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methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-[(2S)-2-hydroxy-5-oxo-2H-furan-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 da278815-2b26-4bf1-93bb-eca0d0c12487
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)-2-hydroxy-5-oxo-2H-furan-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=CC(=O)OC4O)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)C4=CC(=O)O[C@@H]4O)C)C(=O)OC
InChI InChI=1S/C23H28O10/c1-10(24)31-14-8-13(20(28)30-4)22(2)6-5-12-21(29)32-15(11-7-16(25)33-19(11)27)9-23(12,3)18(22)17(14)26/h7,12-15,18-19,27H,5-6,8-9H2,1-4H3/t12-,13-,14-,15-,18-,19-,22-,23-/m0/s1
InChI Key ODUBJIUOBWNPLK-COGSXQLLSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C23H28O10
Molecular Weight 464.50 g/mol
Exact Mass 464.16824709 g/mol
Topological Polar Surface Area (TPSA) 143.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.84
H-Bond Acceptor 10
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-[(2S)-2-hydroxy-5-oxo-2H-furan-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 + 0.9713 97.13%
Caco-2 - 0.6875 68.75%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.8047 80.47%
OATP2B1 inhibitior - 0.8615 86.15%
OATP1B1 inhibitior + 0.7843 78.43%
OATP1B3 inhibitior + 0.8452 84.52%
MATE1 inhibitior - 0.6200 62.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.5947 59.47%
P-glycoprotein inhibitior + 0.6935 69.35%
P-glycoprotein substrate + 0.6051 60.51%
CYP3A4 substrate + 0.7188 71.88%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8946 89.46%
CYP3A4 inhibition - 0.7657 76.57%
CYP2C9 inhibition - 0.9259 92.59%
CYP2C19 inhibition - 0.9240 92.40%
CYP2D6 inhibition - 0.9516 95.16%
CYP1A2 inhibition - 0.7432 74.32%
CYP2C8 inhibition - 0.6936 69.36%
CYP inhibitory promiscuity - 0.8973 89.73%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4540 45.40%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.9118 91.18%
Skin irritation - 0.5234 52.34%
Skin corrosion - 0.9057 90.57%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3656 36.56%
Micronuclear - 0.6800 68.00%
Hepatotoxicity + 0.5375 53.75%
skin sensitisation - 0.8835 88.35%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.8266 82.66%
Acute Oral Toxicity (c) I 0.7051 70.51%
Estrogen receptor binding + 0.8635 86.35%
Androgen receptor binding + 0.6955 69.55%
Thyroid receptor binding + 0.6023 60.23%
Glucocorticoid receptor binding + 0.7899 78.99%
Aromatase binding + 0.5501 55.01%
PPAR gamma + 0.6319 63.19%
Honey bee toxicity - 0.6878 68.78%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9780 97.80%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.60% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.25% 94.45%
CHEMBL237 P41145 Kappa opioid receptor 96.48% 98.10%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.23% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.20% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.44% 85.14%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 86.72% 94.33%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.56% 82.69%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 86.22% 96.38%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.97% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.17% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.12% 100.00%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 85.09% 85.30%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.91% 92.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.53% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 83.91% 91.19%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.64% 99.23%
CHEMBL3524 P56524 Histone deacetylase 4 83.48% 92.97%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.20% 97.14%

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 162960097
LOTUS LTS0146201
wikiData Q105190040