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[(1S,1'R,3aR,4R,4'S,5S,5aS,8'S,8aR,9S,9aR)-4-hydroxy-8'-(2-hydroxypropan-2-yl)-2',5,8a-trimethyl-2,8-dioxospiro[3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-1,5'-bicyclo[2.2.2]oct-2-ene]-9-yl] (Z)-2-methylbut-2-enoate

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 b9fd3bf8-6724-4d40-bff1-ba8e716c362d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
IUPAC Name [(1S,1'R,3aR,4R,4'S,5S,5aS,8'S,8aR,9S,9aR)-4-hydroxy-8'-(2-hydroxypropan-2-yl)-2',5,8a-trimethyl-2,8-dioxospiro[3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-1,5'-bicyclo[2.2.2]oct-2-ene]-9-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C30H40O7/c1-8-14(2)26(33)37-25-22-24(23(32)16(4)18-9-10-21(31)29(18,25)7)36-27(34)30(22)13-17-12-19(28(5,6)35)20(30)11-15(17)3/h8-11,16-20,22-25,32,35H,12-13H2,1-7H3/b14-8-/t16-,17+,18-,19-,20-,22-,23+,24+,25-,29-,30-/m0/s1
InChI Key GBSPBHYJLFGEFU-PUBIIICBSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C30H40O7
Molecular Weight 512.60 g/mol
Exact Mass 512.27740361 g/mol
Topological Polar Surface Area (TPSA) 110.00 Ų
XlogP 2.90
Atomic LogP (AlogP) 3.54
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,1'R,3aR,4R,4'S,5S,5aS,8'S,8aR,9S,9aR)-4-hydroxy-8'-(2-hydroxypropan-2-yl)-2',5,8a-trimethyl-2,8-dioxospiro[3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-1,5'-bicyclo[2.2.2]oct-2-ene]-9-yl] (Z)-2-methylbut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9914 99.14%
Caco-2 - 0.6439 64.39%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7430 74.30%
OATP2B1 inhibitior - 0.8586 85.86%
OATP1B1 inhibitior + 0.8488 84.88%
OATP1B3 inhibitior - 0.2187 21.87%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.7722 77.22%
P-glycoprotein inhibitior + 0.8061 80.61%
P-glycoprotein substrate + 0.6416 64.16%
CYP3A4 substrate + 0.7059 70.59%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9028 90.28%
CYP3A4 inhibition - 0.8949 89.49%
CYP2C9 inhibition - 0.7655 76.55%
CYP2C19 inhibition - 0.7605 76.05%
CYP2D6 inhibition - 0.9225 92.25%
CYP1A2 inhibition - 0.7982 79.82%
CYP2C8 inhibition + 0.5360 53.60%
CYP inhibitory promiscuity - 0.7187 71.87%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5018 50.18%
Eye corrosion - 0.9838 98.38%
Eye irritation - 0.9184 91.84%
Skin irritation - 0.6417 64.17%
Skin corrosion - 0.9337 93.37%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4202 42.02%
Micronuclear - 0.5600 56.00%
Hepatotoxicity + 0.6158 61.58%
skin sensitisation - 0.6994 69.94%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.6721 67.21%
Acute Oral Toxicity (c) III 0.3771 37.71%
Estrogen receptor binding + 0.7655 76.55%
Androgen receptor binding + 0.6215 62.15%
Thyroid receptor binding + 0.5956 59.56%
Glucocorticoid receptor binding + 0.7615 76.15%
Aromatase binding + 0.7020 70.20%
PPAR gamma + 0.7120 71.20%
Honey bee toxicity - 0.6841 68.41%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9941 99.41%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.05% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.83% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.81% 86.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 92.21% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.22% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.95% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 90.81% 97.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.10% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.74% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 89.44% 97.79%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 88.16% 90.93%
CHEMBL2581 P07339 Cathepsin D 87.82% 98.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 86.63% 97.21%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.55% 94.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.23% 96.77%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.87% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.63% 93.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.29% 94.45%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.18% 100.00%
CHEMBL2964 P36507 Dual specificity mitogen-activated protein kinase kinase 2 81.48% 80.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.07% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.47% 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.
Gaillardia aestivalis

Cross-Links

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PubChem 162916113
LOTUS LTS0009949
wikiData Q105006072