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(1S,4R,7S,8aR)-4-{[(2E,4S)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

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 4ae90346-602b-4ebd-ae39-b298f1af225a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
IUPAC Name (1S,4R,7S,8aR)-4-[(E,4S)-2,4-dimethyloct-2-enoyl]oxy-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylic acid
SMILES (Canonical) CCCCC(C)C=C(C)C(=O)OC1CCC(C2(C1=CC(=O)C(C2)C(=C)C=O)C)C(=O)O
SMILES (Isomeric) CCCC[C@H](C)/C=C(\C)/C(=O)O[C@@H]1CC[C@@H]([C@@]2(C1=CC(=O)[C@@H](C2)C(=C)C=O)C)C(=O)O
InChI InChI=1S/C25H34O6/c1-6-7-8-15(2)11-16(3)24(30)31-22-10-9-19(23(28)29)25(5)13-18(17(4)14-26)21(27)12-20(22)25/h11-12,14-15,18-19,22H,4,6-10,13H2,1-3,5H3,(H,28,29)/b16-11+/t15-,18-,19+,22+,25+/m0/s1
InChI Key UIXJDFDDMXCJCT-DVRXSGNOSA-N
Popularity 6 references in papers

Physical and Chemical Properties

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Molecular Formula C25H34O6
Molecular Weight 430.50 g/mol
Exact Mass 430.23553880 g/mol
Topological Polar Surface Area (TPSA) 97.70 Ų
XlogP 4.20
Atomic LogP (AlogP) 4.44
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 9

Synonyms

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(1S,4R,7S,8aR)-4-{[(2E,4S)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid
CHEBI:66081
Q27134594

2D Structure

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2D Structure of (1S,4R,7S,8aR)-4-{[(2E,4S)-2,4-dimethyloct-2-enoyl]oxy}-8a-methyl-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9941 99.41%
Caco-2 - 0.6911 69.11%
Blood Brain Barrier + 0.8750 87.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.8150 81.50%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8116 81.16%
OATP1B3 inhibitior + 0.7878 78.78%
MATE1 inhibitior - 0.5200 52.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9134 91.34%
P-glycoprotein inhibitior + 0.6670 66.70%
P-glycoprotein substrate + 0.5378 53.78%
CYP3A4 substrate + 0.6816 68.16%
CYP2C9 substrate - 0.8046 80.46%
CYP2D6 substrate - 0.9081 90.81%
CYP3A4 inhibition + 0.5471 54.71%
CYP2C9 inhibition - 0.8619 86.19%
CYP2C19 inhibition - 0.8152 81.52%
CYP2D6 inhibition - 0.9227 92.27%
CYP1A2 inhibition - 0.8322 83.22%
CYP2C8 inhibition + 0.4773 47.73%
CYP inhibitory promiscuity - 0.8246 82.46%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9743 97.43%
Carcinogenicity (trinary) Non-required 0.6760 67.60%
Eye corrosion - 0.9925 99.25%
Eye irritation - 0.9401 94.01%
Skin irritation + 0.5900 59.00%
Skin corrosion - 0.9594 95.94%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4175 41.75%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5524 55.24%
skin sensitisation - 0.7473 74.73%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.5395 53.95%
Acute Oral Toxicity (c) III 0.7508 75.08%
Estrogen receptor binding + 0.7197 71.97%
Androgen receptor binding + 0.6309 63.09%
Thyroid receptor binding - 0.5657 56.57%
Glucocorticoid receptor binding + 0.8021 80.21%
Aromatase binding + 0.5446 54.46%
PPAR gamma + 0.6143 61.43%
Honey bee toxicity - 0.8286 82.86%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6100 61.00%
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
CHEMBL2581 P07339 Cathepsin D 98.57% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.94% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.88% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.90% 96.09%
CHEMBL3359 P21462 Formyl peptide receptor 1 93.07% 93.56%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 91.98% 93.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.72% 99.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.58% 97.25%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.20% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 90.03% 91.19%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 88.25% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 86.94% 90.17%
CHEMBL4227 P25090 Lipoxin A4 receptor 86.20% 100.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.80% 82.69%
CHEMBL2001 Q9H244 Purinergic receptor P2Y12 84.73% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.27% 95.89%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.13% 95.50%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 82.42% 96.47%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.09% 97.09%

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.
There are no matching plants.

Cross-Links

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PubChem 44550889
LOTUS LTS0242371
wikiData Q27134594