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(2R,4S,7R,8S,9S,10S,12R,13R,16R,17S,18R)-16-acetyloxy-10-hydroxy-2,9,13,17-tetramethyl-7-(4-methyl-2-oxopent-3-enyl)-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-17-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 d71f89f7-0be5-4c64-bfc5-2323eac70025
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2R,4S,7R,8S,9S,10S,12R,13R,16R,17S,18R)-16-acetyloxy-10-hydroxy-2,9,13,17-tetramethyl-7-(4-methyl-2-oxopent-3-enyl)-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-17-carboxylic acid
SMILES (Canonical) CC(=CC(=O)CC1C2C(CC3(C2(C(CC4C3=CCC5C4(CCC(C5(C)C(=O)O)OC(=O)C)C)O)C)C)OC1=O)C
SMILES (Isomeric) CC(=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3([C@]2([C@H](C[C@H]4C3=CC[C@@H]5[C@@]4(CC[C@H]([C@@]5(C)C(=O)O)OC(=O)C)C)O)C)C)OC1=O)C
InChI InChI=1S/C32H44O8/c1-16(2)12-18(34)13-19-26-22(40-27(19)36)15-30(5)20-8-9-23-29(4,21(20)14-24(35)32(26,30)7)11-10-25(39-17(3)33)31(23,6)28(37)38/h8,12,19,21-26,35H,9-11,13-15H2,1-7H3,(H,37,38)/t19-,21+,22+,23-,24+,25-,26-,29-,30-,31+,32+/m1/s1
InChI Key PGGDNFLHYMDIRS-QYWQWFLASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C32H44O8
Molecular Weight 556.70 g/mol
Exact Mass 556.30361836 g/mol
Topological Polar Surface Area (TPSA) 127.00 Ų
XlogP 3.90
Atomic LogP (AlogP) 4.64
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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BDBM50269527
(1S,2R,4aR,4bR,6S,6aS,6bS,7R,9aS,10aR,12aR)-2-Acetoxy-6-hydroxy-1,4a,6a,10a-tetramethyl-7-(4-methyl-2-oxo-pent-3-enyl)-8-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10,10a,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthrene-1-carboxylic acid
3alpha-Acetoxy-12alpha,16beta-dihydroxy-23-oxo-5alpha-eupha-7,24-diene-21,28-dioic acid 21,16-lactone

2D Structure

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2D Structure of (2R,4S,7R,8S,9S,10S,12R,13R,16R,17S,18R)-16-acetyloxy-10-hydroxy-2,9,13,17-tetramethyl-7-(4-methyl-2-oxopent-3-enyl)-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-17-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 + 0.9886 98.86%
Caco-2 - 0.7510 75.10%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7994 79.94%
OATP2B1 inhibitior - 0.7183 71.83%
OATP1B1 inhibitior + 0.8048 80.48%
OATP1B3 inhibitior + 0.8911 89.11%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.9750 97.50%
P-glycoprotein inhibitior + 0.7845 78.45%
P-glycoprotein substrate + 0.5134 51.34%
CYP3A4 substrate + 0.6990 69.90%
CYP2C9 substrate - 0.8000 80.00%
CYP2D6 substrate - 0.9089 90.89%
CYP3A4 inhibition + 0.6364 63.64%
CYP2C9 inhibition - 0.8053 80.53%
CYP2C19 inhibition - 0.8962 89.62%
CYP2D6 inhibition - 0.9395 93.95%
CYP1A2 inhibition - 0.6820 68.20%
CYP2C8 inhibition + 0.5835 58.35%
CYP inhibitory promiscuity - 0.7819 78.19%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4945 49.45%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.9212 92.12%
Skin irritation + 0.6612 66.12%
Skin corrosion - 0.9246 92.46%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4354 43.54%
Micronuclear - 0.7200 72.00%
Hepatotoxicity + 0.5408 54.08%
skin sensitisation - 0.8172 81.72%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity + 0.5339 53.39%
Acute Oral Toxicity (c) I 0.6986 69.86%
Estrogen receptor binding + 0.7569 75.69%
Androgen receptor binding + 0.7531 75.31%
Thyroid receptor binding + 0.5204 52.04%
Glucocorticoid receptor binding + 0.8169 81.69%
Aromatase binding + 0.7892 78.92%
PPAR gamma + 0.6814 68.14%
Honey bee toxicity - 0.7762 77.62%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9957 99.57%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL204 P00734 Thrombin 90 nM
90 nM
 IC50
IC50
 PMID: 8340925
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.48% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.49% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.45% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.05% 86.33%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 90.06% 93.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 89.68% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.66% 89.00%
CHEMBL340 P08684 Cytochrome P450 3A4 88.82% 91.19%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.49% 96.77%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.44% 97.28%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.14% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.41% 100.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.94% 89.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.89% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.83% 92.62%
CHEMBL5028 O14672 ADAM10 82.25% 97.50%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 80.11% 95.71%

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.
Lantana camara

Cross-Links

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PubChem 10602877
NPASS NPC52634
ChEMBL CHEMBL499564
LOTUS LTS0198281
wikiData Q105208377