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[(1S,2R,4aS,5R,5'S,6S,8S,8aS)-2,8-diacetyloxy-5'-(2-hydroxyethyl)-1,4a,5',6-tetramethyl-7-oxospiro[2,3,4,6,8,8a-hexahydronaphthalene-5,2'-oxolane]-1-yl]methyl acetate

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 eb823c71-6a9f-490f-951a-3b6c40289067
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name [(1S,2R,4aS,5R,5'S,6S,8S,8aS)-2,8-diacetyloxy-5'-(2-hydroxyethyl)-1,4a,5',6-tetramethyl-7-oxospiro[2,3,4,6,8,8a-hexahydronaphthalene-5,2'-oxolane]-1-yl]methyl acetate
SMILES (Canonical) CC1C(=O)C(C2C(C13CCC(O3)(C)CCO)(CCC(C2(C)COC(=O)C)OC(=O)C)C)OC(=O)C
SMILES (Isomeric) C[C@@H]1C(=O)[C@H]([C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CCO)(CC[C@H]([C@]2(C)COC(=O)C)OC(=O)C)C)OC(=O)C
InChI InChI=1S/C26H40O9/c1-15-20(31)21(34-18(4)30)22-24(6,14-32-16(2)28)19(33-17(3)29)8-9-25(22,7)26(15)11-10-23(5,35-26)12-13-27/h15,19,21-22,27H,8-14H2,1-7H3/t15-,19-,21-,22+,23+,24+,25+,26-/m1/s1
InChI Key BTOUAJKAVXLICM-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 [(1S,2R,4aS,5R,5'S,6S,8S,8aS)-2,8-diacetyloxy-5'-(2-hydroxyethyl)-1,4a,5',6-tetramethyl-7-oxospiro[2,3,4,6,8,8a-hexahydronaphthalene-5,2'-oxolane]-1-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9416 94.16%
Caco-2 - 0.6045 60.45%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.7256 72.56%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8126 81.26%
OATP1B3 inhibitior + 0.9509 95.09%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.9149 91.49%
P-glycoprotein inhibitior + 0.7335 73.35%
P-glycoprotein substrate - 0.6253 62.53%
CYP3A4 substrate + 0.6714 67.14%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8451 84.51%
CYP3A4 inhibition - 0.6100 61.00%
CYP2C9 inhibition - 0.8401 84.01%
CYP2C19 inhibition - 0.7974 79.74%
CYP2D6 inhibition - 0.9628 96.28%
CYP1A2 inhibition - 0.8951 89.51%
CYP2C8 inhibition + 0.4711 47.11%
CYP inhibitory promiscuity - 0.9350 93.50%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5881 58.81%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.8837 88.37%
Skin irritation + 0.5000 50.00%
Skin corrosion - 0.9392 93.92%
Ames mutagenesis - 0.6270 62.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4645 46.45%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.6459 64.59%
skin sensitisation - 0.9488 94.88%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.6631 66.31%
Acute Oral Toxicity (c) III 0.4805 48.05%
Estrogen receptor binding + 0.8601 86.01%
Androgen receptor binding + 0.6585 65.85%
Thyroid receptor binding + 0.5622 56.22%
Glucocorticoid receptor binding + 0.7966 79.66%
Aromatase binding + 0.7922 79.22%
PPAR gamma + 0.7412 74.12%
Honey bee toxicity - 0.8179 81.79%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6450 64.50%
Fish aquatic toxicity + 0.9223 92.23%

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 98.41% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.35% 91.11%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 91.97% 82.69%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.53% 97.25%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 89.12% 91.65%
CHEMBL2581 P07339 Cathepsin D 88.34% 98.95%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 87.94% 89.05%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.22% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.64% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 83.77% 91.19%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 83.60% 96.77%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.52% 94.45%
CHEMBL5555 O00767 Acyl-CoA desaturase 83.20% 97.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.99% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.18% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.10% 99.23%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.52% 97.14%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 81.50% 85.14%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.02% 93.04%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.30% 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.
Leonurus macranthus

Cross-Links

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PubChem 122186910
LOTUS LTS0114659
wikiData Q104945781