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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 18:16:22 UTC

Update Date

2023-02-21 17:17:02 UTC

HMDB ID

HMDB0004400

Secondary Accession Numbers

HMDB04400

Metabolite Identification

Common Name

5-Acetylamino-6-amino-3-methyluracil

Description

5-Acetylamino-6-amino-3-methyluracil (AAMU) is one of caffeine major metabolites. Analysis of caffeine and its metabolites is of interest with respect to caffeine exposure, for kinetic and metabolism studies and for opportunistic in vivo estimation of drug metabolizing enzyme activity in humans and animals. Urinary caffeine metabolite ratios are used in humans to assess the activity of cytochrome P450 1A2 (CYP1A2), xanthine oxidase and N-acetyltransferase 2 (NAT2), which are involved in the activation or detoxification of various xenobiotic compounds, including carcinogens. Investigating the activity of these enzymes is of clinical relevance for assessing intra- and inter-individual differences in NAT2- and CYP1A2-mediated drug metabolism, and for evaluating the risk of developing specific exposure-related diseases. (PMID: 3506820 , 15685651 , 12534641 ).

Structure

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


  Mrv1652309121709232D          

 14 14  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
  6 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004400

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)NC(N)=C(NC(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H10N4O3/c1-3(12)9-4-5(8)10-7(14)11(2)6(4)13/h8H2,1-2H3,(H,9,12)(H,10,14)

> <INCHI_KEY>
POQOTWQIYYNXAT-UHFFFAOYSA-N

> <FORMULA>
C7H10N4O3

> <MOLECULAR_WEIGHT>
198.1793

> <EXACT_MASS>
198.075290206

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.36185657836414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-2.197972934

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.509886970218815

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.756465524292572

> <JCHEM_PKA_STRONGEST_BASIC>
-4.511594458108112

> <JCHEM_POLAR_SURFACE_AREA>
104.53

> <JCHEM_REFRACTIVITY>
56.8707

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(4-amino-1-methyl-2,6-dioxo-3H-pyrimidin-5-yl)acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -0.000   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
AAMU	Kegg
5-AMMU	MeSH

Chemical Formula

C₇H₁₀N₄O₃

Average Molecular Weight

198.1793

Monoisotopic Molecular Weight

198.075290206

IUPAC Name

N-(6-amino-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetamide

Traditional Name

N-(4-amino-1-methyl-2,6-dioxo-3H-pyrimidin-5-yl)acetamide

CAS Registry Number

19893-78-8

SMILES

CN1C(=O)NC(N)=C(NC(C)=O)C1=O

InChI Identifier

InChI=1S/C7H10N4O3/c1-3(12)9-4-5(8)10-7(14)11(2)6(4)13/h8H2,1-2H3,(H,9,12)(H,10,14)

InChI Key

POQOTWQIYYNXAT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acetylarylamines. These are acetamides where one or more amide hydrogens is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

N-arylamides

Direct Parent

N-acetylarylamines

Alternative Parents

Substituents

N-acetylarylamine
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Acetamide
Vinylogous amide
Amino acid or derivatives
Carboxamide group
Lactam
Urea
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic oxide
Carbonyl group
Organooxygen compound
Primary amine
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic amide (CHEBI:80473 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004400)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0004400)
Urine (HMDB: HMDB0004400)

