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methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate

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 7f21641b-727b-4387-80a3-cc51a1882019
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
SMILES (Canonical) CC(=O)OC1CC(C2(CCC3C(=O)OC(CC3(C2C1=O)C)C4(C(C(OC4OC)OC)O)O)C)C(=O)OC
SMILES (Isomeric) CC(=O)O[C@H]1C[C@H]([C@@]2(CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]2C1=O)C)[C@]4([C@@H]([C@@H](O[C@@H]4OC)OC)O)O)C)C(=O)OC
InChI InChI=1S/C25H36O12/c1-11(26)35-14-9-13(19(29)32-4)23(2)8-7-12-20(30)36-15(10-24(12,3)17(23)16(14)27)25(31)18(28)21(33-5)37-22(25)34-6/h12-15,17-18,21-22,28,31H,7-10H2,1-6H3/t12-,13-,14-,15-,17-,18+,21+,22-,23-,24-,25+/m0/s1
InChI Key QEBAQEQKIKWXTO-XBKODSCSSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H36O12
Molecular Weight 528.50 g/mol
Exact Mass 528.22067658 g/mol
Topological Polar Surface Area (TPSA) 164.00 Ų
XlogP 0.20
Atomic LogP (AlogP) 0.10
H-Bond Acceptor 12
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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SCHEMBL13312918
BDBM50295161

2D Structure

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2D Structure of methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-dimethoxyoxolan-3-yl]-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8614 86.14%
Caco-2 - 0.7024 70.24%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.8291 82.91%
OATP2B1 inhibitior - 0.8603 86.03%
OATP1B1 inhibitior + 0.7873 78.73%
OATP1B3 inhibitior + 0.8593 85.93%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8321 83.21%
BSEP inhibitior + 0.7069 70.69%
P-glycoprotein inhibitior + 0.6806 68.06%
P-glycoprotein substrate + 0.6485 64.85%
CYP3A4 substrate + 0.7298 72.98%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8962 89.62%
CYP3A4 inhibition - 0.8757 87.57%
CYP2C9 inhibition - 0.8942 89.42%
CYP2C19 inhibition - 0.8822 88.22%
CYP2D6 inhibition - 0.9595 95.95%
CYP1A2 inhibition - 0.8336 83.36%
CYP2C8 inhibition - 0.6567 65.67%
CYP inhibitory promiscuity - 0.9755 97.55%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5651 56.51%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9184 91.84%
Skin irritation - 0.6338 63.38%
Skin corrosion - 0.8857 88.57%
Ames mutagenesis - 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5377 53.77%
Micronuclear - 0.8100 81.00%
Hepatotoxicity - 0.5125 51.25%
skin sensitisation - 0.9181 91.81%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.7704 77.04%
Acute Oral Toxicity (c) I 0.5579 55.79%
Estrogen receptor binding + 0.7829 78.29%
Androgen receptor binding + 0.7039 70.39%
Thyroid receptor binding - 0.5055 50.55%
Glucocorticoid receptor binding + 0.6765 67.65%
Aromatase binding + 0.6772 67.72%
PPAR gamma + 0.6250 62.50%
Honey bee toxicity - 0.6855 68.55%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9489 94.89%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL237 P41145 Kappa opioid receptor 390 nM
 Ki
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.35% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.02% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.06% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.15% 85.14%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 89.90% 96.38%
CHEMBL5255 O00206 Toll-like receptor 4 87.92% 92.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.71% 89.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 87.42% 94.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.05% 92.62%
CHEMBL3922 P50579 Methionine aminopeptidase 2 86.65% 97.28%
CHEMBL340 P08684 Cytochrome P450 3A4 84.89% 91.19%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.68% 100.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 83.51% 91.24%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 83.37% 93.04%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.22% 97.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.18% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.14% 99.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.04% 91.07%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.81% 82.69%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.08% 89.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.80% 95.89%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 80.29% 95.71%

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.
Salvia divinorum

Cross-Links

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PubChem 11214688
LOTUS LTS0240602
wikiData Q105219098