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Showing metabocard for 4-Chlorocatechol (HMDB0041810)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:22 UTC
Update Date2023-02-21 17:28:58 UTC
HMDB IDHMDB0041810
Secondary Accession Numbers
  • HMDB41810
Metabolite Identification
Common Name4-Chlorocatechol
Description4-Chlorocatechol belongs to the class of organic compounds known as 4-chlorocatechols. These are chlorocatechols with the chlorine atom attached at position C4 of the benzene ring. 4-Chlorocatechol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-Chlorocatechol.
Structure
Data?1677000538
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041810 (4-Chlorocatechol)


  Mrv0541 09131211402D          

  9  9  0  0  0  0            999 V2000
    1.4289    0.0000    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
    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 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
    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
Download

3D MOL for HMDB0041810 (4-Chlorocatechol)

HMDB0041810
     RDKit          3D
4-Chlorocatechol
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.6961    1.8560   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    0.9338   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457    1.4051   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128    0.5131    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -0.8522    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8679   -1.9764    0.2203 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -1.2955    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -0.4279   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -0.8598   -0.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    1.5493   -0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    2.4518   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7230    0.8700    0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -2.3527    0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753   -1.8145    0.0121 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  7 13  1  0
  9 14  1  0
M  END
Download

3D SDF for HMDB0041810 (4-Chlorocatechol)


  Mrv0541 09131211402D          

  9  9  0  0  0  0            999 V2000
    1.4289    0.0000    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
    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 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
    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041810

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(O)C=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H

> <INCHI_KEY>
WWOBYPKUYODHDG-UHFFFAOYSA-N

> <FORMULA>
C6H5ClO2

> <MOLECULAR_WEIGHT>
144.556

> <EXACT_MASS>
143.997807111

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.918552350202802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-chlorobenzene-1,2-diol

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.9701598489999999

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.083518697574103

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.667906631147677

> <JCHEM_PKA_STRONGEST_BASIC>
-6.592068932148709

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
34.8246

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chlorocatechol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0041810 (4-Chlorocatechol)

HMDB0041810
     RDKit          3D
4-Chlorocatechol
 14 14  0  0  0  0  0  0  0  0999 V2000
    1.6961    1.8560   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510    0.9338   -0.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6457    1.4051   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128    0.5131    0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -0.8522    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8679   -1.9764    0.2203 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -1.2955    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -0.4279   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -0.8598   -0.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    1.5493   -0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    2.4518   -0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7230    0.8700    0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -2.3527    0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753   -1.8145    0.0121 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  7 13  1  0
  9 14  1  0
M  END
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PDB for HMDB0041810 (4-Chlorocatechol)

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    7                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5    9                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0041810 (4-Chlorocatechol)

COMPND    HMDB0041810
HETATM    1  O1  UNL     1       1.696   1.856  -0.170  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.651   0.934  -0.078  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.646   1.405  -0.057  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.713   0.513   0.034  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.519  -0.852   0.106  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -2.868  -1.976   0.220  1.00  0.00          CL  
HETATM    7  C5  UNL     1      -0.213  -1.296   0.082  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.863  -0.428  -0.008  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.179  -0.860  -0.032  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.660   1.549  -0.188  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.847   2.452  -0.109  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.723   0.870   0.051  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.005  -2.353   0.135  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.475  -1.814   0.012  1.00  0.00           H  
CONECT    1    2   10
CONECT    2    3    3    8
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6    7
CONECT    7    8    8   13
CONECT    8    9
CONECT    9   14
END
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SMILES for HMDB0041810 (4-Chlorocatechol)

OC1=C(O)C=C(Cl)C=C1
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INCHI for HMDB0041810 (4-Chlorocatechol)

InChI=1S/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-Chloro-1,2-benzenediolChEBI
4-ChloropyrocatecholChEBI
4-Chloro-benzene-1,2-diolHMDB
4-Chloro-pyrocatecholHMDB
4-Chlorobenzene-1,2-diolHMDB
Chemical FormulaC6H5ClO2
Average Molecular Weight144.556
Monoisotopic Molecular Weight143.997807111
IUPAC Name4-chlorobenzene-1,2-diol
Traditional Name4-chlorocatechol
CAS Registry Number2138-22-9
SMILES
OC1=C(O)C=C(Cl)C=C1
InChI Identifier
InChI=1S/C6H5ClO2/c7-4-1-2-5(8)6(9)3-4/h1-3,8-9H
InChI KeyWWOBYPKUYODHDG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-chlorocatechols. These are chlorocatechols with the chlorine atom attached at position C4 of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct Parent4-chlorocatechols
Alternative Parents
Substituents
  • 4-chlorocatechol
  • 4-halophenol
  • 3-halophenol
  • 3-chlorophenol
  • 4-chlorophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Halobenzene
  • Chlorobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility28.7 g/LALOGPS
logP1.61ALOGPS
logP1.97ChemAxon
logS-0.7ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.82 m³·mol⁻¹ChemAxon
Polarizability12.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+127.54530932474
DeepCCS[M-H]-123.88130932474
DeepCCS[M-2H]-161.15430932474
DeepCCS[M+Na]+136.69330932474
AllCCS[M+H]+128.932859911
AllCCS[M+H-H2O]+124.232859911
AllCCS[M+NH4]+133.232859911
AllCCS[M+Na]+134.532859911
AllCCS[M-H]-122.232859911
AllCCS[M+Na-2H]-124.332859911
AllCCS[M+HCOO]-126.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.75 minutes32390414
Predicted by Siyang on May 30, 202211.5896 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.33 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid92.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1333.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid421.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid156.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid290.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid302.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid498.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid466.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)227.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid901.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid363.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1057.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid314.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid352.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate613.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA250.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water199.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-ChlorocatecholOC1=C(O)C=C(Cl)C=C12650.5Standard polar33892256
4-ChlorocatecholOC1=C(O)C=C(Cl)C=C11172.3Standard non polar33892256
4-ChlorocatecholOC1=C(O)C=C(Cl)C=C11441.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Chlorocatechol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(Cl)C=C1O1387.4Semi standard non polar33892256
4-Chlorocatechol,1TMS,isomer #2C[Si](C)(C)OC1=CC(Cl)=CC=C1O1381.9Semi standard non polar33892256
4-Chlorocatechol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(Cl)C=C1O[Si](C)(C)C1473.5Semi standard non polar33892256
4-Chlorocatechol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1O1626.8Semi standard non polar33892256
4-Chlorocatechol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(Cl)=CC=C1O1602.6Semi standard non polar33892256
4-Chlorocatechol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1O[Si](C)(C)C(C)(C)C1966.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID15638
KEGG Compound IDC02375
BioCyc IDCPD-9152
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16496
PDB ID4CL
ChEBI ID27772
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available