NP-MRD: Showing NP-Card for 2-Hydroxybenzamide (NP0016018)

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Record Information

Version

2.0

Created at

2021-01-06 01:06:47 UTC

Updated at

2021-08-19 23:59:54 UTC

NP-MRD ID

NP0016018

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxybenzamide

Provided By

NPAtlas

Description

Salicylamide, also known as 2-carbamoylphenol or OHB, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. 2-Hydroxybenzamide is found in Streptomyces cinnamonensis, Streptomyces sp. RM-14-6 and Streptomyces spectabilis. 2-Hydroxybenzamide was first documented in 2004 (PMID: 14729655). Based on a literature review a small amount of articles have been published on Salicylamide (PMID: 22530891) (PMID: 34066719) (PMID: 33895704).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117263D          

 17 17  0  0  0  0            999 V2000
   -2.7407    0.3550    0.0952 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261   -0.7138   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389   -1.8799   -0.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -0.4419   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5108   -1.4887   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -1.2960   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992   -0.0328   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4920    0.9967    0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250    0.8191    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7411    1.8850    0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885    0.5442    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    0.8919   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912   -2.4979   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -2.1309   -0.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    0.1559   -0.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    2.0006    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990    2.8335    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9  4  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0016018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C([H])=C1C(=O)N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10)

> <INCHI_KEY>
SKZKKFZAGNVIMN-UHFFFAOYSA-N

> <FORMULA>
C7H7NO2

> <MOLECULAR_WEIGHT>
137.136

> <EXACT_MASS>
137.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.224969535328583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxybenzamide

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
1.1703207886666664

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.448510775136604

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.211132879966321

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9718542422260034

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
37.1173

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salicylamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -2.741   0.355   0.095  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.826  -0.714  -0.078  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.239  -1.880  -0.243  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.377  -0.442  -0.061  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.511  -1.489  -0.230  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.877  -1.296  -0.224  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.399  -0.033  -0.046  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.492   0.997   0.121  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.125   0.819   0.117  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.741   1.885   0.289  0.00  0.00           O+0
HETATM   11  H   UNK     0      -3.088   0.544   1.073  0.00  0.00           H+0
HETATM   12  H   UNK     0      -3.020   0.892  -0.734  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.091  -2.498  -0.372  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.547  -2.131  -0.358  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.480   0.156  -0.035  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.909   2.001   0.263  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.399   2.833   0.423  0.00  0.00           H+0
CONECT    1    2   11   12                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10    4                                                  
CONECT   10    9   17                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17   10                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Carbamoylphenol	ChEBI
2-Carboxamidophenol	ChEBI
2-Hydroxybenzamide	ChEBI
O-Hydroxybenzamide	ChEBI
OHB	ChEBI
Salicilamida	ChEBI
Salicylamidum	ChEBI
Salicylic acid amide	ChEBI
Salicylate amide	Generator
Salicylamide sulfate	HMDB
Salicylamide, 3H-labeled	HMDB
Salicylamide, monosodium salt	HMDB
Salicylamide, calcium (2:1) salt	HMDB
Salicylamide sodium	HMDB

Chemical Formula

C₇H₇NO₂

Average Mass

137.1360 Da

Monoisotopic Mass

137.04768 Da

IUPAC Name

2-hydroxybenzamide

Traditional Name

salicylamide

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10)

InChI Key

SKZKKFZAGNVIMN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces cinnamonensis	LOTUS Database	35616633
Streptomyces sp. RM-14-6	NPAtlas	28029795
Streptomyces spectabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	142.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	181.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2060 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	1.280	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.74	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.21	ChemAxon
pKa (Strongest Basic)	-0.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.12 m³·mol⁻¹	ChemAxon
Polarizability	13.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA022113

HMDB ID

HMDB0015687

DrugBank ID

DB08797

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Salicylamide

METLIN ID

Not Available

PubChem Compound

5147

PDB ID

Not Available

ChEBI ID

32114

Good Scents ID

rw1281501

References

General References

MacDonald CJ, Ciolino HP, Yeh GC: The drug salicylamide is an antagonist of the aryl hydrocarbon receptor that inhibits signal transduction induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Cancer Res. 2004 Jan 1;64(1):429-34. doi: 10.1158/0008-5472.can-03-0974. [PubMed:14729655 ]
Dundar Y, Ozatik Y, Ozatik O, Ergin V, Onkol T, Menevse A, Erol K, Sahin MF: Synthesis and biological evaluation of the salicylamide and salicylic acid derivatives as anti-estrogen agents. Med Chem. 2012 May;8(3):481-90. doi: 10.2174/1573406411208030481. [PubMed:22530891 ]
Pindelska E, Marczewska-Rak A, Jaskowska J, Madura ID: Solvates of New Arylpiperazine Salicylamide Derivative-a Multi-Technique Approach to the Description of 5 HTR Ligand Structure and Interactions. Int J Mol Sci. 2021 May 8;22(9). pii: ijms22094992. doi: 10.3390/ijms22094992. [PubMed:34066719 ]
Xu J, Wu W, Chen H, Xue Y, Bao X, Zhou J: Substituted N-(4-amino-2-chlorophenyl)-5-chloro-2-hydroxybenzamide analogues potently inhibit respiratory syncytial virus (RSV) replication and RSV infection-associated inflammatory responses. Bioorg Med Chem. 2021 Jun 1;39:116157. doi: 10.1016/j.bmc.2021.116157. Epub 2021 Apr 18. [PubMed:33895704 ]

Showing NP-Card for 2-Hydroxybenzamide (NP0016018)

MOL for NP0016018 (2-Hydroxybenzamide)

3D MOL for NP0016018 (2-Hydroxybenzamide)

3D SDF for NP0016018 (2-Hydroxybenzamide)

3D-SDF for NP0016018 (2-Hydroxybenzamide)

PDB for NP0016018 (2-Hydroxybenzamide)

3D PDB for NP0016018 (2-Hydroxybenzamide)

SMILES for NP0016018 (2-Hydroxybenzamide)

INCHI for NP0016018 (2-Hydroxybenzamide)

Structure for NP0016018 (2-Hydroxybenzamide)

3D Structure for NP0016018 (2-Hydroxybenzamide)