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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] 3-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 b23a266f-9728-440f-99f9-4bc0e2daf6fe
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] 3-methylbutanoate
SMILES (Canonical) CC(C)CC(=O)OC1CC2(C(CCC3(C2C4C1C(=C)C(=O)O4)CO3)OC(=O)C(=C)CO)C
SMILES (Isomeric) CC(C)CC(=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/c1-12(2)8-17(26)30-15-9-23(5)16(31-21(27)13(3)10-25)6-7-24(11-29-24)20(23)19-18(15)14(4)22(28)32-19/h12,15-16,18-20,25H,3-4,6-11H2,1-2,5H3/t15-,16-,18+,19-,20+,23-,24+/m0/s1
InChI Key CZUIWBITAJXBIZ-CUCGTHSTSA-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 2.50
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] 3-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9695 96.95%
Caco-2 - 0.6428 64.28%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.7884 78.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8677 86.77%
OATP1B3 inhibitior + 0.8638 86.38%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.6000 60.00%
BSEP inhibitior - 0.5337 53.37%
P-glycoprotein inhibitior + 0.6399 63.99%
P-glycoprotein substrate + 0.5621 56.21%
CYP3A4 substrate + 0.6993 69.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8828 88.28%
CYP3A4 inhibition - 0.5965 59.65%
CYP2C9 inhibition - 0.7243 72.43%
CYP2C19 inhibition - 0.8161 81.61%
CYP2D6 inhibition - 0.9307 93.07%
CYP1A2 inhibition - 0.7771 77.71%
CYP2C8 inhibition - 0.6071 60.71%
CYP inhibitory promiscuity - 0.8955 89.55%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5120 51.20%
Eye corrosion - 0.9855 98.55%
Eye irritation - 0.8863 88.63%
Skin irritation - 0.6054 60.54%
Skin corrosion - 0.9254 92.54%
Ames mutagenesis - 0.5440 54.40%
Human Ether-a-go-go-Related Gene inhibition - 0.4798 47.98%
Micronuclear - 0.6600 66.00%
Hepatotoxicity + 0.5237 52.37%
skin sensitisation - 0.7903 79.03%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.9008 90.08%
Acute Oral Toxicity (c) III 0.4323 43.23%
Estrogen receptor binding + 0.6948 69.48%
Androgen receptor binding + 0.6805 68.05%
Thyroid receptor binding + 0.5685 56.85%
Glucocorticoid receptor binding + 0.7831 78.31%
Aromatase binding + 0.6282 62.82%
PPAR gamma + 0.6536 65.36%
Honey bee toxicity - 0.7359 73.59%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5750 57.50%
Fish aquatic toxicity + 0.9938 99.38%

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 97.36% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.52% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.54% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 89.93% 97.79%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.92% 99.23%
CHEMBL221 P23219 Cyclooxygenase-1 89.69% 90.17%
CHEMBL2581 P07339 Cathepsin D 89.47% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.90% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.07% 97.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.06% 95.56%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 85.54% 82.69%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.24% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 83.74% 94.75%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.55% 97.25%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.24% 92.62%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 82.58% 98.75%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.08% 95.89%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.73% 97.28%
CHEMBL5028 O14672 ADAM10 81.13% 97.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.84% 100.00%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 80.19% 92.88%

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 162958274
LOTUS LTS0143044
wikiData Q104973150