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Paxilline

AlkaPlorer ID: AK028868

Synonym: None

IUPAC Name: (1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one

Structure

SMILES: CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C(NC6=CC=CC=C56)[C@@]43C)C2=CC1=O

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InChI: InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1

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InChIKey: ACNHBCIZLNNLRS-UBGQALKQSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Aspergillus striatus Aspergillus Aspergillaceae Eurotiales Eurotiomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 435.56400000000014

TPSA？: 82.54999999999998

MolLogP？: 3.9567000000000014

Number of H-Donors: 3

Number of H-Acceptors: 4

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Caenorhabditis elegans Cytoplasmic zinc-finger protein EC50 16719.0 nM None
Caenorhabditis elegans Zinc finger protein mex-5 EC50 12272.0 nM None
Cavia porcellus Ileum Activity 2.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 9.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 11.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 118.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 121.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity 126.0 % 10.1021/np50073a020
Cavia porcellus Ileum Activity nan None 10.1021/np50073a020
Homo sapiens Ataxin-2 Potency 44668.4 nM None
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 35481.3 nM None
Homo sapiens DNA dC->dU-editing enzyme APOBEC-3F Potency 31622.8 nM None
Homo sapiens Geminin Potency 730.8 nM None
Homo sapiens Geminin Potency 2059.6 nM None
Homo sapiens Glucagon-like peptide 1 receptor Potency 14125.4 nM None
Homo sapiens H4 Activity 52.37 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 56.82 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 100.56 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 102.35 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 106.27 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 112.34 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 119.79 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 162.66 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 185.52 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 205.83 % 10.1073/pnas.0709695104
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 31622.8 nM None
Homo sapiens Histone-lysine N-methyltransferase MLL Potency 39810.7 nM None
Homo sapiens Huntingtin Potency 31622.8 nM None
Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Potency 16360.1 nM None
Homo sapiens Lysine-specific demethylase 4A Potency 56234.1 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 25118.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens Mothers against decapentaplegic homolog 3 Potency 35481.3 nM None
Homo sapiens Neuropeptide S receptor Potency 10000.0 nM None
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 35481.3 nM None
Homo sapiens Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 IC50 5000.0 nM 10.1021/acs.jmedchem.9b01509
Homo sapiens Sarcoplasmic/endoplasmic reticulum calcium ATPase 3 IC50 5000.0 nM 10.1021/acs.jmedchem.9b01509
Homo sapiens TAR DNA-binding protein 43 Potency 22387.2 nM None
Homo sapiens Tumor susceptibility gene 101 protein Potency 25118.9 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 20596.2 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 23109.3 nM None
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 17700.0 nM 10.1021/np400304q
Mus musculus Mus musculus ED50 25.0 mg.kg-1 10.1021/np50073a020
Oryctolagus cuniculus Sarcoplasmic/endoplasmic reticulum calcium ATP-ase IC50 5000.0 nM 10.1021/acs.jmedchem.9b01509
Plasmodium falciparum Plasmodium falciparum Potency 11689.1 nM None
Saccharomyces cerevisiae Saccharomyces cerevisiae Potency 35481.3 nM None
Saccharomyces cerevisiae S288c Mitochondrial import inner membrane translocase subunit TIM10 IC50 33550.0 nM None
None Unchecked CC50 40000.0 nM None
None Unchecked EC50 110000.0 nM None
None Unchecked IC50 5000.0 nM 10.1016/j.bmc.2020.115609
None Unchecked IC50 5000.0 nM 10.1021/acs.jmedchem.9b01509
None Unchecked IC50 42160.0 nM None
None Unchecked IC50 48710.0 nM None
None Unchecked Potency 6513.1 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Potency 16360.1 nM None
None Unchecked Potency 35481.3 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT004976 CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O>>CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O RXN-15501
AKRT004980 CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O.CC(C)=CCOP(=O)(O)OP(=O)(O)O.CC(C)=CCOP(=O)(O)OP(=O)(O)O>>CC(C)=CCc1cc2[nH]c3c(c2cc1CC=C(C)C)C[C@@H]1CC[C@@]2(O)C4=CC(=O)[C@@H](C(C)(C)O)O[C@H]4CC[C@]2(C)[C@@]31C RXN-15502
AKRT004981 CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O>>CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=C[C@H]1O R10410