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[(4R,4aR,5R,6S,8aS,9S,9aR)-4-hydroxy-9a-methoxy-3,4a,5-trimethyl-9-(3-methylbut-2-enoyloxy)-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-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 50a4313e-6927-421e-a32d-df9b5710dd80
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name [(4R,4aR,5R,6S,8aS,9S,9aR)-4-hydroxy-9a-methoxy-3,4a,5-trimethyl-9-(3-methylbut-2-enoyloxy)-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CCC2C(C3(C(=C(C(=O)O3)C)C(C2(C1C)C)O)OC)OC(=O)C=C(C)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1CC[C@@H]2[C@@H]([C@]3(C(=C(C(=O)O3)C)[C@@H]([C@@]2([C@H]1C)C)O)OC)OC(=O)C=C(C)C
InChI InChI=1S/C26H36O8/c1-9-14(4)23(29)32-18-11-10-17-22(33-19(27)12-13(2)3)26(31-8)20(15(5)24(30)34-26)21(28)25(17,7)16(18)6/h9,12,16-18,21-22,28H,10-11H2,1-8H3/b14-9-/t16-,17+,18-,21-,22-,25+,26+/m0/s1
InChI Key PRVPRVWGQQSUNW-WIERWUJKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H36O8
Molecular Weight 476.60 g/mol
Exact Mass 476.24101810 g/mol
Topological Polar Surface Area (TPSA) 108.00 Ų
XlogP 3.60
Atomic LogP (AlogP) 3.39
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(4R,4aR,5R,6S,8aS,9S,9aR)-4-hydroxy-9a-methoxy-3,4a,5-trimethyl-9-(3-methylbut-2-enoyloxy)-2-oxo-5,6,7,8,8a,9-hexahydro-4H-benzo[f][1]benzofuran-6-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 + 0.9820 98.20%
Caco-2 - 0.5811 58.11%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7973 79.73%
OATP2B1 inhibitior - 0.8587 85.87%
OATP1B1 inhibitior + 0.8619 86.19%
OATP1B3 inhibitior + 0.9083 90.83%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.9091 90.91%
P-glycoprotein inhibitior + 0.7760 77.60%
P-glycoprotein substrate - 0.5459 54.59%
CYP3A4 substrate + 0.6995 69.95%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8947 89.47%
CYP3A4 inhibition - 0.7389 73.89%
CYP2C9 inhibition - 0.8005 80.05%
CYP2C19 inhibition - 0.8493 84.93%
CYP2D6 inhibition - 0.9025 90.25%
CYP1A2 inhibition - 0.5344 53.44%
CYP2C8 inhibition + 0.5239 52.39%
CYP inhibitory promiscuity - 0.8080 80.80%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Danger 0.4439 44.39%
Eye corrosion - 0.9858 98.58%
Eye irritation - 0.8940 89.40%
Skin irritation - 0.5358 53.58%
Skin corrosion - 0.8633 86.33%
Ames mutagenesis - 0.5596 55.96%
Human Ether-a-go-go-Related Gene inhibition - 0.3965 39.65%
Micronuclear - 0.6600 66.00%
Hepatotoxicity + 0.6419 64.19%
skin sensitisation - 0.7857 78.57%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.7881 78.81%
Acute Oral Toxicity (c) III 0.5550 55.50%
Estrogen receptor binding + 0.8275 82.75%
Androgen receptor binding + 0.6799 67.99%
Thyroid receptor binding + 0.6931 69.31%
Glucocorticoid receptor binding + 0.8351 83.51%
Aromatase binding + 0.6934 69.34%
PPAR gamma + 0.7310 73.10%
Honey bee toxicity - 0.5584 55.84%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9289 92.89%

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 97.84% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.47% 95.56%
CHEMBL2581 P07339 Cathepsin D 92.62% 98.95%
CHEMBL240 Q12809 HERG 92.16% 89.76%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.05% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.38% 94.45%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.27% 97.14%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.87% 92.94%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.79% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 87.64% 91.19%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 87.58% 91.07%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 86.71% 81.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.37% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.23% 89.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.74% 93.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.65% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.35% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 81.86% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.55% 99.23%
CHEMBL221 P23219 Cyclooxygenase-1 80.59% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.00% 95.89%

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.
Farfugium japonicum

Cross-Links

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PubChem 163186648
LOTUS LTS0157569
wikiData Q105213934