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(1R,2R,5S,8R,9R,10R,13R,14R,15R,16R,18R)-16-hydroxy-15-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,14,17,17-pentamethyl-8-prop-1-en-2-ylpentacyclo[11.7.0.02,10.05,9.014,18]icosane-5-carboxylic 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 fdad7a74-e275-48eb-ac0c-670401db036a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,2R,5S,8R,9R,10R,13R,14R,15R,16R,18R)-16-hydroxy-15-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,14,17,17-pentamethyl-8-prop-1-en-2-ylpentacyclo[11.7.0.02,10.05,9.014,18]icosane-5-carboxylic acid
SMILES (Canonical) CC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(C(C(C5(C)C)O)COC(=O)C=CC6=CC=C(C=C6)O)C)C)C(=O)O
SMILES (Isomeric) CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@H]4[C@]([C@@]3(CC2)C)(CC[C@@H]5[C@@]4([C@@H]([C@H](C5(C)C)O)COC(=O)/C=C/C6=CC=C(C=C6)O)C)C)C(=O)O
InChI InChI=1S/C39H54O6/c1-23(2)26-16-19-39(34(43)44)21-20-36(5)27(32(26)39)13-14-30-37(36,6)18-17-29-35(3,4)33(42)28(38(29,30)7)22-45-31(41)15-10-24-8-11-25(40)12-9-24/h8-12,15,26-30,32-33,40,42H,1,13-14,16-22H2,2-7H3,(H,43,44)/b15-10+/t26-,27+,28+,29-,30-,32+,33+,36+,37+,38-,39-/m0/s1
InChI Key MSWXOBSOIDJLPM-IYXPNRLESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C39H54O6
Molecular Weight 618.80 g/mol
Exact Mass 618.39203944 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 9.40
Atomic LogP (AlogP) 7.89
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,2R,5S,8R,9R,10R,13R,14R,15R,16R,18R)-16-hydroxy-15-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-1,2,14,17,17-pentamethyl-8-prop-1-en-2-ylpentacyclo[11.7.0.02,10.05,9.014,18]icosane-5-carboxylic 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 - 0.8365 83.65%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.8922 89.22%
OATP2B1 inhibitior - 0.5698 56.98%
OATP1B1 inhibitior + 0.8287 82.87%
OATP1B3 inhibitior - 0.3555 35.55%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6891 68.91%
BSEP inhibitior + 0.9610 96.10%
P-glycoprotein inhibitior + 0.6692 66.92%
P-glycoprotein substrate + 0.5570 55.70%
CYP3A4 substrate + 0.6959 69.59%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8772 87.72%
CYP3A4 inhibition - 0.7451 74.51%
CYP2C9 inhibition + 0.6249 62.49%
CYP2C19 inhibition - 0.5636 56.36%
CYP2D6 inhibition - 0.9119 91.19%
CYP1A2 inhibition + 0.6615 66.15%
CYP2C8 inhibition + 0.8661 86.61%
CYP inhibitory promiscuity - 0.5621 56.21%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.6355 63.55%
Eye corrosion - 0.9934 99.34%
Eye irritation - 0.9182 91.82%
Skin irritation - 0.6246 62.46%
Skin corrosion - 0.9597 95.97%
Ames mutagenesis - 0.6228 62.28%
Human Ether-a-go-go-Related Gene inhibition + 0.7768 77.68%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.6698 66.98%
skin sensitisation - 0.7980 79.80%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.6407 64.07%
Acute Oral Toxicity (c) I 0.3833 38.33%
Estrogen receptor binding + 0.7866 78.66%
Androgen receptor binding + 0.8040 80.40%
Thyroid receptor binding + 0.5466 54.66%
Glucocorticoid receptor binding + 0.7133 71.33%
Aromatase binding + 0.7146 71.46%
PPAR gamma + 0.7153 71.53%
Honey bee toxicity - 0.6977 69.77%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5200 52.00%
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
CHEMBL1293249 Q13887 Kruppel-like factor 5 97.69% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.24% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.52% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.29% 97.09%
CHEMBL2581 P07339 Cathepsin D 92.63% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.30% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.41% 94.45%
CHEMBL206 P03372 Estrogen receptor alpha 89.03% 97.64%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.96% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 86.85% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.97% 89.00%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 85.00% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 84.75% 97.79%
CHEMBL1951 P21397 Monoamine oxidase A 84.39% 91.49%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.23% 92.94%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.79% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.16% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.15% 99.17%
CHEMBL340 P08684 Cytochrome P450 3A4 81.45% 91.19%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 80.74% 91.71%

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.
Paliurus hemsleyanus

Cross-Links

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PubChem 163186569
LOTUS LTS0273131
wikiData Q105171501