(S)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)pentanoic acid

Details

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Internal ID 7c06a0cb-7ef1-4c5b-9806-ec12e82ef0da
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name 5-(5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl)-3-methylpentanoic acid
SMILES (Canonical) CC(CCC1C(=C)CCC2C1(CCCC2(C)C)C)CC(=O)O
SMILES (Isomeric) CC(CCC1C(=C)CCC2C1(CCCC2(C)C)C)CC(=O)O
InChI InChI=1S/C20H34O2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h14,16-17H,2,6-13H2,1,3-5H3,(H,21,22)
InChI Key NALGVVPRJHXHNM-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H34O2
Molecular Weight 306.50 g/mol
Exact Mass 306.255880323 g/mol
Topological Polar Surface Area (TPSA) 37.30 Ų
XlogP 6.20
Atomic LogP (AlogP) 5.68
H-Bond Acceptor 1
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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(-)-Eperuic acid
Eperuic acid, (-)
SCHEMBL22117111
NALGVVPRJHXHNM-UHFFFAOYSA-N
5.beta.,9.beta.H,10.alpha.-Labd-8(20)-en-15-oic acid, (13S)-(-)-
(S)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)pentanoic acid
1-Naphthalenepentanoic acid, decahydro-.beta.,5,5,8a-tetramethyl-2-methylene-, (.beta.S,1R,4aR,8aR)-
1-Naphthalenepentanoic acid, decahydro-.beta.,5,5,8a-tetramethyl-2-methylene-, [1R-[1.alpha.(S*),4a.beta.,8a.alpha.]]-

2D Structure

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2D Structure of (S)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)pentanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9949 99.49%
Caco-2 + 0.6209 62.09%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability + 0.5429 54.29%
Subcellular localzation Mitochondria 0.4627 46.27%
OATP2B1 inhibitior - 0.8588 85.88%
OATP1B1 inhibitior + 0.8818 88.18%
OATP1B3 inhibitior - 0.2449 24.49%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior - 0.6515 65.15%
P-glycoprotein inhibitior - 0.7611 76.11%
P-glycoprotein substrate - 0.8404 84.04%
CYP3A4 substrate + 0.5917 59.17%
CYP2C9 substrate - 0.5859 58.59%
CYP2D6 substrate - 0.8733 87.33%
CYP3A4 inhibition - 0.8057 80.57%
CYP2C9 inhibition - 0.8155 81.55%
CYP2C19 inhibition - 0.7059 70.59%
CYP2D6 inhibition - 0.9444 94.44%
CYP1A2 inhibition - 0.8516 85.16%
CYP2C8 inhibition - 0.8048 80.48%
CYP inhibitory promiscuity - 0.8349 83.49%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8500 85.00%
Carcinogenicity (trinary) Non-required 0.6897 68.97%
Eye corrosion - 0.9860 98.60%
Eye irritation - 0.5976 59.76%
Skin irritation + 0.5414 54.14%
Skin corrosion - 0.9680 96.80%
Ames mutagenesis - 0.7570 75.70%
Human Ether-a-go-go-Related Gene inhibition - 0.5387 53.87%
Micronuclear - 0.9200 92.00%
Hepatotoxicity - 0.5298 52.98%
skin sensitisation + 0.6928 69.28%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7170 71.70%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.6258 62.58%
Acute Oral Toxicity (c) III 0.8764 87.64%
Estrogen receptor binding + 0.5393 53.93%
Androgen receptor binding + 0.5561 55.61%
Thyroid receptor binding + 0.6394 63.94%
Glucocorticoid receptor binding + 0.6282 62.82%
Aromatase binding - 0.5644 56.44%
PPAR gamma + 0.5394 53.94%
Honey bee toxicity - 0.9120 91.20%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.67% 97.25%
CHEMBL2581 P07339 Cathepsin D 93.49% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 93.40% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.75% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.13% 94.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 90.64% 96.38%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.16% 96.09%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.74% 100.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.67% 90.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.28% 97.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 82.14% 82.69%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.72% 100.00%
CHEMBL340 P08684 Cytochrome P450 3A4 80.68% 91.19%
CHEMBL5028 O14672 ADAM10 80.57% 97.50%
CHEMBL237 P41145 Kappa opioid receptor 80.02% 98.10%

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.
Eperua falcata
Hymenaea courbaril
Moldenhawera nutans

Cross-Links

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PubChem 12309485
LOTUS LTS0009345
wikiData Q105176388