Bovine Metabolome Database: Showing metabocard for Caffeine (BMDB0001847)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:48:07 UTC

Update Date

2020-06-04 20:04:41 UTC

BMDB ID

BMDB0001847

Secondary Accession Numbers

BMDB01847

Metabolite Identification

Common Name

Caffeine

Description

Caffeine, also known as caffeine or 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 a drug which is used for management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants. Caffeine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeine participates in a number of enzymatic reactions, within cattle. In particular, Caffeine can be converted into paraxanthine and formaldehyde through its interaction with the enzyme cytochrome P450 1A2. In addition, Caffeine can be converted into theobromine and formaldehyde; which is mediated by the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In cattle, caffeine is involved in the metabolic pathway called the caffeine metabolism pathway. Caffeine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

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 Molecular Weight

194.1906

Monoisotopic Molecular Weight

194.080375584

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

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	238 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	21.6 mg/mL at 25 °C	Not Available
LogP	-0.07	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)	splash10-0536-3900000000-a9e112713ffae6dabdaa	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)	splash10-0536-2900000000-8cdcd005b2e7622a02a3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-052f-0900000000-f1084acfddb240696073	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-05nf-6900000000-8670a644cee5d9de78d4	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0536-3900000000-4430852b279a72e34822	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-0900000000-51898e93480e848d7da1	View in MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0900000000-2aed5d425b6a95add5db	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-4900000000-3ff72dace6687d242f1f	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-1900000000-2ba1fae6e27c7b836984	View in MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0900000000-fd859aeb416e320d6379	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0536-3900000000-a9e112713ffae6dabdaa	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0536-2900000000-8cdcd005b2e7622a02a3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-0900000000-f1084acfddb240696073	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-05nf-6900000000-8670a644cee5d9de78d4	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0536-3900000000-4430852b279a72e34822	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-0900000000-41f36d541d34d2088964	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0900000000-447fc72b2c709e2e18a9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1900000000-5e3b29de16ad91c79fe0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-d6f6c52ac36c8f25a500	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0006-0900000000-cddd24399d942b1ac97c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - CI-B (Unknown) , Positive	splash10-0002-0900000000-2aed5d425b6a95add5db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-0a4l-4900000000-3ff72dace6687d242f1f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-0006-1900000000-2ba1fae6e27c7b836984	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positive	splash10-0002-0900000000-63b9ef42a3e8d59e9997	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0900000000-185b3d97d8857a0f269d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-0900000000-f8a0c0dd9f5c4a272eaf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000i-1900000000-dd8e35226d0704aa657d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-01x9-9800000000-70e3b0eb52481c39d191	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001l-9100000000-6d428a5571beb0e3fed4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0900000000-98bec16f898808c3de68	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0002-0900000000-b112e4e059e1ecf98c5f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00dr-0900000000-42c6f8fc7b924e9c64f3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-4900000000-a60a480f1340558740a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-695d910d49fc0beb1d54	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-094879886a2e72bf0c56	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-fa38c865089a3a05f287	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000b-0900000000-0e82732a924c974dd0c8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-bfc94c8091471847482b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-1900000000-c8fcf16986c494898203	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-3900000000-9569e0552abb7ebd145a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0900000000-3a924abd44877050c1c9	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-052f-8900000000-68b5e9aa3404fb3d8d3a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Epidermis
Kidney
Liver
Placenta
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Caffeine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details