(1aR,3aR,4R,5R,5'R,7aS,7bS)-5'-(furan-3-yl)-3a-hydroxy-5,7a,7b-trimethylspiro[2,3,5,6-tetrahydro-1aH-naphtho[1,2-b]oxirene-4,3'-oxolane]-2',7-dione

Details

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Internal ID 3268070d-6f55-4e46-b914-2e50618cd00c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name (1aR,3aR,4R,5R,5'R,7aS,7bS)-5'-(furan-3-yl)-3a-hydroxy-5,7a,7b-trimethylspiro[2,3,5,6-tetrahydro-1aH-naphtho[1,2-b]oxirene-4,3'-oxolane]-2',7-dione
SMILES (Canonical) CC1CC(=O)C2(C3(C(O3)CCC2(C14CC(OC4=O)C5=COC=C5)O)C)C
SMILES (Isomeric) C[C@@H]1CC(=O)[C@@]2([C@]3([C@H](O3)CC[C@@]2([C@@]14C[C@@H](OC4=O)C5=COC=C5)O)C)C
InChI InChI=1S/C20H24O6/c1-11-8-14(21)17(2)18(3)15(26-18)4-6-20(17,23)19(11)9-13(25-16(19)22)12-5-7-24-10-12/h5,7,10-11,13,15,23H,4,6,8-9H2,1-3H3/t11-,13-,15-,17-,18-,19+,20-/m1/s1
InChI Key DCWMPDIKJVJVTN-SFNRKBCLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H24O6
Molecular Weight 360.40 g/mol
Exact Mass 360.15728848 g/mol
Topological Polar Surface Area (TPSA) 89.30 Ų
XlogP 0.90
Atomic LogP (AlogP) 2.55
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1aR,3aR,4R,5R,5'R,7aS,7bS)-5'-(furan-3-yl)-3a-hydroxy-5,7a,7b-trimethylspiro[2,3,5,6-tetrahydro-1aH-naphtho[1,2-b]oxirene-4,3'-oxolane]-2',7-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9848 98.48%
Caco-2 + 0.6147 61.47%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7443 74.43%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7867 78.67%
OATP1B3 inhibitior - 0.4199 41.99%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7608 76.08%
BSEP inhibitior - 0.6533 65.33%
P-glycoprotein inhibitior - 0.7417 74.17%
P-glycoprotein substrate - 0.5752 57.52%
CYP3A4 substrate + 0.6492 64.92%
CYP2C9 substrate - 0.8077 80.77%
CYP2D6 substrate - 0.8327 83.27%
CYP3A4 inhibition + 0.6004 60.04%
CYP2C9 inhibition - 0.7452 74.52%
CYP2C19 inhibition - 0.8033 80.33%
CYP2D6 inhibition - 0.9552 95.52%
CYP1A2 inhibition - 0.7721 77.21%
CYP2C8 inhibition + 0.4435 44.35%
CYP inhibitory promiscuity - 0.9698 96.98%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5276 52.76%
Eye corrosion - 0.9914 99.14%
Eye irritation - 0.9669 96.69%
Skin irritation - 0.5945 59.45%
Skin corrosion - 0.8702 87.02%
Ames mutagenesis - 0.6070 60.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7243 72.43%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.7417 74.17%
skin sensitisation - 0.8804 88.04%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.6122 61.22%
Acute Oral Toxicity (c) II 0.3642 36.42%
Estrogen receptor binding + 0.8977 89.77%
Androgen receptor binding + 0.7515 75.15%
Thyroid receptor binding + 0.6568 65.68%
Glucocorticoid receptor binding + 0.7133 71.33%
Aromatase binding + 0.7478 74.78%
PPAR gamma - 0.4886 48.86%
Honey bee toxicity - 0.8789 87.89%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 0.9921 99.21%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.04% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.30% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.81% 97.25%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.42% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.41% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.30% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.82% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.41% 97.09%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 85.24% 100.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.24% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.67% 94.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 82.49% 91.11%
CHEMBL1902 P62942 FK506-binding protein 1A 81.92% 97.05%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.47% 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.
Erigeron canadensis
Microglossa pyrifolia
Microglossa pyrrhopappa
Viola tricolor

Cross-Links

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PubChem 14733476
LOTUS LTS0024109
wikiData Q105263969