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[(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-8-[(2S)-2-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (Z)-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 e67d1f5b-d5dc-4ea8-a15e-a5cab4d021ca
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
IUPAC Name [(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-8-[(2S)-2-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)CC(C4=CC(=O)OC4)OC(=O)C)COC(=O)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1CC[C@]2(CO2)[C@]3([C@H]1[C@@]([C@@H](C[C@@H]3OC(=O)C)C)(C)C[C@@H](C4=CC(=O)OC4)OC(=O)C)COC(=O)C
InChI InChI=1S/C31H42O11/c1-8-17(2)28(36)42-23-9-10-30(15-39-30)31(16-38-19(4)32)25(41-21(6)34)11-18(3)29(7,27(23)31)13-24(40-20(5)33)22-12-26(35)37-14-22/h8,12,18,23-25,27H,9-11,13-16H2,1-7H3/b17-8-/t18-,23-,24+,25+,27-,29+,30+,31-/m1/s1
InChI Key IAAHUGSOWYSQSN-BVGCTOFVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H42O11
Molecular Weight 590.70 g/mol
Exact Mass 590.27271215 g/mol
Topological Polar Surface Area (TPSA) 144.00 Ų
XlogP 2.80
Atomic LogP (AlogP) 3.38
H-Bond Acceptor 11
H-Bond Donor 0
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,4R,4aR,5S,7R,8S,8aR)-5-acetyloxy-4a-(acetyloxymethyl)-8-[(2S)-2-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-1-yl] (Z)-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 + 0.9854 98.54%
Caco-2 - 0.7351 73.51%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7884 78.84%
OATP2B1 inhibitior - 0.7242 72.42%
OATP1B1 inhibitior + 0.8460 84.60%
OATP1B3 inhibitior + 0.9556 95.56%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.5000 50.00%
BSEP inhibitior + 0.9916 99.16%
P-glycoprotein inhibitior + 0.8825 88.25%
P-glycoprotein substrate + 0.6765 67.65%
CYP3A4 substrate + 0.7004 70.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8993 89.93%
CYP3A4 inhibition - 0.8038 80.38%
CYP2C9 inhibition - 0.8158 81.58%
CYP2C19 inhibition - 0.8119 81.19%
CYP2D6 inhibition - 0.9305 93.05%
CYP1A2 inhibition - 0.7755 77.55%
CYP2C8 inhibition + 0.5902 59.02%
CYP inhibitory promiscuity - 0.7950 79.50%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5049 50.49%
Eye corrosion - 0.9857 98.57%
Eye irritation - 0.8935 89.35%
Skin irritation - 0.6041 60.41%
Skin corrosion - 0.9244 92.44%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7708 77.08%
Micronuclear - 0.6200 62.00%
Hepatotoxicity + 0.5399 53.99%
skin sensitisation - 0.8237 82.37%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.7093 70.93%
Acute Oral Toxicity (c) III 0.4086 40.86%
Estrogen receptor binding + 0.8841 88.41%
Androgen receptor binding + 0.7231 72.31%
Thyroid receptor binding + 0.5722 57.22%
Glucocorticoid receptor binding + 0.8316 83.16%
Aromatase binding + 0.7485 74.85%
PPAR gamma + 0.7049 70.49%
Honey bee toxicity - 0.6467 64.67%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.6400 64.00%
Fish aquatic toxicity + 0.9942 99.42%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.99% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.66% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.58% 94.45%
CHEMBL2581 P07339 Cathepsin D 96.31% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 94.50% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.41% 97.25%
CHEMBL221 P23219 Cyclooxygenase-1 94.33% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.36% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.99% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.77% 89.00%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 90.40% 94.80%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.09% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.55% 100.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 85.72% 97.28%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.45% 92.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.98% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.95% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.11% 96.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.09% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 82.89% 91.19%

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 44566350
LOTUS LTS0228739
wikiData Q105297394