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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (12)transporters (1) Show 13 proteins XML

enzymes (12)transporters (1) Show 13 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:10 UTC

Update Date

2023-02-21 17:18:05 UTC

HMDB ID

HMDB0013840

Secondary Accession Numbers

HMDB13840

Metabolite Identification

Common Name

3-Hydroxymethylantipyrine

Description

3-Hydroxymethylantipyrine, also known as 3-HMAP, belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. 3-Hydroxymethylantipyrine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 06191310192D          

 15 16  0  0  0  0            999 V2000
    7.2655   -3.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -3.9107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3850   -3.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1301   -2.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -4.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0501   -3.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051   -2.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1695   -3.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6150   -1.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4320   -5.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -5.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4320   -5.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -5.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -6.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2025   -1.2593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 13 14  1  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013840

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1N(C(=O)C=C1CO)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c1-12-10(8-14)7-11(15)13(12)9-5-3-2-4-6-9/h2-7,14H,8H2,1H3

> <INCHI_KEY>
JBJKAGOWIZGVTR-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.2252

> <EXACT_MASS>
204.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.35738992569093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(hydroxymethyl)-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
0.17206187700000014

> <ALOGPS_LOGS>
-0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.785084559758712

> <JCHEM_PKA_STRONGEST_BASIC>
0.2209613040307593

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
57.96050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(hydroxymethyl)-1-methyl-2-phenylpyrazol-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0      13.562  -6.871   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      16.273  -7.300   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      17.519  -6.395   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      17.043  -4.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.273  -8.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.027  -6.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.503  -4.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.983  -6.871   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.948  -3.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.606  -9.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.939  -9.610   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.606 -11.150   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.939 -11.150   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.273 -11.920   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.178  -2.351   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    5    6                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    7    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    1    2    7                                                  
CONECT    7    4    6                                                       
CONECT    8    3                                                            
CONECT    9    4   15                                                       
CONECT   10    5   12                                                       
CONECT   11    5   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   14                                                       
CONECT   14   12   13                                                       
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0013840
HETATM    1  C1  UNL     1       0.855   1.658  -0.586  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.064   0.358   0.013  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.217  -0.186   0.419  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.559   0.447   0.338  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.553  -0.370   0.840  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.944  -1.437   0.926  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.592  -1.605   0.802  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.103  -2.613   1.141  1.00  0.00           O  
HETATM    9  N2  UNL     1       0.061  -0.496   0.239  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.312  -0.289  -0.051  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.020  -1.153  -0.870  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.350  -0.965  -1.160  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.997   0.115  -0.621  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.341   0.995   0.192  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.994   0.782   0.471  1.00  0.00           C  
HETATM   16  H1  UNL     1       1.724   1.928  -1.222  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.031   1.683  -1.245  1.00  0.00           H  
HETATM   18  H3  UNL     1       0.814   2.459   0.207  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.787   0.592  -0.756  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.546   1.454   0.775  1.00  0.00           H  
HETATM   21  H6  UNL     1       4.582  -1.185   0.297  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.634  -2.163   1.344  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.502  -2.003  -1.292  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.903  -1.634  -1.796  1.00  0.00           H  
HETATM   25  H10 UNL     1      -5.050   0.300  -0.826  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.829   1.848   0.625  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.502   1.479   1.106  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    9
CONECT    3    4    6    6
CONECT    4    5   19   20
CONECT    5   21
CONECT    6    7   22
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   11   15
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-HMAP	HMDB
3-Hydroxymethylantipyrine	MeSH

Chemical Formula

C₁₁H₁₂N₂O₂

Average Molecular Weight

204.2252

Monoisotopic Molecular Weight

204.089877638

IUPAC Name

5-(hydroxymethyl)-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Traditional Name

5-(hydroxymethyl)-1-methyl-2-phenylpyrazol-3-one

CAS Registry Number

18125-49-0

SMILES

CN1N(C(=O)C=C1CO)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12N2O2/c1-12-10(8-14)7-11(15)13(12)9-5-3-2-4-6-9/h2-7,14H,8H2,1H3

InChI Key

JBJKAGOWIZGVTR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
Monocyclic benzene moiety
Pyrazolinone
Benzenoid
Heteroaromatic compound
Vinylogous amide
Lactam
Azacycle
Alcohol
Hydrocarbon derivative
Aromatic alcohol
Organic oxide
Primary alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013840)
Kidney (HMDB: HMDB0013840)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013840)

