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[(1S)-2-[(1S,2R,4S,4aR,5R,8R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethyl-8-(2-methylpropanoyloxy)spiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2R)-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 6f213980-49e5-4bf2-931e-69f2b07154e5
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
IUPAC Name [(1S)-2-[(1S,2R,4S,4aR,5R,8R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethyl-8-(2-methylpropanoyloxy)spiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC(CC1(C(CC(C2(C1C(CCC23CO3)OC(=O)C(C)C)COC(=O)C)OC(=O)C)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]1[C@@H](CC[C@]23CO3)OC(=O)C(C)C)COC(=O)C)OC(=O)C)C)C)C4=CC(=O)OC4
InChI InChI=1S/C33H48O11/c1-9-19(4)30(38)44-25(23-13-27(36)39-15-23)14-31(8)20(5)12-26(42-22(7)35)33(17-40-21(6)34)28(31)24(43-29(37)18(2)3)10-11-32(33)16-41-32/h13,18-20,24-26,28H,9-12,14-17H2,1-8H3/t19-,20-,24-,25+,26+,28-,31+,32+,33-/m1/s1
InChI Key DXRWSWJHXRJGBV-YXQYNZQKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H48O11
Molecular Weight 620.70 g/mol
Exact Mass 620.31966234 g/mol
Topological Polar Surface Area (TPSA) 144.00 Ų
XlogP 4.00
Atomic LogP (AlogP) 4.09
H-Bond Acceptor 11
H-Bond Donor 0
Rotatable Bonds 11

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,8R,8aR)-4-acetyloxy-4a-(acetyloxymethyl)-1,2-dimethyl-8-(2-methylpropanoyloxy)spiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxirane]-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2R)-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 + 0.9911 99.11%
Caco-2 - 0.7666 76.66%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7815 78.15%
OATP2B1 inhibitior - 0.8623 86.23%
OATP1B1 inhibitior + 0.8519 85.19%
OATP1B3 inhibitior + 0.9565 95.65%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.5250 52.50%
BSEP inhibitior + 0.9832 98.32%
P-glycoprotein inhibitior + 0.8652 86.52%
P-glycoprotein substrate + 0.6764 67.64%
CYP3A4 substrate + 0.6987 69.87%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8993 89.93%
CYP3A4 inhibition - 0.7434 74.34%
CYP2C9 inhibition - 0.6909 69.09%
CYP2C19 inhibition - 0.6825 68.25%
CYP2D6 inhibition - 0.9081 90.81%
CYP1A2 inhibition - 0.8053 80.53%
CYP2C8 inhibition + 0.6126 61.26%
CYP inhibitory promiscuity - 0.7019 70.19%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5003 50.03%
Eye corrosion - 0.9855 98.55%
Eye irritation - 0.9039 90.39%
Skin irritation - 0.6451 64.51%
Skin corrosion - 0.9294 92.94%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7043 70.43%
Micronuclear - 0.5900 59.00%
Hepatotoxicity + 0.5625 56.25%
skin sensitisation - 0.7928 79.28%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.5991 59.91%
Acute Oral Toxicity (c) III 0.5316 53.16%
Estrogen receptor binding + 0.8425 84.25%
Androgen receptor binding + 0.7488 74.88%
Thyroid receptor binding + 0.5482 54.82%
Glucocorticoid receptor binding + 0.8121 81.21%
Aromatase binding + 0.7302 73.02%
PPAR gamma + 0.7174 71.74%
Honey bee toxicity - 0.6633 66.33%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5900 59.00%
Fish aquatic toxicity + 0.9971 99.71%

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 98.89% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.18% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.16% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.77% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.73% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.97% 97.09%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 92.32% 82.69%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.86% 85.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.39% 92.62%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 89.70% 94.80%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.92% 100.00%
CHEMBL221 P23219 Cyclooxygenase-1 88.64% 90.17%
CHEMBL3922 P50579 Methionine aminopeptidase 2 88.11% 97.28%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.96% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.71% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.39% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.17% 95.89%
CHEMBL2413 P32246 C-C chemokine receptor type 1 84.28% 89.50%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.82% 96.77%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.80% 94.33%
CHEMBL5255 O00206 Toll-like receptor 4 83.62% 92.50%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 83.16% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.04% 99.23%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.01% 95.89%

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 macrosperma

Cross-Links

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PubChem 162878877
LOTUS LTS0276046
wikiData Q104991170