4)CO3)O
InChI InChI=1S/C19H22O6/c1-8(2)17(21)24-12-5-9(3)11-6-13(20)19(7-23-19)15(11)16-14(12)10(4)18(22)25-16/h11-16,20H,1,3-7H2,2H3/t11-,12-,13-,14+,15-,16+,19+/m0/s1
InChI Key OXOPCSJXUOZWDB-LSYIGHHSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C19H22O6
Molecular Weight 346.40 g/mol
Exact Mass 346.14163842 g/mol
Topological Polar Surface Area (TPSA) 85.40 Ų
XlogP 1.40
Atomic LogP (AlogP) 1.30
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,6aR,8S,9R,9aS,9bR)-8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl] 2-methylprop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9728 97.28%
Caco-2 - 0.6803 68.03%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.7393 73.93%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9009 90.09%
OATP1B3 inhibitior + 0.9597 95.97%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.8572 85.72%
P-glycoprotein inhibitior - 0.8133 81.33%
P-glycoprotein substrate - 0.5932 59.32%
CYP3A4 substrate + 0.6449 64.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8449 84.49%
CYP3A4 inhibition - 0.8605 86.05%
CYP2C9 inhibition - 0.8186 81.86%
CYP2C19 inhibition - 0.8306 83.06%
CYP2D6 inhibition - 0.9299 92.99%
CYP1A2 inhibition - 0.8305 83.05%
CYP2C8 inhibition - 0.6917 69.17%
CYP inhibitory promiscuity - 0.9601 96.01%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5815 58.15%
Eye corrosion - 0.9720 97.20%
Eye irritation - 0.8662 86.62%
Skin irritation - 0.6933 69.33%
Skin corrosion - 0.9128 91.28%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6225 62.25%
Micronuclear - 0.5700 57.00%
Hepatotoxicity + 0.7052 70.52%
skin sensitisation - 0.7667 76.67%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity + 0.8897 88.97%
Acute Oral Toxicity (c) III 0.3686 36.86%
Estrogen receptor binding + 0.7270 72.70%
Androgen receptor binding + 0.6443 64.43%
Thyroid receptor binding - 0.5060 50.60%
Glucocorticoid receptor binding + 0.7710 77.10%
Aromatase binding + 0.5649 56.49%
PPAR gamma + 0.6446 64.46%
Honey bee toxicity - 0.5965 59.65%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9459 94.59%

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 97.48% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.31% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.82% 94.45%
CHEMBL2996 Q05655 Protein kinase C delta 90.60% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 88.89% 90.17%
CHEMBL4040 P28482 MAP kinase ERK2 88.84% 83.82%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.19% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.67% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 87.45% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.43% 97.09%
CHEMBL2581 P07339 Cathepsin D 86.88% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.72% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 80.55% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.35% 86.33%
CHEMBL5028 O14672 ADAM10 80.24% 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.
Pleiotaxis rugosa

Cross-Links

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PubChem 101833765
LOTUS LTS0148691
wikiData Q105202836