Source

Endogenous

Endogenous (HMDB: HMDB0013840)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	74.6 g/L	ALOGPS
logP	0.69	ALOGPS
logP	0.17	ChemAxon
logS	-0.44	ALOGPS
pKa (Strongest Acidic)	14.79	ChemAxon
pKa (Strongest Basic)	0.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.96 m³·mol⁻¹	ChemAxon
Polarizability	21.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	147.68	31661259
DarkChem	[M-H]-	144.511	31661259
DeepCCS	[M+H]+	142.935	30932474
DeepCCS	[M-H]-	140.54	30932474
DeepCCS	[M-2H]-	174.651	30932474
DeepCCS	[M+Na]+	149.165	30932474
AllCCS	[M+H]+	144.8	32859911
AllCCS	[M+H-H2O]+	140.6	32859911
AllCCS	[M+NH4]+	148.7	32859911
AllCCS	[M+Na]+	149.8	32859911
AllCCS	[M-H]-	146.7	32859911
AllCCS	[M+Na-2H]-	146.8	32859911
AllCCS	[M+HCOO]-	147.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.4 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0248 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	900.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	99.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	254.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	309.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	153.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	662.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	266.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	924.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	422.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	204.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	237.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxymethylantipyrine	CN1N(C(=O)C=C1CO)C1=CC=CC=C1	2851.8	Standard polar	33892256
3-Hydroxymethylantipyrine	CN1N(C(=O)C=C1CO)C1=CC=CC=C1	1913.2	Standard non polar	33892256
3-Hydroxymethylantipyrine	CN1N(C(=O)C=C1CO)C1=CC=CC=C1	1924.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxymethylantipyrine,1TMS,isomer #1	CN1C(CO[Si](C)(C)C)=CC(=O)N1C1=CC=CC=C1	1891.8	Semi standard non polar	33892256
3-Hydroxymethylantipyrine,1TBDMS,isomer #1	CN1C(CO[Si](C)(C)C(C)(C)C)=CC(=O)N1C1=CC=CC=C1	2157.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymethylantipyrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bi-3900000000-6524fecf8f2167187b53	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymethylantipyrine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9650000000-b7f2788e446bcf82be39	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxymethylantipyrine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 10V, Positive-QTOF	splash10-0a4i-0090000000-aafa94b64aa167a898a3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 20V, Positive-QTOF	splash10-0ab9-9260000000-d6c5db9f857aa5417e2e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 40V, Positive-QTOF	splash10-00dl-9300000000-4b129ae6e5d87777b792	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 10V, Negative-QTOF	splash10-0uk9-3890000000-6a34930be0e0381cff01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 20V, Negative-QTOF	splash10-00di-2910000000-1218d350688bbd151cb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 40V, Negative-QTOF	splash10-0006-9500000000-a73c7e985279d16006fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 10V, Positive-QTOF	splash10-0a4i-0090000000-82053d3e7735d22e65cf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 20V, Positive-QTOF	splash10-0a4r-2970000000-26ac3a407509d5430224	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 40V, Positive-QTOF	splash10-004l-9100000000-f6af4f352624ce75adfd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 10V, Negative-QTOF	splash10-0udi-0190000000-4dc0ae4b8091b11f4e9f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 20V, Negative-QTOF	splash10-00xu-3910000000-a5f22c78559f8e5c9abf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxymethylantipyrine 40V, Negative-QTOF	splash10-0006-9500000000-f8da02823a15dc9f1453	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123963

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)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Brune K, Neubert A: Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S51-7. [PubMed:11695253 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Lee YS, Kim H, Brahim JS, Rowan J, Lee G, Dionne RA: Acetaminophen selectively suppresses peripheral prostaglandin E2 release and increases COX-2 gene expression in a clinical model of acute inflammation. Pain. 2007 Jun;129(3):279-86. Epub 2006 Dec 18. [PubMed:17175104 ]
Hinz B, Cheremina O, Brune K: Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J. 2008 Feb;22(2):383-90. Epub 2007 Sep 20. [PubMed:17884974 ]
Weinheimer EM, Jemiolo B, Carroll CC, Harber MP, Haus JM, Burd NA, LeMoine JK, Trappe SW, Trappe TA: Resistance exercise and cyclooxygenase (COX) expression in human skeletal muscle: implications for COX-inhibiting drugs and protein synthesis. Am J Physiol Regul Integr Comp Physiol. 2007 Jun;292(6):R2241-8. Epub 2007 Feb 22. [PubMed:17322116 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Brune K, Neubert A: Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S51-7. [PubMed:11695253 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Lee YS, Kim H, Brahim JS, Rowan J, Lee G, Dionne RA: Acetaminophen selectively suppresses peripheral prostaglandin E2 release and increases COX-2 gene expression in a clinical model of acute inflammation. Pain. 2007 Jun;129(3):279-86. Epub 2006 Dec 18. [PubMed:17175104 ]
Hinz B, Cheremina O, Brune K: Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J. 2008 Feb;22(2):383-90. Epub 2007 Sep 20. [PubMed:17884974 ]
Weinheimer EM, Jemiolo B, Carroll CC, Harber MP, Haus JM, Burd NA, LeMoine JK, Trappe SW, Trappe TA: Resistance exercise and cyclooxygenase (COX) expression in human skeletal muscle: implications for COX-inhibiting drugs and protein synthesis. Am J Physiol Regul Integr Comp Physiol. 2007 Jun;292(6):R2241-8. Epub 2007 Feb 22. [PubMed:17322116 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

9. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for 3-Hydroxymethylantipyrine (HMDB0013840)

MOL for HMDB0013840 (3-Hydroxymethylantipyrine)

3D MOL for HMDB0013840 (3-Hydroxymethylantipyrine)

3D SDF for HMDB0013840 (3-Hydroxymethylantipyrine)

3D-SDF for HMDB0013840 (3-Hydroxymethylantipyrine)

PDB for HMDB0013840 (3-Hydroxymethylantipyrine)

3D PDB for HMDB0013840 (3-Hydroxymethylantipyrine)

SMILES for HMDB0013840 (3-Hydroxymethylantipyrine)

INCHI for HMDB0013840 (3-Hydroxymethylantipyrine)

Structure for HMDB0013840 (3-Hydroxymethylantipyrine)

3D Structure for HMDB0013840 (3-Hydroxymethylantipyrine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References

Transporters

References