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(2alpha,3beta)-3-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-2,19-dihydroxyurs-12-en-28-oic acid

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 ae57667c-bdec-46c4-a8b3-56738566120f
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILES (Canonical) CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)OC(=O)C=CC6=CC(=C(C=C6)O)O)O)C)C)C2C1(C)O)C)C(=O)O
SMILES (Isomeric) C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@@H](C5(C)C)OC(=O)/C=C/C6=CC(=C(C=C6)O)O)O)C)C)[C@@H]2[C@]1(C)O)C)C(=O)O
InChI InChI=1S/C39H54O8/c1-22-14-17-39(33(44)45)19-18-36(5)24(31(39)38(22,7)46)10-12-29-35(4)21-27(42)32(34(2,3)28(35)15-16-37(29,36)6)47-30(43)13-9-23-8-11-25(40)26(41)20-23/h8-11,13,20,22,27-29,31-32,40-42,46H,12,14-19,21H2,1-7H3,(H,44,45)/b13-9+/t22-,27-,28+,29-,31-,32+,35+,36-,37-,38-,39+/m1/s1
InChI Key MFPIVTNHMCQSEM-NEXBUHEBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H54O8
Molecular Weight 650.80 g/mol
Exact Mass 650.38186868 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 6.90
Atomic LogP (AlogP) 6.85
H-Bond Acceptor 7
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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DTXSID401113315
(2alpha,3beta)-3-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-2,19-dihydroxyurs-12-en-28-oic acid
144604-16-0

2D Structure

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2D Structure of (2alpha,3beta)-3-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-2,19-dihydroxyurs-12-en-28-oic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9924 99.24%
Caco-2 - 0.8330 83.30%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8720 87.20%
OATP2B1 inhibitior - 0.7174 71.74%
OATP1B1 inhibitior + 0.8544 85.44%
OATP1B3 inhibitior - 0.3830 38.30%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8071 80.71%
BSEP inhibitior + 0.8969 89.69%
P-glycoprotein inhibitior + 0.7471 74.71%
P-glycoprotein substrate + 0.5093 50.93%
CYP3A4 substrate + 0.6963 69.63%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8817 88.17%
CYP3A4 inhibition - 0.7723 77.23%
CYP2C9 inhibition - 0.6860 68.60%
CYP2C19 inhibition - 0.5853 58.53%
CYP2D6 inhibition - 0.9089 90.89%
CYP1A2 inhibition + 0.6455 64.55%
CYP2C8 inhibition + 0.7881 78.81%
CYP inhibitory promiscuity - 0.9248 92.48%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8843 88.43%
Carcinogenicity (trinary) Non-required 0.6578 65.78%
Eye corrosion - 0.9936 99.36%
Eye irritation - 0.9233 92.33%
Skin irritation - 0.5643 56.43%
Skin corrosion - 0.9447 94.47%
Ames mutagenesis - 0.8270 82.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4211 42.11%
Micronuclear - 0.6800 68.00%
Hepatotoxicity - 0.5822 58.22%
skin sensitisation - 0.7435 74.35%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.8263 82.63%
Acute Oral Toxicity (c) III 0.4951 49.51%
Estrogen receptor binding + 0.7726 77.26%
Androgen receptor binding + 0.7868 78.68%
Thyroid receptor binding + 0.5542 55.42%
Glucocorticoid receptor binding + 0.8046 80.46%
Aromatase binding + 0.7185 71.85%
PPAR gamma + 0.7604 76.04%
Honey bee toxicity - 0.7292 72.92%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5455 54.55%
Fish aquatic toxicity + 1.0000 100.00%

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 99.75% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 97.44% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 97.11% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.92% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.07% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.05% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.62% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.60% 97.09%
CHEMBL340 P08684 Cytochrome P450 3A4 90.22% 91.19%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 89.33% 99.15%
CHEMBL241 Q14432 Phosphodiesterase 3A 88.85% 92.94%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 87.95% 91.03%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.60% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.39% 95.89%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 85.71% 91.71%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.55% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.91% 89.00%
CHEMBL221 P23219 Cyclooxygenase-1 83.90% 90.17%

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.
Eriobotrya japonica

Cross-Links

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PubChem 44584640
LOTUS LTS0013851
wikiData Q105162929