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Showing NP-Card for Salicylhydroxamic Acid (NP0002910)

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Record Information
Version2.0
Created at2020-11-23 19:43:25 UTC
Updated at2024-09-03 04:16:35 UTC
NP-MRD IDNP0002910
Natural Product DOIhttps://doi.org/10.57994/0721
Secondary Accession NumbersNone
Natural Product Identification
Common NameSalicylhydroxamic Acid
Provided ByBMRBBMRB logo
DescriptionSalicylhydroxamic acid, also known as 2-hydroxybenzhydroxamate or SHAM, belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid. Salicylhydroxamic Acid was first documented in 1990 (PMID: 16667326). Based on a literature review a small amount of articles have been published on Salicylhydroxamic acid (PMID: 1847381) (PMID: 22554042) (PMID: 23416493).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002910 (Salicylhydroxamic Acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.2990   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 11 18  1  0
M  END
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3D MOL for NP0002910 (Salicylhydroxamic Acid)

NP0002910
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.0335   -0.8682    1.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135   -0.0896    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    0.6929   -0.4604 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518    0.5546   -0.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1828    0.0326    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    0.8800   -0.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.9417   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.1607   -0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749   -0.6823    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7100   -0.7436    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -1.5967    1.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    1.3699   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988   -0.4384   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047    1.4929   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302    1.6070   -1.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6695    0.2079   -0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131   -1.3249    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6718   -2.1964    2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 11 18  1  0
M  END
Download

3D SDF for NP0002910 (Salicylhydroxamic Acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.2990   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    3.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 11 18  1  0
M  END
> <DATABASE_ID>
NP0002910

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ONC(=O)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10)

> <INCHI_KEY>
HBROZNQEVUILML-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.1354

> <EXACT_MASS>
153.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.166873869347885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N,2-dihydroxybenzamide

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
1.1671390613333332

> <ALOGPS_LOGS>
-1.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.851213449003092

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.009476066404712

> <JCHEM_PKA_STRONGEST_BASIC>
-5.262403530561273

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
38.881899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
salicylhydroxamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002910 (Salicylhydroxamic Acid)

NP0002910
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.0335   -0.8682    1.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135   -0.0896    0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    0.6929   -0.4604 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518    0.5546   -0.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1828    0.0326    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    0.8800   -0.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385    0.9417   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.1607   -0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749   -0.6823    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7100   -0.7436    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411   -1.5967    1.7419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    1.3699   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9988   -0.4384   -0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047    1.4929   -1.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302    1.6070   -1.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6695    0.2079   -0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131   -1.3249    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6718   -2.1964    2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  5  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 11 18  1  0
M  END
Download

PDB for NP0002910 (Salicylhydroxamic Acid)

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       5.335   4.620   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002910 (Salicylhydroxamic Acid)

COMPND    NP0002910
HETATM    1  O1  UNL     1       2.033  -0.868   1.156  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.613  -0.090   0.293  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.512   0.693  -0.460  1.00  0.00           N  
HETATM    4  O2  UNL     1       3.852   0.555  -0.198  1.00  0.00           O  
HETATM    5  C2  UNL     1       0.183   0.033   0.040  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.353   0.880  -0.907  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.738   0.942  -1.092  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.586   0.161  -0.336  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.075  -0.682   0.604  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.710  -0.744   0.787  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.141  -1.597   1.742  1.00  0.00           O  
HETATM   12  H1  UNL     1       2.291   1.370  -1.198  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.999  -0.438  -0.180  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.305   1.493  -1.501  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.130   1.607  -1.832  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.669   0.208  -0.480  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.713  -1.325   1.231  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.672  -2.196   2.333  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    5
CONECT    3    4   12
CONECT    4   13
CONECT    5    6    6   10
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8    9   16
CONECT    9   10   10   17
CONECT   10   11
CONECT   11   18
END
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SMILES for NP0002910 (Salicylhydroxamic Acid)

ONC(=O)C1=CC=CC=C1O
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INCHI for NP0002910 (Salicylhydroxamic Acid)

InChI=1S/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10)
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View in JSmol
Synonyms
ValueSource
2-Hydroxybenzhydroxamic acidChEBI
2-Hydroxybenzohydroxamic acidChEBI
O-Hydroxybenzohydroxamic acidChEBI
Salicylohydroximic acidChEBI
SHAMChEBI
2-HydroxybenzhydroxamateGenerator
2-HydroxybenzohydroxamateGenerator
O-HydroxybenzohydroxamateGenerator
SalicylohydroximateGenerator
SalicylhydroxamateGenerator
Chemical FormulaC7H7NO3
Average Mass153.1354 Da
Monoisotopic Mass153.04259 Da
IUPAC NameN,2-dihydroxybenzamide
Traditional Namesalicylhydroxamic acid
CAS Registry NumberNot Available
SMILES
ONC(=O)C1=CC=CC=C1O
InChI Identifier
InChI=1S/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10)
InChI KeyHBROZNQEVUILML-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-04View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylamides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility46600 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.21ALOGPS
logP1.17ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.88 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0257460
DrugBank IDDB03819
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID60011
KEGG Compound IDC11343
BioCyc IDCPD-6543
BiGG IDNot Available
Wikipedia LinkSalicylhydroxamic_acid
METLIN IDNot Available
PubChem Compound66644
PDB IDNot Available
ChEBI ID45615
Good Scents IDrw1281521
References
General References
  1. Goyal A, Tolbert NE: Salicylhydroxamic Acid (SHAM) Inhibition of the Dissolved Inorganic Carbon Concentrating Process in Unicellular Green Algae. Plant Physiol. 1990 Mar;92(3):630-6. doi: 10.1104/pp.92.3.630. [PubMed:16667326 ]
  2. Ikeda-Saito M, Shelley DA, Lu L, Booth KS, Caughey WS, Kimura S: Salicylhydroxamic acid inhibits myeloperoxidase activity. J Biol Chem. 1991 Feb 25;266(6):3611-6. [PubMed:1847381 ]
  3. Xu F, Zhang DW, Zhu F, Tang H, Lv X, Cheng J, Xie HF, Lin HH: A novel role for cyanide in the control of cucumber (Cucumis sativus L.) seedlings response to environmental stress. Plant Cell Environ. 2012 Nov;35(11):1983-97. doi: 10.1111/j.1365-3040.2012.02531.x. Epub 2012 May 28. [PubMed:22554042 ]
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