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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] (2S)-2-methylbutanoate

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 1fa61d65-7428-48d2-b95c-a694806d6a0f
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] (2S)-2-methylbutanoate
SMILES (Canonical) CCC(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) CC[C@H](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/C31H44O11/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/h12,17-18,23-25,27H,8-11,13-16H2,1-7H3/t17-,18+,23+,24-,25-,27+,29-,30-,31+/m0/s1
InChI Key UNNFPBMLPYVEEM-JKZOSZDYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C31H44O11
Molecular Weight 592.70 g/mol
Exact Mass 592.28836222 g/mol
Topological Polar Surface Area (TPSA) 144.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.46
H-Bond Acceptor 11
H-Bond Donor 0
Rotatable Bonds 10

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] (2S)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9910 99.10%
Caco-2 - 0.7410 74.10%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.7421 74.21%
OATP2B1 inhibitior - 0.7262 72.62%
OATP1B1 inhibitior + 0.8556 85.56%
OATP1B3 inhibitior + 0.9687 96.87%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.5000 50.00%
BSEP inhibitior + 0.9867 98.67%
P-glycoprotein inhibitior + 0.8577 85.77%
P-glycoprotein substrate + 0.6796 67.96%
CYP3A4 substrate + 0.6942 69.42%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8993 89.93%
CYP3A4 inhibition - 0.7113 71.13%
CYP2C9 inhibition - 0.7934 79.34%
CYP2C19 inhibition - 0.7359 73.59%
CYP2D6 inhibition - 0.9202 92.02%
CYP1A2 inhibition - 0.7900 79.00%
CYP2C8 inhibition + 0.5887 58.87%
CYP inhibitory promiscuity - 0.6954 69.54%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4988 49.88%
Eye corrosion - 0.9860 98.60%
Eye irritation - 0.8947 89.47%
Skin irritation - 0.5929 59.29%
Skin corrosion - 0.9271 92.71%
Ames mutagenesis - 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7060 70.60%
Micronuclear - 0.6000 60.00%
Hepatotoxicity + 0.6149 61.49%
skin sensitisation - 0.8423 84.23%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.5596 55.96%
Acute Oral Toxicity (c) III 0.5143 51.43%
Estrogen receptor binding + 0.8692 86.92%
Androgen receptor binding + 0.7396 73.96%
Thyroid receptor binding + 0.5317 53.17%
Glucocorticoid receptor binding + 0.8141 81.41%
Aromatase binding + 0.7319 73.19%
PPAR gamma + 0.6999 69.99%
Honey bee toxicity - 0.7153 71.53%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9961 99.61%

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 98.70% 96.09%
CHEMBL2581 P07339 Cathepsin D 98.06% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.71% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.22% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.17% 91.11%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 93.37% 82.69%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.84% 97.09%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 90.16% 94.80%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.36% 100.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 88.28% 97.28%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.09% 85.14%
CHEMBL221 P23219 Cyclooxygenase-1 87.76% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.42% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.13% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.02% 86.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.68% 92.62%
CHEMBL5255 O00206 Toll-like receptor 4 84.01% 92.50%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.91% 89.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.55% 95.89%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.47% 96.77%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.23% 96.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.15% 99.23%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 81.10% 94.23%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.70% 100.00%
CHEMBL340 P08684 Cytochrome P450 3A4 80.06% 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
Ajuga nipponensis

Cross-Links

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PubChem 14314156
LOTUS LTS0270178
wikiData Q105276060