11,12,13-Trihydroxy-4(15),8-eudesmadiene-9-one

Details

Top
Internal ID 39135335-e90a-4056-b4d8-d6c031b10158
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name (4aS,8aS)-8a-methyl-5-methylidene-3-(1,2,3-trihydroxypropan-2-yl)-4a,6,7,8-tetrahydro-4H-naphthalen-1-one
SMILES (Canonical) CC12CCCC(=C)C1CC(=CC2=O)C(CO)(CO)O
SMILES (Isomeric) C[C@]12CCCC(=C)[C@@H]1CC(=CC2=O)C(CO)(CO)O
InChI InChI=1S/C15H22O4/c1-10-4-3-5-14(2)12(10)6-11(7-13(14)18)15(19,8-16)9-17/h7,12,16-17,19H,1,3-6,8-9H2,2H3/t12-,14-/m0/s1
InChI Key PXBZMGHIEDYLOI-JSGCOSHPSA-N
Popularity 1 reference 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) 77.80 Ų
XlogP -0.50
Atomic LogP (AlogP) 0.96
H-Bond Acceptor 4
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

Top
1(4H)-naphthalenone, 3-[1,2-dihydroxy-1-(hydroxymethyl)ethyl]-4a,5,6,7,8,8a-hexahydro-8a-methyl-5-methylene-, (4aS,8aS)-
3-(1,2-Dihdroxy-1-hydroxymethyl-ethyl)-8a-methyl-5-methylene-4a,5,6,7,8,8a-hexayhydro-4H-napthalen-1-one
InChI=1/C15H22O4/c1-10-4-3-5-14(2)12(10)6-11(7-13(14)18)15(19,8-16)9-17/h7,12,16-17,19H,1,3-6,8-9H2,2H3/t12-,14-/m0/s
rel-(4aR,8aR)-3-[1,2-dihydroxy-1-(hydroxymethyl)ethyl]-8a-methyl-5-methylene-4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one

2D Structure

Top
2D Structure of 11,12,13-Trihydroxy-4(15),8-eudesmadiene-9-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9377 93.77%
Caco-2 + 0.6482 64.82%
Blood Brain Barrier + 0.6356 63.56%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.7147 71.47%
OATP2B1 inhibitior - 0.8550 85.50%
OATP1B1 inhibitior + 0.8551 85.51%
OATP1B3 inhibitior + 0.8851 88.51%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6011 60.11%
BSEP inhibitior - 0.8168 81.68%
P-glycoprotein inhibitior - 0.9403 94.03%
P-glycoprotein substrate - 0.8051 80.51%
CYP3A4 substrate + 0.5575 55.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8979 89.79%
CYP3A4 inhibition - 0.9173 91.73%
CYP2C9 inhibition - 0.8788 87.88%
CYP2C19 inhibition - 0.8400 84.00%
CYP2D6 inhibition - 0.9151 91.51%
CYP1A2 inhibition - 0.8684 86.84%
CYP2C8 inhibition - 0.8363 83.63%
CYP inhibitory promiscuity - 0.9589 95.89%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.7084 70.84%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.6573 65.73%
Skin irritation - 0.6162 61.62%
Skin corrosion - 0.9531 95.31%
Ames mutagenesis - 0.8400 84.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7089 70.89%
Micronuclear - 0.9400 94.00%
Hepatotoxicity + 0.5262 52.62%
skin sensitisation - 0.8404 84.04%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity - 0.7138 71.38%
Acute Oral Toxicity (c) III 0.6912 69.12%
Estrogen receptor binding - 0.5888 58.88%
Androgen receptor binding + 0.5930 59.30%
Thyroid receptor binding - 0.5430 54.30%
Glucocorticoid receptor binding + 0.8077 80.77%
Aromatase binding - 0.6173 61.73%
PPAR gamma - 0.6335 63.35%
Honey bee toxicity - 0.8655 86.55%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9740 97.40%

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 96.17% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.62% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.51% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.75% 96.09%
CHEMBL1977 P11473 Vitamin D receptor 91.37% 99.43%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.59% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.76% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.15% 97.09%
CHEMBL1937 Q92769 Histone deacetylase 2 85.71% 94.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.44% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.48% 85.14%
CHEMBL233 P35372 Mu opioid receptor 80.09% 97.93%

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.
Achillea tuzsonii
Asplenium septentrionale
Brachylaena ramiflora
Coespeletia moritziana
Colliguaja salicifolia
Kielmeyera albopunctata
Nuxia oppositifolia
Orbivestus leopoldii
Saussurea parviflora

Cross-Links

Top
PubChem 639678
NPASS NPC273367
LOTUS LTS0080892
wikiData Q105216096