InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

Advertisements

1 hit(s) found in 0.08 seconds
Search term: RYYVLZVUVIJVGH-UHFFFAOYAW
Found by InChIKey (full match)

Please login to be able to add spectra, identifiers, links and publications.

Comments
Image
Spectrum
CIF
Identifier
Description
Format: Insert the DOI number only, not the DOI prefix.
Enter 10.1021/ol702040y not DOI: 10.1021/ol702040y
Use lookup button to fetch DOI record.

Click OK to accept, Cancel to reject fetch result.

OK Cancel
Enter PubMed Id in the text box below. Use lookup button to fetch PubMed record. Click OK to accept, Cancel to reject fetch result.

Click OK to accept, Cancel to reject fetch result.

OK Cancel
Add:

Inherent Properties, Identifiers and References

ChemSpider ID:	2424
Empirical Formula:	C₈H₁₀N₄O₂
Molecular Weight:	194.1906
Nominal Mass:	194 Da
Average Mass:	194.1906 Da
Monoisotopic Mass:	194.080376 Da

Systematic Name:

1,3,7-trimethylpurine-2,6-dione

SMILES:

O=C2N(c1ncn(c1C(=O)N2C)C)C

InChI:

InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

InChIKey:

RYYVLZVUVIJVGH-UHFFFAOYAW

Std. InChI:

InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

Std. InChIKey:

RYYVLZVUVIJVGH-UHFFFAOYSA-N

License

Wikipedia Article(s)

Caffeine is a bitter, white crystalline xanthine alkaloid that is a psychoactive stimulant drug. Caffeine was discovered by a German chemist, Friedrich Ferdinand Runge, in 1819. He coined the term kaffein, a chemical compound in coffee, which in English became caffeine. Caffeine is found in varying quantities in the beans, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants. It is most commonly consumed by humans in infusions extracted from the cherries of the coffee plant and the leaves of the tea bush, as well as from various foods and drinks containing products derived from the kola nut. Other sources include yerba mate, guarana berries, and the Yaupon Holly. In humans, caffeine is a central nervous system (CNS) stimulant, having the effect of temporarily warding off drowsiness and restoring alertness. Beverages containing caffeine, such as coffee, tea, soft drinks, and energy drinks, enjoy great popularity. Caffeine is the world's most widely consumed psychoactive substance, but, unlike many other psychoactive substances, it is legal and unregulated in nearly all jurisdictions. In North America, 90% of adults consume caffeine daily. The U.S. Food and Drug Administration lists caffeine as a "multiple purpose generally recognized as safe food substance". Caffeine has diuretic properties, at least when administered in sufficient doses to subjects that do not have a tolerance for it. Regular users, however, develop a strong tolerance to this effect, Read more... or Edit at Wikipedia...

Associated Data Sources and Commercial Suppliers

Filter

Patents

PubMed Articles

Disclaimer (Details...)

Supplemental Information

Links & References

Johanna Linnankoski, Johanna M Mäkelä, Veli-Pekka Ranta, Arto Urtti, and Marjo Yliperttula. Computational Prediction of Oral Drug Absorption Based on Absorption Rate Constants in Humans, J. Med. Chem., 2006, 49(12), 3674-3681

23 compounds and their Experimental FA values are given in the paper. These have been provided here.

QSAR World - Datasets - Linnankoski

Tapan Sanghvi, Nina Ni, Michael Mayersohn, Samuel H. Yalkowsky. Predicting Passive Intestinal Absorption Using A Single Parameter, QSAR Comb. Sci. 2003, 22(2), 247-257

131 compounds and their 'Fraction Absorbed' values have been obtained from the table given in the paper. Some compounds had multiple values reported (as obtained from various references). These have been averaged and provided by us in the SDF and AMP files. The "Sanghvi_values.txt" file contains all data (as reported in Table 1) and "Sanghvi_avg_values.txt" contains averaged data for compounds with multiple entries (as reported in Table 2). "Benserazide, HCl" was retrieved as "Benserazide", "Ceftriaxone, Na" as "Ceftriaxone", "Foscarnet, Na" as "Foscarnet", "L-Dopa" as "Levodopa", "L-Leucine" as "Leucine" and "Triacrilast" as "Tiacrilast". The last compound was found to be mispelt as checked from the original reference.

QSAR World - Datasets - Sanghvi

Matthew D. Wessel, Peter C. Jurs, John W. Tolan, and Steven M. Muskal. Prediction of Human Intestinal Absorption of Drug Compounds from Molecular Structure, J. Chem. Inf. Comput. Sci., 1998, 38(4), 726-735

A total of 86 drugs and their %HIA (Human Intestinal Absorption) values taken from the table given in the paper. Compound "trovoflaxicin" was retrieved as "trovafloxacin", "acetylsalicylic acid" as "aspirin", and "phenoxymethylpenicillinic acid" as "penicillinv" from ChemIDplus. Fragment removed from "timolol maleate" during "wash". AMP file has a "Label" column indicating 9 compounds used as a "Cross-Validation Set" and 10 compounds used as an "External Prediction Set" by the authors. Rest of the compounds are labeled as "Training Set".

QSAR World - Datasets - Wessel

Oprea, T. I. and Gottfries, J.. Toward Minimalistic Modeling of Oral Drug Absorption, J. Mol. Graphics Modell. 1999, 17 (5-6), 261-274

"The data set consists of 85 compounds, for which Wessel and co-workers gathered %HIA values from the literature. Sixteen of these 85 structures have Caco-2 cell permeability data, originating from Artursson and Karlsson that were used in the QSAR models proposed by Van de Waterbeemd et. al. and by Norinder et. al. In addition, Yazdanian et. al. reported Caco-2 cell permeability data for 29 of these 85 structures. Thus, three experimental measures were used to derive our QSAR model".

QSAR World - Datasets - Oprea

Oleg A. Raevsky, Klaus-J. Schaper, Per Artursson, James W. McFarland. A Novel Approach for Prediction of Intestinal Absorption of Drugs in Humans based on Hydrogen Bond Descriptors and Structural Similarity, Quant. Struct.-Act. Relat. 2002, 20(5-6), 402-413.

[DOI: 10.1002/1521-3838(200112)20:5/6<402::AID-QSAR402>3.0.CO;2-6]

The relationship between gastrointestinal absorption in humans and hydrogen bond descriptors for 100 structurally diverse drugs was studied. The datasets are available from QSAR World here: http://www.qsarworld.com/qsar-datasets-raevsky2.php

William Bains, Antranig Basman and Cat White. hERG binding specificity and binding site structure: evidence from a fragment-based evolutionary computing SAR study, Progress in Biophysics and Molecular Biology 2004, 86 (2), 205-233

[DOI: 10.1016/j.pbiomolbio.2003.09.001]

The authors describe the Tapplication of genetic programming, an evolutionary computing method, to predicting whether small molecules will block the HERG cardiac potassium channel. Models based on a molecular fragment-based descriptor set achieve an accuracy of 85–90% in predicting whether the IC50 of a ‘blind’ set of compounds is <1 μM. The datasets are available from QSAR World at http://www.qsarworld.com/qsar-datasets-bains.php

Jonathan Burns, Donald F. Weaver. A Mathematical Model for Prediction of Drug Molecule Diffusion across the Blood-Brain Barrier, Can. J. Neurol. Sci. 2004, 31, 520-527.