Source

Endogenous

Endogenous (HMDB: HMDB0004400)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Caffeine Metabolism (HMDB: HMDB0004400)
Caffeine Metabolism (HMDB: HMDB0004400)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.5 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.87 m³·mol⁻¹	ChemAxon
Polarizability	18.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.694	31661259
DarkChem	[M-H]-	140.812	31661259
DeepCCS	[M+H]+	136.612	30932474
DeepCCS	[M-H]-	133.837	30932474
DeepCCS	[M-2H]-	169.879	30932474
DeepCCS	[M+Na]+	145.231	30932474
AllCCS	[M+H]+	142.4	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	141.0	32859911
AllCCS	[M+Na-2H]-	141.8	32859911
AllCCS	[M+HCOO]-	142.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Acetylamino-6-amino-3-methyluracil	CN1C(=O)NC(N)=C(NC(C)=O)C1=O	2703.3	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil	CN1C(=O)NC(N)=C(NC(C)=O)C1=O	2106.0	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil	CN1C(=O)NC(N)=C(NC(C)=O)C1=O	2126.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #1	CC(=O)NC1=C(N[Si](C)(C)C)[NH]C(=O)N(C)C1=O	2020.8	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #1	CC(=O)NC1=C(N[Si](C)(C)C)[NH]C(=O)N(C)C1=O	2124.8	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #1	CC(=O)NC1=C(N[Si](C)(C)C)[NH]C(=O)N(C)C1=O	3947.4	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #2	CC(=O)NC1=C(N)N([Si](C)(C)C)C(=O)N(C)C1=O	2026.1	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #2	CC(=O)NC1=C(N)N([Si](C)(C)C)C(=O)N(C)C1=O	2134.8	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #2	CC(=O)NC1=C(N)N([Si](C)(C)C)C(=O)N(C)C1=O	3852.4	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #3	CC(=O)N(C1=C(N)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	1917.2	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #3	CC(=O)N(C1=C(N)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	1991.2	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TMS,isomer #3	CC(=O)N(C1=C(N)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	3261.7	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #1	CC(=O)N(C1=C(N[Si](C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	1904.5	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #1	CC(=O)N(C1=C(N[Si](C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	2123.0	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #1	CC(=O)N(C1=C(N[Si](C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	2881.3	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #2	CC(=O)NC1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N(C)C1=O	1982.4	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #2	CC(=O)NC1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N(C)C1=O	2235.7	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #2	CC(=O)NC1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N(C)C1=O	3530.0	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #3	CC(=O)NC1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O	2083.7	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #3	CC(=O)NC1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O	2236.1	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #3	CC(=O)NC1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O	3460.5	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #4	CC(=O)N(C1=C(N)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	1969.8	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #4	CC(=O)N(C1=C(N)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2070.6	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TMS,isomer #4	CC(=O)N(C1=C(N)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	3045.9	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	1957.3	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	2211.1	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C	2498.9	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #2	CC(=O)N(C1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2041.6	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #2	CC(=O)N(C1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2204.4	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #2	CC(=O)N(C1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2537.7	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #3	CC(=O)NC1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O	2133.4	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #3	CC(=O)NC1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O	2344.6	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TMS,isomer #3	CC(=O)NC1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O	3055.4	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,4TMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2148.9	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,4TMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2321.7	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,4TMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C	2288.1	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #1	CC(=O)NC1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O	2277.9	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #1	CC(=O)NC1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O	2350.1	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #1	CC(=O)NC1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O	3820.7	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #2	CC(=O)NC1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	2265.8	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #2	CC(=O)NC1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	2350.0	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #2	CC(=O)NC1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	3785.4	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #3	CC(=O)N(C1=C(N)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2160.2	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #3	CC(=O)N(C1=C(N)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2206.4	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,1TBDMS,isomer #3	CC(=O)N(C1=C(N)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	3238.0	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #1	CC(=O)N(C1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2357.4	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #1	CC(=O)N(C1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2527.2	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #1	CC(=O)N(C1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2905.5	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #2	CC(=O)NC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O	2469.4	