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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:53:27 UTC

Update Date

2022-09-22 17:44:26 UTC

HMDB ID

HMDB0256439

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenylhydrazine

Description

Phenylhydrazine, also known as hydrazinobenzene or phenyldiazane, belongs to the class of organic compounds known as phenylhydrazines. Phenylhydrazines are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group. Phenylhydrazine has been detected, but not quantified in, sweet bays (Laurus nobilis). This could make phenylhydrazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Phenylhydrazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phenylhydrazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phenylhydrazine 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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-PHENYLHYDRAZINE	ChEBI
Hydrazinobenzene	ChEBI
Hydrazobenzene	ChEBI
Monophenylhydrazine	ChEBI
Phenyldiazane	ChEBI
Phenylhydrazin	ChEBI
PHNHNH2	ChEBI
Phenylhydrazide	MeSH
Phenylhydrazine hydrochloride	MeSH
Phenylhydrazine monohydrochloride	MeSH
Phenylhydrazine monosulfate	MeSH

Chemical Formula

C₆H₈N₂

Average Molecular Weight

108.1411

Monoisotopic Molecular Weight

108.068748266

IUPAC Name

phenylhydrazine

Traditional Name

phenylhydrazine

CAS Registry Number

Not Available

SMILES

NNC1=CC=CC=C1

InChI Identifier

InChI=1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2

InChI Key

HKOOXMFOFWEVGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylhydrazines. Phenylhydrazines are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylhydrazines

Direct Parent

Phenylhydrazines

Alternative Parents

Substituents

Phenylhydrazine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Hydrazine derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylhydrazines (CHEBI:27924 )
a small molecule (PHENYLHYDRAZINE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256439)

Food

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

Insectifuge (HMDB: HMDB0256439)

Industrial application

Agriculture

Pesticide (HMDB: HMDB0256439)