This URL links to the dataset on QSAR world Compounds and their property with respect to crossing of the "Blood-Brain Barrier" (BBB) have been given in the paper. In all 80 compounds with their BBB permabilty have been given in the files provided here. 45 "Cross" the BBB while 35 "Do Not Cross" the BBB

S. Agatonovic-Kustrin, R. Beresford and A. Pauzi M. Yusof. Theoretically-derived molecular descriptors important in human intestinal absorption, J. Pharm. Biomed. Anal. 2001, 44(12), 1927 - 1937

86 drugs and their experimentally-derived Intestinal Absorption (%) values have been given. "Fluconasole" was retrieved as "Fluconazole" and "Hydrocortizone" as "hydrocortisone" from ChemIDplus. Drugs were either part of 'Training and testing data sets' or 'Validation data set'. This scheme has been indicated in a 'Label' column in the AMP file.

QSAR World - Datasets - Kustrin

Zhao YH, Abraham MH, Le J, Hersey A, Luscombe CN, Beck G, Sherborne B, and Cooper I. Rate-limited Steps of Human Oral Absorption and QSAR Studies, Pharm Res., 2002, 19(10), 1446-57

QSAR World - Datasets - Zhao

Igor V. Tetko, Vsevolod Yu. Tanchuk, Tamara N. Kasheva, and Alessandro E. P. Villa. Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices, J. Chem. Inf. Comput. Sci., 2001, 41 (6), pp 1488–1493

[DOI: 10.1021/ci000392t]

The molecular weight and electrotopological E-state indices were used to estimate by Artificial Neural Networks aqueous solubility for a diverse set of 1291 organic compounds. The neural network with 33-4-1 neurons provided highly predictive results with r2 = 0.91 and RMS = 0.62.

Franco Lombardo, R. Scott Obach, Marina Y. Shalaeva, and Feng Gao. Prediction of Human Volume of Distribution Values for Neutral and Basic Drugs. 2. Extended Data Set and Leave-Class-Out Statistics, J. Med. Chem., 2004, 47(5), 1242-1250

[DOI: 10.1021/jm030408h]

In all, 120 compounds, their VDss (volume-of-distribution in steady-state) Fu (fraction unbound in human plasma) values have been given. The same have been provided here in .sdf and .txt files.

Bohn Mathilde. Effects of caffeine on stereoselectivities of high cell density biotransformations of cyclic β-keto esters with Saccharomyces cerevisiae, Organic & Biomolecular Chemistry, 2007

[DOI: 10.1039/b709716f]

Dupre al.. A forward chemical genetic screen reveals an inhibitor of Mre11-Rad50-Nbs1 complex, Nature Chemical Biology, doi: 10.1038/nchembio.63, published online 6 January 2008.

[DOI: 10.1038/nchembio.63]

HPLC Separation of Caffeine on Phenomenex 4u Synergi Hydro-RP with UV Detection

E. L. Willighagen, H. M. G. W. Denissen, R. Wehrens, and L. M. C. Buydens. On the Use of 1H and 13C 1D NMR Spectra as QSPR Descriptors, J. Chem. Inf. Model., 46 (2), 487-494, 2006

[PubMed: 16562976] [DOI: 10.1021/ci050282s]

GC of caffeine on Phenomenex Zebron ZB-1 with MS detection

HPLC Separation of Caffeine on Phenomenex Synergi 2u Fusion-RP with UV Detection

HPLC Separation of Caffeine on Phenomemenx Luna 3u Phenyl-Hexyl MercuryMS Cartridge with UV Detection

User Data

experimental physchem properties

Melting Point: 234-236

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

Melting Point: 234-236

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

Melting Point: 237 C

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

Boiling Point: 178 subl.

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

Boiling Point: 178 subl.

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

Boiling Point: (sublimes)

The boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid. See also: Boiling Point

Specific Gravity: 1.230

Specific gravity is defined as the ratio of the density of a given substance to the density of water, when both are at the same temperature. See also: Specific Gravity

Specific Gravity: 1.230

Specific gravity is defined as the ratio of the density of a given substance to the density of water, when both are at the same temperature. See also: Specific Gravity

Solubility: Soluble in pyrrole, THF-H2O mixture, ethyl acetate

No description available

Solubility: -0.97

No description available

miscellaneous

Appearance: odourless white powder or crystals

Visual appearance of the given substance.

