Showing metabocard for 1,4-Dihydroxy-2-naphthoic acid (MMDBc0029774)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:41:07 UTC
Update Date2024-10-17 15:25:50 UTC
Metabolite IDMMDBc0029774
Metabolite Identification
Common Name1,4-Dihydroxy-2-naphthoic acid
Description1,4-dihydroxy-2-naphthoate is a member of the chemical class known as Naphthalenecarboxylic Acids and Derivatives. These are compounds containing a napthalene moiety with a ring carbon which bears a carboxylic acid group. 1,4-dihydroxy-2-naphthoate is invovled in ubiquinone and other terpenoid-quinone biosynthesis, and the biosynthesis of secondary metabolites. It has been postulated that 1,4-dihydroxy-2-naphthoic acid is the naphthalenic intermediate in the biosynthesis of menaquinone (vitamin K2) in Escherichia coli to which the octaprenyl side chain is attached to from demethylmenaquinone. (PMID 949474 ) It was demonstrated that chorismate is the branch point compound leading to menaquinone, and that 2-succinylbenzoic acid and 1,4-dihydroxy-2-naphthoic acid can serve as menaquinoone precursors in E. (PMID 1091286 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9258112258>

Structure #1
  Mrv0541 02241206302D          

 15 16  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    2.4750    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 15  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9258112258>

HMDB0244212
     RDKit          3D
1,4-Dihydroxy-2-naphthoic acid
 23 24  0  0  0  0  0  0  0  0999 V2000
   -4.1600    0.9819    0.0871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3259    0.0466   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7698   -1.2574   -0.2063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.2857   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578    1.5374    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227    1.7492    0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4458    3.0486    0.3604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132    0.7115    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2830    0.9520    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741   -0.0934   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6521   -1.3520   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2808   -1.6029   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892   -0.5647   -0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828   -0.7748   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298   -2.0123   -0.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809   -1.8582    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354    2.3903    0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597    3.3977    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926    1.9495    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448    0.0656   -0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458   -2.1650   -0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9164   -2.6025   -0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9925   -2.8328   -0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  4  1  0
 13  8  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 15 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9258112258>

Structure #1
  Mrv0541 02241206302D          

 15 16  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    2.4750    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 15  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029774

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C1=C(O)C2=CC=CC=C2C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5,12-13H,(H,14,15)

> <INCHI_KEY>
VOJUXHHACRXLTD-UHFFFAOYSA-N

> <FORMULA>
C11H8O4

> <MOLECULAR_WEIGHT>
204.1788

> <EXACT_MASS>
204.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
19.576522094481

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dihydroxynaphthalene-2-carboxylic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.663174837333333

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.644808371416538

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4402589581288656

> <JCHEM_PKA_STRONGEST_BASIC>
-6.04967030840928

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
53.726200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-dihydroxy-2-naphthoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9258112258>

HMDB0244212
     RDKit          3D
1,4-Dihydroxy-2-naphthoic acid
 23 24  0  0  0  0  0  0  0  0999 V2000
   -4.1600    0.9819    0.0871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3259    0.0466   -0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7698   -1.2574   -0.2063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.2857   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578    1.5374    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227    1.7492    0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4458    3.0486    0.3604 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132    0.7115    0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2830    0.9520    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741   -0.0934   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6521   -1.3520   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2808   -1.6029   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892   -0.5647   -0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828   -0.7748   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298   -2.0123   -0.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809   -1.8582    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354    2.3903    0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3597    3.3977    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6926    1.9495    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2448    0.0656   -0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3458   -2.1650   -0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9164   -2.6025   -0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9925   -2.8328   -0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  4  1  0
 13  8  1  0
  3 16  1  0
  5 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 15 23  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9258112258>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    3    7    9                                                  
CONECT    7    4    6   10                                                  
CONECT    8    5   10   11                                                  
CONECT    9    5    6   12                                                  
CONECT   10    7    8   13                                                  
CONECT   11    8   14   15                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END
Download

3D PDB for #<Metabolite:0x00007f9258112258>

COMPND    HMDB0244212
HETATM    1  O1  UNL     1      -4.160   0.982   0.087  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.326   0.047  -0.035  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.770  -1.257  -0.206  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.885   0.286  -0.003  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.358   1.537   0.161  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.023   1.749   0.190  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.446   3.049   0.360  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.913   0.712   0.054  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.283   0.952   0.086  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.174  -0.093  -0.050  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.652  -1.352  -0.216  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.281  -1.603  -0.249  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.389  -0.565  -0.113  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.983  -0.775  -0.142  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.530  -2.012  -0.304  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.681  -1.858   0.625  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.035   2.390   0.273  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.360   3.398   0.407  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.693   1.950   0.217  1.00  0.00           H  
HETATM   20  H5  UNL     1       4.245   0.066  -0.029  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.346  -2.165  -0.322  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.916  -2.602  -0.380  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.993  -2.833  -0.411  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5    5   14
CONECT    5    6   17
CONECT    6    7    8    8
CONECT    7   18
CONECT    8    9   13
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   13   22
CONECT   13   14   14
CONECT   14   15
CONECT   15   23
END
Download

SMILES for #<Metabolite:0x00007f9258112258>

OC(=O)C1=C(O)C2=CC=CC=C2C(O)=C1
Download

INCHI for #<Metabolite:0x00007f9258112258>

InChI=1S/C11H8O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5,12-13H,(H,14,15)
Download
Synonyms
ValueSource
1,4-Dihydroxy-2-naphthalenecarboxylic acidChEBI
1,4-Dihydroxy-2-naphthoic acidKegg
1,4-Dihydroxy-2-naphthalenecarboxylateGenerator
Molecular FormulaC11H8O4
Average Mass204.1788
Monoisotopic Mass204.042258744
IUPAC Name1,4-dihydroxynaphthalene-2-carboxylic acid
Traditional Name1,4-dihydroxy-2-naphthoic acid
CAS Registry Number31519-22-9
SMILES
OC(=O)C1=C(O)C2=CC=CC=C2C(O)=C1
InChI Identifier
InChI=1S/C11H8O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5,12-13H,(H,14,15)
InChI KeyVOJUXHHACRXLTD-UHFFFAOYSA-N