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	0.95	ALOGPS
logP	1.36	ChemAxon
logS	-0.22	ALOGPS
pKa (Strongest Basic)	5.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	38.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.76 m³·mol⁻¹	ChemAxon
Polarizability	11.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	122.166	30932474
DeepCCS	[M-H]-	119.618	30932474
DeepCCS	[M-2H]-	155.882	30932474
DeepCCS	[M+Na]+	130.54	30932474
AllCCS	[M+H]+	124.1	32859911
AllCCS	[M+H-H2O]+	119.2	32859911
AllCCS	[M+NH4]+	128.7	32859911
AllCCS	[M+Na]+	130.1	32859911
AllCCS	[M-H]-	120.9	32859911
AllCCS	[M+Na-2H]-	123.5	32859911
AllCCS	[M+HCOO]-	126.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylhydrazine	NNC1=CC=CC=C1	1951.5	Standard polar	33892256
Phenylhydrazine	NNC1=CC=CC=C1	1128.6	Standard non polar	33892256
Phenylhydrazine	NNC1=CC=CC=C1	1209.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylhydrazine,1TMS,isomer #1	C[Si](C)(C)NNC1=CC=CC=C1	1420.5	Semi standard non polar	33892256
Phenylhydrazine,1TMS,isomer #1	C[Si](C)(C)NNC1=CC=CC=C1	1266.8	Standard non polar	33892256
Phenylhydrazine,1TMS,isomer #1	C[Si](C)(C)NNC1=CC=CC=C1	1669.3	Standard polar	33892256
Phenylhydrazine,1TMS,isomer #2	C[Si](C)(C)N(N)C1=CC=CC=C1	1330.4	Semi standard non polar	33892256
Phenylhydrazine,1TMS,isomer #2	C[Si](C)(C)N(N)C1=CC=CC=C1	1377.0	Standard non polar	33892256
Phenylhydrazine,1TMS,isomer #2	C[Si](C)(C)N(N)C1=CC=CC=C1	1772.8	Standard polar	33892256
Phenylhydrazine,2TMS,isomer #1	C[Si](C)(C)N(NC1=CC=CC=C1)[Si](C)(C)C	1508.1	Semi standard non polar	33892256
Phenylhydrazine,2TMS,isomer #1	C[Si](C)(C)N(NC1=CC=CC=C1)[Si](C)(C)C	1451.7	Standard non polar	33892256
Phenylhydrazine,2TMS,isomer #1	C[Si](C)(C)N(NC1=CC=CC=C1)[Si](C)(C)C	1660.3	Standard polar	33892256
Phenylhydrazine,2TMS,isomer #2	C[Si](C)(C)NN(C1=CC=CC=C1)[Si](C)(C)C	1461.7	Semi standard non polar	33892256
Phenylhydrazine,2TMS,isomer #2	C[Si](C)(C)NN(C1=CC=CC=C1)[Si](C)(C)C	1401.4	Standard non polar	33892256
Phenylhydrazine,2TMS,isomer #2	C[Si](C)(C)NN(C1=CC=CC=C1)[Si](C)(C)C	1518.3	Standard polar	33892256
Phenylhydrazine,3TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1494.2	Semi standard non polar	33892256
Phenylhydrazine,3TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1520.6	Standard non polar	33892256
Phenylhydrazine,3TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1553.3	Standard polar	33892256
Phenylhydrazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC1=CC=CC=C1	1618.4	Semi standard non polar	33892256
Phenylhydrazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC1=CC=CC=C1	1489.5	Standard non polar	33892256
Phenylhydrazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC1=CC=CC=C1	1841.1	Standard polar	33892256
Phenylhydrazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C1=CC=CC=C1	1517.9	Semi standard non polar	33892256
Phenylhydrazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C1=CC=CC=C1	1567.3	Standard non polar	33892256
Phenylhydrazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C1=CC=CC=C1	1920.9	Standard polar	33892256
Phenylhydrazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1852.2	Semi standard non polar	33892256
Phenylhydrazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1846.2	Standard non polar	33892256
Phenylhydrazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1909.2	Standard polar	33892256
Phenylhydrazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1855.1	Semi standard non polar	33892256
Phenylhydrazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1834.4	Standard non polar	33892256
Phenylhydrazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1832.5	Standard polar	33892256
Phenylhydrazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2118.0	Semi standard non polar	33892256
Phenylhydrazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2105.2	Standard non polar	33892256
Phenylhydrazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1938.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylhydrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9600000000-b78ed4739c4f313d68f5	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylhydrazine 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 - Phenylhydrazine 10V, Positive-QTOF	splash10-0a4i-0900000000-7e4a039ac643774eff4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylhydrazine 20V, Positive-QTOF	splash10-0a4i-5900000000-cdf25c62f80acbfd5ab9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylhydrazine 40V, Positive-QTOF	splash10-014l-9000000000-fb55020d3202a0992e0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylhydrazine 10V, Negative-QTOF	splash10-0a4i-4900000000-c58b776073e02f120c76	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylhydrazine 20V, Negative-QTOF	splash10-0a4i-3900000000-1b3e9a8ecb3130f4a885	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylhydrazine 40V, Negative-QTOF	splash10-056u-9100000000-36873e8e35cb75411c7a	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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

FDB005892

KNApSAcK ID

Not Available

Chemspider ID

7235

KEGG Compound ID

C02304

BioCyc ID

PHENYLHYDRAZINE

BiGG ID

Not Available

Wikipedia Link

Phenylhydrazine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27924

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 ]

Enzymes

Enzyme Details

1. ATP-binding cassette sub-family B member 6, mitochondrial

General function:: Involved in ATP binding
Specific function:: Binds heme and porphyrins and functions in their ATP- dependent uptake into the mitochondria. Plays a crucial role in heme synthesis
Gene Name:: ABCB6
Uniprot ID:: Q9NP58
Molecular weight:: 93884.7

Showing metabocard for Phenylhydrazine (HMDB0256439)

MOL for HMDB0256439 (Phenylhydrazine)

3D MOL for HMDB0256439 (Phenylhydrazine)

3D SDF for HMDB0256439 (Phenylhydrazine)

3D-SDF for HMDB0256439 (Phenylhydrazine)

PDB for HMDB0256439 (Phenylhydrazine)

3D PDB for HMDB0256439 (Phenylhydrazine)

SMILES for HMDB0256439 (Phenylhydrazine)

INCHI for HMDB0256439 (Phenylhydrazine)

Structure for HMDB0256439 (Phenylhydrazine)

3D Structure for HMDB0256439 (Phenylhydrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes