(3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one

Details

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Internal ID 1ba69b2d-efd6-446d-bdce-3e87d9557f6a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
SMILES (Canonical) CC12CCCC(=C)C1C3C(CC2)C(C(=O)O3)COC
SMILES (Isomeric) C[C@]12CCCC(=C)[C@@H]1[C@@H]3[C@@H](CC2)[C@@H](C(=O)O3)COC
InChI InChI=1S/C16H24O3/c1-10-5-4-7-16(2)8-6-11-12(9-18-3)15(17)19-14(11)13(10)16/h11-14H,1,4-9H2,2-3H3/t11-,12-,13+,14-,16+/m0/s1
InChI Key OCZYALGLUPTEFV-JHZZJYKESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C16H24O3
Molecular Weight 264.36 g/mol
Exact Mass 264.17254462 g/mol
Topological Polar Surface Area (TPSA) 35.50 Ų
XlogP 3.00
Atomic LogP (AlogP) 2.95
H-Bond Acceptor 3
H-Bond Donor 0
Rotatable Bonds 2

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9951 99.51%
Caco-2 + 0.8433 84.33%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability + 0.7429 74.29%
Subcellular localzation Mitochondria 0.5983 59.83%
OATP2B1 inhibitior - 0.8522 85.22%
OATP1B1 inhibitior + 0.8807 88.07%
OATP1B3 inhibitior + 0.9277 92.77%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5000 50.00%
BSEP inhibitior - 0.8606 86.06%
P-glycoprotein inhibitior - 0.7853 78.53%
P-glycoprotein substrate - 0.8749 87.49%
CYP3A4 substrate + 0.6404 64.04%
CYP2C9 substrate - 0.8006 80.06%
CYP2D6 substrate - 0.8554 85.54%
CYP3A4 inhibition - 0.6388 63.88%
CYP2C9 inhibition - 0.7253 72.53%
CYP2C19 inhibition - 0.5914 59.14%
CYP2D6 inhibition - 0.8982 89.82%
CYP1A2 inhibition + 0.5129 51.29%
CYP2C8 inhibition - 0.7766 77.66%
CYP inhibitory promiscuity - 0.6341 63.41%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5738 57.38%
Eye corrosion - 0.9774 97.74%
Eye irritation - 0.7279 72.79%
Skin irritation - 0.6842 68.42%
Skin corrosion - 0.9468 94.68%
Ames mutagenesis - 0.7701 77.01%
Human Ether-a-go-go-Related Gene inhibition - 0.6661 66.61%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.6077 60.77%
skin sensitisation - 0.6927 69.27%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.5803 58.03%
Acute Oral Toxicity (c) III 0.4739 47.39%
Estrogen receptor binding - 0.4885 48.85%
Androgen receptor binding + 0.6916 69.16%
Thyroid receptor binding - 0.5141 51.41%
Glucocorticoid receptor binding + 0.6825 68.25%
Aromatase binding - 0.7093 70.93%
PPAR gamma - 0.6257 62.57%
Honey bee toxicity - 0.7120 71.20%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9958 99.58%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.93% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.22% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.24% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.13% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.12% 96.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 88.35% 96.38%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.85% 92.62%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.71% 93.04%
CHEMBL1871 P10275 Androgen Receptor 82.47% 96.43%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.43% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.17% 100.00%
CHEMBL2581 P07339 Cathepsin D 81.30% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.58% 95.89%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 80.57% 94.78%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.07% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.02% 86.33%

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.
Aucklandia costus

Cross-Links

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PubChem 44568209
LOTUS LTS0109015
wikiData Q105189671