InChI=1/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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Inherent Properties, Identifiers and References

ChemSpider ID:	5236
Empirical Formula:	C₇H₈N₄O₂
Molecular Weight:	180.164
Nominal Mass:	180 Da
Average Mass:	180.164 Da
Monoisotopic Mass:	180.064726 Da

Systematic Name:

3,7-dimethylpurine-2,6-dione

SMILES:

O=C2N(c1ncn(c1C(=O)N2)C)C

InChI:

InChI=1/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-UHFFFAOYAW

Original Reference(s)

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Data Source	External ID(s)
AKos	AKI-STT-00189649, AKJ-91967, AKM01295
Alfa Aesar	A11861
CambridgeSoft Corporation	9626
ChEBI	CHEBI:28946
ChemBank	DivK1c_000611, KBio1_000611, KBio2_000433, KBio2_003001, KBio2_005569, KBio3_001258, KBioGR_000666, KBioSS_000433, NINDS_000611, Prestwick0_000874, ...
ChemDB	3968775, 5264045, 5789166
ChemDiv	0342-0017
ChemExper Chemical Directory	Hk\d@DsmB\bbbTrQXUujjUj`@@
ChemIDplus	000083670, 001010599, 006767733, 008048315, 016484858, 017186957, XH2395000
ChemPacific	22310
DiscoveryGate	205018, 24700, 5429
DTP/NCI	221261, 5039
EINECS	N/A
Emory University Molecular Libraries Screening Center	EU-0101187
EPA DSSTox	2130_NTPBSI_v2b
Human Metabolome Database	HMDB02825
Journal of Heterocyclic Chemistry	19711039_I, 19730187_11, 19931221_9
KEGG	C07480
LeadScope	LS-1828, LS-1828
MeSH	Theobromine
Microsource	01500649, 01500649, 01500649, 01500649
MLSMR	MLS000028407
NCGC	NCGC00016023-01, NCGC00016023-02
NIAID	022717
NINDS Approved Drug Screening Program	01500649
NIST	1526284202
NIST Chemistry WebBook	1526284202
PDSP, Pharmacology School of Medicine UNC Chapel Hill	Prestwick_1054
PubChem	5429
PubMed	10048762, 10048796, 10073324, 1008848, 10215755, 10364410, 10376762, 10399816, 10427766, 10445395, ...
Ryan Scientific	LT00000138
San Diego Center for Chemical Genomics	SDCCGMLS-0002875.P003
Sigma-Aldrich	T4500_SIGMA
Single Depositions	Theobromine
SureChem (Patents)	- Patents Exist
Thomson Pharma	00014886, 00029007, 01507320, 02006709
ZINC	ZINC00002151

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Supplemental Information

User Data

experimental physchem properties

Melting Point: 345-350

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

miscellaneous

Safety: WARNING: Irreversible damage risk, protect skin/eyes/lungs.

See Chemical Safety

Source: Camelia, Theobroma, Cola spp

No description available

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-

3,7-Dimethyl-xanthine

83-67-0 [RN]

Diuretin

Theobromine [Wiki]

17186-95-7 [RN]

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-dimethylpurine

2,6-Dihydroxy-3,7-dimethyl-purine

More...

Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

AIDS022717

AIDS-022717

BRN 0016464

C07480

c1095

CCRIS 2350

CHEBI:28946

DivK1c_000611

EU-0101187

FEMA No. 3591

More...

Predicted Properties

LogP:	ACD/LogP: -0.72 XLogP: -0.60 ALOGPS: -0.46	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-0.72	ACD/LogD (pH 7.4):	-0.72
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	9.67	ACD/KOC (pH 7.4):	9.64
#H bond acceptors:	6	#H bond donors:	1
#Freely Rotating Bonds:	0	Polar Surface Area:	58.44 Å²
Index of Refraction:	1.737	Molar Refractivity:	45.05 cm³
Molar Volume:	112 cm³	Polarizability:	17.86 10^-24cm³
Surface Tension:	65.7 dyne/cm	Density:	1.6 g/cm³
Flash Point:	°C	Enthalpy of Vaporization:	kJ/mol
Boiling Point:	°C at 760 mmHg	Vapour Pressure:	mmHg at 25°C

MeSH

MeSH Descriptor Data

MeSH Heading	Theobromine
Concept 1 (Preferred)	Theobromine
	Scope Note	3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9)
	Term	Theobromine
Allowable Qualifiers	AD AE AA AN AI BI BL CF CS CL DF DU EC GE HI IM IP ME PK PD PH PO RE SE ST SD TU TO UR CH CT AG
Pharm. Action	Bronchodilator Agents
	Vasodilator Agents
Registry Number	83-67-0

MeSH Tree Structures

Heterocyclic Compounds [D03]
- Alkaloids [D03.132]
  - Xanthines [D03.132.960]
    - Theobromine [D03.132.960.651]

Heterocyclic Compounds [D03]
- Heterocyclic Compounds, 2-Ring [D03.438]
  - Purines [D03.438.759]
    - Purinones [D03.438.759.758]
      - Xanthines [D03.438.759.758.824]
        
        Theobromine [D03.438.759.758.824.651]

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -0.05
    Log Kow (Exper. database match) =  -0.78
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  483.47  (Adapted Stein & Brown method)
    Melting Pt (deg C):  204.88  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.13E-011  (Modified Grain method)
    MP  (exp database):  357 deg C
    Subcooled liquid VP: 7.17E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.248e+004
       log Kow used: -0.78 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  330 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  32619 mg/L
    Wat Sol (Exper. database match) =  330.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imides
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.63E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.147E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.78  (exp database)
  Log Kaw used:  -9.176  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.396
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6618
   Biowin2 (Non-Linear Model)     :   0.6107
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8010  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5878  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1852
   Biowin6 (MITI Non-Linear Model):   0.0747
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5815
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  9.56E-006 Pa (7.17E-008 mm Hg)
  Log Koa (Koawin est  ): 8.396
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.314 
       Octanol/air (Koa) model:  6.11E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.919 
       Mackay model           :  0.962 
       Octanol/air (Koa) model:  0.00486 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  18.8609 E-12 cm3/molecule-sec
      Half-Life =     0.567 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     6.805 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.94 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: -0.78 (expkow database)

 Volatilization from Water:
    Henry LC:  1.63E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.821E+007  hours   (2.009E+006 days)
    Half-Life from Model Lake :  5.26E+008  hours   (2.192E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.318           13.6         1000       
   Water     40.5            360          1000       
   Soil      59.1            720          1000       
   Sediment  0.0742          3.24e+003    0          
     Persistence Time: 513 hr