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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:20 UTC

Update Date

2023-02-21 17:22:35 UTC

HMDB ID

HMDB0032710

Secondary Accession Numbers

HMDB32710

Metabolite Identification

Common Name

2-(1-Naphthyl)acetamide

Description

2-(1-Naphthyl)acetamide, also known as alpha-naa amide or alpha-naphthaleneacetamide, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review a significant number of articles have been published on 2-(1-Naphthyl)acetamide.

Structure

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

  Mrv0541 02241220342D          

 14 15  0  0  0  0            999 V2000
   -0.7421   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421   -0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846    1.0308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445   -0.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032710

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)CC1=CC=CC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H2,13,14)

> <INCHI_KEY>
XFNJVKMNNVCYEK-UHFFFAOYSA-N

> <FORMULA>
C12H11NO

> <MOLECULAR_WEIGHT>
185.2218

> <EXACT_MASS>
185.084063979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.818852962396743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(naphthalen-1-yl)acetamide

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
1.793528248333333

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.658120408979247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4229039398449586

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
55.638000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-naphthaleneacetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.385  -0.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.385  -1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.617  -2.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.003  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.003  -0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.617   0.384   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.617   1.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.385   2.694   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.001   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.001   0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.385  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.617   0.384   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.771   1.924   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       4.003  -0.384   0.000  0.00  0.00           N+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Naphthylacetamide	ChEBI
alpha-NAA amide	ChEBI
alpha-Naphthaleneacetamide	ChEBI
alpha-Naphthaleneacetic acid amide	ChEBI
alpha-Naphthylacetamide	ChEBI
Amid-thin	ChEBI
Amid-thin W	ChEBI
Dirigol N	ChEBI
Dirigol-N	ChEBI
Frufix	ChEBI
NAAm	ChEBI
Rootone	ChEBI
1-Naphthaleneacetamide	Kegg
a-NAA amide	Generator
Α-naa amide	Generator
a-Naphthaleneacetamide	Generator
Α-naphthaleneacetamide	Generator
a-Naphthaleneacetate amide	Generator
a-Naphthaleneacetic acid amide	Generator
alpha-Naphthaleneacetate amide	Generator
Α-naphthaleneacetate amide	Generator
Α-naphthaleneacetic acid amide	Generator
a-Naphthylacetamide	Generator
Α-naphthylacetamide	Generator
1-Naphthalene acetamide	HMDB
1-Naphthyl-acetamide	HMDB
2-(1-Naphthyl)acetamide, iso	HMDB
N-Acetyl-1-naphthylamine	HMDB
Naphthalene acetamide	HMDB
NAAmide	MeSH
alpha-Naphthalene acetamide	MeSH
Naphthaleneacetamide	MeSH

Chemical Formula

C₁₂H₁₁NO

Average Molecular Weight

185.2218

Monoisotopic Molecular Weight

185.084063979

IUPAC Name

2-(naphthalen-1-yl)acetamide

Traditional Name

1-naphthaleneacetamide

CAS Registry Number

86-86-2

SMILES

NC(=O)CC1=CC=CC2=C1C=CC=C2

InChI Identifier

InChI=1S/C12H11NO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H2,13,14)

InChI Key

XFNJVKMNNVCYEK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenes (CHEBI:81810 )
Auxins (C18533 )
a small molecule (ALPHA-NAPHTHALENEACETAMIDE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032710)
Cytoplasm (HMDB: HMDB0032710)

Source

Exogenous

Exogenous (HMDB: HMDB0032710)

Food

Food (HMDB: HMDB0032710)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032710)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.039 mg/mL at 40 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.79	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16.66	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.64 m³·mol⁻¹	ChemAxon
Polarizability	19.82 Å³	ChemAxon
Number of Rings	2	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]+	141.783	31661259
DarkChem	[M-H]-	137.743	31661259
DeepCCS	[M+H]+	138.027	30932474
DeepCCS	[M-H]-	135.524	30932474
DeepCCS	[M-2H]-	171.038	30932474
DeepCCS	[M+Na]+	146.259	30932474
AllCCS	[M+H]+	140.2	32859911
AllCCS	[M+H-H2O]+	135.8	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	141.8	32859911
AllCCS	[M+Na-2H]-	142.0	32859911
AllCCS	[M+HCOO]-	142.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(1-Naphthyl)acetamide	NC(=O)CC1=CC=CC2=C1C=CC=C2	3304.8	Standard polar	33892256
2-(1-Naphthyl)acetamide	NC(=O)CC1=CC=CC2=C1C=CC=C2	1922.9	Standard non polar	33892256
2-(1-Naphthyl)acetamide	NC(=O)CC1=CC=CC2=C1C=CC=C2	1946.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(1-Naphthyl)acetamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC2=CC=CC=C12	1936.8	Semi standard non polar	33892256
2-(1-Naphthyl)acetamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CC1=CC=CC2=CC=CC=C12	1963.1	Standard non polar	33892256
2-(1-Naphthyl)acetamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C	2044.5	Semi standard non polar	33892256
2-(1-Naphthyl)acetamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C	2133.4	Standard non polar	33892256
2-(1-Naphthyl)acetamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC2=CC=CC=C12	2163.3	Semi standard non polar	33892256
2-(1-Naphthyl)acetamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC2=CC=CC=C12	2148.6	Standard non polar	33892256
2-(1-Naphthyl)acetamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2492.8	Semi standard non polar	33892256
2-(1-Naphthyl)acetamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2565.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(1-Naphthyl)acetamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1900000000-c06434e5e90e566656fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(1-Naphthyl)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-(1-Naphthyl)acetamide 10V, Positive-QTOF	splash10-00kr-0900000000-83acde4005592f3367ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 20V, Positive-QTOF	splash10-014i-0900000000-34773753b20a7508536f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 40V, Positive-QTOF	splash10-014l-2900000000-a2c17c68d8103b39ba5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 10V, Negative-QTOF	splash10-001i-0900000000-e3c56c024c16254df484	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 20V, Negative-QTOF	splash10-000x-1900000000-c2ae5ae2c2bfa32084c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 40V, Negative-QTOF	splash10-0006-9300000000-28b6448af7f8909fbee4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 10V, Positive-QTOF	splash10-000l-0900000000-cdf502567c4f0ef50eb9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 20V, Positive-QTOF	splash10-0006-0900000000-88031e5ffecfa93f4c74	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 40V, Positive-QTOF	splash10-0006-1900000000-89f1cf8c1d03619f0324	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 10V, Negative-QTOF	splash10-000x-0900000000-0bc130e61efbd9476b57	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 20V, Negative-QTOF	splash10-0006-4900000000-587af4a310de55aa1818	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(1-Naphthyl)acetamide 40V, Negative-QTOF	splash10-0006-8900000000-118feedcfbb375f8d09d	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+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

FDB010671

KNApSAcK ID

Not Available

Chemspider ID

6600

KEGG Compound ID

C18533

BioCyc ID

ALPHA-NAPHTHALENEACETAMIDE

BiGG ID

Not Available

Wikipedia Link

1-Naphthaleneacetamide

METLIN ID

Not Available

PubChem Compound

6861

PDB ID

Not Available

ChEBI ID

81810

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1155541

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-(1-Naphthyl)acetamide (HMDB0032710)

MOL for HMDB0032710 (2-(1-Naphthyl)acetamide)

3D MOL for HMDB0032710 (2-(1-Naphthyl)acetamide)

3D SDF for HMDB0032710 (2-(1-Naphthyl)acetamide)

3D-SDF for HMDB0032710 (2-(1-Naphthyl)acetamide)

PDB for HMDB0032710 (2-(1-Naphthyl)acetamide)

3D PDB for HMDB0032710 (2-(1-Naphthyl)acetamide)

SMILES for HMDB0032710 (2-(1-Naphthyl)acetamide)

INCHI for HMDB0032710 (2-(1-Naphthyl)acetamide)

Structure for HMDB0032710 (2-(1-Naphthyl)acetamide)

3D Structure for HMDB0032710 (2-(1-Naphthyl)acetamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra