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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:41 UTC

Update Date

2023-02-21 17:22:26 UTC

HMDB ID

HMDB0032595

Secondary Accession Numbers

HMDB32595

Metabolite Identification

Common Name

1-(4-Methoxyphenyl)-2-nitroethylene

Description

1-(4-Methoxyphenyl)-2-nitroethylene, also known as -(2-nitrovinyl)anisole or -methoxy-b-nitrostyrene, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Based on a literature review very few articles have been published on 1-(4-Methoxyphenyl)-2-nitroethylene.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    2    3    6                                                  
CONECT    9    4    5   13                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
-(2-Nitrovinyl)anisole	HMDB
-(4-Methoxyphenyl)-2-nitroethene	HMDB
-Methoxy-4-(2-nitrovinyl)benzene	HMDB
-Methoxy-b-nitrostyrene	HMDB
-Methoxy-W-nitrostyrene	HMDB
1-(4-Methoxyphenyl)-2-nitroethene	HMDB
1-Methoxy-4-(2-nitroethenyl)-benzene	HMDB
1-Methoxy-4-(2-nitrovinyl)benzene	HMDB
1-Methoxy-4-[(e)-2-nitroethenyl]benzene	HMDB
2'-Nitro vinyl anisole	HMDB
4-(2-Nitrovinyl)anisole	HMDB
4-Methoxy-b-nitrostyrene	HMDB
4-Methoxy-laquo omegaraquo -nitrostyrene	HMDB
4-Methoxy-W-nitrostyrene	HMDB
Anisylidenenitromethane	HMDB
Ethene,-1-(4-methoxyphenyl)-2-nitro	HMDB
p-(2-Nitrovinyl)-anisole	HMDB
p-(2-Nitrovinyl)-nisole	HMDB
p-(2-Nitrovinyl)anisole	HMDB
p-Methoxy-b-nitrostyrene	HMDB
trans-4-Methoxy-beta-nitrostyrene	HMDB
trans-4-Methyl-beta-nitrostyrene	HMDB
4-Methoxy-beta-nitrostyrene	HMDB
T4MeN compound	HMDB
4-Methyl-beta-nitrostyrene	HMDB
T4MN Compound	HMDB

Chemical Formula

C₉H₉NO₃

Average Molecular Weight

179.1727

Monoisotopic Molecular Weight

179.058243159

IUPAC Name

1-methoxy-4-[(E)-2-nitroethenyl]benzene

Traditional Name

4-methoxy-B-nitrostyrene

CAS Registry Number

3179-10-0

SMILES

COC1=CC=C(\C=C\N(=O)=O)C=C1

InChI Identifier

InChI=1S/C9H9NO3/c1-13-9-4-2-8(3-5-9)6-7-10(11)12/h2-7H,1H3/b7-6+

InChI Key

JKQUXSHVQGBODD-VOTSOKGWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Styrene
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
C-nitro compound
Organic nitro compound
Ether
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032595)
Cytoplasm (HMDB: HMDB0032595)

Source

Endogenous

Endogenous (HMDB: HMDB0032595)

Exogenous

Food

Food (HMDB: HMDB0032595)

Exogenous (HMDB: HMDB0032595)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	88 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.20	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	2.25	ALOGPS
logP	1.97	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.51 m³·mol⁻¹	ChemAxon
Polarizability	17.72 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
DarkChem	[M+H]+	142.375	31661259
DarkChem	[M-H]-	141.87	31661259
DeepCCS	[M+H]+	139.217	30932474
DeepCCS	[M-H]-	136.822	30932474
DeepCCS	[M-2H]-	171.741	30932474
DeepCCS	[M+Na]+	146.799	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	138.8	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.26 minutes	32390414
Predicted by Siyang on May 30, 2022	12.601 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1842.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	432.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	260.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	432.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1101.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1093.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	62.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(4-Methoxyphenyl)-2-nitroethylene	COC1=CC=C(\C=C\N(=O)=O)C=C1	2644.6	Standard polar	33892256
1-(4-Methoxyphenyl)-2-nitroethylene	COC1=CC=C(\C=C\N(=O)=O)C=C1	1594.1	Standard non polar	33892256
1-(4-Methoxyphenyl)-2-nitroethylene	COC1=CC=C(\C=C\N(=O)=O)C=C1	1729.6	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 - 1-(4-Methoxyphenyl)-2-nitroethylene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01si-0900000000-d21811240dc912b7ebe1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 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 - 1-(4-Methoxyphenyl)-2-nitroethylene 10V, Positive-QTOF	splash10-001i-0900000000-d2c1915d3835578dbb04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 20V, Positive-QTOF	splash10-0fk9-0900000000-944c4381e6a9ce4966b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 40V, Positive-QTOF	splash10-0kou-0900000000-e06d90c4cb831e63b790	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 10V, Negative-QTOF	splash10-004i-0900000000-298190dadaca02d166f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 20V, Negative-QTOF	splash10-004i-1900000000-db09a2d9d0264608088b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 40V, Negative-QTOF	splash10-00fr-4900000000-97d50821ca71402cbf63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 10V, Negative-QTOF	splash10-004i-0900000000-f7139a1e768d1e55c0da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 20V, Negative-QTOF	splash10-002b-7900000000-12a183129706ea042ab2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 40V, Negative-QTOF	splash10-0002-9100000000-4dfba43304ac4a0efb25	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 10V, Positive-QTOF	splash10-001i-0900000000-904131a9fd847f721e45	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 20V, Positive-QTOF	splash10-001i-0900000000-ba59201c8598c8309340	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(4-Methoxyphenyl)-2-nitroethylene 40V, Positive-QTOF	splash10-004i-9300000000-4ac6915ab5c33c3c1123	2021-09-25	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+Na]+)	2023-02-04	FELIX 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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010532

KNApSAcK ID

Not Available

Chemspider ID

608130

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

697963

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

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

Showing metabocard for 1-(4-Methoxyphenyl)-2-nitroethylene (HMDB0032595)

MOL for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

3D MOL for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

3D SDF for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

3D-SDF for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

PDB for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

3D PDB for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

SMILES for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

INCHI for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

Structure for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

3D Structure for HMDB0032595 (1-(4-Methoxyphenyl)-2-nitroethylene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra