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name Structure Reference Source Properties Activities Metabolism

phenethylbiguanide

AlkaPlorer ID: AK071495

Synonym: None

IUPAC Name: 1-(diaminomethylidene)-2-(2-phenylethyl)guanidine

Structure

SMILES: N=C(N)N=C(N)NCCC1=CC=CC=C1

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InChI: InChI=1S/C10H15N5/c11-9(12)15-10(13)14-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H6,11,12,13,14,15)

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InChIKey: ICFJFFQQTFMIBG-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 205.265

TPSA？: 100.28

MolLogP？: 0.0268700000000008

Number of H-Donors: 4

Number of H-Acceptors: 1

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cavia porcellus Cavia porcellus Decrease in blood glucose 70.0 % 10.1021/jm00148a011
Cavia porcellus Cavia porcellus MED 7.5 mg 10.1016/j.ejmech.2021.113726
Cavia porcellus Cavia porcellus Reduction 46.0 % 10.1021/jm00144a031
Cavia porcellus Cavia porcellus Reduction 46.0 % 10.1021/jm00346a006
Cercopithecidae Monkey Reduction 50.0 % 10.1021/jm00346a006
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 15000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 6711.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 15000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-3 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 Bile salt export pump IC50 135000.0 nM 10.1093/toxsci/kfq269
Homo sapiens Bile salt export pump IC50 1000000.0 nM 10.1124/dmd.112.047068
Homo sapiens Bradykinin B1 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 Canalicular multispecific organic anion transporter 1 Activity 88.0 % 10.1021/jm7015683
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 Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Carbonic anhydrase I Ki 50000.0 nM 10.1016/j.ejmech.2016.10.037
Homo sapiens Carbonic anhydrase II Ki 50000.0 nM 10.1016/j.ejmech.2016.10.037
Homo sapiens Carbonic anhydrase IX Ki 50000.0 nM 10.1016/j.ejmech.2016.10.037
Homo sapiens Carbonic anhydrase XII Ki 50000.0 nM 10.1016/j.ejmech.2016.10.037
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 Corticotropin releasing factor receptor 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Corticotropin releasing factor receptor 2 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 Cytochrome P450 1A2 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2D6 AC50 10000.0 nM None
Homo sapiens Cytochrome P450 2D6 IC50 27000.0 nM 10.1021/jm0209578
Homo sapiens Cytochrome P450 2D6 Potency 10000.0 nM None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dihydrofolate reductase Ki 140000.0 nM 10.1021/acs.jmedchem.0c00546
Homo sapiens Dopamine D1 receptor AC50 10000.0 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 25200.0 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 Endothelin receptor ET-B 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 Estrogen receptor beta AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Gastric inhibitory polypeptide receptor 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 Glucagon 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 nan None 10.1016/j.ejmech.2016.10.037
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 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -9.26 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 3.23 % 10.6019/CHEMBL4808148
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 6309.6 nM None
Homo sapiens Kappa opioid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 4 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Multidrug resistance-associated protein 4 IC50 133000.0 nM 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 10000.0 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 10000.0 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 Neuropeptide Y receptor type 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neurotensin receptor 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 18335.2 nM 10.1038/s41467-023-40064-9
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 38570.8 nM None
Homo sapiens Phosphodiesterase 3A AC50 21999.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Prelamin-A/C Potency 398.1 nM None
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 8904.9 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 10000.0 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 22 member 1 Drug uptake 570.0 pmol/mg 10.1021/jm400966v
Homo sapiens Solute carrier family 22 member 1 FC 39.0 None 10.1021/jm400966v
Homo sapiens Solute carrier family 22 member 1 IC50 10000.0 nM 10.1023/a:1019870831174
Homo sapiens Solute carrier family 22 member 2 Drug uptake 450.0 pmol/mg 10.1021/jm400966v
Homo sapiens Solute carrier family 22 member 2 FC 35.0 None 10.1021/jm400966v
Homo sapiens Solute carrier family 22 member 2 IC50 65000.0 nM 10.1023/a:1019870831174
Homo sapiens Solute carrier family 22 member 3 Ratio 32.2 None 10.1021/acs.jmedchem.2c01075
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 34.5 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition -2.3 % 10.1021/jm300212s
Homo sapiens Solute carrier organic anion transporter family member 2B1 Inhibition 16.7 % 10.1021/jm300212s
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thyroid stimulating hormone receptor Potency 7943.3 nM None
Homo sapiens Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 39810.7 nM None
Homo sapiens UMUC3 IC50 250000.0 nM 10.1021/acs.jmedchem.2c01244
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 Mus musculus Activity -3.4 % 10.1021/jm8011933
Mus musculus Mus musculus Activity -0.14 % 10.1021/jm8011933
Mus musculus Mus musculus Activity 106.0 % 10.1021/jm8011933
Mus musculus Mus musculus Activity nan None 10.1021/jm8011933
Mus musculus Mus musculus Inhibition 21.0 % 10.1021/jm00189a022
Mus musculus Mus musculus LD50 160.0 mg.kg-1 10.1021/jm00144a031
Mus musculus Mus musculus LD50 900.0 mg.kg-1 10.1021/jm00144a031
Nakaseomyces glabratus Nakaseomyces glabratus FICI 0.5 None 10.1016/j.ejmech.2021.113293
Plasmodium falciparum Plasmodium falciparum IC50 0.0 nM 10.1016/j.bmc.2010.01.068
Plasmodium falciparum Plasmodium falciparum Potency 8087.5 nM None
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 Cytochrome P450 2D1 Inhibition nan % 10.1021/jm0209578
Rattus norvegicus Cytochrome P450 2D18 IC50 833000.0 nM 10.1021/jm0209578
Rattus norvegicus Cytochrome P450 2D2 IC50 45400.0 nM 10.1021/jm0209578
Rattus norvegicus Cytochrome P450 2D3 IC50 1927000.0 nM 10.1021/jm0209578
Rattus norvegicus GABA receptor alpha-1 subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 2321.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Peripheral myelin protein 22 Potency 13789.4 nM None
Rattus norvegicus Rattus norvegicus Blood glucose 5.52 mM l-1 10.1021/jm00361a007
Rattus norvegicus Rattus norvegicus Blood lactate 12.2 mg dl-1 10.1021/jm00167a022
Rattus norvegicus Rattus norvegicus Change -10.0 % 10.1021/jm00361a007
Rattus norvegicus Rattus norvegicus Change -6.0 % 10.1021/jm00361a007
Rattus norvegicus Rattus norvegicus ED20 0.16 mM kg-1 10.1021/jm00361a006
Rattus norvegicus Rattus norvegicus ED20 1.0 mM kg-1 10.1021/jm00361a006
Rattus norvegicus Rattus norvegicus ED50 1000.0 umol.kg-1 10.1021/jm00361a006
Rattus norvegicus Rattus norvegicus Glucose rise 21.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 26.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 31.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 35.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 58.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 61.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 63.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 68.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 70.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 84.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 98.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 101.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Glucose rise 129.0 mg dl-1 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus IC50 180000.0 nM 10.1021/jm00361a007
Rattus norvegicus Rattus norvegicus Inhibition 0.0 % 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Inhibition 57.0 % 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Inhibition 64.0 % 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Inhibition 71.0 % 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus Inhibition 81.0 % 10.1021/jm00129a015
Rattus norvegicus Rattus norvegicus LD50 160.0 mg.kg-1 10.1021/jm00346a006
Rattus norvegicus Rattus norvegicus LD50 900.0 mg.kg-1 10.1021/jm00346a006
Rattus norvegicus Rattus norvegicus Plasma glucose level 85.0 mg dl-1 10.1021/jm00167a022
Rattus norvegicus Rattus norvegicus Plasma Insulin 86.1 pM l-1 10.1021/jm00361a007
Rattus norvegicus Rattus norvegicus Reduction 0.0 % 10.1021/jm00144a031
Rattus norvegicus Rattus norvegicus Reduction 0.0 % 10.1021/jm00346a006
Rattus norvegicus Rattus norvegicus Reduction 25.3 % 10.1021/jm00144a031
Rattus norvegicus Rattus norvegicus Reduction 52.9 % 10.1021/jm00144a031
Rattus norvegicus Rattus norvegicus Reduction 62.0 % 10.1021/jm00144a031
Rattus norvegicus Rattus norvegicus Reduction 62.0 % 10.1021/jm00346a006
Rattus norvegicus Solute carrier family 22 member 1 Km 15600.0 nM 10.1124/jpet.102.034140
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Voltage-gated N-type calcium channel alpha-1B subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
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
None ADMET Activity nan None 10.1021/jm8011933
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx900326k
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) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 0.0 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 Potency 14950.2 nM None
None NON-PROTEIN TARGET Potency 21117.7 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) 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 IC50 3800.0 nM 10.1021/acs.jmedchem.1c01509
None Unchecked IC50 170000.0 nM 10.1021/acs.jmedchem.0c00546
None Unchecked IC50 570000.0 nM 10.1021/acs.jmedchem.2c01244

Metabolism Information