NP-MRD: Showing NP-Card for Caffeine (NP0000009)

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Record Information

Version

2.0

Created at

2006-02-16 08:53:46 UTC

Updated at

2025-02-11 15:42:35 UTC

NP-MRD ID

NP0000009

Natural Product DOI

https://doi.org/10.57994/0546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caffeine

Description

Caffeine is a methyl xanthine alkaloid that is also classified as a purine. Formally, caffeine 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. Caffeine is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, nuts, or leaves of a number of plants native to Africa, East Asia and South America and helps to protect them against predator insects and to prevent germination of nearby seeds. The most well-known source of caffeine is the coffee bean. Caffeine is the most widely consumed psychostimulant drug in the world. 85% Of American adults consumed some form of caffeine daily, consuming 164 mg on average. Caffeine is mostly is consumed in the form of coffee. Caffeine is a central nervous system stimulant that reduces fatigue and drowsiness. At normal doses, caffeine has variable effects on learning and memory, but it generally improves reaction time, wakefulness, concentration, and motor coordination. Caffeine is a proven ergogenic aid in humans. Caffeine improves athletic performance in aerobic (especially endurance sports) and anaerobic conditions. Moderate doses of caffeine (around 5 mg/kg) can improve sprint performance, cycling and running time trial performance, endurance and cycling power output (PMID: 32551869 ). At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance, studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption. (PMID: 16540173 ). Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form 5-acetylamino-6-amino-3-methyluracil. Caffeine concentrations in coffee beverages can be quite variable. A standard cup of coffee is often assumed to provide 100 mg of caffeine, but a recent analysis of 14 different specialty coffees purchased at coffee shops in the US found that the amount of caffeine in 8 oz (=240 ml) of brewed coffee ranged from 72 to 130 mg. Caffeine in espresso coffees ranged from 58 to 76 mg in a single shot. (PMID: 16507475 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

201
  Mrv1652305201900032D          

 14 15  0  0  0  0            999 V2000
    3.0791    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741    0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4  7  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=NC2=C1C(=O)N(C)C(=O)N2C

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

> <INCHI_KEY>
RYYVLZVUVIJVGH-UHFFFAOYSA-N

> <FORMULA>
C8H10N4O2

> <MOLECULAR_WEIGHT>
194.1906

> <EXACT_MASS>
194.080375584

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.9549309213843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-0.5456455916666669

> <ALOGPS_LOGS>
-1.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9241843687844741

> <JCHEM_POLAR_SURFACE_AREA>
58.440000000000005

> <JCHEM_REFRACTIVITY>
49.8312

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 201                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748   3.080   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -1.540   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748  -1.540   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.538   1.239   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.414   0.770   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.538  -1.239   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.437   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.017   2.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    8   10   12                                                  
CONECT    4    7   11   13                                                  
CONECT    5    9   10   14                                                  
CONECT    6    8   11                                                       
CONECT    7    4    8    9                                                  
CONECT    8    3    6    7                                                  
CONECT    9    1    5    7                                                  
CONECT   10    2    3    5                                                  
CONECT   11    4    6                                                       
CONECT   12    3                                                            
CONECT   13    4                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
1,3,7-Trimethyl-2,6-dioxopurine	ChEBI
1,3,7-Trimethylpurine-2,6-dione	ChEBI
1,3,7-Trimethylxanthine	ChEBI
1-Methyltheobromine	ChEBI
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion	ChEBI
7-Methyltheophylline	ChEBI
Anhydrous caffeine	ChEBI
Cafeina	ChEBI
Cafeine	ChEBI
Coffein	ChEBI
Guaranine	ChEBI
Koffein	ChEBI
Mateina	ChEBI
Methyltheobromine	ChEBI
Teina	ChEBI
Thein	ChEBI
Theine	ChEBI
Respia	Kegg
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione	HMDB
1-Methyl-theobromine	HMDB
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione	HMDB
7-Methyl theophylline	HMDB
Anhydrous caffeine (JP15)	HMDB
Hycomine	HMDB
Lanorinal	HMDB
Methyltheobromide	HMDB
Methylxanthine theophylline	HMDB
Monohydrate caffeine	HMDB
Propoxyphene	HMDB
Merck dura brand OF caffeine	HMDB
Thompson brand 1 OF caffeine	HMDB
Bristol-myers squibb brand OF caffeine	HMDB
Caffedrine	HMDB
Dexitac	HMDB
Percoffedrinol N	HMDB
Pierre fabre brand OF caffeine	HMDB
Republic drug brand OF caffeine	HMDB
Thompson brand 2 OF caffeine	HMDB
Vivarin	HMDB
Coffeinum N	HMDB
Coffeinum purrum	HMDB
Durvitan	HMDB
GlaxoSmithKline brand OF caffeine	HMDB
No doz	HMDB
Percutaféine	HMDB
Quick-pep	HMDB
Seid brand OF caffeine	HMDB
Berlin-chemie brand OF caffeine	HMDB
Passauer brand OF caffeine	HMDB
Quick pep	HMDB
QuickPep	HMDB

Chemical Formula

C₈H₁₀N₄O₂

Average Mass

194.1906 Da

Monoisotopic Mass

194.08038 Da

IUPAC Name

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

Traditional Name

caffeine

CAS Registry Number

58-08-2

SMILES

CN1C=NC2=C1C(=O)N(C)C(=O)N2C

InChI Identifier

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

InChI Key

RYYVLZVUVIJVGH-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Varshavi.d26			2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Varshavi.d26			2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	Varshavi.d26			2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Varshavi.d26			2021-10-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Varshavi.d26			2021-10-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-21	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-21	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-10-12	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	USDA
Abramis brama	FooDB	USDA
Acacia polyacantha	LOTUS Database	35616633
Acipenser	FooDB	USDA
Acipenseridae	FooDB	USDA
Agave	FooDB	USDA
Allium ampeloprasum	FooDB	USDA
Allium ascalonicum	FooDB	USDA
Allium cepa	FooDB	USDA
Allium fistulosum	FooDB	USDA
Allium sativum	FooDB	USDA
Allium schoenoprasum	FooDB	USDA
Allium tuberosum	FooDB	USDA
Alosa sapidissima	FooDB	USDA
Anacardium occidentale	FooDB	USDA
Ananas comosus	FooDB	USDA
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	USDA
Anguilla	FooDB	USDA
Anguilliformes	FooDB	USDA
Annona cherimola	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona muricata	FooDB	USDA
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	USDA
Apium graveolens	FooDB	USDA
Apium graveolens var. dulce	FooDB	USDA
Apium graveolens var. rapaceum	FooDB	USDA
Arachis hypogaea	FooDB	USDA
Arctium lappa	FooDB	USDA
Armoracia rusticana	FooDB	USDA
Artocarpus altilis	FooDB	USDA
Aspalathus linearis	LOTUS Database	35616633
Asparagus officinalis	FooDB	USDA
Astacidea	FooDB	USDA
Avena sativa L.	FooDB	USDA
Averrhoa carambola	FooDB	USDA
Bertholletia excelsa	FooDB	USDA
Beta vulgaris	FooDB	USDA
Beta vulgaris ssp. cicla	FooDB	USDA
Bidens pilosa	LOTUS Database	35616633
Bison bison	FooDB	USDA
Bos taurus	FooDB	USDA
Bos taurus X Bison bison	FooDB	FooDB
Brassica alboglabra	FooDB	USDA
Brassica juncea	FooDB	USDA
Brassica napus	FooDB	USDA
Brassica oleracea	FooDB	USDA
Brassica oleracea var. botrytis	FooDB	USDA
Brassica oleracea var. capitata	FooDB	USDA
Brassica oleracea var. gemmifera	FooDB	USDA
Brassica oleracea var. gongylodes	FooDB	USDA
Brassica oleracea var. sabauda	FooDB	USDA
Brassica rapa	FooDB	USDA
Brassica rapa ssp. chinensis	FooDB	USDA
Brassica rapa var. rapa	FooDB	USDA
Bubalus bubalis	FooDB	FooDB
Buccinidae	FooDB	USDA
Camellia assamica	KNApSAcK Database	22123792
