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: cn(C)c; cnc; c=O; c[nH]c
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, Theobromine
External chemical identifiers:
CID:CID_5429; ChEMBL:CHEMBL1114; ChEBI: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
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 0.562472


Theobromine
ADME 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
Number of Brenk structural alerts SwissADME 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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140BindingDB, ChEMBL
TAR_EXP_000204ENSG00000170425ADORA2B136BindingDB
TAR_EXP_000203ENSG00000128271ADORA2A135BindingDB, ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134BindingDB, ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001060ENSG00000105650PDE4C5143ChEMBL
TAR_EXP_001057ENSG00000184588PDE4B5142ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL