(3S,4aS,6Z,8E,12aR)-3-(furan-3-yl)-4a-methyl-10-methylidene-1-oxo-3,4,5,11,12,12a-hexahydrocyclodeca[c]pyran-9-carboxylic acid

Details

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Internal ID 6941ee04-f1cd-44f4-b302-62fd2001e503
Taxonomy Organoheterocyclic compounds > Lactones > Delta valerolactones
IUPAC Name (3S,4aS,6Z,8E,12aR)-3-(furan-3-yl)-4a-methyl-10-methylidene-1-oxo-3,4,5,11,12,12a-hexahydrocyclodeca[c]pyran-9-carboxylic acid
SMILES (Canonical) CC12CC=CC=C(C(=C)CCC1C(=O)OC(C2)C3=COC=C3)C(=O)O
SMILES (Isomeric) C[C@@]12C/C=C\C=C(/C(=C)CC[C@H]1C(=O)O[C@@H](C2)C3=COC=C3)\C(=O)O
InChI InChI=1S/C20H22O5/c1-13-6-7-16-19(23)25-17(14-8-10-24-12-14)11-20(16,2)9-4-3-5-15(13)18(21)22/h3-5,8,10,12,16-17H,1,6-7,9,11H2,2H3,(H,21,22)/b4-3-,15-5+/t16-,17-,20-/m0/s1
InChI Key CWQAKZVVQWOLKL-PTIGVWBYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H22O5
Molecular Weight 342.40 g/mol
Exact Mass 342.14672380 g/mol
Topological Polar Surface Area (TPSA) 76.70 Ų
XlogP 3.40
Atomic LogP (AlogP) 4.20
H-Bond Acceptor 4
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 (3S,4aS,6Z,8E,12aR)-3-(furan-3-yl)-4a-methyl-10-methylidene-1-oxo-3,4,5,11,12,12a-hexahydrocyclodeca[c]pyran-9-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9807 98.07%
Caco-2 - 0.6687 66.87%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.8013 80.13%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7499 74.99%
OATP1B3 inhibitior + 0.7971 79.71%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior - 0.6649 66.49%
P-glycoprotein inhibitior - 0.7803 78.03%
P-glycoprotein substrate - 0.7351 73.51%
CYP3A4 substrate + 0.6200 62.00%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8990 89.90%
CYP3A4 inhibition - 0.6483 64.83%
CYP2C9 inhibition - 0.8842 88.42%
CYP2C19 inhibition - 0.8655 86.55%
CYP2D6 inhibition - 0.9467 94.67%
CYP1A2 inhibition + 0.5839 58.39%
CYP2C8 inhibition - 0.5720 57.20%
CYP inhibitory promiscuity - 0.9289 92.89%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5012 50.12%
Eye corrosion - 0.9857 98.57%
Eye irritation - 0.9631 96.31%
Skin irritation - 0.5267 52.67%
Skin corrosion - 0.8590 85.90%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7338 73.38%
Micronuclear - 0.7400 74.00%
Hepatotoxicity + 0.7315 73.15%
skin sensitisation - 0.8264 82.64%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.6461 64.61%
Acute Oral Toxicity (c) II 0.3695 36.95%
Estrogen receptor binding + 0.7868 78.68%
Androgen receptor binding - 0.5129 51.29%
Thyroid receptor binding - 0.6597 65.97%
Glucocorticoid receptor binding + 0.5957 59.57%
Aromatase binding + 0.7601 76.01%
PPAR gamma + 0.5173 51.73%
Honey bee toxicity - 0.9005 90.05%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9956 99.56%

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
CHEMBL4040 P28482 MAP kinase ERK2 96.36% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.15% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.69% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.41% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.86% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.64% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.49% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.17% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.29% 85.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.00% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.40% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.00% 89.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.53% 93.00%
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.
Lomatia tinctoria
Nidorella welwitschii
Tecomella undulata

Cross-Links

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PubChem 102057014
LOTUS LTS0092136
wikiData Q105162356