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(E)-2-Methyl-2-butenoic acid (3R)-6,7-(carbonyloxy)-9beta-[(S)-[(3R)-2,7-dioxo-3alpha,9-dimethyl-4alpha-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3alpha,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4alpha-yl ester

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 9b37287e-8cdb-418b-a955-08dac3a72979
Taxonomy Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
IUPAC Name [(1S,2R,5R,6R,7R,14S)-14-[(S)-[(3R,3aR,4R,9aS,9bR)-3,9-dimethyl-4-[(E)-2-methylbut-2-enoyl]oxy-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-6-yl]-hydroxymethyl]-5,14-dimethyl-4,10-dioxo-3,11-dioxatetracyclo[7.5.1.02,6.012,15]pentadeca-9(15),12-dien-7-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC2=C3C(C4C1C(C(=O)O4)C)C(C=C3OC2=O)(C)C(C5=C6C(C7C(C(C(=O)O7)C)C(C5)OC(=O)C(=CC)C)C(=CC6=O)C)O
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H]1CC2=C3[C@@H]([C@@H]4[C@@H]1[C@H](C(=O)O4)C)[C@](C=C3OC2=O)(C)[C@@H](C5=C6[C@@H]([C@@H]7[C@H]([C@H](C(=O)O7)C)[C@@H](C5)OC(=O)/C(=C/C)/C)C(=CC6=O)C)O
InChI InChI=1S/C40H44O12/c1-9-15(3)35(43)48-23-12-20(29-22(41)11-17(5)26(29)32-27(23)18(6)37(45)51-32)34(42)40(8)14-25-30-21(39(47)50-25)13-24(49-36(44)16(4)10-2)28-19(7)38(46)52-33(28)31(30)40/h9-11,14,18-19,23-24,26-28,31-34,42H,12-13H2,1-8H3/b15-9+,16-10+/t18-,19-,23-,24-,26+,27-,28-,31+,32-,33+,34-,40-/m1/s1
InChI Key RKYYJTTWXWMMIE-NPCVJFMNSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C40H44O12
Molecular Weight 716.80 g/mol
Exact Mass 716.28327683 g/mol
Topological Polar Surface Area (TPSA) 169.00 Ų
XlogP 3.40
Atomic LogP (AlogP) 4.08
H-Bond Acceptor 12
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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[[(S)-[(3R,3aR,4R,9aS,9bR)-3,9-dimethyl-4-[(E)-2-methylbut-2-enoyl]oxy-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-6-yl]-hydroxy-methyl]-dimethyl-dioxo-[?]yl] (E)-2-methylbut-2-enoate

2D Structure

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2D Structure of (E)-2-Methyl-2-butenoic acid (3R)-6,7-(carbonyloxy)-9beta-[(S)-[(3R)-2,7-dioxo-3alpha,9-dimethyl-4alpha-(tigloyloxy)-2,3,3abeta,4,5,7,9abeta,9balpha-octahydroazuleno[4,5-b]furan-6-yl]hydroxymethyl]-2-oxo-3alpha,9-dimethyl-2,3,3abeta,4,5,9,9abeta,9balpha-octahydroazuleno[4,5-b]furan-4alpha-yl ester

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9849 98.49%
Caco-2 - 0.8288 82.88%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7224 72.24%
OATP2B1 inhibitior + 0.5783 57.83%
OATP1B1 inhibitior + 0.8451 84.51%
OATP1B3 inhibitior + 0.8573 85.73%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.8703 87.03%
P-glycoprotein inhibitior + 0.8394 83.94%
P-glycoprotein substrate + 0.6326 63.26%
CYP3A4 substrate + 0.6993 69.93%
CYP2C9 substrate - 0.8000 80.00%
CYP2D6 substrate - 0.9000 90.00%
CYP3A4 inhibition - 0.7620 76.20%
CYP2C9 inhibition - 0.8159 81.59%
CYP2C19 inhibition - 0.8926 89.26%
CYP2D6 inhibition - 0.9613 96.13%
CYP1A2 inhibition - 0.7557 75.57%
CYP2C8 inhibition + 0.5696 56.96%
CYP inhibitory promiscuity - 0.9142 91.42%
UGT catelyzed - 0.9000 90.00%
Carcinogenicity (binary) - 0.9368 93.68%
Carcinogenicity (trinary) Danger 0.4567 45.67%
Eye corrosion - 0.9644 96.44%
Eye irritation - 0.9152 91.52%
Skin irritation - 0.6220 62.20%
Skin corrosion - 0.8703 87.03%
Ames mutagenesis + 0.5146 51.46%
Human Ether-a-go-go-Related Gene inhibition + 0.6890 68.90%
Micronuclear - 0.5100 51.00%
Hepatotoxicity + 0.6836 68.36%
skin sensitisation - 0.7292 72.92%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.6875 68.75%
Acute Oral Toxicity (c) III 0.3931 39.31%
Estrogen receptor binding + 0.8320 83.20%
Androgen receptor binding + 0.7765 77.65%
Thyroid receptor binding + 0.5465 54.65%
Glucocorticoid receptor binding + 0.8349 83.49%
Aromatase binding + 0.6575 65.75%
PPAR gamma + 0.7462 74.62%
Honey bee toxicity - 0.6192 61.92%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.8541 85.41%

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 98.78% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.89% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.75% 94.45%
CHEMBL2265 P23141 Acyl coenzyme A:cholesterol acyltransferase 93.07% 85.94%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.20% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.09% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.23% 99.23%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 90.23% 94.80%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 87.07% 96.47%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.44% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 83.53% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.33% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.74% 99.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.00% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.71% 89.00%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 81.26% 83.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.33% 93.56%

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.
Hunteria zeylanica
Pseudognaphalium affine
Vernonia pachyclada

Cross-Links

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PubChem 53231631
NPASS NPC173972