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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:15:45 UTC

Update Date

2023-02-21 17:30:18 UTC

HMDB ID

HMDB0061058

Secondary Accession Numbers

HMDB61058

Metabolite Identification

Common Name

triazolopropionic acid

Description

triazolopropionic acid is a metabolite of trazodone. Trazodone (also sold under the brand names Desyrel, Oleptro, Beneficat, Deprax, Desirel, Molipaxin, Thombran, Trazorel, Trialodine, Trittico, and Mesyrel) is an antidepressant of the serotonin antagonist and reuptake inhibitor (SARI) class. It is a phenylpiperazine compound. Trazodone also has anxiolytic and hypnotic effects. Trazodone has considerably fewer prominent anticholinergic and sexual side effects than most of the tricyclic antidepressants (TCAs). (Wikipedia)

Structure

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


  Mrv0541 07091309152D          

 15 16  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  5  2  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061058

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCN1N=C2C=CC=CN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9N3O3/c13-8(14)4-6-12-9(15)11-5-2-1-3-7(11)10-12/h1-3,5H,4,6H2,(H,13,14)

> <INCHI_KEY>
DXVGDKXFBVHCCE-UHFFFAOYSA-N

> <FORMULA>
C9H9N3O3

> <MOLECULAR_WEIGHT>
207.1861

> <EXACT_MASS>
207.064391169

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.751231569448194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propanoic acid

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
0.4259639230000002

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.111194474164884

> <JCHEM_PKA_STRONGEST_BASIC>
-4.60656416982977

> <JCHEM_POLAR_SURFACE_AREA>
73.21000000000001

> <JCHEM_REFRACTIVITY>
52.425700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       3.590   3.613   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       1.220   2.843   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      -3.400   0.175   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.400   2.843   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    7                                                       
CONECT    4    6    8                                                       
CONECT    5    2   11                                                       
CONECT    6    4   12                                                       
CONECT    7    3   10   11                                                  
CONECT    8    4   13   14                                                  
CONECT    9   11   12   15                                                  
CONECT   10    7   12                                                       
CONECT   11    5    7    9                                                  
CONECT   12    6    9   10                                                  
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Triazolopropionate	Generator
beta-(3-oxo-S-Triazolo)-(4,3a)-pyridin-2-yl-propionic acid	HMDB

Chemical Formula

C₉H₉N₃O₃

Average Molecular Weight

207.1861

Monoisotopic Molecular Weight

207.064391169

IUPAC Name

3-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propanoic acid

Traditional Name

3-{3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCN1N=C2C=CC=CN2C1=O

InChI Identifier

InChI=1S/C9H9N3O3/c13-8(14)4-6-12-9(15)11-5-2-1-3-7(11)10-12/h1-3,5H,4,6H2,(H,13,14)

InChI Key

DXVGDKXFBVHCCE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl 1,2,4-triazolones. These are aromatic heterocyclic compounds containing a 1,2,4-triazolone moiety that is substituted at the 5-position with an aryl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Triazoles

Direct Parent

Aryl 1,2,4-triazolones

Alternative Parents

Substituents

Aryl 1,2,4-triazol-3-one
Triazolopyridine
Pyridinone
Pyridine
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0061058)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061058)

Organ

Kidney (HMDB: HMDB0061058)
Liver (HMDB: HMDB0061058)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061058)

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	7.44 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	0.43	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.21 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.43 m³·mol⁻¹	ChemAxon
Polarizability	19.75 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]+	145.3	31661259
DarkChem	[M-H]-	143.255	31661259
DeepCCS	[M+H]+	137.488	30932474
DeepCCS	[M-H]-	134.929	30932474
DeepCCS	[M-2H]-	170.519	30932474
DeepCCS	[M+Na]+	145.993	30932474
AllCCS	[M+H]+	143.9	32859911
AllCCS	[M+H-H2O]+	139.8	32859911
AllCCS	[M+NH4]+	147.7	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	144.4	32859911
AllCCS	[M+Na-2H]-	144.5	32859911
AllCCS	[M+HCOO]-	144.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
triazolopropionic acid	OC(=O)CCN1N=C2C=CC=CN2C1=O	2866.3	Standard polar	33892256
triazolopropionic acid	OC(=O)CCN1N=C2C=CC=CN2C1=O	1468.5	Standard non polar	33892256
triazolopropionic acid	OC(=O)CCN1N=C2C=CC=CN2C1=O	2030.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
triazolopropionic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCN1N=C2C=CC=CN2C1=O	1995.2	Semi standard non polar	33892256
triazolopropionic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN1N=C2C=CC=CN2C1=O	2288.3	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 - triazolopropionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-3900000000-bbbf4f384305e61943bc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - triazolopropionic acid GC-MS (1 TMS) - 70eV, Positive	splash10-022m-9820000000-0532a56abdce4174e210	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - triazolopropionic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - triazolopropionic acid 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 - triazolopropionic acid 10V, Positive-QTOF	splash10-0006-0920000000-35081e0693dc89c3c288	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 20V, Positive-QTOF	splash10-06y6-3910000000-44ad8cb0615e1b9cd668	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 40V, Positive-QTOF	splash10-00b9-9300000000-248e80c3ee33fdce9e85	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 10V, Negative-QTOF	splash10-0a4i-1790000000-0b9bbb3f6a94e3b5dddc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 20V, Negative-QTOF	splash10-001i-5920000000-f6dcd140596d85d24e79	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 40V, Negative-QTOF	splash10-057i-9700000000-43d271db3a3776e210d6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 10V, Negative-QTOF	splash10-0a59-0590000000-48983d8bab7b732491b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 20V, Negative-QTOF	splash10-053r-0900000000-52692d656491b5345e6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 40V, Negative-QTOF	splash10-0a4i-3900000000-0ec9ef106d6594190d22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 10V, Positive-QTOF	splash10-0a4i-0090000000-3359e47bd0aa06e169ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 20V, Positive-QTOF	splash10-0c01-1920000000-167dce464ce1601fe3e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - triazolopropionic acid 40V, Positive-QTOF	splash10-001i-9500000000-b5a8a7905b111363619c	2021-09-23	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

198292

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

Showing metabocard for triazolopropionic acid (HMDB0061058)

MOL for HMDB0061058 (triazolopropionic acid)

3D MOL for HMDB0061058 (triazolopropionic acid)

3D SDF for HMDB0061058 (triazolopropionic acid)

3D-SDF for HMDB0061058 (triazolopropionic acid)

PDB for HMDB0061058 (triazolopropionic acid)

3D PDB for HMDB0061058 (triazolopropionic acid)

SMILES for HMDB0061058 (triazolopropionic acid)

INCHI for HMDB0061058 (triazolopropionic acid)

Structure for HMDB0061058 (triazolopropionic acid)

3D Structure for HMDB0061058 (triazolopropionic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra