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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-07-16 16:50:56 UTC

Update Date

2022-03-07 03:18:16 UTC

HMDB ID

HMDB0240370

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Hydroxy-N-(2-hydroxyphenyl)acetamide

Description

2-Hydroxy-N-(2-hydroxyphenyl)acetamide, also known as HHPAA, belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. Based on a literature review very few articles have been published on 2-Hydroxy-N-(2-hydroxyphenyl)acetamide.

Structure

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

HEADER    PROTEIN                                 16-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-19         0                                  
HETATM    1  C   UNK     0      -6.917   2.457   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.250   1.687   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.250   0.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.917  -0.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.583   0.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.583   1.687   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.917   3.997   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -4.249   2.457   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.916   1.687   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.916   0.147   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.582   2.457   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.248   1.687   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    8                                                  
CONECT    7    1                                                            
CONECT    8    6    9                                                       
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
HHPAA	HMDB
2-Hydroxy-N-(2-hydroxyphenyl)acetamide	HMDB

Chemical Formula

C₈H₉NO₃

Average Molecular Weight

167.164

Monoisotopic Molecular Weight

167.058243154

IUPAC Name

2-hydroxy-N-(2-hydroxyphenyl)acetamide

Traditional Name

2-hydroxy-N-(2-hydroxyphenyl)acetamide

CAS Registry Number

78958-15-3

SMILES

OCC(=O)NC1=CC=CC=C1O

InChI Identifier

InChI=1S/C8H9NO3/c10-5-8(12)9-6-3-1-2-4-7(6)11/h1-4,10-11H,5H2,(H,9,12)

InChI Key

OYHOCUAXXOWENX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
N-arylamide
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 26264776)

Source

Exogenous

Exogenous (HMDB: HMDB0240370)

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	0.28	ALOGPS
logP	0.09	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.6 m³·mol⁻¹	ChemAxon
Polarizability	16.35 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]+	134.543	30932474
DeepCCS	[M-H]-	131.969	30932474
DeepCCS	[M-2H]-	168.118	30932474
DeepCCS	[M+Na]+	143.278	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-N-(2-hydroxyphenyl)acetamide	OCC(=O)NC1=CC=CC=C1O	2676.5	Standard polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide	OCC(=O)NC1=CC=CC=C1O	1794.4	Standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide	OCC(=O)NC1=CC=CC=C1O	1759.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,1TMS,isomer #1	C[Si](C)(C)OCC(=O)NC1=CC=CC=C1O	1795.4	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,1TMS,isomer #2	C[Si](C)(C)OC1=CC=CC=C1NC(=O)CO	1769.7	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,1TMS,isomer #3	C[Si](C)(C)N(C(=O)CO)C1=CC=CC=C1O	1671.4	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,2TMS,isomer #1	C[Si](C)(C)OCC(=O)NC1=CC=CC=C1O[Si](C)(C)C	1873.1	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,2TMS,isomer #2	C[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O)[Si](C)(C)C	1707.0	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,2TMS,isomer #3	C[Si](C)(C)OC1=CC=CC=C1N(C(=O)CO)[Si](C)(C)C	1704.8	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,3TMS,isomer #1	C[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O[Si](C)(C)C)[Si](C)(C)C	1773.2	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,3TMS,isomer #1	C[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O[Si](C)(C)C)[Si](C)(C)C	1823.0	Standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,3TMS,isomer #1	C[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O[Si](C)(C)C)[Si](C)(C)C	1892.0	Standard polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)NC1=CC=CC=C1O	2056.3	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1NC(=O)CO	2031.7	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)CO)C1=CC=CC=C1O	1892.1	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)NC1=CC=CC=C1O[Si](C)(C)C(C)(C)C	2362.0	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O)[Si](C)(C)C(C)(C)C	2178.6	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1N(C(=O)CO)[Si](C)(C)C(C)(C)C	2147.7	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2396.4	Semi standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2452.8	Standard non polar	33892256
2-Hydroxy-N-(2-hydroxyphenyl)acetamide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)N(C1=CC=CC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2295.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 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-Hydroxy-N-(2-hydroxyphenyl)acetamide 10V, Positive-QTOF	splash10-014i-1900000000-f04e075705782038c9af	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 20V, Positive-QTOF	splash10-0ldi-3900000000-f822b2d7957746cd9b93	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 40V, Positive-QTOF	splash10-06si-9200000000-1dd62b4e69f4580733ae	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 10V, Negative-QTOF	splash10-014i-0900000000-67419f648e415323a1c8	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 20V, Negative-QTOF	splash10-0aor-0900000000-2e29a5fd5b28e33dbce9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 40V, Negative-QTOF	splash10-0a4i-9800000000-f0be8320d96ca91d1184	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 10V, Positive-QTOF	splash10-03di-0900000000-258c0bf9c6647cf961f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 20V, Positive-QTOF	splash10-03di-2900000000-c6b58521f15d439b8f88	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 40V, Positive-QTOF	splash10-001i-9200000000-1c01cd96639040040e71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 10V, Negative-QTOF	splash10-05mk-0900000000-1f90077a6d4a403f0429	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 20V, Negative-QTOF	splash10-0a4l-2900000000-03d654a82e54120aef56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-N-(2-hydroxyphenyl)acetamide 40V, Negative-QTOF	splash10-0a4i-7900000000-05048effb426c439f6ba	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26264776	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14978638

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12748684

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

Hanhineva K, Brunius C, Andersson A, Marklund M, Juvonen R, Keski-Rahkonen P, Auriola S, Landberg R: Discovery of urinary biomarkers of whole grain rye intake in free-living subjects using nontargeted LC-MS metabolite profiling. Mol Nutr Food Res. 2015 Nov;59(11):2315-25. doi: 10.1002/mnfr.201500423. Epub 2015 Sep 10. [PubMed:26264776 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Showing metabocard for 2-Hydroxy-N-(2-hydroxyphenyl)acetamide (HMDB0240370)

MOL for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

3D MOL for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

3D SDF for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

3D-SDF for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

PDB for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

3D PDB for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

SMILES for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

INCHI for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

Structure for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

3D Structure for HMDB0240370 (2-Hydroxy-N-(2-hydroxyphenyl)acetamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra