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[(1S,2S,3R,4aR,5R,6S,8S,8aR)-5-[(5S)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] propanoate

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 00621691-622e-4c7f-a100-800f87b845c7
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(1S,2S,3R,4aR,5R,6S,8S,8aR)-5-[(5S)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] propanoate
SMILES (Canonical) CCC(=O)OC1C(CC2C(C(CC(C2(C13CO3)COC(=O)C)OC(=O)C)C)(C)C4CC5C=COC5O4)O
SMILES (Isomeric) CCC(=O)O[C@H]1[C@@H](C[C@@H]2[C@]([C@H](C[C@@H]([C@]2([C@]13CO3)COC(=O)C)OC(=O)C)C)(C)[C@@H]4CC5C=COC5O4)O
InChI InChI=1S/C27H38O10/c1-6-22(31)37-23-18(30)11-19-25(5,20-10-17-7-8-32-24(17)36-20)14(2)9-21(35-16(4)29)26(19,12-33-15(3)28)27(23)13-34-27/h7-8,14,17-21,23-24,30H,6,9-13H2,1-5H3/t14-,17?,18+,19+,20-,21-,23-,24?,25+,26-,27-/m0/s1
InChI Key NZOCASSHWUPPDP-HNBMZQHKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H38O10
Molecular Weight 522.60 g/mol
Exact Mass 522.24649740 g/mol
Topological Polar Surface Area (TPSA) 130.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.26
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2S,3R,4aR,5R,6S,8S,8aR)-5-[(5S)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] propanoate

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 - 0.7396 73.96%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6991 69.91%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8425 84.25%
OATP1B3 inhibitior + 0.8863 88.63%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9474 94.74%
P-glycoprotein inhibitior + 0.6791 67.91%
P-glycoprotein substrate + 0.6203 62.03%
CYP3A4 substrate + 0.6954 69.54%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8590 85.90%
CYP3A4 inhibition + 0.5254 52.54%
CYP2C9 inhibition - 0.7881 78.81%
CYP2C19 inhibition - 0.7968 79.68%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.9200 92.00%
CYP2C8 inhibition + 0.6488 64.88%
CYP inhibitory promiscuity - 0.8247 82.47%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.4986 49.86%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9217 92.17%
Skin irritation - 0.5890 58.90%
Skin corrosion - 0.9380 93.80%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4789 47.89%
Micronuclear - 0.5800 58.00%
Hepatotoxicity - 0.7250 72.50%
skin sensitisation - 0.8624 86.24%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.5797 57.97%
Acute Oral Toxicity (c) I 0.5975 59.75%
Estrogen receptor binding + 0.8876 88.76%
Androgen receptor binding + 0.6793 67.93%
Thyroid receptor binding + 0.5249 52.49%
Glucocorticoid receptor binding + 0.7434 74.34%
Aromatase binding + 0.7197 71.97%
PPAR gamma + 0.7051 70.51%
Honey bee toxicity - 0.7160 71.60%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5287 52.87%
Fish aquatic toxicity + 0.9913 99.13%

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 98.76% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.24% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.82% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.38% 91.11%
CHEMBL340 P08684 Cytochrome P450 3A4 91.83% 91.19%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 91.08% 97.21%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.02% 97.09%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 89.32% 96.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 88.37% 82.69%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.74% 86.33%
CHEMBL2581 P07339 Cathepsin D 86.61% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.14% 85.14%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 85.77% 98.75%
CHEMBL5255 O00206 Toll-like receptor 4 85.46% 92.50%
CHEMBL2996 Q05655 Protein kinase C delta 85.22% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 85.15% 90.17%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.93% 94.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.73% 89.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.34% 92.94%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.99% 89.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.68% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.11% 100.00%

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 lupulina

Cross-Links

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PubChem 101041507
LOTUS LTS0233677
wikiData Q105188342