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Squalamine

AlkaPlorer ID: AK024532

Synonym: None

IUPAC Name: [(3R,6R)-6-[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-[3-(4-aminobutylamino)propylamino]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptan-3-yl] hydrogen sulfate

Structure

SMILES: CC(C)[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@H]4C[C@@H](NCCCNCCCCN)CC[C@]4(C)[C@H]3CC[C@]12C)OS(=O)(=O)O

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InChI: InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-/m1/s1

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InChIKey: UIRKNQLZZXALBI-MSVGPLKSSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Squalus acanthias Squalus Squalidae Squaliformes Chondrichthyes Chordata Metazoa Eukaryota

Properties Information

Molecule Weight: 627.9770000000005

TPSA？: 133.91

MolLogP？: 5.553200000000005

Number of H-Donors: 5

Number of H-Acceptors: 7

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis MIC 3.13 ug.mL-1 10.1016/s0960-894x(01)00632-1
Burkholderia cepacia Burkholderia cepacia MIC 40.0 ug.mL-1 10.1021/jm200506x
Candida albicans Candida albicans MIC 8.0 ug.mL-1 10.1016/j.bmcl.2004.06.010
Candida albicans Candida albicans MIC 16.0 ug.mL-1 10.1021/np990514f
Candida albicans Candida albicans MIC 4000.0 nM 10.1016/j.bmc.2015.10.034
Escherichia coli Escherichia coli Activity 35.0 % 10.1021/jm200506x
Escherichia coli Escherichia coli Activity nan None 10.1021/jm200506x
Escherichia coli Escherichia coli MIC 0.03 ug.mL-1 10.1021/acs.jmedchem.8b01781
Escherichia coli Escherichia coli MIC 0.06 ug.mL-1 10.1021/acs.jmedchem.8b01781
Escherichia coli Escherichia coli MIC 0.125 ug.mL-1 10.1021/acs.jmedchem.8b01781
Escherichia coli Escherichia coli MIC 0.5 ug.mL-1 10.1021/acs.jmedchem.8b01781
Escherichia coli Escherichia coli MIC 2.5 ug.mL-1 10.1021/jm200506x
Escherichia coli Escherichia coli MIC 4.0 ug.mL-1 10.1021/np990514f
Escherichia coli Escherichia coli MIC 5.0 ug.mL-1 10.1021/jm200506x
Escherichia coli Escherichia coli MIC 32.0 ug.mL-1 10.1021/jm200506x
Escherichia coli Escherichia coli MIC 100.0 ug.mL-1 10.1016/j.bmcl.2004.06.010
Escherichia coli Escherichia coli MIC 100.0 ug.mL-1 10.1016/s0960-894x(01)00632-1
Escherichia coli Escherichia coli MIC 256.0 ug.mL-1 10.1021/acs.jmedchem.8b01781
Escherichia coli Escherichia coli MIC 1000.0 nM 10.1016/j.bmc.2015.10.034
Escherichia coli Escherichia coli Ratio 4.0 None 10.1021/jm200506x
Klebsiella aerogenes Klebsiella aerogenes MIC 0.015 ug.mL-1 10.1021/acs.jmedchem.8b01781
Klebsiella aerogenes Klebsiella aerogenes MIC 0.03 ug.mL-1 10.1021/acs.jmedchem.8b01781
Klebsiella aerogenes Klebsiella aerogenes MIC 0.25 ug.mL-1 10.1021/acs.jmedchem.8b01781
Klebsiella aerogenes Klebsiella aerogenes MIC 128.0 ug.mL-1 10.1021/acs.jmedchem.8b01781
Klebsiella pneumoniae Klebsiella pneumoniae MIC 12.5 ug.mL-1 10.1016/s0960-894x(01)00632-1
Micrococcus luteus Micrococcus luteus MIC 3.13 ug.mL-1 10.1016/s0960-894x(01)00632-1
Proteus mirabilis Proteus mirabilis MIC 100.0 ug.mL-1 10.1016/s0960-894x(01)00632-1
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 1.0 ug.mL-1 10.1021/acs.jmedchem.8b01781
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 2.5 ug.mL-1 10.1021/jm200506x
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 4.0 ug.mL-1 10.1021/acs.jmedchem.8b01781
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 5.0 ug.mL-1 10.1021/jm200506x
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 16.0 ug.mL-1 10.1021/acs.jmedchem.8b01781
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 16.0 ug.mL-1 10.1021/np990514f
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 100.0 ug.mL-1 10.1016/s0960-894x(01)00632-1
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 256.0 ug.mL-1 10.1021/acs.jmedchem.8b01781
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 4000.0 nM 10.1016/j.bmc.2015.10.034
Salmonella enterica subsp. enterica serovar Typhimurium Salmonella typhimurium MIC 100.0 ug.mL-1 10.1016/s0960-894x(01)00632-1
Serratia marcescens Serratia marcescens MIC 100.0 ug.mL-1 10.1016/s0960-894x(01)00632-1
Staphylococcus aureus Staphylococcus aureus Activity 80.0 % 10.1021/jm200506x
Staphylococcus aureus Staphylococcus aureus Activity 100.0 % 10.1021/jm200506x
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1016/j.bmc.2019.04.004
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/jm200506x
Staphylococcus aureus Staphylococcus aureus MIC 0.3 ug.mL-1 10.1021/jm200506x
Staphylococcus aureus Staphylococcus aureus MIC 1.0 ug.mL-1 10.1021/np990514f
Staphylococcus aureus Staphylococcus aureus MIC 1.25 ug.mL-1 10.1021/jm200506x
Staphylococcus aureus Staphylococcus aureus MIC 1.56 ug.mL-1 10.1016/j.bmcl.2004.06.010
Staphylococcus aureus Staphylococcus aureus MIC 6.25 ug.mL-1 10.1016/s0960-894x(01)00632-1
Staphylococcus aureus Staphylococcus aureus MIC 1000.0 nM 10.1016/j.bmc.2015.10.034
None ADMET CL 1.2 mL.min-1.kg-1 10.1124/dmd.108.020479
None ADMET MRT 3.2 hr 10.1124/dmd.108.020479
None ADMET T1/2 9.5 hr 10.1124/dmd.108.020479
None ADMET Vdss 0.23 L.kg-1 10.1124/dmd.108.020479
None NON-PROTEIN TARGET Hepatotoxicity (acute) 38.5 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 1.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET MIC 5.0 ug.mL-1 10.1021/jm200506x
None Unchecked Hepatotoxicity (acute) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked MHC nan None 10.1016/s0960-894x(01)00632-1
None Unchecked MIC 3.13 ug.mL-1 10.1016/s0960-894x(01)00632-1

Metabolism Information