Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 21:00:21 UTC

Update Date

2022-09-22 18:34:54 UTC

HMDB ID

HMDB0341409

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zolpidem phenyl-4-carboxylic acid

Description

Zolpidem Carboxylic Acid, also known as zolpidem carboxylate or ZCA CPD, belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond. Zolpidem Carboxylic Acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 09051316162D          

 25 27  0  0  0  0            999 V2000
    3.4722    0.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740   -1.9816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5358    1.5287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740   -0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8305    0.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795    0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -2.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1182   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9848    2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3431    1.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7682   -2.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7682   -0.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4 13  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 15  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  2  0  0  0  0
 11 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 14  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341409

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H19N3O3/c1-12-4-9-16-20-18(13-5-7-14(8-6-13)19(24)25)15(22(16)11-12)10-17(23)21(2)3/h4-9,11H,10H2,1-3H3,(H,24,25)

> <INCHI_KEY>
FELZONDEFBLTSP-UHFFFAOYSA-N

> <FORMULA>
C19H19N3O3

> <MOLECULAR_WEIGHT>
337.3725

> <EXACT_MASS>
337.142641489

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.224192296536984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{3-[(dimethylcarbamoyl)methyl]-6-methylimidazo[1,2-a]pyridin-2-yl}benzoic acid

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
0.6062335556595199

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8744141468723288

> <JCHEM_PKA_STRONGEST_BASIC>
5.661457722771263

> <JCHEM_POLAR_SURFACE_AREA>
74.91

> <JCHEM_REFRACTIVITY>
95.7987

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{3-[(dimethylcarbamoyl)methyl]-6-methylimidazo[1,2-a]pyridin-2-yl}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-13         0                                  
HETATM    1  O   UNK     0       6.481   1.072   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.081  -1.690   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.538  -3.699   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.467   2.854   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.538  -1.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.437  -2.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -3.230   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.017   0.243   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.977  -2.460   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -0.920   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -4.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.988   1.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.747  -3.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.747  -1.126   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -0.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.057  -2.460   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.287  -3.793   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.287  -1.126   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.438   4.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.974   3.171   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.597  -2.460   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.367  -3.793   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.367  -1.126   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    5    7   10                                                  
CONECT    3    6    7                                                       
CONECT    4   13   21   22                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5    9                                                  
CONECT    7    2    3   12                                                  
CONECT    8    5   13                                                       
CONECT    9    6   15   16                                                  
CONECT   10    2   11                                                       
CONECT   11   10   14   17                                                  
CONECT   12    7   14                                                       
CONECT   13    1    4    8                                                  
CONECT   14   11   12                                                       
CONECT   15    9   19                                                       
CONECT   16    9   20                                                       
CONECT   17   11                                                            
CONECT   18   19   20   23                                                  
CONECT   19   15   18                                                       
CONECT   20   16   18                                                       
CONECT   21    4                                                            
CONECT   22    4                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Zolpidem carboxylate	Generator
ZCA CPD	MeSH
4-{3-[(dimethylcarbamoyl)methyl]-6-methylimidazo[1,2-a]pyridin-2-yl}benzoate	Generator

Chemical Formula

C₁₉H₁₉N₃O₃

Average Molecular Weight

337.3725

Monoisotopic Molecular Weight

337.142641489

IUPAC Name

4-{3-[(dimethylcarbamoyl)methyl]-6-methylimidazo[1,2-a]pyridin-2-yl}benzoic acid

Traditional Name

4-{3-[(dimethylcarbamoyl)methyl]-6-methylimidazo[1,2-a]pyridin-2-yl}benzoic acid

CAS Registry Number

Not Available

SMILES

CN(C)C(=O)CC1=C(N=C2C=CC(C)=CN12)C1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C19H19N3O3/c1-12-4-9-16-20-18(13-5-7-14(8-6-13)19(24)25)15(22(16)11-12)10-17(23)21(2)3/h4-9,11H,10H2,1-3H3,(H,24,25)

InChI Key

FELZONDEFBLTSP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylimidazoles. These are polycyclic aromatic compounds containing a benzene ring linked to an imidazole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Phenylimidazoles

Alternative Parents

Substituents

5-phenylimidazole
4-phenylimidazole
Benzoic acid or derivatives
Imidazo[1,2-a]pyridine
Benzoic acid
Imidazopyridine
Benzoyl
Methylpyridine
Monocyclic benzene moiety
N-substituted imidazole
Benzenoid
Pyridine
Heteroaromatic compound
Tertiary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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
logP	2.5	ALOGPS
logP	0.61	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	5.66	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.8 m³·mol⁻¹	ChemAxon
Polarizability	36.22 Å³	ChemAxon
Number of Rings	3	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 Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

11966044

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

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for Zolpidem phenyl-4-carboxylic acid (HMDB0341409)

MOL for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

3D MOL for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

3D SDF for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

3D-SDF for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

PDB for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

3D PDB for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

SMILES for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

INCHI for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

Structure for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

3D Structure for HMDB0341409 (Zolpidem phenyl-4-carboxylic acid)

Predicted Kovats Retention Indices