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[(1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-1,2,3,4,5,6,8,8a-octahydronaphthalen-1-yl] (E)-3-methylpent-2-enoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 821df54c-dc2c-41e8-a4d5-d78a540db759
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
IUPAC Name [(1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-1,2,3,4,5,6,8,8a-octahydronaphthalen-1-yl] (E)-3-methylpent-2-enoate
SMILES (Canonical) CCC(=CC(=O)OC1C2CC(=O)CC(C2(CC(C1O)C3(CO3)C)C)C)C
SMILES (Isomeric) CC/C(=C/C(=O)O[C@H]1[C@H]2CC(=O)C[C@@H]([C@]2(C[C@@H]([C@H]1O)[C@@]3(CO3)C)C)C)/C
InChI InChI=1S/C21H32O5/c1-6-12(2)7-17(23)26-19-15-9-14(22)8-13(3)20(15,4)10-16(18(19)24)21(5)11-25-21/h7,13,15-16,18-19,24H,6,8-11H2,1-5H3/b12-7+/t13-,15+,16-,18+,19-,20+,21-/m0/s1
InChI Key WQPOYRBZCATNLX-LKERXJEMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H32O5
Molecular Weight 364.50 g/mol
Exact Mass 364.22497412 g/mol
Topological Polar Surface Area (TPSA) 76.10 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.05
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,3S,4aR,5S,8aS)-2-hydroxy-4a,5-dimethyl-3-[(2R)-2-methyloxiran-2-yl]-7-oxo-1,2,3,4,5,6,8,8a-octahydronaphthalen-1-yl] (E)-3-methylpent-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9895 98.95%
Caco-2 + 0.6528 65.28%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.7653 76.53%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8600 86.00%
OATP1B3 inhibitior + 0.9132 91.32%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9114 91.14%
BSEP inhibitior + 0.8613 86.13%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate - 0.5644 56.44%
CYP3A4 substrate + 0.6662 66.62%
CYP2C9 substrate - 0.8007 80.07%
CYP2D6 substrate - 0.8953 89.53%
CYP3A4 inhibition - 0.6604 66.04%
CYP2C9 inhibition - 0.7201 72.01%
CYP2C19 inhibition - 0.7538 75.38%
CYP2D6 inhibition - 0.9481 94.81%
CYP1A2 inhibition - 0.8080 80.80%
CYP2C8 inhibition - 0.5816 58.16%
CYP inhibitory promiscuity - 0.7161 71.61%
UGT catelyzed + 1.0000 100.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6321 63.21%
Eye corrosion - 0.9884 98.84%
Eye irritation - 0.9612 96.12%
Skin irritation - 0.6195 61.95%
Skin corrosion - 0.9541 95.41%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5805 58.05%
Micronuclear - 0.5600 56.00%
Hepatotoxicity + 0.5500 55.00%
skin sensitisation - 0.8423 84.23%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.8836 88.36%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.5554 55.54%
Acute Oral Toxicity (c) III 0.4287 42.87%
Estrogen receptor binding + 0.8020 80.20%
Androgen receptor binding + 0.5299 52.99%
Thyroid receptor binding + 0.6291 62.91%
Glucocorticoid receptor binding + 0.8520 85.20%
Aromatase binding + 0.5948 59.48%
PPAR gamma - 0.5000 50.00%
Honey bee toxicity - 0.6391 63.91%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9968 99.68%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.53% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.04% 94.45%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 93.90% 89.34%
CHEMBL2581 P07339 Cathepsin D 90.47% 98.95%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 89.08% 96.77%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.75% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.10% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.16% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.40% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.20% 100.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 84.30% 89.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.87% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 83.37% 94.73%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 82.79% 94.80%
CHEMBL4208 P20618 Proteasome component C5 81.32% 90.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 80.76% 91.07%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.58% 91.24%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.45% 99.17%
CHEMBL5255 O00206 Toll-like receptor 4 80.45% 92.50%

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.
Euryops algoensis

Cross-Links

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PubChem 162842670
LOTUS LTS0154147
wikiData Q105310906