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[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4a-(acetyloxymethyl)-4-hydroxy-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (E)-2-methylbut-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 0a50a288-be52-4116-9494-2f454c312be9
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4a-(acetyloxymethyl)-4-hydroxy-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC(CC1(C(CC(C2(C1CCCC23CO3)COC(=O)C)O)C)C)C4=CC(=O)OC4
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H](C[C@]1([C@@H](C[C@@H]([C@@]2([C@@H]1CCC[C@]23CO3)COC(=O)C)O)C)C)C4=CC(=O)OC4
InChI InChI=1S/C27H38O8/c1-6-16(2)24(31)35-20(19-11-23(30)32-13-19)12-25(5)17(3)10-22(29)27(15-33-18(4)28)21(25)8-7-9-26(27)14-34-26/h6,11,17,20-22,29H,7-10,12-15H2,1-5H3/b16-6+/t17-,20+,21-,22+,25+,26+,27+/m1/s1
InChI Key SCADEYICDOGWSG-YUMWEXGASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H38O8
Molecular Weight 490.60 g/mol
Exact Mass 490.25666817 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 3.26
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4a-(acetyloxymethyl)-4-hydroxy-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (E)-2-methylbut-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 + 0.9809 98.09%
Caco-2 - 0.6310 63.10%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8184 81.84%
OATP2B1 inhibitior - 0.8607 86.07%
OATP1B1 inhibitior + 0.8489 84.89%
OATP1B3 inhibitior + 0.9441 94.41%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5771 57.71%
BSEP inhibitior + 0.9882 98.82%
P-glycoprotein inhibitior + 0.7984 79.84%
P-glycoprotein substrate + 0.6337 63.37%
CYP3A4 substrate + 0.6874 68.74%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8932 89.32%
CYP3A4 inhibition - 0.6678 66.78%
CYP2C9 inhibition - 0.7170 71.70%
CYP2C19 inhibition - 0.8449 84.49%
CYP2D6 inhibition - 0.9413 94.13%
CYP1A2 inhibition - 0.8560 85.60%
CYP2C8 inhibition + 0.4921 49.21%
CYP inhibitory promiscuity - 0.9025 90.25%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4941 49.41%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9301 93.01%
Skin irritation - 0.5168 51.68%
Skin corrosion - 0.9346 93.46%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7641 76.41%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.5076 50.76%
skin sensitisation - 0.8820 88.20%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.4711 47.11%
Acute Oral Toxicity (c) I 0.5424 54.24%
Estrogen receptor binding + 0.8794 87.94%
Androgen receptor binding + 0.7131 71.31%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.8589 85.89%
Aromatase binding + 0.8150 81.50%
PPAR gamma + 0.6392 63.92%
Honey bee toxicity - 0.6689 66.89%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9896 98.96%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.15% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.28% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.19% 96.09%
CHEMBL2581 P07339 Cathepsin D 95.90% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 95.80% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.24% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.32% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.09% 89.00%
CHEMBL221 P23219 Cyclooxygenase-1 91.64% 90.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.52% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.20% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.37% 95.89%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 87.09% 94.80%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.19% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.12% 96.77%
CHEMBL1937 Q92769 Histone deacetylase 2 85.08% 94.75%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.72% 92.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.65% 99.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.44% 91.07%
CHEMBL340 P08684 Cytochrome P450 3A4 81.34% 91.19%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.06% 95.71%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.92% 96.00%

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.
Ajuga decumbens

Cross-Links

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PubChem 24882073
LOTUS LTS0063262
wikiData Q105249827