[(3aS,4R,5R,6E,9S,10E,11aR)-5-acetyloxy-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID 06989d9c-5adf-49b9-9cfd-fb0ba74e54ca
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4R,5R,6E,9S,10E,11aR)-5-acetyloxy-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(C=C(C(CC=C(C1OC(=O)C)C)O)C)OC(=O)C2=C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1[C@@H]2[C@@H](/C=C(/[C@H](C/C=C(/[C@H]1OC(=O)C)\C)O)\C)OC(=O)C2=C
InChI InChI=1S/C22H28O7/c1-7-11(2)21(25)29-20-18-14(5)22(26)28-17(18)10-13(4)16(24)9-8-12(3)19(20)27-15(6)23/h7-8,10,16-20,24H,5,9H2,1-4,6H3/b11-7-,12-8+,13-10+/t16-,17+,18-,19+,20+/m0/s1
InChI Key NFWWXOKMAAKPNX-GGNPVZBNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28O7
Molecular Weight 404.50 g/mol
Exact Mass 404.18350323 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 2.00
Atomic LogP (AlogP) 2.55
H-Bond Acceptor 7
H-Bond Donor 1
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,6E,9S,10E,11aR)-5-acetyloxy-9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-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 + 0.9879 98.79%
Caco-2 + 0.6555 65.55%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.5544 55.44%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8753 87.53%
OATP1B3 inhibitior + 0.9141 91.41%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior + 0.6932 69.32%
P-glycoprotein inhibitior + 0.6402 64.02%
P-glycoprotein substrate - 0.6795 67.95%
CYP3A4 substrate + 0.6040 60.40%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9014 90.14%
CYP3A4 inhibition - 0.8250 82.50%
CYP2C9 inhibition - 0.9532 95.32%
CYP2C19 inhibition - 0.8871 88.71%
CYP2D6 inhibition - 0.9474 94.74%
CYP1A2 inhibition - 0.7654 76.54%
CYP2C8 inhibition - 0.7559 75.59%
CYP inhibitory promiscuity - 0.9528 95.28%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5323 53.23%
Eye corrosion - 0.9397 93.97%
Eye irritation - 0.8592 85.92%
Skin irritation - 0.5997 59.97%
Skin corrosion - 0.9207 92.07%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4590 45.90%
Micronuclear - 0.5700 57.00%
Hepatotoxicity + 0.6500 65.00%
skin sensitisation - 0.7181 71.81%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.5886 58.86%
Acute Oral Toxicity (c) IV 0.3704 37.04%
Estrogen receptor binding + 0.6404 64.04%
Androgen receptor binding - 0.5698 56.98%
Thyroid receptor binding - 0.5191 51.91%
Glucocorticoid receptor binding + 0.6184 61.84%
Aromatase binding - 0.6578 65.78%
PPAR gamma + 0.6009 60.09%
Honey bee toxicity - 0.6480 64.80%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9079 90.79%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.97% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.82% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.11% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.85% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.43% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.15% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 85.86% 94.73%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 84.15% 81.11%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.89% 93.03%
CHEMBL2581 P07339 Cathepsin D 82.76% 98.95%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.36% 97.21%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.15% 94.00%

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.
Balsamorhiza sagittata
Isodon lophanthoides

Cross-Links

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PubChem 162992084
LOTUS LTS0152165
wikiData Q105366395