Theobromine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Theobromine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Theobromine?

The molecule Theobromine presents a molecular formula of C7H8N4O2 and its IUPAC name is 3,7-dimethylpurine-2,6-dione.

Theobromine is a molecule found in the cacao plant. It's also found in other foods like tea and coffee. Theobromine is structurally similar to caffeine, but it has a weaker effect on the human body. Theobromine is a bitter alkaloid that's used as a bronchodilator, diuretic, and vasodilator. It's also used to treat heartburn and asthma. Theobromine belongs in chocolate, which is why eating chocolate can make you feel alert and energetic. Theobromine can also be found in some energy drinks..

3D structure

Cartesian coordinates

Geometry of Theobromine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Theobromine YAPQBXQYLJRXSA-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Theobromine

 

Molecule descriptors

 
IUPAC name3,7-dimethylpurine-2,6-dione
InChI codeInChI=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 KeyYAPQBXQYLJRXSA-UHFFFAOYSA-N
SMILESCn1cnc2c1c(=O)[nH]c(=O)n2C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1H-Purine-2, 3,7-dihydro-3,7-dimethyl-
  • 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-
  • 1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI)
  • 2,6-Dihydroxy-3,7-dimethyl-purine
  • 2,6-Dihydroxy-3,7-dimethylpurine
  • 3, 7-Dimethylxanthine
  • 3,7-DIMETHYLXANTHINE; 3,7-DIMETHYLPURINE-2,6-DIONE
  • 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione
  • 3,7-Dimethyl-1H-purine-2,6(3H,7H)-dione
  • 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione
  • 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione #
  • 3,7-Dimethylxanthine
  • 3,7-dimethyl-1,3,7-trihydropurine-2,6-dione
  • 3,7-dimethyl-1H-purine-2,6-dione
  • 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
  • 3,7-dimethylpurine-2,6-dione
  • 3,7-dimethylxanthin
  • 37T
  • 5-26-13-00553 (Beilstein)
  • 519-41-5
  • 7-Dimethylxanthine
  • 83-67-0
  • AB00052141
  • AB00052141_12
  • AC-11381
  • AC-34381
  • AS-13904
  • BBL034679
  • BDBM50014260
  • BPBio1_001043
  • BRN 0016464
  • BSPBio_000947
  • BSPBio_001758
  • C07480
  • CCG-40078
  • CCRIS 2350
  • CEC63CCA-3B4B-4F4F-92C1-1789DF3C880A
  • CS-7972
  • Cocoa Theobromine
  • D71206
  • DB01412
  • DSSTox_CID_6132
  • DSSTox_GSID_26132
  • DSSTox_RID_78030
  • Diurobromine
  • DivK1c_000611
  • EU-0101187
  • FEMA No. 3591
  • FT-0660435
  • FT-0675138
  • HMS1570P09
  • HMS1921O13
  • HMS2092G04
  • HMS2097P09
  • HMS3263N15
  • HMS3714P09
  • HMS501O13
  • HSDB 7332
  • HY-N0138
  • IDI1_000611
  • KBio1_000611
  • KBio2_000433
  • KBio2_003001
  • KBio2_005569
  • KBio3_001258
  • KBioGR_000666
  • KBioSS_000433
  • LP01187
  • LS00156
  • Lopac-T-4500
  • Lopac0_001187
  • MFCD00022830
  • MLS000028407
  • N1573
  • NCGC00016023-01
  • NCGC00016023-02
  • NCGC00016023-03
  • NCGC00016023-04
  • NCGC00016023-05
  • NCGC00016023-06
  • NCGC00016023-07
  • NCGC00016023-08
  • NCGC00016023-09
  • NCGC00016023-10
  • NCGC00016023-11
  • NCGC00016023-12
  • NCGC00016023-13
  • NCGC00016023-14
  • NCGC00016023-15
  • NCGC00016023-17
  • NCGC00016023-18
  • NCGC00016023-26
  • NCGC00024123-03
  • NCGC00024123-04
  • NCGC00024123-05
  • NCGC00024123-06
  • NCGC00024123-07
  • NCGC00024123-08
  • NCGC00179030-01
  • NCGC00179030-02
  • NCGC00253943-01
  • NCGC00261872-01
  • NINDS_000611
  • NSC 5039
  • NSC-5039
  • NSC-757407
  • NSC5039
  • NSC757407
  • OBD445WZ5P
  • PDSP1_001017
  • PDSP2_001001
  • Pharmakon1600-01500649
  • Prestwick0_000874
  • Prestwick1_000874
  • Prestwick2_000874
  • Prestwick3_000874
  • Prestwick_1054
  • Q-100848
  • Q206844
  • SBI-0051154.P003
  • SC 15090
  • SC-15090
  • SDCCGMLS-0002875.P003
  • SDCCGSBI-0051154.P004
  • SMR000058357
  • SPECTRUM1500649
  • SR-01000000069
  • SR-01000000069-10
  • SR-01000000069-2
  • SR-01000000069-4
  • SR-01000000069-7
  • SR-01000000069-8
  • SR-01000000069-9
  • STL419465
  • SY048379
  • Santheose
  • T 4500
  • T0178
  • Teobromin
  • Theobromin
  • Theobromine
  • Theobromine (3,7-Dimethylxanthine)
  • Theobromine 0.1 mg/ml in Methanol
  • Theobromine;
  • Theobrominum
  • Theosalvose
  • Theostene
  • Thesal
  • Thesodate
  • WLN: T56 BN DN FNVMVJ B1 F1
  • Xantheose
  • Xanthine, 3,7-dimethyl-
  • YAPQBXQYLJRXSA-UHFFFAOYSA-
  • Z56347209
  • s2368
  • theobromine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2151
  • CAS-83-67-0
  • UNII-OBD445WZ5P
  • AKOS000121558
  • BRD-K34888156-001-08-8
  • DTXSID9026132
  • CHEMBL1114
  • CHEBI:28946
  • Tox21_110284
  • Tox21_300016
  • Tox21_501187
  • Tox21_110284_1
  • EINECS 201-494-2
  • SPBio_001049
  • SPBio_002868
  • SCHEMBL3184
  • Spectrum_000053
  • Spectrum2_000985
  • Spectrum3_000279
  • Spectrum4_000403
  • Spectrum5_001387

Physico-Chemical properties

IUPAC name3,7-dimethylpurine-2,6-dione
Molecular formulaC7H8N4O2
Molecular weight180.164
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity47.14
LogP-1.0
Topological polar surface area72.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.