IMPPAT Phytochemical information: 
Theobromine

Theobromine
Summary

SMILES: Cn1cnc2c1c(=O)[nH]c(=O)n2C
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)
InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N
DeepSMILES: Cncncc5c=O)[nH]c=O)n6C
Scaffold Graph/Node/Bond level: O=c1[nH]c(=O)c2[nH]cnc2[nH]1
Scaffold Graph/Node level: OC1NC(O)C2NCNC2N1
Scaffold Graph level: CC1CC(C)C2CCCC2C1
Functional groups: c=O; c[nH]c; cn(c)C; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Imidazopyrimidines
ClassyFire Subclass: Purines and purine derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
theobromin, theobromine
External chemical identifiers:
CID:5429; ChEMBL:CHEMBL1114; ChEBI:28946; ZINC:ZINC000000002151; FDASRS:OBD445WZ5P; SureChEMBL:SCHEMBL3184; MolPort-000-514-708
Chemical structure download


Theobromine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 180.17
Log P RDKit -1.04
Topological polar surface area (Å2) RDKit 72.68
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 7
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Theobromine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5625


Theobromine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.95
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Theobromine
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000252945CYP2E1733
ENSP00000308549ADORA1814
ENSP00000332116PDE4B819
ENSP00000336630ADORA2A834
ENSP00000342007CYP1A2938
ENSP00000368727XDH800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.