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name Structure Reference Source Properties Activities Metabolism

Theobromine

AlkaPlorer ID: AK001702

Synonym: None

IUPAC Name: 3,7-dimethylpurine-2,6-dione

Structure

SMILES: CN1C=NC2=C1C(O)=NC(=O)N2C

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InChI: InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)

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InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Ilex paraguariensis Ilex Aquifoliaceae Aquifoliales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 180.167

TPSA？: 72.94

MolLogP？: -0.6274000000000004

Number of H-Donors: 1

Number of H-Acceptors: 6

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Electrophorus electricus Acetylcholinesterase Inhibition 39.37 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 3.88 % 10.1016/j.bmc.2012.09.040
Homo sapiens Adenosine A1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A1 receptor IC50 105000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Adenosine A1 receptor Ki 105000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Adenosine A2a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor IC50 250000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Adenosine A2a receptor Ki 250000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Adenosine A2b receptor IC50 130000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Adenosine A3 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor IC50 100000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Adenosine A3 receptor Ki 103000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Alpha-1a adrenergic receptor AC50 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 10000.0 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 Bradykinin B2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cerebroside-sulfatase Potency 84.9 nM None
Homo sapiens Cholecystokinin A receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Chromobox protein homolog 1 Potency 39810.7 nM None
Homo sapiens Cyclooxygenase-2 AC50 10000.0 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 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 Potency 25118.9 nM None
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ghrelin receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG Potency 25118.9 nM None
Homo sapiens Histamine H1 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -28.11 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -3.54 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 11220.2 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 17782.8 nM None
Homo sapiens Kappa opioid receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens MAP kinase ERK2 Potency 4.0 nM None
Homo sapiens Melanocortin receptor 3 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 4 AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 10000.0 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 10000.0 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 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Potency 37933.0 nM None
Homo sapiens Peripheral myelin protein 22 Potency 84921.4 nM None
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4 IC50 100000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Phosphodiesterase 4 Ki 100000.0 nM 10.1021/acs.jmedchem.1c00261
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Retinoid X receptor alpha Potency 25118.9 nM None
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 10000.0 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 10000.0 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 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 93.41 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 101.26 % 10.1124/mol.112.084152
Homo sapiens Thromboxane A2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 35481.3 nM None
Homo sapiens Vasopressin V1a receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Mus musculus Mus musculus Activity nan None 10.1021/jm100490m
Plasmodium falciparum Plasmodium falciparum Potency 369.6 nM None
Plasmodium falciparum Plasmodium falciparum Potency 465.4 nM None
Rattus norvegicus Adenosine A1 receptor Ki 105000.0 nM 10.1021/jm00074a015
Rattus norvegicus Adenosine A1 receptor Ki 105000.0 nM 10.1021/jm00172a022
Rattus norvegicus Adenosine A2 receptor Inhibition 40.0 % 10.1021/jm00074a015
Rattus norvegicus Adenosine A2 receptor Inhibition 40.0 % 10.1021/jm00172a022
Rattus norvegicus Adenosine A2 receptor Ki 250000.0 nM 10.1021/jm00172a022
Rattus norvegicus Androgen Receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 10000.0 nM 10.1038/s41467-023-40064-9
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 10000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Muscarinic acetylcholine receptor M1 Potency 11.2 nM None
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 10000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 17.53 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.2208 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 0.2 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 18.79 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition index 0.04567 None 10.1101/2020.04.03.023846
Trypanosoma brucei 6-phospho-1-fructokinase Potency 26854.5 nM None
None No relevant target LogP -0.78 None 10.1016/j.bmcl.2021.128318
None No relevant target LogP 0.1 None 10.1021/jm00379a002
None No relevant target Rm 0.26 None 10.1016/j.bmcl.2021.128318
None Nucleic Acid K ass 94.5 M-1 10.1021/jm9904708
None Unchecked Ac50 3.981 uM None
None Unchecked Ac50 10.0 uM None
None Unchecked Ac50 39.81 uM None
None Unchecked AC50 3981.1 nM None
None Unchecked AC50 10000.0 nM None
None Unchecked AC50 39810.7 nM None
None Unchecked IC50 420000.0 nM 10.1016/j.bmcl.2009.11.017
None Unchecked IC50 580000.0 nM 10.1016/j.bmcl.2009.11.017
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Potency 1995.3 nM None
None Unchecked Potency 4109.5 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT014610 C[SAH].Cn1c(=O)[nH]c(=O)c2[nH]cnc21>>Cn1cnc2c1c(=O)[nH]c(=O)n2C RXN-7603
AKRT014617 C[SAH].Cn1cnc2[nH]c(=O)[nH]c(=O)c21>>Cn1cnc2c1c(=O)[nH]c(=O)n2C RXN-7598
AKRT014618 C[SAH].Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1c(=O)c2c(ncn2C)n(C)c1=O RXN-7599
AKRT015524 Cn1c(=O)c2c(ncn2C)n(C)c1=O>>Cn1cnc2c1c(=O)[nH]c(=O)n2C RXN-11513
AKRT015551 Cn1cnc2c1c(=O)[nH]c(=O)n2C>>C=O RXN-11516
AKRT015552 Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1c(=O)[nH]c(=O)c2c1[nH]c(=O)n2C RXN-11519
AKRT015553 Cn1cnc2c1c(=O)[nH]c(=O)n2C>>Cn1cnc2[nH]c(=O)[nH]c(=O)c21 RXN-11516