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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:57:17 UTC

Update Date

2023-02-21 17:25:56 UTC

HMDB ID

HMDB0037693

Secondary Accession Numbers

HMDB37693

Metabolite Identification

Common Name

2-Propenyl 2-aminobenzoate

Description

2-Propenyl 2-aminobenzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. 2-Propenyl 2-aminobenzoate is a floral, grape, and green tasting compound. Based on a literature review very few articles have been published on 2-Propenyl 2-aminobenzoate.

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   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.335   9.240   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    7                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    2   13                                                       
CONECT    8    5    9   10                                                  
CONECT    9    6    8   11                                                  
CONECT   10    8   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13    7   10                                                       
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
2-Propenyl 2-aminobenzoic acid	Generator
2-Propen-1-yl 2-aminobenzoate	HMDB
2-Propen-1-yl anthranilate	HMDB
Allyl 2-aminobenzoate	HMDB
Allyl anthranilate	HMDB
Allyl O-aminobenzoate	HMDB
Anthranilic acid, allyl ester	HMDB
Anthranilic acid, allyl ester (8ci)	HMDB
Benzoic acid, 2-amino-, 2-propenyl ester	HMDB
Vinyl carbinyl anthranilate	HMDB
Prop-2-en-1-yl 2-aminobenzoic acid	Generator
Allyl anthranilic acid	Generator

Chemical Formula

C₁₀H₁₁NO₂

Average Molecular Weight

177.1998

Monoisotopic Molecular Weight

177.078978601

IUPAC Name

prop-2-en-1-yl 2-aminobenzoate

Traditional Name

prop-2-en-1-yl 2-aminobenzoate

CAS Registry Number

7493-63-2

SMILES

NC1=CC=CC=C1C(=O)OCC=C

InChI Identifier

InChI=1S/C10H11NO2/c1-2-7-13-10(12)8-5-3-4-6-9(8)11/h2-6H,1,7,11H2

InChI Key

UCANFCXAKYMFGA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037693)
Cytoplasm (HMDB: HMDB0037693)

Source

Exogenous

Exogenous (HMDB: HMDB0037693)

Food

Food (HMDB: HMDB0037693)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037693)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	105.00 °C. @ 2.00 mm Hg	The Good Scents Company Information System
Water Solubility	125.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.945 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.05 g/L	ALOGPS
logP	1.76	ALOGPS
logP	2.53	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	19.39	ChemAxon
pKa (Strongest Basic)	2.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.95 m³·mol⁻¹	ChemAxon
Polarizability	18.7 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]+	140.372	31661259
DarkChem	[M-H]-	135.976	31661259
DeepCCS	[M+H]+	137.624	30932474
DeepCCS	[M-H]-	135.154	30932474
DeepCCS	[M-2H]-	170.801	30932474
DeepCCS	[M+Na]+	145.974	30932474
AllCCS	[M+H]+	139.0	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	142.9	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	139.4	32859911
AllCCS	[M+HCOO]-	140.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl 2-aminobenzoate	NC1=CC=CC=C1C(=O)OCC=C	2511.7	Standard polar	33892256
2-Propenyl 2-aminobenzoate	NC1=CC=CC=C1C(=O)OCC=C	1469.7	Standard non polar	33892256
2-Propenyl 2-aminobenzoate	NC1=CC=CC=C1C(=O)OCC=C	1525.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl 2-aminobenzoate,1TMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C	1665.1	Semi standard non polar	33892256
2-Propenyl 2-aminobenzoate,1TMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C	1658.3	Standard non polar	33892256
2-Propenyl 2-aminobenzoate,2TMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1666.8	Semi standard non polar	33892256
2-Propenyl 2-aminobenzoate,2TMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C	1730.7	Standard non polar	33892256
2-Propenyl 2-aminobenzoate,1TBDMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1870.5	Semi standard non polar	33892256
2-Propenyl 2-aminobenzoate,1TBDMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C	1869.3	Standard non polar	33892256
2-Propenyl 2-aminobenzoate,2TBDMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2094.9	Semi standard non polar	33892256
2-Propenyl 2-aminobenzoate,2TBDMS,isomer #1	C=CCOC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2133.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 2-aminobenzoate EI-B (Non-derivatized)	splash10-0103-3900000000-12a46495a65d9dee99e0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 2-aminobenzoate EI-B (Non-derivatized)	splash10-01dl-7900000000-b1419121142cd4687b33	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 2-aminobenzoate EI-B (Non-derivatized)	splash10-0103-3900000000-12a46495a65d9dee99e0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl 2-aminobenzoate EI-B (Non-derivatized)	splash10-01dl-7900000000-b1419121142cd4687b33	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2-aminobenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9400000000-75ed8033f672d4836b7b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2-aminobenzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 2-aminobenzoate 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 - 2-Propenyl 2-aminobenzoate 10V, Positive-QTOF	splash10-01tc-3900000000-293d19497d1ce9de67a6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 20V, Positive-QTOF	splash10-0006-9400000000-1f6caf2e4cf352ac7e22	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 40V, Positive-QTOF	splash10-0006-9300000000-0a86d2a7c694d759049c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 10V, Negative-QTOF	splash10-004i-3900000000-8b065f796a9a1be1ad0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 20V, Negative-QTOF	splash10-000f-8900000000-af5f5d929c8b4ce3db27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 40V, Negative-QTOF	splash10-0006-9200000000-0cc8276ac3562d5184db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 10V, Positive-QTOF	splash10-00di-0900000000-44c1c438f145d51074dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 20V, Positive-QTOF	splash10-00di-1900000000-95280826d65ad3d1bf69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 40V, Positive-QTOF	splash10-0006-9300000000-ec952da2bcda5a766b4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 10V, Negative-QTOF	splash10-054x-7900000000-d6e9ef0e5ce849a25ca1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 20V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl 2-aminobenzoate 40V, Negative-QTOF	splash10-0006-9000000000-eef4c1f804c025cbb978	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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
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

FDB016821

KNApSAcK ID

Not Available

Chemspider ID

22541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24116

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1002291

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 2-Propenyl 2-aminobenzoate (HMDB0037693)

MOL for HMDB0037693 (2-Propenyl 2-aminobenzoate)

3D MOL for HMDB0037693 (2-Propenyl 2-aminobenzoate)

3D SDF for HMDB0037693 (2-Propenyl 2-aminobenzoate)

3D-SDF for HMDB0037693 (2-Propenyl 2-aminobenzoate)

PDB for HMDB0037693 (2-Propenyl 2-aminobenzoate)

3D PDB for HMDB0037693 (2-Propenyl 2-aminobenzoate)

SMILES for HMDB0037693 (2-Propenyl 2-aminobenzoate)

INCHI for HMDB0037693 (2-Propenyl 2-aminobenzoate)

Structure for HMDB0037693 (2-Propenyl 2-aminobenzoate)

3D Structure for HMDB0037693 (2-Propenyl 2-aminobenzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra