(4R,4aR,5S,8aR,9aS)-4-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-2-one

Details

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Internal ID 9f43f783-7aef-42ee-8e66-91090b98af83
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name (4R,4aR,5S,8aR,9aS)-4-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][1]benzofuran-2-one
SMILES (Canonical) CC1CCCC2C1(C(C3=C(C(=O)OC3C2)C)O)C
SMILES (Isomeric) C[C@H]1CCC[C@H]2[C@@]1([C@H](C3=C(C(=O)O[C@H]3C2)C)O)C
InChI InChI=1S/C15H22O3/c1-8-5-4-6-10-7-11-12(9(2)14(17)18-11)13(16)15(8,10)3/h8,10-11,13,16H,4-7H2,1-3H3/t8-,10+,11-,13-,15+/m0/s1
InChI Key YDCNBSJHGGIZNP-NOWRLKFISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H22O3
Molecular Weight 250.33 g/mol
Exact Mass 250.15689456 g/mol
Topological Polar Surface Area (TPSA) 46.50 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.44
H-Bond Acceptor 3
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (4R,4aR,5S,8aR,9aS)-4-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,8a,9,9a-octahydrobenzo[f][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 + 0.9950 99.50%
Caco-2 + 0.9047 90.47%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability + 0.6429 64.29%
Subcellular localzation Mitochondria 0.5975 59.75%
OATP2B1 inhibitior - 0.8530 85.30%
OATP1B1 inhibitior + 0.9282 92.82%
OATP1B3 inhibitior + 0.9715 97.15%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior + 0.7250 72.50%
BSEP inhibitior - 0.8872 88.72%
P-glycoprotein inhibitior - 0.8929 89.29%
P-glycoprotein substrate - 0.8366 83.66%
CYP3A4 substrate + 0.5674 56.74%
CYP2C9 substrate - 0.7907 79.07%
CYP2D6 substrate - 0.8724 87.24%
CYP3A4 inhibition - 0.7214 72.14%
CYP2C9 inhibition - 0.8950 89.50%
CYP2C19 inhibition - 0.7761 77.61%
CYP2D6 inhibition - 0.9587 95.87%
CYP1A2 inhibition + 0.7052 70.52%
CYP2C8 inhibition - 0.8897 88.97%
CYP inhibitory promiscuity - 0.8734 87.34%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4413 44.13%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9174 91.74%
Skin irritation + 0.6760 67.60%
Skin corrosion - 0.9100 91.00%
Ames mutagenesis - 0.7264 72.64%
Human Ether-a-go-go-Related Gene inhibition - 0.5800 58.00%
Micronuclear - 0.8300 83.00%
Hepatotoxicity + 0.6575 65.75%
skin sensitisation - 0.7440 74.40%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.6359 63.59%
Acute Oral Toxicity (c) III 0.5812 58.12%
Estrogen receptor binding + 0.6308 63.08%
Androgen receptor binding - 0.5781 57.81%
Thyroid receptor binding + 0.5926 59.26%
Glucocorticoid receptor binding + 0.5957 59.57%
Aromatase binding - 0.7121 71.21%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.9149 91.49%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9910 99.10%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.25% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.23% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.55% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.31% 99.23%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.33% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.74% 100.00%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 84.09% 96.47%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 84.07% 93.03%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.56% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 81.87% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.75% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.19% 92.94%
CHEMBL2581 P07339 Cathepsin D 80.10% 98.95%

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.
Ligularia muliensis
Ligularia virgaurea

Cross-Links

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PubChem 102384814
LOTUS LTS0023893
wikiData Q105346645