Camellia irawadiensis	KNApSAcK Database	22123792
Camellia kissi	KNApSAcK Database	22123792
Camellia ptilophylla	LOTUS Database	35616633
Camellia sinensis	KNApSAcK Database	22123792
Camellia sinensis var. assamica	Plant	KNApSAcK
Camellia sinensis var. sinensis	KNApSAcK Database	22123792
Camellia taliensis	KNApSAcK Database	22123792
Camellia thea	KNApSAcK Database	22123792
Camellia toliensis	KNApSAcK Database	22123792
Cammellia assamica var.kucha	-	KNApSAcK
Capparis spinosa	FooDB	USDA
Capra aegagrus hircus	FooDB	USDA
Capsicum annuum	FooDB	All-Creatures
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	FooDB	USDA
Caridea	FooDB	USDA
Carum carvi	FooDB	USDA
Carya illinoinensis	FooDB	USDA
Ceratonia siliqua	FooDB	USDA
Cervidae	FooDB	USDA
Cervus canadensis	FooDB	USDA
Chamaemelum nobile	FooDB	USDA
Chondrus crispus	FooDB	USDA
Cicer arietinum	FooDB	USDA
Cichlidae	FooDB	USDA
Cichorium endivia	FooDB	USDA
Cichorium intybus	FooDB	USDA
Cinnamomum	FooDB	USDA
Citrullus lanatus	FooDB	USDA
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	USDA
Citrus aurantiifolia	FooDB	USDA
Citrus aurantium	LOTUS Database	35616633
Citrus latifolia	FooDB	USDA
Citrus limon	KNApSAcK Database	22123792
Citrus maxima	KNApSAcK Database	22123792
Citrus paradisi	KNApSAcK Database	22123792
Citrus reticulata	FooDB	USDA
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clupea harengus harengus	FooDB	USDA
Cocos nucifera	FooDB	USDA
Coffea arabica	KNApSAcK Database	22123792
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	KNApSAcK Database	22123792
Coffea dewevrei	KNApSAcK Database	22123792
Coffea eugeniodes	KNApSAcK Database	22123792
Coffea eugenioides	KNApSAcK Database	22123792
Coffea excelsa	KNApSAcK Database	22123792
Coffea kianjavatensis	KNApSAcK Database	22123792
Coffea liberica	KNApSAcK Database	22123792
Coffea racemosa	KNApSAcK Database	22123792
Coffea salvatrix	KNApSAcK Database	22123792
Coffea spp	KNApSAcK Database	22123792
Coffea spp.	KNApSAcK Database	22123792
Coffea, Thea	-	KNApSAcK
Coffee arabica	-	KNApSAcK
Cola acuminata	KNApSAcK Database	22123792
Cola nitida	LOTUS Database	35616633
Cola sp.	KNApSAcK Database	22123792
Cola spp.	KNApSAcK Database	22123792
Colocasia esculenta	FooDB	USDA
Columba	FooDB	FooDB
Columbidae	FooDB	USDA
Coregonus	FooDB	USDA
Coriandrum sativum L.	FooDB	USDA
Corylus	FooDB	USDA
Corylus avellana	FooDB	USDA
Crassostrea gigas	FooDB	USDA
Crassostrea virginica	FooDB	USDA
Crocus sativus	FooDB	USDA
Cucumis melo	FooDB	USDA
Cucumis sativus L.	FooDB	USDA
Cucurbita maxima	FooDB	USDA
Cucurbita moschata	FooDB	USDA
Cuminum cyminum	FooDB	USDA
Curcuma longa	FooDB	USDA
Cyprinus carpio	FooDB	USDA
Dioscorea	FooDB	USDA
Dioscorea pentaphylla	FooDB	USDA
Diospyros kaki	FooDB	USDA
Dromaius novaehollandiae	FooDB	USDA
Elaeis	FooDB	USDA
