Showing metabocard for biphenyl-2,3-diol (MMDBc0054370)

Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:09:26 UTC
Update Date2025-10-07 16:08:29 UTC
Metabolite IDMMDBc0054370
Metabolite Identification
Common Namebiphenyl-2,3-diol
DescriptionBiphenyl-2,3-diol is a biphenyl derivative classified as a metabolite involved in the degradation of aromatic compounds. Its chemical structure features two phenyl rings connected by a single bond, with hydroxyl groups positioned at the 2 and 3 carbon atoms of one of the rings. This compound plays a significant role in microbial bioremediation pathways, particularly in the degradation of polychlorinated biphenyls (PCBs) and other polycyclic aromatic hydrocarbons (PAHs). For instance, biphenyl-2,3-diol 1,2-dioxygenase (bphC) is crucial for the enzymatic breakdown of biphenyl, as evidenced by its expression in the presence of phenanthrene (PHE) (PMID:37214282 ). Additionally, the transformation of tetrachlorobiphenyl in soybean root nodules involves biphenyl-2,3-diol as an intermediate, mediated by specific enzymes including bphC (PMID:38823562 ). The compound also participates in the extradiol cleavage pathway, where its dioxygenase activity is upregulated in response to PAHs (PMID:24608660 ). Furthermore, structural genes encoding various enzymes related to biphenyl degradation have been identified, highlighting its importance in environmental detoxification processes (PMID:8344527 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f9aad17d848>

BPY
  Mrv1652305062021422D          

 14 15  0  0  0  0            999 V2000
   -1.1069    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069   -1.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213   -0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366   -0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069   -2.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221   -1.2582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9aad17d848>

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3D SDF for #<Metabolite:0x00007f9aad17d848>
BPY
  Mrv1652305062021422D          

 14 15  0  0  0  0            999 V2000
   -1.1069    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3924   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069   -1.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8213   -0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7510    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366   -0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069   -2.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221   -1.2582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 14  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054370

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O2/c13-11-8-4-7-10(12(11)14)9-5-2-1-3-6-9/h1-8,13-14H

> <INCHI_KEY>
YKOQAAJBYBTSBS-UHFFFAOYSA-N

> <FORMULA>
C12H10O2

> <MOLECULAR_WEIGHT>
186.2066

> <EXACT_MASS>
186.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.683880787878255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[1,1'-biphenyl]-2,3-diol

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
3.013340534666666

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.547348050699604

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.154614348698352

> <JCHEM_PKA_STRONGEST_BASIC>
-6.30384536415754

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
55.156000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxybiphenyl

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f9aad17d848>
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PDB for #<Metabolite:0x00007f9aad17d848>
HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: BPY                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0      -2.066   0.731   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.732  -0.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.732  -1.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.066  -2.349   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.400  -1.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.400  -0.039   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.601   0.731   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.601   2.271   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.935   3.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.269   2.271   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.269   0.731   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.935  -0.039   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.066  -3.889   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.601  -2.349   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11                                                       
CONECT   13    4                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for #<Metabolite:0x00007f9aad17d848>
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SMILES for #<Metabolite:0x00007f9aad17d848>
OC1=C(O)C(=CC=C1)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f9aad17d848>
InChI=1S/C12H10O2/c13-11-8-4-7-10(12(11)14)9-5-2-1-3-6-9/h1-8,13-14H
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Synonyms
ValueSource
(1,1'-Biphenyl)-2,3-diolChEBI
2,3-BiphenyldiolChEBI
2,3-DihydroxybiphenylChEBI
3-PhenylcatecholChEBI
Molecular FormulaC12H10O2
Average Mass186.2066
Monoisotopic Mass186.068079564
IUPAC Name[1,1'-biphenyl]-2,3-diol
Traditional Name2,3-dihydroxybiphenyl
CAS Registry NumberNot Available
SMILES
OC1=C(O)C(=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H10O2/c13-11-8-4-7-10(12(11)14)9-5-2-1-3-6-9/h1-8,13-14H
InChI KeyYKOQAAJBYBTSBS-UHFFFAOYSA-N