Theobromine (Compound)

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ID	1579
Name	Theobromine
Synonyms	3,7-Dimethylxanthine
Structure	MOL SDF PDB SMILES InChI Structure for EE001579 (Theobromine) 3D Structure for EE001579 (Theobromine) Mrv1652309042000272D 13 14 0 0 0 0 999 V2000 -0.3984 0.7541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3556 -2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6284 -0.6979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6411 -0.2854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6411 -1.1104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3556 0.1271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0701 -1.1104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1435 -1.3654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0701 -0.2854 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1435 -0.0305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3556 -1.5229 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3556 0.9521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7845 -1.5229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 4 2 0 0 0 0 6 4 1 0 0 0 0 8 3 2 0 0 0 0 8 5 1 0 0 0 0 9 6 2 0 0 0 0 9 7 1 0 0 0 0 10 1 1 0 0 0 0 10 3 1 0 0 0 0 10 4 1 0 0 0 0 11 2 1 0 0 0 0 11 5 1 0 0 0 0 11 7 1 0 0 0 0 12 6 1 0 0 0 0 13 7 2 0 0 0 0 M END > <DATABASE_ID> EE001579 > <DATABASE_NAME> ExposomeExplorer > <SMILES> CN1C=NC2=C1C(O)=NC(=O)N2C > <INCHI_IDENTIFIER> 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) > <INCHI_KEY> YAPQBXQYLJRXSA-UHFFFAOYSA-N > <FORMULA> C7H8N4O2 > <MOLECULAR_WEIGHT> 180.164 > <EXACT_MASS> 180.06472552 > <JCHEM_ACCEPTOR_COUNT> 3 > <JCHEM_ATOM_COUNT> 21 > <JCHEM_AVERAGE_POLARIZABILITY> 16.84759944556188 > <JCHEM_BIOAVAILABILITY> 1 > <JCHEM_DONOR_COUNT> 1 > <JCHEM_FORMAL_CHARGE> 0 > <JCHEM_GHOSE_FILTER> 0 > <JCHEM_IUPAC> 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione > <ALOGPS_LOGP> -0.78 > <JCHEM_LOGP> -0.7693216573333334 > <ALOGPS_LOGS> -1.37 > <JCHEM_MDDR_LIKE_RULE> 0 > <JCHEM_NUMBER_OF_RINGS> 2 > <JCHEM_PHYSIOLOGICAL_CHARGE> 0 > <JCHEM_PKA_STRONGEST_ACIDIC> 9.28030481882757 > <JCHEM_PKA_STRONGEST_BASIC> -0.9071824149877291 > <JCHEM_POLAR_SURFACE_AREA> 67.23 > <JCHEM_REFRACTIVITY> 44.9345 > <JCHEM_ROTATABLE_BOND_COUNT> 0 > <JCHEM_RULE_OF_FIVE> 1 > <ALOGPS_SOLUBILITY> 7.76e+00 g/l > <JCHEM_TRADITIONAL_IUPAC> theobromine > <JCHEM_VEBER_RULE> 0 $$$$
Description	Found in cacao plant, chocolate and a number of other foods.
Classification	Compounds > Chemical entities > Organic compounds > Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Xanthines
CAS number	83-67-0
PubChem ID	5429
ChEBI ID	28946
FooDB ID	FDB000455
HMDB ID	HMDB0002825

Chemical data

MolDBi data

IUPAC Name	3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional IUPAC Name	theobromine
Formula	C7H8N4O2
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)
InChI Key	YAPQBXQYLJRXSA-UHFFFAOYSA-N
Molecular weight	180.164
Exact mass	180.06472552
SMILES	CN1C=NC2=C1C(=O)NC(=O)N2C

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Imidazopyrimidines
Sub Class	Purines and purine derivatives
Direct Parent	Xanthines
Alternative Parents	6-oxopurines Alkaloids and derivatives Pyrimidones N-substituted imidazoles Vinylogous amides Heteroaromatic compounds Ureas Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives

Publications with Theobromine

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of Theobromine in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of Theobromine with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of Theobromine with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of Theobromine exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of Theobromine exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication