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Isopenicin A

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 9c2eb1d7-17c7-4965-95bc-fc3f8aab5347
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesterterpenoids > Cheilanthane sesterterpenoids
IUPAC Name methyl (5R)-2-[(2R)-2-[(3S,5R,8S,9R,10S,13R,14R,16R)-3-acetyloxy-10-formyl-14-methoxycarbonyl-4,4,8,12,13,16-hexamethyl-15,17-dioxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthren-16-yl]propyl]-5-[(1E,3E)-hexa-1,3-dienyl]-5-methyl-4-oxofuran-3-carboxylate
SMILES (Canonical) CCC=CC=CC1(C(=O)C(=C(O1)CC(C)C2(C(=O)C3(C(=CC4C(C3(C2=O)C(=O)OC)(CCC5C4(CCC(C5(C)C)OC(=O)C)C=O)C)C)C)C)C(=O)OC)C
SMILES (Isomeric) CC/C=C/C=C/[C@@]1(C(=O)C(=C(O1)C[C@@H](C)[C@@]2(C(=O)[C@@]3(C(=C[C@@H]4[C@@]([C@@]3(C2=O)C(=O)OC)(CC[C@H]5[C@]4(CC[C@@H](C5(C)C)OC(=O)C)C=O)C)C)C)C)C(=O)OC)C
InChI InChI=1S/C44H58O11/c1-13-14-15-16-19-40(8)33(47)32(34(48)52-11)28(55-40)22-25(2)41(9)35(49)42(10)26(3)23-30-39(7,44(42,36(41)50)37(51)53-12)20-17-29-38(5,6)31(54-27(4)46)18-21-43(29,30)24-45/h14-16,19,23-25,29-31H,13,17-18,20-22H2,1-12H3/b15-14+,19-16+/t25-,29-,30-,31+,39+,40-,41-,42+,43+,44-/m1/s1
InChI Key IPRUCLFQELTKPQ-KUKUZQMVSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C44H58O11
Molecular Weight 762.90 g/mol
Exact Mass 762.39791266 g/mol
Topological Polar Surface Area (TPSA) 156.00 Ų
XlogP 6.90
Atomic LogP (AlogP) 6.57
H-Bond Acceptor 11
H-Bond Donor 0
Rotatable Bonds 10

Synonyms

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Methyl (5R)-2-((2R)-2-((1R,2S,5S,7R,10S,11R,13R,15R)-5-(acetyloxy)-2-formyl-11-(methoxycarbonyl)-6,6,10,13,15,16-hexamethyl-12,14-dioxotetracyclo(8.7.0.0,.0,)heptadec-16-en-13-yl)propyl)-5-((1E,3E)-hexa-1,3-dien-1-yl)-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid
methyl (5R)-2-((2R)-2-((3S,5R,8S,9R,10S,13R,14R,16R)-3-acetyloxy-10-formyl-14-methoxycarbonyl-4,4,8,12,13,16-hexamethyl-15,17-dioxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta(a)phenanthren-16-yl)propyl)-5-((1E,3E)-hexa-1,3-dienyl)-5-methyl-4-oxofuran-3-carboxylate
Methyl (5R)-2-[(2R)-2-[(1R,2S,5S,7R,10S,11R,13R,15R)-5-(acetyloxy)-2-formyl-11-(methoxycarbonyl)-6,6,10,13,15,16-hexamethyl-12,14-dioxotetracyclo[8.7.0.0,.0,]heptadec-16-en-13-yl]propyl]-5-[(1E,3E)-hexa-1,3-dien-1-yl]-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid
methyl (5R)-2-[(2R)-2-[(3S,5R,8S,9R,10S,13R,14R,16R)-3-acetyloxy-10-formyl-14-methoxycarbonyl-4,4,8,12,13,16-hexamethyl-15,17-dioxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthren-16-yl]propyl]-5-[(1E,3E)-hexa-1,3-dienyl]-5-methyl-4-oxofuran-3-carboxylate
RefChem:149704
CHEMBL5278189
CHEBI:209347
methyl (5R)-2-[(2R)-2-[(3S,5R,8S,9R,10S,13R,14R,16R)-3-acetyloxy-10-ormyl-14-methoxycarbonyl-4,4,8,12,13,16-hexamethyl-15,17-dioxo-2,3,5,6,7,9-hexahydro-1H-cyclopenta[a]phenanthren-16-yl]propyl]-5-[(1E,3E)-hexa-1,3-dienyl]-5-methyl-4-oxouran-3-carboxylate

2D Structure

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2D Structure of Isopenicin A

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9949 99.49%
Caco-2 - 0.8241 82.41%
Blood Brain Barrier + 0.8750 87.50%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6755 67.55%
OATP2B1 inhibitior + 0.5505 55.05%
OATP1B1 inhibitior + 0.7561 75.61%
OATP1B3 inhibitior + 0.9349 93.49%
MATE1 inhibitior - 0.7200 72.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.9901 99.01%
P-glycoprotein inhibitior + 0.8257 82.57%
P-glycoprotein substrate + 0.6779 67.79%
CYP3A4 substrate + 0.7351 73.51%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9007 90.07%
CYP3A4 inhibition - 0.5070 50.70%
CYP2C9 inhibition - 0.7852 78.52%
CYP2C19 inhibition - 0.6514 65.14%
CYP2D6 inhibition - 0.9331 93.31%
CYP1A2 inhibition - 0.7930 79.30%
CYP2C8 inhibition + 0.8225 82.25%
CYP inhibitory promiscuity - 0.6599 65.99%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5758 57.58%
Eye corrosion - 0.9885 98.85%
Eye irritation - 0.9095 90.95%
Skin irritation - 0.5928 59.28%
Skin corrosion - 0.9344 93.44%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6482 64.82%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.6323 63.23%
skin sensitisation - 0.8115 81.15%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.6499 64.99%
Acute Oral Toxicity (c) III 0.4930 49.30%
Estrogen receptor binding + 0.7924 79.24%
Androgen receptor binding + 0.7556 75.56%
Thyroid receptor binding + 0.6590 65.90%
Glucocorticoid receptor binding + 0.8183 81.83%
Aromatase binding + 0.7082 70.82%
PPAR gamma + 0.7701 77.01%
Honey bee toxicity - 0.7116 71.16%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity + 0.9956 99.56%

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
CHEMBL4072 P07858 Cathepsin B 97.90% 93.67%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.16% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.56% 94.45%
CHEMBL261 P00915 Carbonic anhydrase I 96.40% 96.76%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.87% 91.11%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 93.70% 91.07%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.40% 97.09%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 88.06% 92.62%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.99% 99.23%
CHEMBL2581 P07339 Cathepsin D 87.33% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.15% 95.89%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 84.82% 96.38%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 84.63% 95.71%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.58% 94.33%
CHEMBL340 P08684 Cytochrome P450 3A4 84.48% 91.19%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 83.91% 92.88%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 82.86% 89.34%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.80% 97.14%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 82.13% 91.65%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 81.97% 91.24%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 81.54% 96.90%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 81.26% 96.47%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 81.01% 95.71%
CHEMBL3401 O75469 Pregnane X receptor 80.75% 94.73%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.02% 96.77%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 146683135
LOTUS LTS0010892
wikiData Q105117455