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[5-acetyloxy-4a-(hydroxymethyl)-8-[2-hydroxy-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] 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 084a6404-d04e-474c-9765-83357addc4af
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [5-acetyloxy-4a-(hydroxymethyl)-8-[2-hydroxy-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] 2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)CC(C4=CC(=O)OC4)O)CO
SMILES (Isomeric) CCC(C)C(=O)OC1CCC2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)CC(C4=CC(=O)OC4)O)CO
InChI InChI=1S/C27H40O9/c1-6-15(2)24(32)36-20-7-8-26(14-34-26)27(13-28)21(35-17(4)29)9-16(3)25(5,23(20)27)11-19(30)18-10-22(31)33-12-18/h10,15-16,19-21,23,28,30H,6-9,11-14H2,1-5H3
InChI Key WOINILMQIFGCGI-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H40O9
Molecular Weight 508.60 g/mol
Exact Mass 508.26723285 g/mol
Topological Polar Surface Area (TPSA) 132.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.31
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [5-acetyloxy-4a-(hydroxymethyl)-8-[2-hydroxy-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] 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 + 0.9811 98.11%
Caco-2 - 0.6568 65.68%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7644 76.44%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8537 85.37%
OATP1B3 inhibitior + 0.9499 94.99%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.9540 95.40%
P-glycoprotein inhibitior + 0.6365 63.65%
P-glycoprotein substrate + 0.6316 63.16%
CYP3A4 substrate + 0.6931 69.31%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8929 89.29%
CYP3A4 inhibition + 0.7274 72.74%
CYP2C9 inhibition - 0.7618 76.18%
CYP2C19 inhibition - 0.8706 87.06%
CYP2D6 inhibition - 0.9271 92.71%
CYP1A2 inhibition - 0.8611 86.11%
CYP2C8 inhibition + 0.5665 56.65%
CYP inhibitory promiscuity - 0.8186 81.86%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Danger 0.4346 43.46%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9464 94.64%
Skin irritation + 0.5173 51.73%
Skin corrosion - 0.9380 93.80%
Ames mutagenesis - 0.5970 59.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4286 42.86%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.5274 52.74%
skin sensitisation - 0.9061 90.61%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.5978 59.78%
Acute Oral Toxicity (c) III 0.4118 41.18%
Estrogen receptor binding + 0.8715 87.15%
Androgen receptor binding + 0.7419 74.19%
Thyroid receptor binding - 0.5408 54.08%
Glucocorticoid receptor binding + 0.8000 80.00%
Aromatase binding + 0.7669 76.69%
PPAR gamma + 0.5899 58.99%
Honey bee toxicity - 0.7194 71.94%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9878 98.78%

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 99.07% 96.09%
CHEMBL2581 P07339 Cathepsin D 98.23% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.17% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.83% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.78% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.58% 85.14%
CHEMBL221 P23219 Cyclooxygenase-1 93.50% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.32% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.95% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.42% 89.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 88.99% 89.50%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.04% 82.69%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 85.21% 100.00%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 85.09% 94.80%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.81% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.65% 92.62%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 82.85% 82.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.84% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.94% 95.56%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.93% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.31% 92.50%
CHEMBL5555 O00767 Acyl-CoA desaturase 80.61% 97.50%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 80.53% 94.23%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.44% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 80.14% 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 ciliata

Cross-Links

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PubChem 14356971
LOTUS LTS0038851
wikiData Q105309518