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[(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4a-(acetyloxymethyl)-4-hydroxy-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (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 61db5fc8-6902-43fe-befd-99138c3a0912
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(1S)-2-[(1S,2R,4S,4aR,5R,8aR)-4a-(acetyloxymethyl)-4-hydroxy-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC(CC1(C(CC(C2(C1CCCC23CO3)COC(=O)C)O)C)C)C4=CC(=O)OC4
SMILES (Isomeric) CC[C@H](C)C(=O)O[C@@H](C[C@]1([C@@H](C[C@@H]([C@@]2([C@@H]1CCC[C@]23CO3)COC(=O)C)O)C)C)C4=CC(=O)OC4
InChI InChI=1S/C27H40O8/c1-6-16(2)24(31)35-20(19-11-23(30)32-13-19)12-25(5)17(3)10-22(29)27(15-33-18(4)28)21(25)8-7-9-26(27)14-34-26/h11,16-17,20-22,29H,6-10,12-15H2,1-5H3/t16-,17+,20-,21+,22-,25-,26-,27-/m0/s1
InChI Key DLWHBMFPGCORJS-JFTREPHWSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H40O8
Molecular Weight 492.60 g/mol
Exact Mass 492.27231823 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.34
H-Bond Acceptor 8
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)-2-[(1S,2R,4S,4aR,5R,8aR)-4a-(acetyloxymethyl)-4-hydroxy-1,2-dimethylspiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (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 + 0.9889 98.89%
Caco-2 - 0.6097 60.97%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7781 77.81%
OATP2B1 inhibitior - 0.8639 86.39%
OATP1B1 inhibitior + 0.8495 84.95%
OATP1B3 inhibitior + 0.9522 95.22%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.9774 97.74%
P-glycoprotein inhibitior + 0.7538 75.38%
P-glycoprotein substrate + 0.6345 63.45%
CYP3A4 substrate + 0.6836 68.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8932 89.32%
CYP3A4 inhibition + 0.5109 51.09%
CYP2C9 inhibition - 0.6945 69.45%
CYP2C19 inhibition - 0.8094 80.94%
CYP2D6 inhibition - 0.9304 93.04%
CYP1A2 inhibition - 0.8708 87.08%
CYP2C8 inhibition + 0.4503 45.03%
CYP inhibitory promiscuity - 0.8394 83.94%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4903 49.03%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9222 92.22%
Skin irritation + 0.5121 51.21%
Skin corrosion - 0.9333 93.33%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7047 70.47%
Micronuclear - 0.6700 67.00%
Hepatotoxicity + 0.5024 50.24%
skin sensitisation - 0.8899 88.99%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.6573 65.73%
Acute Oral Toxicity (c) III 0.3987 39.87%
Estrogen receptor binding + 0.8755 87.55%
Androgen receptor binding + 0.7402 74.02%
Thyroid receptor binding - 0.5201 52.01%
Glucocorticoid receptor binding + 0.8609 86.09%
Aromatase binding + 0.8080 80.80%
PPAR gamma + 0.6396 63.96%
Honey bee toxicity - 0.6971 69.71%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9930 99.30%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 98.19% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.82% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.79% 96.09%
CHEMBL2581 P07339 Cathepsin D 97.62% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.64% 91.11%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 94.70% 82.69%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 92.49% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.09% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.08% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 90.77% 96.77%
CHEMBL1994 P08235 Mineralocorticoid receptor 90.62% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.47% 95.89%
CHEMBL226 P30542 Adenosine A1 receptor 85.87% 95.93%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.80% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.59% 86.33%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 83.98% 94.80%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.73% 89.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.66% 94.33%
CHEMBL221 P23219 Cyclooxygenase-1 83.42% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.39% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.19% 99.23%
CHEMBL1937 Q92769 Histone deacetylase 2 83.02% 94.75%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 82.91% 95.71%
CHEMBL5255 O00206 Toll-like receptor 4 82.57% 92.50%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.30% 100.00%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 81.16% 98.75%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.08% 90.24%
CHEMBL5028 O14672 ADAM10 80.06% 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 ciliata

Cross-Links

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PubChem 14356985
LOTUS LTS0091333
wikiData Q104984788