[(E)-2-[(3S,4R,5S,7S)-7-hydroxy-5-methyl-5-(4-methylpent-3-enyl)-3-(2-oxopropyl)-3,4,6,7-tetrahydro-1H-2-benzofuran-4-yl]ethenyl] 3-methylbut-2-enoate

Details

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Internal ID 3903d3b2-33f6-4e07-9998-67264d99e72a
Taxonomy Organoheterocyclic compounds > Isobenzofurans
IUPAC Name [(E)-2-[(3S,4R,5S,7S)-7-hydroxy-5-methyl-5-(4-methylpent-3-enyl)-3-(2-oxopropyl)-3,4,6,7-tetrahydro-1H-2-benzofuran-4-yl]ethenyl] 3-methylbut-2-enoate
SMILES (Canonical) CC(=CCCC1(CC(C2=C(C1C=COC(=O)C=C(C)C)C(OC2)CC(=O)C)O)C)C
SMILES (Isomeric) CC(=CCC[C@]1(C[C@@H](C2=C([C@@H]1/C=C/OC(=O)C=C(C)C)[C@@H](OC2)CC(=O)C)O)C)C
InChI InChI=1S/C25H36O5/c1-16(2)8-7-10-25(6)14-21(27)19-15-30-22(13-18(5)26)24(19)20(25)9-11-29-23(28)12-17(3)4/h8-9,11-12,20-22,27H,7,10,13-15H2,1-6H3/b11-9+/t20-,21-,22-,25-/m0/s1
InChI Key DOUGJCUAIIVOOP-XFTRUYOKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H36O5
Molecular Weight 416.50 g/mol
Exact Mass 416.25627424 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 3.20
Atomic LogP (AlogP) 4.82
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 8

Synonyms

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DTXSID201100152
(1E)-2-[(3S,4R,5S,7S)-1,3,4,5,6,7-Hexahydro-7-hydroxy-5-methyl-5-(4-methyl-3-penten-1-yl)-3-(2-oxopropyl)-4-isobenzofuranyl]ethenyl 3-methyl-2-butenoate
205514-80-3

2D Structure

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2D Structure of [(E)-2-[(3S,4R,5S,7S)-7-hydroxy-5-methyl-5-(4-methylpent-3-enyl)-3-(2-oxopropyl)-3,4,6,7-tetrahydro-1H-2-benzofuran-4-yl]ethenyl] 3-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 + 0.9926 99.26%
Caco-2 + 0.5592 55.92%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.8782 87.82%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8593 85.93%
OATP1B3 inhibitior + 0.9285 92.85%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5364 53.64%
BSEP inhibitior + 0.9030 90.30%
P-glycoprotein inhibitior + 0.7680 76.80%
P-glycoprotein substrate + 0.5082 50.82%
CYP3A4 substrate + 0.6514 65.14%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9019 90.19%
CYP3A4 inhibition - 0.6161 61.61%
CYP2C9 inhibition - 0.5553 55.53%
CYP2C19 inhibition - 0.8750 87.50%
CYP2D6 inhibition - 0.9487 94.87%
CYP1A2 inhibition - 0.6676 66.76%
CYP2C8 inhibition + 0.4682 46.82%
CYP inhibitory promiscuity - 0.8671 86.71%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5843 58.43%
Eye corrosion - 0.9882 98.82%
Eye irritation - 0.9439 94.39%
Skin irritation + 0.5345 53.45%
Skin corrosion - 0.9399 93.99%
Ames mutagenesis + 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8457 84.57%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.8692 86.92%
Respiratory toxicity - 0.6000 60.00%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity - 0.6359 63.59%
Acute Oral Toxicity (c) III 0.4937 49.37%
Estrogen receptor binding + 0.6980 69.80%
Androgen receptor binding + 0.5231 52.31%
Thyroid receptor binding + 0.6435 64.35%
Glucocorticoid receptor binding + 0.8350 83.50%
Aromatase binding + 0.6090 60.90%
PPAR gamma + 0.6404 64.04%
Honey bee toxicity - 0.7058 70.58%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.5155 51.55%
Fish aquatic toxicity + 0.9914 99.14%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.50% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.11% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.81% 94.45%
CHEMBL2581 P07339 Cathepsin D 84.36% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.21% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 82.02% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.77% 99.17%
CHEMBL3430907 Q96GD4 Aurora kinase B/Inner centromere protein 81.64% 97.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.53% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 81.38% 90.17%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.75% 94.33%

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.
Berberis japonica
Isodon nervosus
Isodon xerophilus
Lonicera macrantha

Cross-Links

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PubChem 10645581
NPASS NPC113472