(5aR,6R,9R)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

Details

Top
Internal ID e84f911b-3bd3-4df4-850d-d8a203fa3787
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name (5aR,6R,9R)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one
SMILES (Canonical) CC12CCC3C(C1C(CCC2O)(C)O)OC(=O)C3=C
SMILES (Isomeric) C[C@@]12CCC3C(C1[C@](CC[C@H]2O)(C)O)OC(=O)C3=C
InChI InChI=1S/C15H22O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h9-12,16,18H,1,4-7H2,2-3H3/t9?,10-,11?,12?,14+,15-/m1/s1
InChI Key LVABKRFKENTQBT-VWNUJFTMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C15H22O4
Molecular Weight 266.33 g/mol
Exact Mass 266.15180918 g/mol
Topological Polar Surface Area (TPSA) 66.80 Ų
XlogP 1.40
Atomic LogP (AlogP) 1.41
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 0

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (5aR,6R,9R)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-2-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9905 99.05%
Caco-2 + 0.6432 64.32%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.6937 69.37%
OATP2B1 inhibitior - 0.8542 85.42%
OATP1B1 inhibitior + 0.8981 89.81%
OATP1B3 inhibitior + 0.8475 84.75%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6170 61.70%
BSEP inhibitior - 0.9633 96.33%
P-glycoprotein inhibitior - 0.9147 91.47%
P-glycoprotein substrate - 0.8658 86.58%
CYP3A4 substrate + 0.6389 63.89%
CYP2C9 substrate - 0.8038 80.38%
CYP2D6 substrate - 0.8527 85.27%
CYP3A4 inhibition - 0.5612 56.12%
CYP2C9 inhibition - 0.9247 92.47%
CYP2C19 inhibition - 0.8848 88.48%
CYP2D6 inhibition - 0.9517 95.17%
CYP1A2 inhibition - 0.6883 68.83%
CYP2C8 inhibition - 0.8361 83.61%
CYP inhibitory promiscuity - 0.9169 91.69%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4952 49.52%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.8593 85.93%
Skin irritation + 0.6326 63.26%
Skin corrosion - 0.8995 89.95%
Ames mutagenesis - 0.7500 75.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5741 57.41%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.8875 88.75%
skin sensitisation - 0.7613 76.13%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity + 0.5196 51.96%
Acute Oral Toxicity (c) I 0.5236 52.36%
Estrogen receptor binding + 0.7480 74.80%
Androgen receptor binding + 0.6255 62.55%
Thyroid receptor binding + 0.5360 53.60%
Glucocorticoid receptor binding + 0.6944 69.44%
Aromatase binding - 0.5810 58.10%
PPAR gamma - 0.6807 68.07%
Honey bee toxicity - 0.8650 86.50%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9953 99.53%

Targets

Top

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 94.44% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.43% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.70% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.38% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.59% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.89% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.90% 99.23%
CHEMBL2581 P07339 Cathepsin D 83.12% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.25% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.60% 95.89%

Plants that contains it

Top
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.
Gynochthodes umbellata

Cross-Links

Top
PubChem 5318148
NPASS NPC163651