Navigation

name Structure Reference Source Properties Activities Metabolism

Pentostatin

AlkaPlorer ID: AK006313

Synonym: None

IUPAC Name: (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-8-ol

Structure

SMILES: OC[C@H]1O[C@@H](N2C=NC3=C2NC=NC[C@H]3O)C[C@@H]1O

copy

InChI: InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1

copy

InChIKey: FPVKHBSQESCIEP-JQCXWYLXSA-N

copy

Source

Species Genus Family Order Class Phylum Kingdom Domain
Narcissus pseudonarcissus Narcissus Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Streptomyces antibioticus Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria
Artemisia iwayomogi Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Myxococcus xanthus Myxococcus Myxococcaceae Myxococcales Myxococcia Myxococcota None Bacteria
Lithospermum carolinense Lithospermum Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Drimia altissima Drimia Hyacinthaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Taxus wallichiana Taxus Taxaceae Cupressales Pinopsida Streptophyta Viridiplantae Eukaryota
Evasterias retifera Evasterias Asteriidae Forcipulatida Asteroidea Echinodermata Metazoa Eukaryota
Sideritis glacialis Sideritis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Aconitum umbrosum Aconitum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Helenium amarum Helenium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Scutellaria viscidula Scutellaria Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Uperoleia rugosa Uperoleia Myobatrachidae Anura Amphibia Chordata Metazoa Eukaryota
Bolboschoenus maritimus Bolboschoenus Cyperaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ligularia lankongensis Ligularia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Allium ampeloprasum Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Maytenus disticha Maytenus Celastraceae Celastrales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Conyza pallidiflora Conyza Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Senecio retrorsus Senecio Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lonicera nitida Lonicera Caprifoliaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 268.273

TPSA？: 112.13

MolLogP？: -0.9890000000000004

Number of H-Donors: 4

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Adenosine deaminase Ki 0.001 nM 10.1021/jm00027a026
Bos taurus Adenosine deaminase Ki 0.001 nM 10.1021/jm0304257
Bos taurus Adenosine deaminase Ki 0.0025 nM 10.1021/jm00100a025
Bos taurus Adenosine deaminase Ki 0.01 nM 10.1016/s0960-894x(01)00591-1
Bos taurus Adenosine deaminase Ki nan nM 10.1021/jm00369a008
Bos taurus Adenosine deaminase REA 2800000.0 None 10.1021/jm00347a023
Bos taurus Monoamine oxidase A Activity nan None 10.1021/jm800656v
Homo sapiens Adenosine A1 receptor AC50 410.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 3400.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 3600.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine deaminase Ki 0.0001 nM 10.1016/j.bmcl.2012.09.053
Homo sapiens Adenosine deaminase Ki 0.0025 nM 10.1016/j.ejmech.2021.113877
Homo sapiens Adenosine deaminase Ki 0.0025 nM 10.1021/jm00364a022
Homo sapiens Adenosine deaminase Ki 0.026 nM 10.1021/acs.jmedchem.9b00182
Homo sapiens Adenosine deaminase Ki 0.033 nM 10.1016/s0960-894x(03)00026-x
Homo sapiens Adenosine deaminase Ki 0.1 nM 10.1021/jm00144a002
Homo sapiens Adenosine deaminase Ki 0.5 nM 10.1021/acs.jmedchem.9b00182
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 Bile salt export pump IC50 133000.0 nM 10.1093/toxsci/kft176
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Canalicular multispecific organic anion transporter 1 IC50 nan None 10.1093/toxsci/kft176
Homo sapiens Canalicular multispecific organic anion transporter 2 IC50 nan None 10.1093/toxsci/kft176
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 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 Equilibrative nucleoside transporter 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 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 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 -12.9 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -1.74 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 3.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Kappa opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 Multidrug resistance-associated protein 4 IC50 nan None 10.1093/toxsci/kft176
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 Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Peroxisome proliferator-activated receptor gamma AC50 30000.0 nM 10.1038/s41467-023-40064-9
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 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 10000.0 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 T47D Inhibition nan % 10.1016/j.ejmech.2014.10.080
Homo sapiens Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
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
Mus musculus L1210 IC50 250.0 nM 10.1021/jm00160a046
Mus musculus L1210 IC50 1900.0 nM 10.1021/jm00160a046
Mus musculus Mus musculus AUC 9500.0 ng.hr.mL-1 10.1016/s0960-894x(03)00026-x
Mus musculus Mus musculus Cmax 45476.57 nM 10.1016/s0960-894x(03)00026-x
Mus musculus Mus musculus MST 28.5 day 10.1021/jm0499559
Mus musculus Mus musculus MST 34.0 day 10.1021/jm0499559
Mus musculus Mus musculus MST 34.0 day 10.1021/jm050413g
Mus musculus Mus musculus MST 42.5 day 10.1021/jm0499559
Mus musculus Mus musculus MST 42.5 day 10.1021/jm050413g
Plasmodium falciparum Adenosine deaminase Ki 0.038 nM 10.1021/acs.jmedchem.9b00182
Plasmodium falciparum Adenosine deaminase Ki 8.2 nM 10.1021/acs.jmedchem.9b00182
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 6599.9 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
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 10.69 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 13.02 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.0932 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 -0.07 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.02 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 3.17 % 10.21203/rs.3.rs-23951/v1
None Hepatotoxicity Alkaline Phosphatase Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity Alkaline Phosphatase Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Alkaline Phosphatase Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Active 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Marginal 0.0 None 10.2174/1570163043334794
None Hepatotoxicity Composite Activity - Score nan None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity GGT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
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 3.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_elevated liver function tests 1.0 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 1.0 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 1.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity LDH Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity LDH Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity LDH Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity SGOT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Activity Score nan None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Index Value 0.0 None 10.2174/1570163043334794
None Hepatotoxicity SGPT Increase - Number of Reports 4.0 None 10.2174/1570163043334794
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) 16.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 81.3 % 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 Inhibition nan % 10.1016/j.ejmech.2014.10.080
None No relevant target LogP -1.1 None 10.1016/j.ejmech.2009.12.043
None Unchecked Ac50 1.0 uM None
None Unchecked Ac50 3.548 uM None
None Unchecked AC50 1000.0 nM None
None Unchecked AC50 3548.1 nM None
None Unchecked Hepatotoxicity (acute) 1.0 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) 1.0 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) 2.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 1.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT023566 O=C1CN=CNc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1>>OC[C@H]1O[C@@H](n2cnc3c2NC=NC[C@H]3O)C[C@@H]1O enzymemap_3192
AKRT024842 OC[C@H]1O[C@@H](n2cnc3c2NC=NC[C@H]3O)C[C@@H]1O>>O=C1CN=CNc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1 enzymemap_3192