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #2	CC(=O)NC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O	2668.6	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #2	CC(=O)NC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O	3417.7	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #3	CC(=O)NC1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	2563.5	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #3	CC(=O)NC1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	2657.8	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #3	CC(=O)NC1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	3331.2	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #4	CC(=O)N(C1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2441.3	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #4	CC(=O)N(C1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2521.3	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,2TBDMS,isomer #4	CC(=O)N(C1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	3047.0	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2606.9	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2826.4	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2754.6	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #2	CC(=O)N(C1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2672.2	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #2	CC(=O)N(C1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2819.3	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #2	CC(=O)N(C1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2775.2	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #3	CC(=O)NC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	2765.8	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #3	CC(=O)NC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	2942.9	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,3TBDMS,isomer #3	CC(=O)NC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O	3062.3	Standard polar	33892256
5-Acetylamino-6-amino-3-methyluracil,4TBDMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2927.2	Semi standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,4TBDMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	3078.3	Standard non polar	33892256
5-Acetylamino-6-amino-3-methyluracil,4TBDMS,isomer #1	CC(=O)N(C1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N(C)C1=O)[Si](C)(C)C(C)(C)C	2711.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-2900000000-2d2fce0f3b41d6ee5ed5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 20V, Negative-QTOF	splash10-006y-9200000000-bc1b2146eec01e767a75	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Negative-QTOF	splash10-002e-4900000000-1d19aed0d341cc4d9210	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Positive-QTOF	splash10-0a4i-1900000000-c3d8379066da662149e1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 30V, Positive-QTOF	splash10-007o-9400000000-ea9d970e92f2c9069413	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Positive-QTOF	splash10-0002-9000000000-e51004c20cbfc1d4f944	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 0V, Positive-QTOF	splash10-0gx1-0920000000-1c3930bbd99354dc64bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 30V, Positive-QTOF	splash10-0cdi-5900000000-049dcbea7599c459514b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 0V, Positive-QTOF	splash10-001i-0900000000-9f886b28f5f0dc3c490d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 30V, Negative-QTOF	splash10-006y-9000000000-5981916c239c2705d949	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 40V, Negative-QTOF	splash10-0006-9000000000-c0932a165f81ee34af30	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Positive-QTOF	splash10-052b-0900000000-6d6bb4381c239bd1e83f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 20V, Positive-QTOF	splash10-0a4i-2900000000-72b405e1279632249e5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 40V, Positive-QTOF	splash10-0007-9100000000-b93fa98027956aaaa8f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Negative-QTOF	splash10-0udi-1900000000-1c50114eb8bce95366bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 20V, Negative-QTOF	splash10-004i-9800000000-91e073b0e556bcd2bd2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 40V, Negative-QTOF	splash10-01bc-9000000000-1cc734e6cf6743ce30a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Negative-QTOF	splash10-0002-1900000000-5e285a4ce72c0d3495bf	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 20V, Negative-QTOF	splash10-002b-3900000000-5e5f9a546b5f48946784	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 40V, Negative-QTOF	splash10-052f-9100000000-27fd0995b1c229e56123	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 10V, Positive-QTOF	splash10-0002-0900000000-ca06f4616042dc126edc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 20V, Positive-QTOF	splash10-052b-0900000000-5d50721d3d88998cf657	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetylamino-6-amino-3-methyluracil 40V, Positive-QTOF	splash10-00di-9100000000-3452e3a490e46f193900	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Caffeine Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	5.06 +/- 0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	11393735	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023371

KNApSAcK ID

Not Available

Chemspider ID

79659

KEGG Compound ID

C16366

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

88299

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
Weimann A, Sabroe M, Poulsen HE: Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry. J Mass Spectrom. 2005 Mar;40(3):307-16. [PubMed:15685651 ]
Nyeki A, Buclin T, Biollaz J, Decosterd LA: NAT2 and CYP1A2 phenotyping with caffeine: head-to-head comparison of AFMU vs. AAMU in the urine metabolite ratios. Br J Clin Pharmacol. 2003 Jan;55(1):62-7. [PubMed:12534641 ]

Showing metabocard for 5-Acetylamino-6-amino-3-methyluracil (HMDB0004400)

MOL for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

3D MOL for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

3D SDF for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

3D-SDF for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

PDB for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

3D PDB for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

SMILES for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

INCHI for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

Structure for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

3D Structure for HMDB0004400 (5-Acetylamino-6-amino-3-methyluracil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra