(1R,4S,8S,9S,10S)-9-[2-(furan-3-yl)ethyl]-9,10-dihydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one

Details

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Internal ID 895784d2-d1c7-4f88-b736-827c8322a415
Taxonomy Organoheterocyclic compounds > Lactones > Gamma butyrolactones
IUPAC Name (1R,4S,8S,9S,10S)-9-[2-(furan-3-yl)ethyl]-9,10-dihydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one
SMILES (Canonical) CC12CCCC3(C1C(CC(C3(CCC4=COC=C4)O)(C)O)OC2=O)C
SMILES (Isomeric) C[C@]12CCC[C@]3(C1[C@@H](C[C@]([C@@]3(CCC4=COC=C4)O)(C)O)OC2=O)C
InChI InChI=1S/C20H28O5/c1-17-7-4-8-18(2)15(17)14(25-16(17)21)11-19(3,22)20(18,23)9-5-13-6-10-24-12-13/h6,10,12,14-15,22-23H,4-5,7-9,11H2,1-3H3/t14-,15?,17+,18+,19+,20+/m1/s1
InChI Key FJNCXZZQNBKEJT-LIFSKISDSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C20H28O5
Molecular Weight 348.40 g/mol
Exact Mass 348.19367399 g/mol
Topological Polar Surface Area (TPSA) 79.90 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.84
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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26549-00-8

2D Structure

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2D Structure of (1R,4S,8S,9S,10S)-9-[2-(furan-3-yl)ethyl]-9,10-dihydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9530 95.30%
Caco-2 + 0.7118 71.18%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.7131 71.31%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7062 70.62%
OATP1B3 inhibitior + 0.8125 81.25%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.6156 61.56%
P-glycoprotein inhibitior - 0.7180 71.80%
P-glycoprotein substrate - 0.7087 70.87%
CYP3A4 substrate + 0.6529 65.29%
CYP2C9 substrate - 0.5928 59.28%
CYP2D6 substrate - 0.8003 80.03%
CYP3A4 inhibition - 0.5987 59.87%
CYP2C9 inhibition - 0.9012 90.12%
CYP2C19 inhibition - 0.8379 83.79%
CYP2D6 inhibition - 0.9636 96.36%
CYP1A2 inhibition - 0.8076 80.76%
CYP2C8 inhibition - 0.6584 65.84%
CYP inhibitory promiscuity - 0.9629 96.29%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4921 49.21%
Eye corrosion - 0.9949 99.49%
Eye irritation - 0.9590 95.90%
Skin irritation + 0.5699 56.99%
Skin corrosion - 0.9050 90.50%
Ames mutagenesis - 0.5970 59.70%
Human Ether-a-go-go-Related Gene inhibition - 0.3864 38.64%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.7250 72.50%
skin sensitisation - 0.8906 89.06%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.6032 60.32%
Acute Oral Toxicity (c) I 0.3917 39.17%
Estrogen receptor binding + 0.9098 90.98%
Androgen receptor binding + 0.7497 74.97%
Thyroid receptor binding + 0.6276 62.76%
Glucocorticoid receptor binding + 0.8178 81.78%
Aromatase binding + 0.8076 80.76%
PPAR gamma - 0.5184 51.84%
Honey bee toxicity - 0.8707 87.07%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9834 98.34%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.98% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.13% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.29% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.76% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.51% 85.14%
CHEMBL2581 P07339 Cathepsin D 90.05% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.39% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.26% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.16% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.51% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.71% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.20% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 80.23% 94.73%

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.
Leonurus sibiricus

Cross-Links

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PubChem 101306752
NPASS NPC65090
LOTUS LTS0129513
wikiData Q104996233