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Valinomycin

AlkaPlorer ID: AK003303

Synonym: None

IUPAC Name: (3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nona(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone

Structure

SMILES: CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O

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InChI: InChI=1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1

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InChIKey: FCFNRCROJUBPLU-DNDCDFAISA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
None Bacillus Bacillidae Phasmatodea Insecta Arthropoda Metazoa Eukaryota

Properties Information

Molecule Weight: 1111.3379999999995

TPSA？: 332.3999999999999

MolLogP？: 2.343300000000008

Number of H-Donors: 6

Number of H-Acceptors: 18

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacteria Cell membrane Activity nan None 10.1016/j.bmcl.2023.129210
Chlorocebus sabaeus Vero CC50 67500.0 nM 10.1021/jm070295s
Chlorocebus sabaeus Vero C1008 CC50 68000.0 nM 10.1021/acs.jmedchem.0c00626
Electrophorus electricus Acetylcholinesterase Inhibition 16.65 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition -1.5 % 10.1016/j.bmc.2012.09.040
Escherichia coli Escherichia coli Activity nan None 10.1021/acs.jmedchem.7b00453
Homo sapiens A2780 Activity nan None 10.1021/ml400300q
Homo sapiens A2780 IC50 2180.0 nM 10.1021/ml400300q
Homo sapiens A2780 Ratio IC50 3.0 None 10.1021/ml400300q
Homo sapiens Bile salt export pump Activity nan None 10.1023/a:1023278211849
Homo sapiens Bile salt export pump IC50 1560.0 nM 10.1093/toxsci/kft176
Homo sapiens Bile salt export pump IC50 1600.0 nM 10.1093/toxsci/kfq269
Homo sapiens Bile salt export pump IC50 7200.0 nM 10.1023/a:1023278211849
Homo sapiens BXPC-3 GI50 0.0019 ug.mL-1 10.1021/np800603u
Homo sapiens Canalicular multispecific organic anion transporter 1 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Canalicular multispecific organic anion transporter 2 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens DU-145 GI50 0.0035 ug.mL-1 10.1021/np800603u
Homo sapiens HEK-293T Activity nan None 10.1021/jm200364n
Homo sapiens HeLa IC50 1.0 nM 10.1021/jm061162u
Homo sapiens HepG2 Activity 40.3 % 10.1021/np400653p
Homo sapiens HepG2 Activity nan None 10.1021/ml400300q
Homo sapiens HepG2 IC50 0.8 nM 10.1021/ml400300q
Homo sapiens HepG2 Ratio IC50 3.0 None 10.1021/ml400300q
Homo sapiens HUVEC Activity nan None 10.1016/j.ejmech.2016.02.062
Homo sapiens KM-20L2 GI50 0.0008 ug.mL-1 10.1021/np800603u
Homo sapiens MCF7 Activity 16.0 % 10.1021/ml400300q
Homo sapiens MCF7 Activity 18.15 % 10.1021/ml400300q
Homo sapiens MCF7 Activity 25.79 % 10.1021/ml400300q
Homo sapiens MCF7 Activity 56.07 % 10.1021/ml400300q
Homo sapiens MCF7 Activity nan None 10.1021/ml400300q
Homo sapiens MCF7 GI50 0.001 ug.mL-1 10.1021/np800603u
Homo sapiens MCF7 IC50 500.0 nM 10.1021/jm061162u
Homo sapiens MCF7 IC50 1770.0 nM 10.1021/ml400300q
Homo sapiens MIA PaCa-2 Activity 12.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 18.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 19.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 23.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 24.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 35.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 42.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 49.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 60.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 62.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity 63.0 % 10.1021/jm061162u
Homo sapiens MIA PaCa-2 Activity nan None 10.1021/jm061162u
Homo sapiens MIA PaCa-2 IC50 1.0 nM 10.1021/jm061162u
Homo sapiens Multidrug resistance-associated protein 4 IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens NCI-H460 GI50 0.0025 ug.mL-1 10.1021/np800603u
Homo sapiens NCI-H460 IC50 1.0 nM 10.1021/jm061162u
Homo sapiens P-glycoprotein 1 Activity nan None 10.1016/j.bbrc.2004.01.156
Homo sapiens P-glycoprotein 1 IC50 3200.0 nM 10.1021/tx010125x
Homo sapiens P-glycoprotein 1 Km 1000.0 nM 10.1074/jbc.271.6.3163
Homo sapiens SF-268 GI50 0.0027 ug.mL-1 10.1021/np800603u
Homo sapiens SK-MEL-28 Activity nan None 10.1016/j.ejmech.2016.02.062
Homo sapiens SW-620 IC50 0.1 nM 10.1021/jm061162u
Leishmania major Leishmania major EC50 110.0 nM 10.1021/acs.jnatprod.8b00159
Mus musculus L1210 Log CR 0.59 None 10.1021/jm00169a014
Mus musculus P388 ED50 0.12 ug ml-1 10.1021/np800603u
Mycobacterium tuberculosis Mycobacterium tuberculosis FC 2.0 None 10.1128/aac.00550-09
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 0.4 ug.mL-1 10.1128/aac.00550-09
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC nan None 10.1128/aac.00550-09
Mycobacterium tuberculosis variant bovis BCG Mycobacterium tuberculosis variant bovis BCG MIC 0.2 ug.mL-1 10.1128/aac.00550-09
Mycobacterium tuberculosis variant bovis BCG Mycobacterium tuberculosis variant bovis BCG MIC 0.4 ug.mL-1 10.1128/aac.00550-09
Mycolicibacterium smegmatis Mycolicibacterium smegmatis Activity nan None 10.1021/jm500131s
Rattus norvegicus C6 Activity nan None 10.1021/ml400300q
Rattus norvegicus C6 IC50 0.4 nM 10.1021/ml400300q
Rattus norvegicus C6 Ratio IC50 3.0 None 10.1021/ml400300q
Severe acute respiratory syndrome-related coronavirus SARS-CoV EC50 1630.0 nM 10.1021/jm070295s
Severe acute respiratory syndrome-related coronavirus SARS-CoV IC50 850.0 nM 10.1021/acs.jmedchem.0c00626
Severe acute respiratory syndrome-related coronavirus SARS-CoV Inhibition 25.0 % 10.1021/jm070295s
Severe acute respiratory syndrome-related coronavirus SARS-CoV Inhibition 50.0 % 10.1021/jm070295s
Staphylococcus aureus Quinolone resistance protein norA Inhibition nan % 10.1016/j.bmc.2012.05.025
Staphylococcus aureus Staphylococcus aureus Activity 40.0 % 10.1128/aac.00887-08
Staphylococcus epidermidis Staphylococcus epidermidis Activity 40.0 % 10.1128/aac.00887-08
Trypanosoma brucei Trypanosoma brucei Activity 97.3 % 10.1128/aac.00423-07
Trypanosoma brucei brucei Trypanosoma brucei brucei Activity 70.0 % 10.1128/aac.00642-07
Trypanosoma brucei brucei Trypanosoma brucei brucei Activity nan None 10.1021/acs.jmedchem.6b01740
Trypanosoma brucei brucei Trypanosoma brucei brucei EC50 3.2 nM 10.1021/acs.jnatprod.8b00159
None ADMET Survival 50.0 % 10.1021/ml400300q
None No relevant target LogD 3.24 None 10.1021/jm00169a014
None Unchecked Ratio CC50/EC50 41.4 None 10.1021/jm070295s
None Unchecked Ratio CC50/EC50 80.0 None 10.1021/acs.jmedchem.0c00626

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000663 *N[C@@H](COC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(*)=O>>CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O RXN-22840