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[(1S,2S,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-2,5-diacetyloxy-3-hydroxy-7,8-dimethyl-1-[(E)-2-methylbut-2-enoxy]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate

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 4b95c37d-5a51-4002-811e-e0be40e75df7
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(1S,2S,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-2,5-diacetyloxy-3-hydroxy-7,8-dimethyl-1-[(E)-2-methylbut-2-enoxy]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
SMILES (Canonical) CC=C(C)COC1C(C(C2(CO2)C3(C1C(C(CC3OC(=O)C)C)(C)C4CC5C=COC5O4)COC(=O)C)O)OC(=O)C
SMILES (Isomeric) C/C=C(\C)/CO[C@@H]1[C@H]([C@@H]([C@]2(CO2)[C@]3([C@H]1[C@@]([C@@H](C[C@@H]3OC(=O)C)C)(C)C4C[C@H]5C=CO[C@H]5O4)COC(=O)C)O)OC(=O)C
InChI InChI=1S/C31H44O11/c1-8-16(2)13-37-24-25(41-20(6)34)27(35)31(15-39-31)30(14-38-18(4)32)23(40-19(5)33)11-17(3)29(7,26(24)30)22-12-21-9-10-36-28(21)42-22/h8-10,17,21-28,35H,11-15H2,1-7H3/b16-8+/t17-,21-,22?,23+,24-,25-,26-,27+,28+,29-,30-,31-/m1/s1
InChI Key RSIGSVUKLTUZCW-QSXUDRCFSA-N
Popularity 1 reference 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) 139.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.83
H-Bond Acceptor 11
H-Bond Donor 1
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2S,3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-2,5-diacetyloxy-3-hydroxy-7,8-dimethyl-1-[(E)-2-methylbut-2-enoxy]spiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9791 97.91%
Caco-2 - 0.7851 78.51%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.8228 82.28%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8329 83.29%
OATP1B3 inhibitior + 0.8921 89.21%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9539 95.39%
P-glycoprotein inhibitior + 0.7557 75.57%
P-glycoprotein substrate + 0.6255 62.55%
CYP3A4 substrate + 0.6982 69.82%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8643 86.43%
CYP3A4 inhibition - 0.6989 69.89%
CYP2C9 inhibition - 0.7494 74.94%
CYP2C19 inhibition - 0.8126 81.26%
CYP2D6 inhibition - 0.9534 95.34%
CYP1A2 inhibition - 0.8879 88.79%
CYP2C8 inhibition + 0.6304 63.04%
CYP inhibitory promiscuity - 0.7878 78.78%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5158 51.58%
Eye corrosion - 0.9876 98.76%
Eye irritation - 0.9049 90.49%
Skin irritation - 0.6310 63.10%
Skin corrosion - 0.9419 94.19%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6924 69.24%
Micronuclear - 0.6100 61.00%
Hepatotoxicity - 0.6500 65.00%
skin sensitisation - 0.8620 86.20%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6875 68.75%
Nephrotoxicity + 0.6172 61.72%
Acute Oral Toxicity (c) I 0.7329 73.29%
Estrogen receptor binding + 0.8591 85.91%
Androgen receptor binding + 0.6735 67.35%
Thyroid receptor binding + 0.5926 59.26%
Glucocorticoid receptor binding + 0.7300 73.00%
Aromatase binding + 0.7260 72.60%
PPAR gamma + 0.7274 72.74%
Honey bee toxicity - 0.7197 71.97%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5055 50.55%
Fish aquatic toxicity + 0.9949 99.49%

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 98.32% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.20% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.68% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.63% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 89.36% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.37% 97.09%
CHEMBL2581 P07339 Cathepsin D 85.35% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.16% 82.69%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.58% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.67% 95.56%
CHEMBL221 P23219 Cyclooxygenase-1 83.10% 90.17%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.45% 99.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.16% 100.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.15% 96.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.10% 89.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 80.40% 95.50%
CHEMBL5028 O14672 ADAM10 80.29% 97.50%

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 reptans

Cross-Links

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PubChem 100955945
LOTUS LTS0238044
wikiData Q105244673