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[(2R,3S,4S,5R)-6-[2-[(1aR,2R,4aR,7R,8aR)-2,7-dihydroxy-4a-methyl-8-methylidene-1a,3,4,5,6,7-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yloxy]-4-acetyloxy-2-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyoxan-3-yl] (Z)-2-methylbut-2-enoate

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 e8464e26-e4b3-455a-9fa2-80dc8a01ccf8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
IUPAC Name [(2R,3S,4S,5R)-6-[2-[(1aR,2R,4aR,7R,8aR)-2,7-dihydroxy-4a-methyl-8-methylidene-1a,3,4,5,6,7-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yloxy]-4-acetyloxy-2-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyoxan-3-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C33H48O11/c1-11-17(3)26(36)41-23-20(6)39-28(25(24(23)40-21(7)34)42-27(37)18(4)12-2)43-30(8,9)32(38)16-15-31(10)14-13-22(35)19(5)33(31)29(32)44-33/h11-12,20,22-25,28-29,35,38H,5,13-16H2,1-4,6-10H3/b17-11-,18-12-/t20-,22-,23+,24+,25-,28?,29-,31-,32-,33-/m1/s1
InChI Key AKACNUARSZZVHH-FYJKLWJNSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C33H48O11
Molecular Weight 620.70 g/mol
Exact Mass 620.31966234 g/mol
Topological Polar Surface Area (TPSA) 150.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.59
H-Bond Acceptor 11
H-Bond Donor 2
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5R)-6-[2-[(1aR,2R,4aR,7R,8aR)-2,7-dihydroxy-4a-methyl-8-methylidene-1a,3,4,5,6,7-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yloxy]-4-acetyloxy-2-methyl-5-[(Z)-2-methylbut-2-enoyl]oxyoxan-3-yl] (Z)-2-methylbut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9658 96.58%
Caco-2 - 0.8185 81.85%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7152 71.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8379 83.79%
OATP1B3 inhibitior + 0.8905 89.05%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior + 0.9221 92.21%
P-glycoprotein inhibitior + 0.7741 77.41%
P-glycoprotein substrate - 0.5098 50.98%
CYP3A4 substrate + 0.7077 70.77%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8891 88.91%
CYP3A4 inhibition - 0.5402 54.02%
CYP2C9 inhibition - 0.7869 78.69%
CYP2C19 inhibition - 0.8556 85.56%
CYP2D6 inhibition - 0.9429 94.29%
CYP1A2 inhibition - 0.7896 78.96%
CYP2C8 inhibition + 0.4818 48.18%
CYP inhibitory promiscuity - 0.9744 97.44%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6499 64.99%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9055 90.55%
Skin irritation - 0.5723 57.23%
Skin corrosion - 0.9185 91.85%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4256 42.56%
Micronuclear - 0.6500 65.00%
Hepatotoxicity - 0.5449 54.49%
skin sensitisation - 0.7500 75.00%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity + 0.6801 68.01%
Acute Oral Toxicity (c) III 0.4348 43.48%
Estrogen receptor binding + 0.7219 72.19%
Androgen receptor binding + 0.7142 71.42%
Thyroid receptor binding + 0.5233 52.33%
Glucocorticoid receptor binding + 0.7259 72.59%
Aromatase binding + 0.7263 72.63%
PPAR gamma + 0.6991 69.91%
Honey bee toxicity - 0.7365 73.65%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9913 99.13%

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 97.72% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.84% 96.09%
CHEMBL340 P08684 Cytochrome P450 3A4 91.66% 91.19%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 91.33% 91.03%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.92% 89.00%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 88.98% 83.00%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 87.55% 98.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.22% 94.45%
CHEMBL2581 P07339 Cathepsin D 86.97% 98.95%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 85.48% 82.50%
CHEMBL5028 O14672 ADAM10 85.28% 97.50%
CHEMBL259 P32245 Melanocortin receptor 4 84.80% 95.38%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.73% 92.94%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.41% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.26% 100.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.96% 100.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.51% 89.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.48% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.45% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.96% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.89% 95.56%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 82.77% 98.99%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.14% 86.33%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.04% 96.77%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.44% 93.04%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.66% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.32% 97.25%
CHEMBL4015 P41597 C-C chemokine receptor type 2 80.22% 98.57%

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.
Calendula arvensis

Cross-Links

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PubChem 162987380
LOTUS LTS0201099
wikiData Q104913498