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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:41 UTC

Update Date

2022-03-07 02:53:08 UTC

HMDB ID

HMDB0031822

Secondary Accession Numbers

HMDB31822

Metabolite Identification

Common Name

Nitarsone

Description

Nitarsone, also known as histostat or 4-O2c6h4aso3h2, belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. Based on a literature review a significant number of articles have been published on Nitarsone.

Structure

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

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7 As   UNK     0       1.334  -2.310   0.000  0.00  0.00          As+0
HETATM    8  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    5                                                       
CONECT    3    1    6                                                       
CONECT    4    2    6                                                       
CONECT    5    1    2    7                                                  
CONECT    6    3    4    8                                                  
CONECT    7    5    9   10   11                                             
CONECT    8    6   12   13                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(p-Nitrophenyl)arsonic acid	ChEBI
4-Nitrobenzenearsonic acid	ChEBI
4-Nitrophenylarsonic acid	ChEBI
4-O2c6h4AsO3h2	ChEBI
Histostat	ChEBI
Nitarson	ChEBI
Nitarsonum	ChEBI
p-Nitrobenzenearsonic acid	ChEBI
p-Nitrophenylarsonic acid	ChEBI
(p-Nitrophenyl)arsonate	Generator
4-Nitrobenzenearsonate	Generator
4-Nitrophenylarsonate	Generator
p-Nitrobenzenearsonate	Generator
p-Nitrophenylarsonate	Generator
(4-Nitrophenyl)-arsonic acid	HMDB
4-(Hydroxy(oxido)amino)phenylarsonic acid	HMDB
Arsonic acid, 4-nitrophenyl	HMDB
C6H6AsNO5	HMDB
Hep-a-stat	HMDB
Histostat 50	HMDB
Histostat-50	HMDB
Nitarsone(usan)	HMDB
Nitarsone, inn, usan	HMDB
NSC 5085	HMDB
p-Nitro-benzenearsonic acid	HMDB
p-Nitrobenzenearsonic acid, 8ci	HMDB
Nitarsone, monosodium salt	HMDB
Nitarsone, disodium salt	HMDB

Chemical Formula

C₆H₆AsNO₅

Average Molecular Weight

247.0371

Monoisotopic Molecular Weight

246.946193724

IUPAC Name

(4-nitrophenyl)arsonic acid

Traditional Name

histostat

CAS Registry Number

98-72-6

SMILES

O[As](O)(=O)C1=CC=C(C=C1)N(=O)=O

InChI Identifier

InChI=1S/C6H6AsNO5/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4H,(H2,9,10,11)

InChI Key

FUUFQLXAIUOWML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Nitroaromatic compound
Pentaorganoarsane
C-nitro compound
Organic nitro compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Oxygen-containing organoarsenic compound
Propargyl-type 1,3-dipolar organic compound
Organic metalloid salt
Organic 1,3-dipolar compound
Organic nitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organoarsenic compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:62629 )
organoarsonic acid (CHEBI:62629 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Hepatobiliary disorder

Hepatitis (HMDB: HMDB0031822)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Confusion (HMDB: HMDB0031822)
Hallucinations (HMDB: HMDB0031822)

Circulatory system disorder

Vascular disorder

Hypotension (HMDB: HMDB0031822)

Cardiac disorder

Cardiomyopathy (HMDB: HMDB0031822)

Renal system and urinary system

Renal disorder

Renal failure (HMDB: HMDB0031822)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031822)
Cytoplasm (HMDB: HMDB0031822)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0031822)
Inhalation (HMDB: HMDB0031822)

Enteral

Ingestion (HMDB: HMDB0031822)

Source

Endogenous

Endogenous (HMDB: HMDB0031822)

Exogenous

Food

Food (HMDB: HMDB0031822)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0031822)
antiprotozoal drug (HMDB: HMDB0031822)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

agrochemical (HMDB: HMDB0031822)

Biological role

Modulator

antiprotozoal drug (HMDB: HMDB0031822)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	298 - 300 °C	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	3.83 g/L	ALOGPS
logP	0.06	ALOGPS
logP	0.88	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39.37 m³·mol⁻¹	ChemAxon
Polarizability	17.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	144.4	32859911
AllCCS	[M+H-H2O]+	140.8	32859911
AllCCS	[M+NH4]+	147.8	32859911
AllCCS	[M+Na]+	148.8	32859911
AllCCS	[M-H]-	143.0	32859911
AllCCS	[M+Na-2H]-	143.8	32859911
AllCCS	[M+HCOO]-	144.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitarsone	O[As](O)(=O)C1=CC=C(C=C1)N(=O)=O	3010.0	Standard polar	33892256
Nitarsone	O[As](O)(=O)C1=CC=C(C=C1)N(=O)=O	2425.6	Standard non polar	33892256
Nitarsone	O[As](O)(=O)C1=CC=C(C=C1)N(=O)=O	1963.3	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 - Nitarsone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2890000000-a3acf3293eae7a0684b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitarsone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitarsone 90V, Negative-QTOF	splash10-0ab9-0900000000-45a948d2717ab2be4295	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitarsone 75V, Negative-QTOF	splash10-0ab9-0900000000-263eb9e558df28fec9f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitarsone 60V, Negative-QTOF	splash10-0ab9-0900000000-6cadf14a24708ad0c1c2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitarsone 45V, Negative-QTOF	splash10-059i-0900000000-1063733419b9b33d41fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitarsone 15V, Negative-QTOF	splash10-000b-0690000000-66b62c233912e541cc3b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitarsone 30V, Negative-QTOF	splash10-000i-0910000000-7020a4100304636dcc5b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 10V, Positive-QTOF	splash10-0002-0090000000-62891226aa9ca258ede2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 20V, Positive-QTOF	splash10-00dl-0090000000-2d936ca40f0bface1726	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 40V, Positive-QTOF	splash10-00kb-1970000000-dfc529b0f93c6dcc8d1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 10V, Negative-QTOF	splash10-000i-0090000000-a16175bbc62ffed663b0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 20V, Negative-QTOF	splash10-0002-0090000000-0cadf4e759362c6d473e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 40V, Negative-QTOF	splash10-000i-1930000000-16f839acf98e7ba63149	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 10V, Positive-QTOF	splash10-0002-0090000000-f19674757ba09d0dcef8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 20V, Positive-QTOF	splash10-0002-0090000000-e6f3ecb68157bd1c3bc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 40V, Positive-QTOF	splash10-0w29-9200000000-a95e0c2ae27fd12d23bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 10V, Negative-QTOF	splash10-0002-0090000000-29d79b09c2e5f484e536	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 20V, Negative-QTOF	splash10-0002-0090000000-29d79b09c2e5f484e536	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitarsone 40V, Negative-QTOF	splash10-00di-0940000000-0009cbf993e797ddc523	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11437

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008500

KNApSAcK ID

Not Available

Chemspider ID

60190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitarsone

METLIN ID

Not Available

PubChem Compound

66826

PDB ID

Not Available

ChEBI ID

62629

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Nitarsone (HMDB0031822)

MOL for HMDB0031822 (Nitarsone)

3D MOL for HMDB0031822 (Nitarsone)

3D SDF for HMDB0031822 (Nitarsone)

3D-SDF for HMDB0031822 (Nitarsone)

PDB for HMDB0031822 (Nitarsone)

3D PDB for HMDB0031822 (Nitarsone)

SMILES for HMDB0031822 (Nitarsone)

INCHI for HMDB0031822 (Nitarsone)

Structure for HMDB0031822 (Nitarsone)

3D Structure for HMDB0031822 (Nitarsone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra