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18172-33-3

AlkaPlorer ID: AK043781

Synonym: 'Iso-α-cyclopiazonic acid'

IUPAC Name: (2R,3S,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.02,9.03,7.015,18]octadeca-1(17),4,11(18),12,14-pentaen-6-one

Structure

SMILES: CC(=O)C1=C(O)[C@@H]2[C@H]3C4=CNC5=C4C(=CC=C5)C[C@H]3C(C)(C)N2C1=O

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InChI: InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1

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InChIKey: SZINUGQCTHLQAZ-DQYPLSBCSA-N

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Source

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

Properties Information

Molecule Weight: 336.3910000000001

TPSA？: 73.4

MolLogP？: 2.8279000000000014

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 56234.1 nM None
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 89125.1 nM None
Cavia porcellus Ileum Activity 52.3 % 10.1021/np060073h
Electrophorus electricus Acetylcholinesterase Inhibition -13.39 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 6.85 % 10.1016/j.bmc.2012.09.040
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 35481.3 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 44668.4 nM None
Homo sapiens H4 Activity 30.54 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 33.06 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 41.44 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 96.32 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 96.45 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 97.66 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 103.58 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 112.62 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 162.66 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 178.53 % 10.1073/pnas.0709695104
Homo sapiens H4 Activity 186.44 % 10.1073/pnas.0709695104
Homo sapiens HeLa S3 Activity nan None 10.1016/j.bmcl.2015.09.044
Homo sapiens Histone deacetylase 6 Inhibition -1.23 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 2.95 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 25118.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 8912.5 nM None
Homo sapiens Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 Ki 1800.0 nM 10.1016/j.bmcl.2017.12.050
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 5804.8 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 8313.2 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 10465.7 nM None
Homo sapiens Vitamin D receptor Potency 56234.1 nM None
Plasmodium falciparum Plasmodium falciparum IC50 3240.0 nM 10.1126/science.1193225
Plasmodium falciparum Plasmodium falciparum IC50 3417.0 nM 10.1126/science.1193225
Plasmodium falciparum Plasmodium falciparum IC50 3460.0 nM 10.1126/science.1193225
Plasmodium falciparum Plasmodium falciparum IC50 4160.0 nM 10.1126/science.1193225
Plasmodium falciparum Plasmodium falciparum IC50 4900.0 nM 10.1016/j.bmcl.2017.12.050
Plasmodium falciparum Plasmodium falciparum IC50 8800.0 nM 10.1016/j.bmcl.2017.12.050
Rattus norvegicus Rattus norvegicus LC50 30.0 mg kg-1 10.1016/j.bmc.2008.02.069
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition -0.2776 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.89 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 2.4 % 10.6019/CHEMBL4495565
None Unchecked IC50 10.0 nM 10.1016/j.bmc.2011.06.001
None Unchecked IC50 120.0 nM 10.1016/j.bmc.2008.12.010
None Unchecked Potency 12589.3 nM None

Metabolism Information