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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:16:24 UTC

Update Date

2021-09-26 23:06:52 UTC

HMDB ID

HMDB0253570

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Iproniazid

Description

Iproniazid belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. Iproniazid is a drug which is used for the treatment of depression (originally intended to treat tuberculosis). Iproniazid is a strong basic compound (based on its pKa). Hepatic necrosis was found in rats with doses as low as 10 mg/kg. This compound has been identified in human blood as reported by (PMID: 31557052 ). Iproniazid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Iproniazid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4818                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   0.770   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   2.310   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748   0.770   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.414  -4.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.081   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -3.850   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3    5                                                       
CONECT    3    2    8                                                       
CONECT    4   12   13                                                       
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12    4   10                                                       
CONECT   13    4   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Iproniazide	ChEMBL
Iprazid	MeSH

Chemical Formula

C₉H₁₃N₃O

Average Molecular Weight

179.219

Monoisotopic Molecular Weight

179.105862053

IUPAC Name

N'-(propan-2-yl)pyridine-4-carbohydrazide

Traditional Name

iproniazid

CAS Registry Number

Not Available

SMILES

CC(C)NNC(=O)C1=CC=NC=C1

InChI Identifier

InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)

InChI Key

NYMGNSNKLVNMIA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids and derivatives

Alternative Parents

Substituents

Pyridine carboxylic acid or derivatives
Heteroaromatic compound
Carboxylic acid hydrazide
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbohydrazide (CHEBI:5958 )
pyridines (CHEBI:5958 )
a small molecule (IPRONIAZID )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	0.02	ALOGPS
logP	0.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	3.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.02 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.96 m³·mol⁻¹	ChemAxon
Polarizability	19.19 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	139.253	30932474
DeepCCS	[M-H]-	136.375	30932474
DeepCCS	[M-2H]-	172.929	30932474
DeepCCS	[M+Na]+	148.467	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.4	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	141.5	32859911
AllCCS	[M+Na-2H]-	142.5	32859911
AllCCS	[M+HCOO]-	143.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Iproniazid	CC(C)NNC(=O)C1=CC=NC=C1	2263.2	Standard polar	33892256
Iproniazid	CC(C)NNC(=O)C1=CC=NC=C1	1589.9	Standard non polar	33892256
Iproniazid	CC(C)NNC(=O)C1=CC=NC=C1	1628.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Iproniazid,1TMS,isomer #1	CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C	1692.5	Semi standard non polar	33892256
Iproniazid,1TMS,isomer #1	CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C	1773.2	Standard non polar	33892256
Iproniazid,1TMS,isomer #1	CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C	2214.2	Standard polar	33892256
Iproniazid,1TMS,isomer #2	CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1635.7	Semi standard non polar	33892256
Iproniazid,1TMS,isomer #2	CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	1714.0	Standard non polar	33892256
Iproniazid,1TMS,isomer #2	CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C	2118.2	Standard polar	33892256
Iproniazid,2TMS,isomer #1	CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)[Si](C)(C)C	1685.8	Semi standard non polar	33892256
Iproniazid,2TMS,isomer #1	CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)[Si](C)(C)C	1793.2	Standard non polar	33892256
Iproniazid,2TMS,isomer #1	CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)[Si](C)(C)C	2032.1	Standard polar	33892256
Iproniazid,1TBDMS,isomer #1	CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	1937.7	Semi standard non polar	33892256
Iproniazid,1TBDMS,isomer #1	CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	1947.1	Standard non polar	33892256
Iproniazid,1TBDMS,isomer #1	CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2328.5	Standard polar	33892256
Iproniazid,1TBDMS,isomer #2	CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	1851.0	Semi standard non polar	33892256
Iproniazid,1TBDMS,isomer #2	CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	1925.1	Standard non polar	33892256
Iproniazid,1TBDMS,isomer #2	CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2241.5	Standard polar	33892256
Iproniazid,2TBDMS,isomer #1	CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2161.9	Semi standard non polar	33892256
Iproniazid,2TBDMS,isomer #1	CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2193.5	Standard non polar	33892256
Iproniazid,2TBDMS,isomer #1	CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2276.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Iproniazid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-8900000000-d786226d5db93593d8de	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Iproniazid 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 - Iproniazid 10V, Positive-QTOF	splash10-001r-0900000000-49e950c0a9fa3a055b3c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 20V, Positive-QTOF	splash10-000i-1900000000-8affb6a605c559ecb93d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 40V, Positive-QTOF	splash10-0a4u-9500000000-ef4944e3da7f09e3f333	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 10V, Negative-QTOF	splash10-004i-1900000000-70c20dd8c669b103896b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 20V, Negative-QTOF	splash10-004i-4900000000-f332cce024a43397b9d5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 40V, Negative-QTOF	splash10-0006-9100000000-380364d4d62d96f3f0c6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 10V, Positive-QTOF	splash10-001i-0900000000-eeed42b0f7d83a85dffb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 20V, Positive-QTOF	splash10-0a4i-0900000000-9a58baefb65b09e234e4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 40V, Positive-QTOF	splash10-003r-9200000000-cce8a523785f5ede4bce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 10V, Negative-QTOF	splash10-004i-0900000000-139fe46b0bf366caedda	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 20V, Negative-QTOF	splash10-002f-9100000000-bd9f875c29ef9d0121dc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Iproniazid 40V, Negative-QTOF	splash10-002f-9000000000-990dd797d2e961cdcaad	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04818

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11777

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iproniazid

METLIN ID

Not Available

PubChem Compound

3748

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Iproniazid (HMDB0253570)

MOL for HMDB0253570 (Iproniazid)

3D MOL for HMDB0253570 (Iproniazid)

3D SDF for HMDB0253570 (Iproniazid)

3D-SDF for HMDB0253570 (Iproniazid)

PDB for HMDB0253570 (Iproniazid)

3D PDB for HMDB0253570 (Iproniazid)

SMILES for HMDB0253570 (Iproniazid)

INCHI for HMDB0253570 (Iproniazid)

Structure for HMDB0253570 (Iproniazid)

3D Structure for HMDB0253570 (Iproniazid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra