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Gutolactone

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 295479e9-f8a1-4a7a-a023-7e7f3fb71750
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
IUPAC Name [(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-en-3-yl] 3-methylbut-2-enoate
SMILES (Canonical) CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C)(OC5)C)O)O)C)O
SMILES (Isomeric) CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)C=C(C)C)(OC5)C)O)O)C)O
InChI InChI=1S/C25H32O9/c1-10(2)6-15(27)34-17-19-24(5)21(30)16(28)18-23(4)12(11(3)7-13(26)20(23)29)8-14(33-22(17)31)25(18,19)9-32-24/h6-7,12,14,16-21,28-30H,8-9H2,1-5H3/t12-,14+,16+,17+,18+,19-,20+,21-,23-,24-,25+/m0/s1
InChI Key WSUNNCJENRRPLS-DQVMPRLHSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C25H32O9
Molecular Weight 476.50 g/mol
Exact Mass 476.20463259 g/mol
Topological Polar Surface Area (TPSA) 140.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 0.45
H-Bond Acceptor 9
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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152369-48-7
Gurolactone
(+)-Gurolactone
CHEBI:65989
DTXSID90934486
Q27134490
(1beta,11beta,12alpha,13beta,15beta)-1,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-15-yl 3-methylbut-2-enoate
(1beta,11beta,12alpha,15beta)-13,20-Epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)picras-3-ene-2,16-dione
13,20-Epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)picras-3-ene-2,16-dione (1beta,11beta,12alpha,15beta)-
Picras-3-ene-2,16-dione, 13,20-epoxy-1,11,12-trihydroxy-15-((3-methyl-1-oxo-2-butenyl)oxy)-, (1beta,11beta,12alpha,15beta)-

2D Structure

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2D Structure of Gutolactone

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9154 91.54%
Caco-2 - 0.7783 77.83%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.8329 83.29%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8615 86.15%
OATP1B3 inhibitior + 0.9439 94.39%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.9370 93.70%
P-glycoprotein inhibitior - 0.4324 43.24%
P-glycoprotein substrate + 0.8606 86.06%
CYP3A4 substrate + 0.6958 69.58%
CYP2C9 substrate - 0.8217 82.17%
CYP2D6 substrate - 0.8936 89.36%
CYP3A4 inhibition - 0.8506 85.06%
CYP2C9 inhibition - 0.8361 83.61%
CYP2C19 inhibition - 0.8372 83.72%
CYP2D6 inhibition - 0.9254 92.54%
CYP1A2 inhibition - 0.8206 82.06%
CYP2C8 inhibition - 0.5804 58.04%
CYP inhibitory promiscuity - 0.8625 86.25%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5061 50.61%
Eye corrosion - 0.9874 98.74%
Eye irritation - 0.9278 92.78%
Skin irritation - 0.6273 62.73%
Skin corrosion - 0.9176 91.76%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4153 41.53%
Micronuclear - 0.6000 60.00%
Hepatotoxicity - 0.5132 51.32%
skin sensitisation - 0.8068 80.68%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.7513 75.13%
Acute Oral Toxicity (c) III 0.5770 57.70%
Estrogen receptor binding + 0.7649 76.49%
Androgen receptor binding + 0.6301 63.01%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7388 73.88%
Aromatase binding + 0.6646 66.46%
PPAR gamma + 0.6639 66.39%
Honey bee toxicity - 0.6254 62.54%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.9791 97.91%

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 97.49% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.63% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.50% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.89% 89.00%
CHEMBL2581 P07339 Cathepsin D 88.71% 98.95%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 87.86% 96.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.68% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.30% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.74% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.72% 96.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.29% 99.23%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.31% 91.07%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 85.02% 94.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 84.81% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.26% 97.09%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 81.77% 97.21%
CHEMBL3922 P50579 Methionine aminopeptidase 2 81.77% 97.28%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.03% 97.14%

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.
Simaba guianensis

Cross-Links

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PubChem 70697826
LOTUS LTS0069290
wikiData Q27134490