Stability: Stable. Incompatible with strong acids, strong bases, strongoxidizing agents, iodine, silver salts, tannins. Weakly light sensitive in solution.

Chemical stability occurs when a substance is in a (dynamic) chemical equilibrium with its environment. See also: Chemical Stability

Toxicity: ORL-RAT LD50 192 mg kg-1, IPR-RAT LD50 260 mg kg-1, IVN-RAT LD50 105 mg kg-1, SCU-RAT LD50 170 mg kg-1

Toxicity is the degree to which something is able to produce illness or damage to an exposed organism. See also: Toxicity and list of used abbreviations.

Safety: DANGER: POISON, irritates skin, eyes, lungs

See Chemical Safety

Safety: WARNING: Causes CNS effects, skin and eye irritation

See Chemical Safety

Safety: Safety glasses.

See Chemical Safety

Source: Cofea, Theobroma, Camelia and Cola spp

No description available

Chemical Class: alkaloid

No description available

Names and Synonyms

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

1,3,7-Trimethyl-3,7-dihydro-1H-purin-2,6-dion

1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione

1,3,7-Triméthyl-3,7-dihydro-1H-purine-2,6-dione

1H-purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-

1-methyl-Theobromine

5743-12-4 [RN]

7-methyl Theophylline

Caffeina [Italian]

Shape Plus

58-08-2

More...

Database ID(s)

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

ACD/Labs Predicted Properties

ACD/LogP:	-0.13	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-0.13	ACD/LogD (pH 7.4):	-0.13
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	20.22	ACD/KOC (pH 7.4):	20.22
#H bond acceptors:	6	#H bond donors:	0
#Freely Rotating Bonds:	0	Polar Surface Area:	58.44 Å²
Index of Refraction:	1.679	Molar Refractivity:	50.38 cm³
Molar Volume:	133.3 cm³	Polarizability:	19.97 10^-24cm³
Surface Tension:	55.7 dyne/cm	Density:	1.45 g/cm³
Flash Point:	205.9 °C	Enthalpy of Vaporization:	67.01 kJ/mol
Boiling Point:	416.8 °C at 760 mmHg	Vapour Pressure:	3.72E-07 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.16
    Log Kow (Exper. database match) =  -0.07
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  430.85  (Adapted Stein & Brown method)
    Melting Pt (deg C):  180.30  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.33E-009  (Modified Grain method)
    MP  (exp database):  238 deg C
    Subcooled liquid VP: 1.46E-006 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):  2632
       log Kow used: -0.07 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2.16e+004 mg/L (25 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  11308 mg/L
    Wat Sol (Exper. database match) =  21600.00
       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 :   3.58E-011  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  7.116E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -0.07  (exp database)
  Log Kaw used:  -8.835  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  8.765
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6551
   Biowin2 (Non-Linear Model)     :   0.5625
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7700  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5676  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1439
   Biowin6 (MITI Non-Linear Model):   0.0521
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.5019
 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):  0.000195 Pa (1.46E-006 mm Hg)
  Log Koa (Koawin est  ): 8.765
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0154 
       Octanol/air (Koa) model:  0.000143 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.358 
       Mackay model           :  0.552 
       Octanol/air (Koa) model:  0.0113 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  19.4185 E-12 cm3/molecule-sec
      Half-Life =     0.551 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     6.610 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.455 (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: -0.07 (expkow database)

 Volatilization from Water:
    Henry LC:  3.58E-011 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.279E+007  hours   (9.496E+005 days)
    Half-Life from Model Lake : 2.486E+008  hours   (1.036E+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       0.00382         13.2         1000       
   Water     38.6            360          1000       
   Soil      61.4            720          1000       
   Sediment  0.0711          3.24e+003    0          
     Persistence Time: 581 hr

Spectra