Showing metabocard for 4-Aminobenzoate (MMDBc0049933)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:46:34 UTC
Update Date2022-09-01 02:17:26 UTC
Metabolite IDMMDBc0049933
Metabolite Identification
Common Name4-Aminobenzoate
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:0x00007fecfcffa2f8>


  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
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3D MOL for #<Metabolite:0x00007fecfcffa2f8>

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
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3D SDF for #<Metabolite:0x00007fecfcffa2f8>


  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>
MMDBc0049933

> <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

$$$$
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3D-SDF for #<Metabolite:0x00007fecfcffa2f8>

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
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PDB for #<Metabolite:0x00007fecfcffa2f8>

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
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3D PDB for #<Metabolite:0x00007fecfcffa2f8>

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
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SMILES for #<Metabolite:0x00007fecfcffa2f8>

NC1=CC=C(C=C1)C(O)=O
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INCHI for #<Metabolite:0x00007fecfcffa2f8>

InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
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Synonyms
ValueSource
1-Amino-4-carboxybenzeneChEBI
4-Amino-benzoic acidChEBI
4-AminobenzoesaeureChEBI
4-CarboxyanilineChEBI
4-CarboxyphenylamineChEBI
ABEEChEBI
gamma-Aminobenzoic acidChEBI
p-AminobenzoesaeureChEBI
p-CarboxyanilineChEBI
p-CarboxyphenylamineChEBI
PABAChEBI
Para-aminobenzoic acidChEBI
4-Aminobenzoic acidKegg
p-AminobenzoateKegg
RVPaba lipstickKegg
4-Amino-benzoateGenerator
g-AminobenzoateGenerator
g-Aminobenzoic acidGenerator
gamma-AminobenzoateGenerator
Γ-aminobenzoateGenerator
Γ-aminobenzoic acidGenerator
Para-aminobenzoateGenerator
4-AminobenzoateGenerator
acido P-AminobenzoicoHMDB
Acidum paraminobenzoicumHMDB
ActipolHMDB
AmbenHMDB
AminobenzoateHMDB
Aminobenzoic acidHMDB, MeSH
Aniline-4-carboxylateHMDB
Aniline-4-carboxylic acidHMDB
Anti-chromotrichia factorHMDB
Anticanitic vitaminHMDB
Anticantic vitaminHMDB
Antichromotrichia factorHMDB
Bacterial vitamin H1HMDB
Chromotrichia factorHMDB
HacheminaHMDB, MeSH
Kyselina P-aminobenzoovaHMDB
P-amino-BenzoateHMDB
P-amino-Benzoic acidHMDB
PABHMDB
PabacydHMDB
PabafilmHMDB
PabagelHMDB
PabamineHMDB
PabanolHMDB
PapacidumHMDB
ParaminolHMDB, MeSH
ParanateHMDB
PotabaHMDB, MeSH
RomavitHMDB
RvpabaHMDB
SunbrellaHMDB
Super shade by coppertoneHMDB
Trichochromogenic factorHMDB
Trochromogenic factorHMDB
Vitamin BXHMDB
Vitamin h'HMDB
4 Aminobenzoic acidMeSH, HMDB
4 Aminobenzoic acid, potassium saltMeSH, HMDB
EpitelplastMeSH, HMDB
Jumer brand OF aminobenzoic acidMeSH, HMDB
Medea brand OF aminobenzoic acidMeSH, HMDB
ParaminanMeSH, HMDB
4-Aminobenzoate, potassiumMeSH, HMDB
Epit vitMeSH, HMDB
Llorens brand OF aminobenzoic acidMeSH, HMDB
PabasanMeSH, HMDB
Potassium aminobenzoateMeSH, HMDB
4-Aminobenzoic acid, potassium saltMeSH, HMDB
Aminobenzoate, potassiumMeSH, HMDB
Glenwood brand OF potassium aminobezoateMeSH, HMDB
Llorens brand OF aminobenzoic acid sodium saltMeSH, HMDB
Magnesium para-aminobenzoateMeSH, HMDB
Potassium 4 aminobenzoateMeSH, HMDB
Potassium 4-aminobenzoateMeSH, HMDB
P Aminobenzoic acidMeSH, HMDB
Para aminobenzoic acidMeSH, HMDB
Para-aminobenzoate, magnesiumMeSH, HMDB
p-Aminobenzoic acidChEBI
Molecular FormulaC7H7NO2
Average Mass137.136
Monoisotopic Mass137.047678473
IUPAC Name4-aminobenzoic acid
Traditional Namesunbrella
CAS Registry NumberNot Available
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