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[(3aR,4S,5aR,6S,9S,9aS,9bS)-6-[2-(hydroxymethyl)prop-2-enoyloxy]-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-4-yl] (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 6aed720d-50c1-4aa3-820f-1efca5438005
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,5aR,6S,9S,9aS,9bS)-6-[2-(hydroxymethyl)prop-2-enoyloxy]-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-4-yl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1CC2(C(CCC3(C2C4C1C(=C)C(=O)O4)CO3)OC(=O)C(=C)CO)C
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@H]1C[C@]2([C@H](CC[C@]3([C@@H]2[C@@H]4[C@@H]1C(=C)C(=O)O4)CO3)OC(=O)C(=C)CO)C
InChI InChI=1S/C24H32O8/c1-6-12(2)20(26)30-15-9-23(5)16(31-21(27)13(3)10-25)7-8-24(11-29-24)19(23)18-17(15)14(4)22(28)32-18/h12,15-19,25H,3-4,6-11H2,1-2,5H3/t12-,15+,16+,17-,18+,19-,23+,24-/m1/s1
InChI Key FHXZHXYEUJMURM-NCEGOPNLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C24H32O8
Molecular Weight 448.50 g/mol
Exact Mass 448.20971797 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.09
H-Bond Acceptor 8
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 [(3aR,4S,5aR,6S,9S,9aS,9bS)-6-[2-(hydroxymethyl)prop-2-enoyloxy]-5a-methyl-3-methylidene-2-oxospiro[3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-9,2'-oxirane]-4-yl] (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 + 0.9798 97.98%
Caco-2 - 0.5975 59.75%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6916 69.16%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8701 87.01%
OATP1B3 inhibitior + 0.9325 93.25%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.5250 52.50%
BSEP inhibitior + 0.5908 59.08%
P-glycoprotein inhibitior + 0.6432 64.32%
P-glycoprotein substrate + 0.5154 51.54%
CYP3A4 substrate + 0.6893 68.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8828 88.28%
CYP3A4 inhibition + 0.5914 59.14%
CYP2C9 inhibition - 0.7946 79.46%
CYP2C19 inhibition - 0.8026 80.26%
CYP2D6 inhibition - 0.9293 92.93%
CYP1A2 inhibition - 0.7773 77.73%
CYP2C8 inhibition + 0.4639 46.39%
CYP inhibitory promiscuity - 0.8421 84.21%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5020 50.20%
Eye corrosion - 0.9860 98.60%
Eye irritation - 0.8920 89.20%
Skin irritation - 0.5445 54.45%
Skin corrosion - 0.9267 92.67%
Ames mutagenesis - 0.6140 61.40%
Human Ether-a-go-go-Related Gene inhibition - 0.4262 42.62%
Micronuclear - 0.6500 65.00%
Hepatotoxicity + 0.5112 51.12%
skin sensitisation - 0.8489 84.89%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.7548 75.48%
Acute Oral Toxicity (c) III 0.5401 54.01%
Estrogen receptor binding + 0.8002 80.02%
Androgen receptor binding + 0.6824 68.24%
Thyroid receptor binding + 0.5951 59.51%
Glucocorticoid receptor binding + 0.8456 84.56%
Aromatase binding + 0.6905 69.05%
PPAR gamma + 0.6898 68.98%
Honey bee toxicity - 0.7418 74.18%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6050 60.50%
Fish aquatic toxicity + 0.9945 99.45%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.73% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.43% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.23% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.76% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.91% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 91.57% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 91.46% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.00% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.43% 97.09%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 86.94% 98.75%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.85% 92.62%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.11% 82.69%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.77% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 85.66% 94.75%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.61% 97.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.08% 95.56%
CHEMBL299 P17252 Protein kinase C alpha 82.95% 98.03%
CHEMBL3922 P50579 Methionine aminopeptidase 2 82.55% 97.28%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.99% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.79% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.40% 100.00%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.34% 94.08%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.21% 89.50%

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.
Dimerostemma brasilianum

Cross-Links

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PubChem 163033917
LOTUS LTS0023644
wikiData Q104995504