Engraulidae	FooDB	USDA
Engraulis encrasicolus	FooDB	USDA
Equus caballus	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	USDA
Esox lucius	FooDB	USDA
Eucheuma	FooDB	USDA
Eutrema japonicum	FooDB	USDA
Fagopyrum esculentum	FooDB	USDA
Festuca rubra	LOTUS Database	35616633
Firmiana simplex	KNApSAcK Database	22123792
Foeniculum vulgare	FooDB	USDA
Gadiformes	FooDB	USDA
Gadus	FooDB	USDA
Gadus macrocephalus	FooDB	USDA
Gadus morhua	FooDB	USDA
Gallus gallus	FooDB	FooDB
Gastropoda	FooDB	USDA
Glycine max	FooDB	USDA
Grifola frondosa	FooDB	USDA
Helianthus tuberosus	FooDB	USDA
Herreania sp.	-	KNApSAcK
Hibiscus sabbariffa	FooDB	USDA
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	USDA
Hippoglossus stenolepis	FooDB	USDA
Homarus americanus	FooDB	USDA
Hoplostethus atlanticus	FooDB	USDA
Hordeum vulgare	FooDB	USDA
Ictalurus punctatus	FooDB	USDA
Ilex cornuta	KNApSAcK Database	22123792
Ilex dumosa	LOTUS Database	35616633
Ilex paraguariensis	KNApSAcK Database	22123792
Ilex paraguayensis	KNApSAcK Database	22123792
Illicium verum	FooDB	USDA
Ipomoea batatas	FooDB	USDA
Juglans	FooDB	USDA
Juglans nigra L.	FooDB	USDA
Juglans regia	FooDB	USDA
Lablab purpureus	FooDB	USDA
Lagenaria siceraria	FooDB	USDA
Lagopus muta	FooDB	FooDB
Laminaria	FooDB	USDA
Lens culinaris	FooDB	USDA
Lepidium sativum	FooDB	USDA
Leporidae	FooDB	USDA
Lepus timidus	FooDB	FooDB
Linum usitatissimum	FooDB	USDA
Litchi chinensis	FooDB	USDA
Lupinus	FooDB	USDA
Lutjanidae	FooDB	USDA
Macadamia	FooDB	USDA
Macadamia tetraphylla	FooDB	USDA
Malus pumila	FooDB	USDA
Mangifera indica	FooDB	USDA
Manihot esculenta	FooDB	USDA
Matricaria recutita	FooDB	USDA
Medicago sativa	FooDB	USDA
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	USDA
Merlangius merlangus	FooDB	USDA
Micropogonias undulatus	FooDB	USDA
Microstomus kitt	FooDB	USDA
Mugil cephalus	FooDB	USDA
Murraya exotica	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	USDA
Myristica fragrans	FooDB	USDA
Mytilidae	FooDB	USDA
Mytilus edulis	FooDB	USDA
Nelumbo	FooDB	USDA
Nephropidae	FooDB	USDA
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	USDA
Ocimum basilicum	FooDB	USDA
Octopus vulgaris	FooDB	USDA
Odocoileus	FooDB	FooDB
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus keta	FooDB	USDA
Oncorhynchus kisutch	FooDB	USDA
Oncorhynchus mykiss	FooDB	USDA
Oncorhynchus nerka	FooDB	USDA
Oncorhynchus tshawytscha	FooDB	USDA
Opuntia cochenillifera	FooDB	USDA
Origanum majorana	FooDB	USDA
Origanum vulgare	FooDB	USDA
Origanum X majoricum	FooDB	USDA
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	USDA
Oryza sativa	FooDB	USDA
Osmeridae	FooDB	USDA
Osmerus mordax	FooDB	USDA
Ovis aries	FooDB	FooDB
Pachyrhizus erosus	FooDB	USDA
Panicum miliaceum	FooDB	USDA
Paramuricea clavata	LOTUS Database	35616633
Passiflora edulis	FooDB	USDA
