2-[(2'S,3R,4S,4aS,5S,7S,8R,8aS)-5-acetyloxy-4-(acetyloxymethyl)-3-hydroxy-2',4,7,8a-tetramethyl-6-oxospiro[1,2,3,4a,5,7-hexahydronaphthalene-8,5'-oxolane]-2'-yl]ethyl acetate

Details

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Internal ID 75346321-711b-4fca-8de5-76d99a508f59
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name 2-[(2'S,3R,4S,4aS,5S,7S,8R,8aS)-5-acetyloxy-4-(acetyloxymethyl)-3-hydroxy-2',4,7,8a-tetramethyl-6-oxospiro[1,2,3,4a,5,7-hexahydronaphthalene-8,5'-oxolane]-2'-yl]ethyl acetate
SMILES (Canonical) CC1C(=O)C(C2C(C13CCC(O3)(C)CCOC(=O)C)(CCC(C2(C)COC(=O)C)O)C)OC(=O)C
SMILES (Isomeric) C[C@@H]1C(=O)[C@H]([C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CCOC(=O)C)(CC[C@H]([C@]2(C)COC(=O)C)O)C)OC(=O)C
InChI InChI=1S/C26H40O9/c1-15-20(31)21(34-18(4)29)22-24(6,14-33-17(3)28)19(30)8-9-25(22,7)26(15)11-10-23(5,35-26)12-13-32-16(2)27/h15,19,21-22,30H,8-14H2,1-7H3/t15-,19-,21-,22+,23+,24+,25+,26-/m1/s1
InChI Key FHAIKNSLRUWPRQ-GCDFGGQNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C26H40O9
Molecular Weight 496.60 g/mol
Exact Mass 496.26723285 g/mol
Topological Polar Surface Area (TPSA) 125.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.74
H-Bond Acceptor 9
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-[(2'S,3R,4S,4aS,5S,7S,8R,8aS)-5-acetyloxy-4-(acetyloxymethyl)-3-hydroxy-2',4,7,8a-tetramethyl-6-oxospiro[1,2,3,4a,5,7-hexahydronaphthalene-8,5'-oxolane]-2'-yl]ethyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9792 97.92%
Caco-2 - 0.6710 67.10%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7875 78.75%
OATP2B1 inhibitior - 0.8631 86.31%
OATP1B1 inhibitior + 0.8476 84.76%
OATP1B3 inhibitior + 0.9545 95.45%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.9086 90.86%
P-glycoprotein inhibitior + 0.6896 68.96%
P-glycoprotein substrate - 0.5354 53.54%
CYP3A4 substrate + 0.6966 69.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8283 82.83%
CYP3A4 inhibition - 0.7521 75.21%
CYP2C9 inhibition - 0.8043 80.43%
CYP2C19 inhibition - 0.8096 80.96%
CYP2D6 inhibition - 0.9729 97.29%
CYP1A2 inhibition - 0.9191 91.91%
CYP2C8 inhibition - 0.5658 56.58%
CYP inhibitory promiscuity - 0.9661 96.61%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6159 61.59%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.8962 89.62%
Skin irritation - 0.6068 60.68%
Skin corrosion - 0.9385 93.85%
Ames mutagenesis - 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4611 46.11%
Micronuclear - 0.8200 82.00%
Hepatotoxicity - 0.5709 57.09%
skin sensitisation - 0.9446 94.46%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.6178 61.78%
Acute Oral Toxicity (c) III 0.3992 39.92%
Estrogen receptor binding + 0.8093 80.93%
Androgen receptor binding + 0.6692 66.92%
Thyroid receptor binding + 0.5877 58.77%
Glucocorticoid receptor binding + 0.8379 83.79%
Aromatase binding + 0.7905 79.05%
PPAR gamma + 0.6257 62.57%
Honey bee toxicity - 0.7544 75.44%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5650 56.50%
Fish aquatic toxicity + 0.9588 95.88%

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 96.91% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.48% 98.95%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 91.47% 82.69%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.03% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.65% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.17% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.78% 94.45%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 86.15% 91.65%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.46% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.44% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.12% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.03% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.97% 99.23%
CHEMBL5028 O14672 ADAM10 81.71% 97.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.82% 85.14%

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.
Leonurus macranthus

Cross-Links

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PubChem 122186907
LOTUS LTS0152104
wikiData Q104995152