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methyl (2Z)-2-[(2R,8S,9R,10S,12R,13S,14S,16S,17S,19R,20S,21R)-9-(acetyloxymethyl)-16,21-dihydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.02,6.02,14.08,13.010,12.017,19.020,24]tetracosa-1(24),5-dien-23-ylidene]propanoate

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 90e93cad-ed50-401b-8cba-688340b5ae82
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name methyl (2Z)-2-[(2R,8S,9R,10S,12R,13S,14S,16S,17S,19R,20S,21R)-9-(acetyloxymethyl)-16,21-dihydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.02,6.02,14.08,13.010,12.017,19.020,24]tetracosa-1(24),5-dien-23-ylidene]propanoate
SMILES (Canonical) CC(=C1C(=O)C(C2(C3CC3C4(C2=C1C56C(C4)C7(C8CC8C(C7CC5=C(C(=O)O6)CO)COC(=O)C)C)O)C)O)C(=O)OC
SMILES (Isomeric) C/C(=C\1/C(=O)[C@@H]([C@]2([C@@H]3C[C@@H]3[C@@]4(C2=C1[C@@]56[C@@H](C4)[C@]7([C@@H]8C[C@@H]8[C@H]([C@@H]7CC5=C(C(=O)O6)CO)COC(=O)C)C)O)C)O)/C(=O)OC
InChI InChI=1S/C33H38O10/c1-12(28(38)41-5)23-24-26-31(4,27(37)25(23)36)20-8-21(20)32(26,40)9-22-30(3)17-6-14(17)16(11-42-13(2)35)18(30)7-19-15(10-34)29(39)43-33(19,22)24/h14,16-18,20-22,27,34,37,40H,6-11H2,1-5H3/b23-12-/t14-,16-,17-,18+,20-,21+,22+,27+,30+,31+,32+,33+/m1/s1
InChI Key IXFDRCYQIQGSHW-YJZJOYDFSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C33H38O10
Molecular Weight 594.60 g/mol
Exact Mass 594.24649740 g/mol
Topological Polar Surface Area (TPSA) 157.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.56
H-Bond Acceptor 10
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (2Z)-2-[(2R,8S,9R,10S,12R,13S,14S,16S,17S,19R,20S,21R)-9-(acetyloxymethyl)-16,21-dihydroxy-5-(hydroxymethyl)-13,20-dimethyl-4,22-dioxo-3-oxaoctacyclo[14.7.1.02,6.02,14.08,13.010,12.017,19.020,24]tetracosa-1(24),5-dien-23-ylidene]propanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9724 97.24%
Caco-2 - 0.7854 78.54%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.7823 78.23%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8107 81.07%
OATP1B3 inhibitior + 0.9542 95.42%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.7132 71.32%
P-glycoprotein inhibitior + 0.7006 70.06%
P-glycoprotein substrate + 0.6643 66.43%
CYP3A4 substrate + 0.7394 73.94%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9052 90.52%
CYP3A4 inhibition - 0.6241 62.41%
CYP2C9 inhibition - 0.8488 84.88%
CYP2C19 inhibition - 0.8722 87.22%
CYP2D6 inhibition - 0.9395 93.95%
CYP1A2 inhibition - 0.8412 84.12%
CYP2C8 inhibition + 0.6737 67.37%
CYP inhibitory promiscuity - 0.8485 84.85%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4897 48.97%
Eye corrosion - 0.9877 98.77%
Eye irritation - 0.9212 92.12%
Skin irritation - 0.5961 59.61%
Skin corrosion - 0.9437 94.37%
Ames mutagenesis - 0.5048 50.48%
Human Ether-a-go-go-Related Gene inhibition - 0.5424 54.24%
Micronuclear - 0.6400 64.00%
Hepatotoxicity - 0.5625 56.25%
skin sensitisation - 0.8772 87.72%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.5415 54.15%
Acute Oral Toxicity (c) III 0.3848 38.48%
Estrogen receptor binding + 0.7372 73.72%
Androgen receptor binding + 0.7442 74.42%
Thyroid receptor binding - 0.5555 55.55%
Glucocorticoid receptor binding + 0.7309 73.09%
Aromatase binding + 0.7268 72.68%
PPAR gamma + 0.6519 65.19%
Honey bee toxicity - 0.6977 69.77%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5700 57.00%
Fish aquatic toxicity + 0.9528 95.28%

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 99.44% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.63% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.53% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.31% 97.25%
CHEMBL2581 P07339 Cathepsin D 92.76% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.59% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.22% 97.09%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 90.03% 96.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.31% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.75% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.58% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 86.68% 91.19%
CHEMBL226 P30542 Adenosine A1 receptor 86.04% 95.93%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 86.01% 97.14%
CHEMBL221 P23219 Cyclooxygenase-1 83.03% 90.17%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.94% 82.69%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.10% 99.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.95% 86.33%

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.
Actinidia chinensis var. deliciosa
Lepidium apetalum

Cross-Links

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PubChem 54671541
NPASS NPC56592