Pastinaca sativa	FooDB	USDA
Paullinia cupana	KNApSAcK Database	22123792
Paullinia trifoliata	KNApSAcK Database	22123792
Pectinidae	FooDB	USDA
Perciformes	FooDB	USDA
Persea americana	FooDB	USDA
Petroselinum crispum	FooDB	USDA
Phaseolus lunatus	FooDB	USDA
Phaseolus vulgaris	FooDB	USDA
Phasianidae	FooDB	USDA
Phasianus colchicus	FooDB	FooDB
Phyllostachys edulis	FooDB	USDA
Pimenta dioica	FooDB	USDA
Pimpinella anisum	FooDB	USDA
Pinus	FooDB	USDA
Piper nigrum L.	FooDB	USDA
Pistacia vera	FooDB	USDA
Pisum sativum	FooDB	USDA
Pleuronectiformes	FooDB	USDA
Pleurotus ostreatus	FooDB	USDA
Pollachius pollachius	FooDB	USDA
Portulaca oleracea	FooDB	USDA
Prunus armeniaca	FooDB	USDA
Prunus domestica	FooDB	PHYTOHUB
Prunus dulcis	FooDB	USDA
Prunus virginiana	FooDB	USDA
Pseudo-nitzschia multistriata	LOTUS Database	35616633
Psidium guajava	FooDB	USDA
Psophocarpus tetragonolobus	FooDB	USDA
Punica granatum	FooDB	USDA
Pyrus pyrifolia	FooDB	USDA
Ranidae	FooDB	USDA
Raphanus sativus	FooDB	USDA
Raphanus sativus var. longipinnatus	FooDB	USDA
Reinhardtius hippoglossoides	FooDB	USDA
Rheum rhabarbarum	FooDB	USDA
Ribes nigrum	FooDB	PHYTOHUB
Ribes rubrum	FooDB	USDA
Ribes uva-crispa	FooDB	USDA
Scomberomorus maculatus	FooDB	USDA
Scurrula atropurpurea	KNApSAcK Database	22123792
Scurrura atropurpurea	-	KNApSAcK
Sebastes	FooDB	USDA
Sebastes alutus	FooDB	USDA
Secale cereale	FooDB	USDA
Sechium edule	FooDB	USDA
Sesamum indicum	FooDB	USDA
Sinomenium acutum	LOTUS Database	35616633
Solanum melongena	FooDB	USDA
Solanum tuberosum	FooDB	USDA
Soleidae	FooDB	USDA
Spinacia oleracea	FooDB	USDA
Spirulina	FooDB	USDA
Squaliformes	FooDB	USDA
Stenodus leucichthys	FooDB	USDA
Stenotomus chrysops	FooDB	USDA
Strombidae	FooDB	USDA
Struthio camelus	FooDB	USDA
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	USDA
Syzygium aromaticum	FooDB	USDA
Tamarindus indica	FooDB	USDA
Taraxacum officinale	FooDB	USDA
Tetragonia tetragonioides	FooDB	USDA
Teuthida	FooDB	USDA
Thea siensis	KNApSAcK Database	22123792
Theobroma angustifolium	LOTUS Database	35616633
Theobroma cacao	KNApSAcK Database	22123792
Theobroma grandiflorum	KNApSAcK Database	22123792
Thunnus albacares	FooDB	USDA
Thunnus thynnus	FooDB	USDA
Thymus vulgaris	FooDB	USDA
Trachinotus carolinus	FooDB	USDA
Trachurus symmetricus	FooDB	USDA
Trewia nudiflora	LOTUS Database	35616633
Triticum	FooDB	USDA
Triticum aestivum	FooDB	USDA
Triticum durum	FooDB	USDA
Undaria pinnatifida	FooDB	USDA
Vaccinium macrocarpon	FooDB	USDA
Vaccinium ovalifolium	FooDB	USDA
Vanilla	FooDB	USDA
Vicia faba	FooDB	USDA
Vigna mungo	FooDB	USDA
Vigna radiata	FooDB	USDA
Vigna unguiculata ssp. unguiculata	FooDB	USDA
Virola surinamensis	FooDB	USDA
Vitis	FooDB	USDA
Xiphias gladius	FooDB	USDA
Zea mays L.	FooDB	USDA
Zingiber officinale	FooDB	USDA
Zizania	FooDB	USDA

