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Showing NP-Card for 3-chloro-2,6-dihydroxy-4-methylbenzaldehyde (NP0211397)

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Record Information
Version2.0
Created at2022-09-05 09:39:58 UTC
Updated at2022-09-05 09:39:58 UTC
NP-MRD IDNP0211397
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-chloro-2,6-dihydroxy-4-methylbenzaldehyde
Description3-Chloro-2,6-dihydroxy-4-methylbenzaldehyde, also known as chloroatranol, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. 3-chloro-2,6-dihydroxy-4-methylbenzaldehyde is found in Evernia prunastri and Platismatia glauca. 3-Chloro-2,6-dihydroxy-4-methylbenzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)


  Mrv1533004171517442D          

 12 12  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    2.7253   -0.5296   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3366   -0.2406   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    0.9179    0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157    1.2210    0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4250    2.4026    1.4144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    0.3812    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    0.6282    0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5491   -0.1973    0.6312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798   -0.7925   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0533   -1.6625   -0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2881   -1.0936   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6194   -2.5752   -1.5441 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -1.5704   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340    0.1256   -0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -0.2847   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8773    1.6367    0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    2.6380    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136    1.5069    1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590   -2.5116   -0.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  6  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11  2  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)


  Mrv1533004171517442D          

 12 12  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C(C=O)C(O)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C8H7ClO3/c1-4-2-6(11)5(3-10)8(12)7(4)9/h2-3,11-12H,1H3

> <INCHI_KEY>
IOTAGSGSURFFDS-UHFFFAOYSA-N

> <FORMULA>
C8H7ClO3

> <MOLECULAR_WEIGHT>
186.59

> <EXACT_MASS>
186.0083718

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.99821891127073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-chloro-2,6-dihydroxy-4-methylbenzaldehyde

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
3.496083583

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.782957719983822

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.091186196229533

> <JCHEM_PKA_STRONGEST_BASIC>
-5.980330488822664

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
46.4498

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-2,6-dihydroxy-4-methylbenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)

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PDB for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)
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SMILES for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)
CC1=CC(O)=C(C=O)C(O)=C1Cl
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INCHI for NP0211397 (3-chloro-2,6-dihydroxy-4-methylbenzaldehyde)
InChI=1S/C8H7ClO3/c1-4-2-6(11)5(3-10)8(12)7(4)9/h2-3,11-12H,1H3
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View in JSmol
Synonyms
ValueSource
ChloroatranolMeSH
Chemical FormulaC8H7ClO3
Average Mass186.5900 Da
Monoisotopic Mass186.00837 Da
IUPAC Name3-chloro-2,6-dihydroxy-4-methylbenzaldehyde
Traditional Name3-chloro-2,6-dihydroxy-4-methylbenzaldehyde
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=C(C=O)C(O)=C1Cl
InChI Identifier
InChI=1S/C8H7ClO3/c1-4-2-6(11)5(3-10)8(12)7(4)9/h2-3,11-12H,1H3
InChI KeyIOTAGSGSURFFDS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Evernia prunastriLOTUS Database
Platismatia glaucaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentHydroxybenzaldehydes  
Alternative Parents
Substituents
  • Hydroxybenzaldehyde
    • 

  • 4-halophenol
    • 

  • 2-halophenol
    • 

  • M-cresol
    • 

  • 2-chlorophenol
    • 

  • Benzoyl
    • 

  • 4-chlorophenol
    • 

  • Resorcinol
    • 

  • Halobenzene
    • 

  • Phenol
    • 

  • Chlorobenzene
    • 

  • Toluene
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Aryl halide
    • 

  • Aryl chloride
    • 

  • Vinylogous acid
    • 

  • Organochloride
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organohalogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.97ALOGPS
logP3.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.45 m³·mol⁻¹ChemAxon
Polarizability17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6426722  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]