Showing metabocard for p-Aminobenzoic acid (MMDBc0000191)

Show more...
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:39:12 UTC
Update Date2024-10-06 23:15:23 UTC
Metabolite IDMMDBc0000191
Metabolite Identification
Common Namep-Aminobenzoic acid
Descriptionp-Aminobenzoic acid, also known as 4-aminobenzoic acid or PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid. PABA is an essential nutrient for some bacteria and is sometimes called vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. PABA is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria. Certain bacteria in the human intestinal tract such as E. coli generate PABA from chorismate. Humans lack the enzymes to convert PABA into folate, and therefore require folate from dietary sources such as green leafy vegetables. Although some intestinal bacteria can synthesize folate from PABA and some E. coli can synthesize folate this requires six enzymatic activities in folate synthesis which are not all done in the same bacteria. PABA used to be a common sunscreen agent until it was found to also be a sensitizer. The potassium salt of PABA is used therapeutically in fibrotic skin disorders. PABA can also be found in Acetobacter (DOI: 10.3181/00379727-52-14147).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005623081bc750>

  Mrv1652309042000222D          

 10 10  0  0  0  0            999 V2000
   -0.7698   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133   -1.6843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -0.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005623081bc750>

HMDB0001392
     RDKit          3D
p-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.0541    0.0130   -0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6318    0.0160    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    1.1435    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    1.1829    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084    0.0857    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.1409    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    1.1590    0.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913   -0.9366   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -1.0468   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -1.0776   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930   -0.0311   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334    0.0593    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    1.9903    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8814    2.0912    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8520   -0.8861   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.9253   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3832   -1.9782   -0.7779 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
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005623081bc750>

  Mrv1652309042000222D          

 10 10  0  0  0  0            999 V2000
   -0.7698   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1989   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -1.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698   -1.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133   -1.6843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -0.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -0.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000191

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)

> <INCHI_KEY>
ALYNCZNDIQEVRV-UHFFFAOYSA-N

> <FORMULA>
C7H7NO2

> <MOLECULAR_WEIGHT>
137.136

> <EXACT_MASS>
137.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.44348919384024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-aminobenzoic acid

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.8019027699999998

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.769893805764377

> <JCHEM_PKA_STRONGEST_BASIC>
2.6912772144052126

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
38.0146

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sunbrella

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00005623081bc750>

HMDB0001392
     RDKit          3D
p-Aminobenzoic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.0541    0.0130   -0.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6318    0.0160    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    1.1435    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    1.1829    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1084    0.0857    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.1409    0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    1.1590    0.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913   -0.9366   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4666   -1.0468   -0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -1.0776   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930   -0.0311   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5334    0.0593    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    1.9903    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8814    2.0912    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8520   -0.8861   -1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.9253   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3832   -1.9782   -0.7779 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
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

PDB for #<Metabolite:0x00005623081bc750>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.437  -0.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.771  -0.064   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.104  -0.834   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.105  -2.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.771  -3.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.437  -2.374   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.438  -3.144   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.103  -0.064   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.103   1.476   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.230  -0.834   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
Download

3D PDB for #<Metabolite:0x00005623081bc750>

COMPND    HMDB0001392
HETATM    1  N1  UNL     1       3.054   0.013  -0.026  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.632   0.016   0.012  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.984   1.143   0.478  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.390   1.183   0.529  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.108   0.086   0.109  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.542   0.141   0.168  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.115   1.159   0.589  1.00  0.00           O  
HETATM    8  O2  UNL     1      -3.291  -0.937  -0.243  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.467  -1.047  -0.359  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.912  -1.078  -0.406  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.593  -0.031  -0.911  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.533   0.059   0.921  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.571   1.990   0.801  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.881   2.091   0.904  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.852  -0.886  -1.090  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.015  -1.925  -0.696  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.383  -1.978  -0.778  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    3   10
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   15
CONECT    9   10   10   16
CONECT   10   17
END
Download

SMILES for #<Metabolite:0x00005623081bc750>

NC1=CC=C(C=C1)C(O)=O
Download

INCHI for #<Metabolite:0x00005623081bc750>

InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
Download
Synonyms
Molecular FormulaC7H7NO2
Average Mass137.136
Monoisotopic Mass137.047678473
IUPAC Name4-aminobenzoic acid
Traditional Namesunbrella
CAS Registry Number150-13-0
SMILES
NC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyALYNCZNDIQEVRV-UHFFFAOYSA-N