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical 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

Substituents

Xanthine
Purinone
6-oxopurine
Alkaloid or derivatives
Pyrimidone
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Vinylogous amide
Imidazole
Azole
Urea
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine alkaloid (CHEBI:27732 )
trimethylxanthine (CHEBI:27732 )
Purine alkaloids (C07481 )
a small molecule (1-3-7-TRIMETHYLXANTHINE )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	238 °C	https://pubchem.ncbi.nlm.nih.gov/compound/caffeine#section=Melting-Point
Boiling Point	178 °C	https://pubchem.ncbi.nlm.nih.gov/compound/caffeine#section=Boiling-Point
Water Solubility	21.6 mg/mL at 25 °C	Not Available
LogP	-0.07	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	11 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-0.55	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.83 m³·mol⁻¹	ChemAxon
Polarizability	18.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001847

DrugBank ID

DB00201

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

1-3-7-TRIMETHYLXANTHINE

BiGG ID

Not Available

Wikipedia Link

Caffeine

METLIN ID

1455

PubChem Compound

2519

PDB ID

Not Available

ChEBI ID

27732

Good Scents ID

rw1014161

References

General References

Wilkinson SC, Maas WJ, Nielsen JB, Greaves LC, van de Sandt JJ, Williams FM: Interactions of skin thickness and physicochemical properties of test compounds in percutaneous penetration studies. Int Arch Occup Environ Health. 2006 May;79(5):405-13. Epub 2006 Jan 25. [PubMed:16435152 ]
Ayotte P, Dewailly E, Lambert GH, Perkins SL, Poon R, Feeley M, Larochelle C, Pereg D: Biomarker measurements in a coastal fish-eating population environmentally exposed to organochlorines. Environ Health Perspect. 2005 Oct;113(10):1318-24. [PubMed:16203240 ]
Horrigan LA, Kelly JP, Connor TJ: Immunomodulatory effects of caffeine: friend or foe? Pharmacol Ther. 2006 Sep;111(3):877-92. Epub 2006 Mar 15. [PubMed:16540173 ]
Rodrigues IM, Klein LC: Boiled or filtered coffee? Effects of coffee and caffeine on cholesterol, fibrinogen and C-reactive protein. Toxicol Rev. 2006;25(1):55-69. [PubMed:16856769 ]
Lamarine RJ: Selected health and behavioral effects related to the use of caffeine. J Community Health. 1994 Dec;19(6):449-66. [PubMed:7844249 ]
James JE: Critical review of dietary caffeine and blood pressure: a relationship that should be taken more seriously. Psychosom Med. 2004 Jan-Feb;66(1):63-71. [PubMed:14747639 ]
Higdon JV, Frei B: Coffee and health: a review of recent human research. Crit Rev Food Sci Nutr. 2006;46(2):101-23. [PubMed:16507475 ]
Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [PubMed:1356551 ]
Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. [PubMed:2010614 ]
Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [PubMed:6207592 ]
Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. [PubMed:15549276 ]
Haskell CF, Kennedy DO, Wesnes KA, Milne AL, Scholey AB: A double-blind, placebo-controlled, multi-dose evaluation of the acute behavioural effects of guarana in humans. J Psychopharmacol. 2007 Jan;21(1):65-70. Epub 2006 Mar 13. [PubMed:16533867 ]
Ferreira TT, da Silva JVF, Bueno NB: Effects of caffeine supplementation on muscle endurance, maximum strength, and perceived exertion in adults submitted to strength training: a systematic review and meta-analyses. Crit Rev Food Sci Nutr. 2020 Jun 18:1-14. doi: 10.1080/10408398.2020.1781051. [PubMed:32551869 ]

Showing NP-Card for Caffeine (NP0000009)

MOL for NP0000009 (Caffeine)

3D MOL for NP0000009 (Caffeine)

3D SDF for NP0000009 (Caffeine)

3D-SDF for NP0000009 (Caffeine)

PDB for NP0000009 (Caffeine)

3D PDB for NP0000009 (Caffeine)

SMILES for NP0000009 (Caffeine)

INCHI for NP0000009 (Caffeine)

Structure for NP0000009 (Caffeine)

3D Structure for NP0000009 (Caffeine)