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Showing NP-Card for benzamide (NP0002841)

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Record Information
Version1.0
Created at2020-11-23 19:41:46 UTC
Updated at2024-04-19 09:50:46 UTC
NP-MRD IDNP0002841
Secondary Accession NumbersNone
Natural Product Identification
Common Namebenzamide
Provided ByBMRBBMRB logo
DescriptionBenzamide, also known as PHC(=o)NH2 or phenylcarboxamide, belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Benzamide exists in all living organisms, ranging from bacteria to humans. Benzamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. benzamide is found in Colchicum autumnale, Haplophyllum obtusifolium, Homo sapiens, Houttuynia cordata, Paeonia peregrina and Sarcomelicope argyrophylla. It was first documented in 1987 (PMID: 2443639). Based on a literature review a significant number of articles have been published on Benzamide (PMID: 17984079) (PMID: 12769385) (PMID: 14522364) (PMID: 16386474).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002841 (benzamide)


     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.9428    0.3202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8881   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -2.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371   -0.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407    1.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    1.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650    0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3939   -0.0599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5465    1.7669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954    2.1470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    2.9072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160    0.7741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1234   -2.1193    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -2.8796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
Download

3D MOL for NP0002841 (benzamide)

NP0002841
     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.7346    0.4997   -0.2217 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -0.4770    0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3454   -1.4776    0.8413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -0.2699    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855    0.8569   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    1.1051   -0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3184    0.1538   -0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -0.9933    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040   -1.1866    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    1.4378    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    0.2393   -1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    1.6045   -0.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138    1.9937   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    0.3244   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575   -1.7487    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -2.0622    1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
Download

3D SDF for NP0002841 (benzamide)


     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.9428    0.3202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8881   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -2.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371   -0.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407    1.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103    1.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650    0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3939   -0.0599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5465    1.7669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954    2.1470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066    2.9072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9160    0.7741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1234   -2.1193    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -2.8796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
> <DATABASE_ID>
NP0002841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)

> <INCHI_KEY>
KXDAEFPNCMNJSK-UHFFFAOYSA-N

> <FORMULA>
C7H7NO

> <MOLECULAR_WEIGHT>
121.1366

> <EXACT_MASS>
121.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
12.38029881491579

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzamide

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.8238861103333335

> <ALOGPS_LOGS>
-1.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.561712990542674

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2412468419680267

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
35.136399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002841 (benzamide)

NP0002841
     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.7346    0.4997   -0.2217 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -0.4770    0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3454   -1.4776    0.8413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050   -0.2699    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855    0.8569   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    1.1051   -0.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3184    0.1538   -0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -0.9933    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040   -1.1866    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8611    1.4378    0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    0.2393   -1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    1.6045   -0.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138    1.9937   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    0.3244   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575   -1.7487    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1084   -2.0622    1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
M  END
Download

PDB for NP0002841 (benzamide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      22.321  -4.907   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      24.988  -4.907   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      23.654  -5.677   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.654  -7.217   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.988  -7.987   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.321  -7.987   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.988  -9.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.321  -9.527   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.654 -10.297   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    3                                                            
CONECT    3    1    2    4                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6    9                                                       
CONECT    9    7    8                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0002841 (benzamide)

COMPND    NP0002841
HETATM    1  N1  UNL     1       2.735   0.500  -0.222  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.841  -0.477   0.292  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.345  -1.478   0.841  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.405  -0.270   0.158  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.086   0.857  -0.460  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.432   1.105  -0.615  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.318   0.154  -0.115  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.879  -0.993   0.513  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.504  -1.187   0.639  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.861   1.438   0.177  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.296   0.239  -1.060  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.614   1.605  -0.853  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.814   1.994  -1.102  1.00  0.00           H  
HETATM   14  H5  UNL     1      -3.399   0.324  -0.224  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.557  -1.749   0.910  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.108  -2.062   1.119  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3    3    4
CONECT    4    5    5    9
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9    9   15
CONECT    9   16
END
Download

SMILES for NP0002841 (benzamide)

NC(=O)C1=CC=CC=C1
Download

INCHI for NP0002841 (benzamide)

InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
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View in JSmol
Synonyms
ValueSource
BenzenecarboxamideChEBI
Benzoic acid amideChEBI
BenzoylamideChEBI
PHC(=O)NH2ChEBI
PHC(O)NH2ChEBI
PhenylcarboxamideChEBI
PhenylcarboxyamideChEBI
Benzoate amideGenerator
Amid kyseliny benzooveHMDB
Benzamide (acd/name 4.0)HMDB
BenzoateHMDB
Benzoic acidHMDB
Phenyl carboxyamideHMDB
TiganHMDB
Trimethobenzamide hydrochlorideHMDB
Chemical FormulaC7H7NO
Average Mass121.1366 Da
Monoisotopic Mass121.05276 Da
IUPAC Namebenzamide
Traditional Namebenzamide
CAS Registry NumberNot Available
SMILES
NC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)
InChI KeyKXDAEFPNCMNJSK-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, ethanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, ethanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, ethanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Boronella koniambiensisKNApSAcK Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Colchicum autumnaleLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Haplophyllum obtusifoliumLOTUS Database
Homo sapiensLOTUS Database
Houttuynia cordataLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Paeonia peregrinaLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Sarcomelicope argyrophyllaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzamides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point129.10 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point290.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility13500 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP0.640The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.51ALOGPS
logP0.82ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)14.56ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.14 m³·mol⁻¹ChemAxon
Polarizability12.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004461
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023373
KNApSAcK IDC00042277
Chemspider ID2241
KEGG Compound IDC09815
BioCyc IDSAM
BiGG IDNot Available
Wikipedia LinkBenzamide
METLIN IDNot Available
PubChem Compound2331
PDB IDUNU
ChEBI ID28179
Good Scents IDrw1221711
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Chiba R, Ogasawara A, Kubo T, Yamazaki H, Umino M, Ishizuka Y: Direct determination of benzamides in serum by column-switching high-performance liquid chromatography. Anal Sci. 2003 May;19(5):785-9. doi: 10.2116/analsci.19.785. [PubMed:12769385 ]
  3. Yamamoto T, Hanioka N, Maeda Y, Imazumi K, Hamada K, Matsuo M, Manda T, Mutoh S: Contribution of tachykinin receptor subtypes to micturition reflex in guinea pigs. Eur J Pharmacol. 2003 Sep 23;477(3):253-9. doi: 10.1016/j.ejphar.2003.08.028. [PubMed:14522364 ]
  4. Gschwend MH, Arnold P, Ring J, Martin W: Selective and sensitive determination of amisulpride in human plasma by liquid chromatography-tandem mass spectrometry with positive electrospray ionisation and multiple reaction monitoring. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):132-9. doi: 10.1016/j.jchromb.2005.11.042. Epub 2005 Dec 28. [PubMed:16386474 ]
  5. Coyle JD, MacKichan JJ, Boudoulas H, Lima JJ: Reversed-phase liquid chromatography method for measurement of procainamide and three metabolites in serum and urine: percent of dose excreted as deethyl metabolites. J Pharm Sci. 1987 May;76(5):402-5. doi: 10.1002/jps.2600760513. [PubMed:2443639 ]