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name Structure Reference Source Properties Activities Metabolism

5-Amino-4-oxopentanoic acid; Hydrochloride

AlkaPlorer ID: AK001872

Synonym: Aminolevulinic acid hydrochloride, Levulan

IUPAC Name: 5-amino-4-oxopentanoic acid

Structure

SMILES: NCC(=O)CCC(=O)O

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InChI: InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)

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InChIKey: ZGXJTSGNIOSYLO-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 131.131

TPSA？: 80.39

MolLogP？: -0.6210000000000004

Number of H-Donors: 2

Number of H-Acceptors: 3

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Acinetobacter baumannii Acinetobacter baumannii Inhibition 27.7 % 10.6019/CHEMBL4513141
Candida albicans Candida albicans Inhibition 0.21 % 10.6019/CHEMBL4513141
Cricetulus griseus CHO Inhibition nan % None
Cryptococcus neoformans Cryptococcus neoformans Inhibition -6.69 % 10.6019/CHEMBL4513141
Escherichia coli Escherichia coli Activity 5.4 pmol 10.1128/aac.01372-07
Escherichia coli Escherichia coli Activity 7.5 pmol 10.1128/aac.01372-07
Escherichia coli Escherichia coli Activity nan None 10.1128/aac.01372-07
Escherichia coli Escherichia coli GI nan None 10.1128/aac.01372-07
Escherichia coli Escherichia coli Inhibition 5.31 % 10.6019/CHEMBL4513141
Escherichia coli Escherichia coli Ratio 5e-05 None 10.1128/aac.01372-07
Escherichia coli Escherichia coli Ratio 0.00048 None 10.1128/aac.01372-07
Escherichia coli K-12 Beta-lactamase AmpC Potency 22387.2 nM None
Helicobacter pylori Helicobacter pylori Activity 66.0 % 10.1016/j.ejmech.2019.04.057
Helicobacter pylori Helicobacter pylori Activity 85.0 % 10.1016/j.ejmech.2019.04.057
Homo sapiens A-375 Activity 60.0 % 10.1016/j.ejmech.2019.111582
Homo sapiens A-431 Inhibition 31.0 % 10.1016/j.bmc.2016.05.015
Homo sapiens A-431 Inhibition 43.0 % 10.1016/j.bmc.2016.05.015
Homo sapiens A-431 Inhibition nan % 10.1016/j.bmc.2016.05.015
Homo sapiens A549 Activity 80.0 % 10.1016/j.ejmech.2019.111582
Homo sapiens A549 Activity nan None 10.1039/C6MD00040A
Homo sapiens A549 Drug uptake 0.08 ug 10.1021/jm900224r
Homo sapiens A549 Drug uptake 39.88 ng 10.1021/jm900224r
Homo sapiens A549 Flu intensity 17.7 a.u. 10.1039/C6MD00040A
Homo sapiens A549 Flu intensity 42.1 a.u. 10.1039/C6MD00040A
Homo sapiens A549 Flu intensity 77.8 a.u. 10.1039/C6MD00040A
Homo sapiens A549 Survival 18.4 % 10.1039/C6MD00040A
Homo sapiens A549 Survival 54.7 % 10.1039/C6MD00040A
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-1 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bromodomain adjacent to zinc finger domain protein 2B Potency 707.9 nM None
Homo sapiens Caco-2 Drug uptake 2.66 ug 10.1021/jm900224r
Homo sapiens Caco-2 Drug uptake 603.45 ng 10.1021/jm900224r
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin A receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin B receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens CNE-2 LD80 0.75 mM 10.1021/acs.jmedchem.7b00346
Homo sapiens Cyclooxygenase-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endothelin receptor ET-A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens GABA receptor rho-1 subunit IC50 12900.0 nM 10.1021/jm7015842
Homo sapiens Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Geminin Potency 125.9 nM None
Homo sapiens Ghrelin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HCT-116 Activity 80.0 % 10.1016/j.ejmech.2019.111582
Homo sapiens HeLa Activity nan None 10.1016/j.ejmech.2019.111582
Homo sapiens HeLa Activity nan None 10.1039/C6MD00040A
Homo sapiens HeLa IC50 230000.0 nM 10.1016/j.ejmech.2019.111582
Homo sapiens HeLa Survival 26.9 % 10.1039/C6MD00040A
Homo sapiens HeLa Survival 58.6 % 10.1039/C6MD00040A
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition 4.51 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 10.48 % 10.6019/CHEMBL4808148
Homo sapiens HL-60 IC50 1570000.0 nM 10.1021/jm8008794
Homo sapiens Kappa opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens KB Activity nan None 10.1021/acs.jmedchem.7b00346
Homo sapiens KB LD50 124.0 uM 10.1021/acs.jmedchem.7b00346
Homo sapiens KB Survival 52.6 % 10.1039/C6MD00040A
Homo sapiens LNCaP Activity nan None 10.1039/C6MD00040A
Homo sapiens LNCaP Flu intensity 17.3 a.u. 10.1039/C6MD00040A
Homo sapiens LNCaP Flu intensity 31.3 a.u. 10.1039/C6MD00040A
Homo sapiens LNCaP Flu intensity 46.0 a.u. 10.1039/C6MD00040A
Homo sapiens LNCaP Survival 33.1 % 10.1039/C6MD00040A
Homo sapiens LNCaP Survival 61.9 % 10.1039/C6MD00040A
Homo sapiens MCF7 Activity nan None 10.1021/acs.jmedchem.7b00346
Homo sapiens MCF7 Activity nan None 10.1039/C6MD00040A
Homo sapiens MCF7 IC50 1735000.0 nM 10.1021/jm8008794
Homo sapiens MCF7 LD50 131.2 uM 10.1021/acs.jmedchem.7b00346
Homo sapiens MCF7 Survival 26.7 % 10.1039/C6MD00040A
Homo sapiens MCF7R Activity nan None 10.1021/acs.jmedchem.7b00346
Homo sapiens MCF7R LD50 122.5 uM 10.1021/acs.jmedchem.7b00346
Homo sapiens MDA-MB-435 Activity nan None 10.1039/C6MD00040A
Homo sapiens MDA-MB-435 Survival 28.9 % 10.1039/C6MD00040A
Homo sapiens MDA-MB-435 Survival 61.4 % 10.1039/C6MD00040A
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Oligopeptide transporter small intestine isoform Activity nan None 10.1038/nrd3028
Homo sapiens Oligopeptide transporter small intestine isoform Ki 790000.0 nM 10.1021/jm030976x
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Porphobilinogen synthase k cat 0.803 s-1 10.1016/0960-894X(96)00199-0
Homo sapiens Porphobilinogen synthase Km 253000.0 nM 10.1016/0960-894X(96)00199-0
Homo sapiens Porphobilinogen synthase Retention 80.0 % 10.1016/0960-894X(95)00357-Y
Homo sapiens Pregnane X receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2c (5-HT2c) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier family 15 member 2 Activity nan None 10.1038/nrd3028
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens U-251 Activity 2.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 3.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 5.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 6.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 7.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 14.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 17.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 76.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 78.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity 130.0 % 10.1021/jm8008794
Homo sapiens U-251 Activity nan None 10.1021/jm8008794
Homo sapiens U-251 FC 2.0 None 10.1021/jm8008794
Homo sapiens U-251 FC 3.0 None 10.1021/jm8008794
Homo sapiens U-251 FC 7.2 None 10.1021/jm8008794
Homo sapiens U-251 IC50 2665000.0 nM 10.1021/jm8008794
Homo sapiens U-251 IC50 2715000.0 nM 10.1021/jm8008794
Homo sapiens U-251 IC50 2719000.0 nM 10.1021/jm8008794
Homo sapiens Uracil nucleotide/cysteinyl leukotriene receptor Inhibition nan % None
Homo sapiens Vasopressin V1a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Xaa-Pro dipeptidase Ki 960000.0 nM 10.1016/0960-894X(95)00494-E
Klebsiella pneumoniae Klebsiella pneumoniae Inhibition 13.51 % 10.6019/CHEMBL4513141
Mus musculus PAM212 Activity 11.0 % 10.1021/jm900224r
Mus musculus PAM212 Activity nan None 10.1021/jm900224r
Mus musculus PAM212 Drug uptake 0.81 ug 10.1021/jm900224r
Mus musculus PAM212 Drug uptake 3.41 ug 10.1021/jm900224r
Mus musculus PAM212 Drug uptake 108.19 ng 10.1021/jm900224r
Mus musculus PAM212 Drug uptake 309.54 ng 10.1021/jm900224r
Plasmodium falciparum Plasmodium falciparum Potency 10417.9 nM None
Pseudomonas aeruginosa Pseudomonas aeruginosa Activity 34.5 pmol 10.1128/aac.01372-07
Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition 12.16 % 10.6019/CHEMBL4513141
Pseudomonas aeruginosa Pseudomonas aeruginosa Ratio 0.0019 None 10.1128/aac.01372-07
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Oligopeptide transporter, kidney isoform Ki 230000.0 nM 10.1007/s004240000339
Rattus norvegicus Solute carrier family 15 member 1 Ki 2200000.0 nM 10.1007/s004240000339
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 31.45 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.04501 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.08 % 10.6019/CHEMBL4495565
Staphylococcus aureus Staphylococcus aureus Activity 6.6 pmol 10.1128/aac.01372-07
Staphylococcus aureus Staphylococcus aureus Inhibition 8.53 % 10.6019/CHEMBL4513141
Staphylococcus aureus Staphylococcus aureus Ratio 5e-06 None 10.1128/aac.01372-07
None ADMET Activity 0.0 % 10.1021/jm901654x
None ADMET Activity 23.0 % 10.1021/jm901654x
None ADMET Activity nan None 10.1039/C6MD00040A
None ADMET Drug metabolism nan None 10.1016/j.ejmech.2019.111582
None ADMET Drug metabolism nan None 10.1021/acs.jmedchem.7b00346
None ADMET permeability 0.0 10'6cm/s 10.1021/jm901654x
None ADMET Survival 70.8 % 10.1039/C6MD00040A
None ADMET Survival 81.9 % 10.1039/C6MD00040A
None Hepatotoxicity HepSE_bilirubinemia 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholecystitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholelithiasis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cirrhosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_Combined Scores 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_elevated liver function tests 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic failure 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic necrosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatomegaly 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_jaundice 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver disease 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver fatty 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver function tests abnormal 0.0 None 10.1371/journal.pcbi.1002310
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 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) 7.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 66.7 % 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 IC50 3475000.0 nM 10.1021/jm8008794
None No relevant target LogP -1.52 None 10.1016/j.ejmech.2019.111582
None No relevant target LogP -1.5 None 10.1016/j.ejmech.2009.12.043
None No relevant target Stability nan % 10.1016/j.ejmech.2019.111582
None Unchecked Activity nan None 10.1021/jm8008794
None Unchecked Hepatotoxicity (acute) 0.0 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) 0.0 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) 0.0 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 Inhibition 100.0 % 10.1021/jm8008794
None Unchecked Inhibition 102.0 % 10.1021/jm8008794

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT017491 NCC(=O)CCC(=O)O.NCC(=O)CCC(=O)O>>NCc1[nH]cc(CCC(=O)O)c1CC(=O)O PORPHOBILSYNTH-RXN
AKRT017492 NCC(=O)CCC(=O)O.O=C=O>>NC(C(=O)O)C(=O)CCC(=O)O MNXR134309
AKRT017493 NCC(=O)CCC(=O)O.O=C=O>>NCC(=O)O.O=C(O)CCC(=O)[32S] None
AKRT017494 NCC(=O)CCC(=O)O>>NCC(=O)CCC(=O)[CoA] RXN-15714
AKRT017495 NCC(=O)CCC(=O)O>>N[C@H](C=O)CCC(=O)O enzymemap_88267
AKRT017496 NCC(=O)CCC(=O)O>>O=CC(=O)CCC(=O)O R02271
AKRT017699 NCC(=O)O.O=C(O)CCC(=O)[CoA]>>NCC(=O)CCC(=O)O 5-AMINOLEVULINIC-ACID-SYNTHASE-RXN
AKRT020207 N[C@H](C=O)CCC(=O)O>>NCC(=O)CCC(=O)O GSAAMINOTRANS-RXN
AKRT022750 O=C(O)CCC(=O)[CoA].NCC(=O)O>>NCC(=O)CCC(=O)O enzymemap_30777
AKRT023659 O=CC(=O)CCC(=O)O>>NCC(=O)CCC(=O)O R02271