(2alpha,3beta)-2-[(3,4-Dihydroxybenzoyl)oxy]-3-hydroxylup-20(29)-en-28-oic acid

Details

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Internal ID e7794caf-3050-4352-be81-d9ca3b6c8b07
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (1R,3aS,5aR,5bR,7aR,9R,10R,11aR,11bR,13aR,13bR)-10-(3,4-dihydroxybenzoyl)oxy-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
SMILES (Canonical) CC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)O)OC(=O)C6=CC(=C(C=C6)O)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[C@H]([C@@H](C5(C)C)O)OC(=O)C6=CC(=C(C=C6)O)O)C)C)C(=O)O
InChI InChI=1S/C37H52O7/c1-20(2)22-12-15-37(32(42)43)17-16-35(6)23(29(22)37)9-11-28-34(5)19-26(44-31(41)21-8-10-24(38)25(39)18-21)30(40)33(3,4)27(34)13-14-36(28,35)7/h8,10,18,22-23,26-30,38-40H,1,9,11-17,19H2,2-7H3,(H,42,43)/t22-,23+,26+,27-,28+,29+,30-,34-,35+,36+,37-/m0/s1
InChI Key MKDOBXUKRMFQNI-JFJOLGLVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C37H52O7
Molecular Weight 608.80 g/mol
Exact Mass 608.37130399 g/mol
Topological Polar Surface Area (TPSA) 124.00 Ų
XlogP 8.80
Atomic LogP (AlogP) 7.34
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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DTXSID901149692
(2alpha,3beta)-2-[(3,4-Dihydroxybenzoyl)oxy]-3-hydroxylup-20(29)-en-28-oic acid
182682-95-7

2D Structure

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2D Structure of (2alpha,3beta)-2-[(3,4-Dihydroxybenzoyl)oxy]-3-hydroxylup-20(29)-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 + 0.9879 98.79%
Caco-2 - 0.8319 83.19%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8722 87.22%
OATP2B1 inhibitior - 0.5687 56.87%
OATP1B1 inhibitior + 0.8674 86.74%
OATP1B3 inhibitior - 0.5000 50.00%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7571 75.71%
BSEP inhibitior + 0.7356 73.56%
P-glycoprotein inhibitior + 0.6720 67.20%
P-glycoprotein substrate - 0.5233 52.33%
CYP3A4 substrate + 0.7102 71.02%
CYP2C9 substrate - 0.6370 63.70%
CYP2D6 substrate - 0.8609 86.09%
CYP3A4 inhibition - 0.7711 77.11%
CYP2C9 inhibition - 0.6281 62.81%
CYP2C19 inhibition - 0.5390 53.90%
CYP2D6 inhibition - 0.9183 91.83%
CYP1A2 inhibition + 0.7156 71.56%
CYP2C8 inhibition + 0.8441 84.41%
CYP inhibitory promiscuity - 0.8616 86.16%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9100 91.00%
Carcinogenicity (trinary) Non-required 0.6371 63.71%
Eye corrosion - 0.9933 99.33%
Eye irritation - 0.9170 91.70%
Skin irritation - 0.5667 56.67%
Skin corrosion - 0.9399 93.99%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7658 76.58%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.7125 71.25%
skin sensitisation - 0.7640 76.40%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.7046 70.46%
Acute Oral Toxicity (c) III 0.4711 47.11%
Estrogen receptor binding + 0.7649 76.49%
Androgen receptor binding + 0.7831 78.31%
Thyroid receptor binding - 0.5162 51.62%
Glucocorticoid receptor binding + 0.7365 73.65%
Aromatase binding + 0.7865 78.65%
PPAR gamma + 0.7108 71.08%
Honey bee toxicity - 0.6941 69.41%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5900 59.00%
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
CHEMBL1951 P21397 Monoamine oxidase A 99.04% 91.49%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.59% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.83% 86.33%
CHEMBL2581 P07339 Cathepsin D 92.34% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 91.97% 91.19%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.82% 96.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.23% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.88% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.48% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.32% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 87.30% 97.79%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 85.97% 94.97%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.06% 97.09%
CHEMBL3194 P02766 Transthyretin 84.84% 90.71%
CHEMBL221 P23219 Cyclooxygenase-1 83.19% 90.17%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 83.10% 93.03%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.65% 90.71%
CHEMBL2095172 P14867 GABA-A receptor; alpha-1/beta-2/gamma-2 82.19% 92.67%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 80.83% 97.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.81% 99.17%

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.
Ziziphus jujuba

Cross-Links

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PubChem 102247122
LOTUS LTS0269150
wikiData Q105165837