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[(3aS,4R,5R,6S,6aR,8R,9bS)-5-acetyloxy-6,8-dihydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-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 cc4553f1-27e2-4993-9163-ee4cfb450ff7
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
IUPAC Name [(3aS,4R,5R,6S,6aR,8R,9bS)-5-acetyloxy-6,8-dihydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(C3=C(C(CC3C(C1OC(=O)C)(C)O)O)C)OC(=O)C2=C
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H]1[C@@H]2[C@@H](C3=C([C@@H](C[C@H]3[C@]([C@@H]1OC(=O)C)(C)O)O)C)OC(=O)C2=C
InChI InChI=1S/C22H28O8/c1-7-9(2)20(25)30-18-16-11(4)21(26)29-17(16)15-10(3)14(24)8-13(15)22(6,27)19(18)28-12(5)23/h7,13-14,16-19,24,27H,4,8H2,1-3,5-6H3/b9-7+/t13-,14-,16+,17-,18-,19-,22+/m1/s1
InChI Key YKMGQINTLWXISC-YASIBEGASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28O8
Molecular Weight 420.50 g/mol
Exact Mass 420.17841785 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 0.50
Atomic LogP (AlogP) 1.36
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4R,5R,6S,6aR,8R,9bS)-5-acetyloxy-6,8-dihydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-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 + 0.9850 98.50%
Caco-2 - 0.5517 55.17%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.5684 56.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8400 84.00%
OATP1B3 inhibitior + 0.8912 89.12%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.7299 72.99%
P-glycoprotein inhibitior - 0.4664 46.64%
P-glycoprotein substrate - 0.6347 63.47%
CYP3A4 substrate + 0.6448 64.48%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9069 90.69%
CYP3A4 inhibition - 0.6464 64.64%
CYP2C9 inhibition - 0.8280 82.80%
CYP2C19 inhibition - 0.8525 85.25%
CYP2D6 inhibition - 0.9437 94.37%
CYP1A2 inhibition - 0.7047 70.47%
CYP2C8 inhibition - 0.6930 69.30%
CYP inhibitory promiscuity - 0.9488 94.88%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4825 48.25%
Eye corrosion - 0.9749 97.49%
Eye irritation - 0.8667 86.67%
Skin irritation - 0.5697 56.97%
Skin corrosion - 0.8804 88.04%
Ames mutagenesis - 0.6678 66.78%
Human Ether-a-go-go-Related Gene inhibition - 0.4861 48.61%
Micronuclear - 0.5700 57.00%
Hepatotoxicity + 0.7033 70.33%
skin sensitisation - 0.7383 73.83%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.5795 57.95%
Acute Oral Toxicity (c) III 0.3717 37.17%
Estrogen receptor binding + 0.7267 72.67%
Androgen receptor binding + 0.5738 57.38%
Thyroid receptor binding + 0.5169 51.69%
Glucocorticoid receptor binding + 0.6715 67.15%
Aromatase binding - 0.5070 50.70%
PPAR gamma + 0.6597 65.97%
Honey bee toxicity - 0.6300 63.00%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9382 93.82%

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 97.76% 91.11%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 94.18% 95.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.61% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 92.45% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.20% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.43% 97.25%
CHEMBL2581 P07339 Cathepsin D 88.06% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 87.37% 97.79%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.26% 93.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.11% 91.07%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.09% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.46% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.26% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.61% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 84.70% 91.19%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.07% 99.23%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 82.64% 89.34%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.10% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.69% 94.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.01% 96.95%

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.
Anthemis cretica subsp. carpatica

Cross-Links

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PubChem 101047221
LOTUS LTS0099582
wikiData Q105349775