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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] 2-methylpropanoate

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 b63c0b42-2896-48f1-94c2-3eafc17b0724
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] 2-methylpropanoate
SMILES (Canonical) CC1=C2C(CC1O)C(C(C(C3C2OC(=O)C3=C)OC(=O)C(C)C)OC(=O)C)(C)O
SMILES (Isomeric) CC1=C2[C@@H](C[C@H]1O)[C@]([C@@H]([C@@H]([C@@H]3[C@@H]2OC(=O)C3=C)OC(=O)C(C)C)OC(=O)C)(C)O
InChI InChI=1S/C21H28O8/c1-8(2)19(24)29-17-15-10(4)20(25)28-16(15)14-9(3)13(23)7-12(14)21(6,26)18(17)27-11(5)22/h8,12-13,15-18,23,26H,4,7H2,1-3,5-6H3/t12-,13-,15+,16-,17-,18-,21+/m1/s1
InChI Key COXOHTLJKLXHPR-SHTDPRGMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H28O8
Molecular Weight 408.40 g/mol
Exact Mass 408.17841785 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 0.30
Atomic LogP (AlogP) 1.05
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] 2-methylpropanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9863 98.63%
Caco-2 - 0.6036 60.36%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6138 61.38%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8601 86.01%
OATP1B3 inhibitior + 0.8706 87.06%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.8714 87.14%
P-glycoprotein inhibitior - 0.5206 52.06%
P-glycoprotein substrate - 0.6659 66.59%
CYP3A4 substrate + 0.6364 63.64%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8903 89.03%
CYP3A4 inhibition - 0.6566 65.66%
CYP2C9 inhibition - 0.7666 76.66%
CYP2C19 inhibition - 0.8213 82.13%
CYP2D6 inhibition - 0.9302 93.02%
CYP1A2 inhibition - 0.7300 73.00%
CYP2C8 inhibition - 0.7289 72.89%
CYP inhibitory promiscuity - 0.9343 93.43%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.4963 49.63%
Eye corrosion - 0.9754 97.54%
Eye irritation - 0.8133 81.33%
Skin irritation - 0.5992 59.92%
Skin corrosion - 0.8861 88.61%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5668 56.68%
Micronuclear - 0.6300 63.00%
Hepatotoxicity + 0.7461 74.61%
skin sensitisation - 0.6939 69.39%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.5000 50.00%
Acute Oral Toxicity (c) III 0.4080 40.80%
Estrogen receptor binding + 0.7560 75.60%
Androgen receptor binding + 0.6203 62.03%
Thyroid receptor binding - 0.5484 54.84%
Glucocorticoid receptor binding + 0.5597 55.97%
Aromatase binding - 0.5249 52.49%
PPAR gamma + 0.6483 64.83%
Honey bee toxicity - 0.6395 63.95%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.9560 95.60%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.76% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.63% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.74% 85.14%
CHEMBL2996 Q05655 Protein kinase C delta 95.11% 97.79%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.72% 94.45%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 94.07% 95.50%
CHEMBL2581 P07339 Cathepsin D 92.69% 98.95%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 90.98% 96.47%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.85% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.36% 95.56%
CHEMBL299 P17252 Protein kinase C alpha 89.14% 98.03%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.99% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 88.75% 90.17%
CHEMBL340 P08684 Cytochrome P450 3A4 87.76% 91.19%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.74% 92.62%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 84.22% 98.75%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.86% 91.07%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 82.79% 95.71%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.51% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.36% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.56% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.92% 94.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.48% 97.14%

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 101047220
LOTUS LTS0262682
wikiData Q104967360