NP-MRD: Showing NP-Card for tetrahydrofolate (NP0334556)

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Record Information

Version

2.0

Created at

2024-09-10 18:53:15 UTC

Updated at

2024-09-10 18:53:15 UTC

NP-MRD ID

NP0334556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tetrahydrofolate

Description

Tetrahydrofolic acid, also known as (6S)-tetrahydrofolate or (6S)-thfa, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Methotrexate acts on dihydrofolate reductase, like pyrimethamine or trimethoprim, as an inhibitor and thus reduces the amount of tetrahydrofolate made. Tetrahydrofolic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. A shortage in tetrahydrofolic acid (FH4) can cause megaloblastic anemia. Tetrahydrofolic acid (THFA), or tetrahydrofolate, is a folic acid derivative. Tetrahydrofolic acid is a strong basic compound (based on its pKa). Tetrahydrofolic acid may be a unique S. Cerevisiae (yeast) metabolite. Within humans, tetrahydrofolic acid participates in a number of enzymatic reactions. In particular, tetrahydrofolic acid can be converted into dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, tetrahydrofolic acid and formic acid can be converted into 10-formyltetrahydrofolate through the action of the enzyme C-1-tetrahydrofolate synthase, cytoplasmic. Tetrahydrofolic acid is a cofactor in many reactions, especially in the synthesis (or anabolism) of amino acids and nucleic acids. Tetrahydrofolic acid is involved in the conversion of formiminoglutamic acid to glutamic acid; this may reduce the amount of histidine available for decarboxylation and protein synthesis, and hence the urinary histamine and formiminoglutamic acid may be decreased. 10-Formyltetrahydrofolate acts as a donor of a group with one carbon atom. In humans, tetrahydrofolic acid is involved in the metabolic disorder called the methylenetetrahydrofolate reductase deficiency (mthfrd) pathway. Outside of the human body, Tetrahydrofolic acid has been detected, but not quantified in, several different foods, such as teffs, common verbena, redcurrants, lettuces, and common sages. This could make tetrahydrofolic acid a potential biomarker for the consumption of these foods. Many bacteria use dihydropteroate synthetase to produce dihydropteroate, a molecule without function in humans. This may result in megaloblastic anemia.

Structure

MOL SDF PDB SMILES InChI

116
  Mrv0541 02231214272D          

 32 34  0  0  1  0            999 V2000
    3.5220   -0.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9988    1.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598    0.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1501   -0.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8502    2.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4213    2.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -1.0107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -2.7179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504   -1.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7180   -0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -1.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -2.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633   -1.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4309    0.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4277    1.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5793   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8601   -0.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890   -0.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2922   -1.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5730    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019    0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1374    2.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2 30  2  0  0  0  0
  3 31  1  0  0  0  0
  4 31  2  0  0  0  0
  5 32  1  0  0  0  0
  6 32  2  0  0  0  0
  7 14  1  0  0  0  0
  7 17  1  0  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  9 16  1  0  0  0  0
  9 19  1  0  0  0  0
 10 18  1  0  0  0  0
 10 21  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  2  0  0  0  0
 22 12  1  1  0  0  0
 12 30  1  0  0  0  0
 13 21  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 24  2  0  0  0  0
 19 25  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  1  0  0  0  0
 23 29  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 30  1  0  0  0  0
 29 32  1  0  0  0  0
M  END

116
  Mrv0541 02231214272D          

 32 34  0  0  1  0            999 V2000
    3.5220   -0.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9988    1.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598    0.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1501   -0.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8502    2.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4213    2.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -1.0107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -2.7179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504   -1.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7180   -0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -1.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -2.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633   -1.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4309    0.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4277    1.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5793   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8601   -0.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890   -0.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2922   -1.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5730    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019    0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1374    2.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2 30  2  0  0  0  0
  3 31  1  0  0  0  0
  4 31  2  0  0  0  0
  5 32  1  0  0  0  0
  6 32  2  0  0  0  0
  7 14  1  0  0  0  0
  7 17  1  0  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  9 16  1  0  0  0  0
  9 19  1  0  0  0  0
 10 18  1  0  0  0  0
 10 21  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  2  0  0  0  0
 22 12  1  1  0  0  0
 12 30  1  0  0  0  0
 13 21  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 24  2  0  0  0  0
 19 25  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  1  0  0  0  0
 23 29  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 30  1  0  0  0  0
 29 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334556

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1

> <INCHI_KEY>
MSTNYGQPCMXVAQ-KIYNQFGBSA-N

> <FORMULA>
C19H23N7O6

> <MOLECULAR_WEIGHT>
445.4292

> <EXACT_MASS>
445.170981503

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
42.9531289011855

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-4.212630310185438

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.863700981959142

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5095693878577654

> <JCHEM_PKA_STRONGEST_BASIC>
3.5846826310688993

> <JCHEM_POLAR_SURFACE_AREA>
207.27000000000004

> <JCHEM_REFRACTIVITY>
121.3866

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrofolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 116                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.574  -0.400   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.664   1.973   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      24.005   0.453   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      22.680  -1.862   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      23.987   5.073   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      21.320   5.063   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       9.285  -1.887   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.285  -5.073   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.347  -2.668   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       6.574  -5.020   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       5.241  -2.710   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      20.007  -0.332   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.907  -5.020   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      10.680  -2.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.680  -4.282   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.011  -1.903   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -2.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.908  -4.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.678  -1.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -1.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241  -4.250   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.338   0.443   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.332   1.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.015  -2.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.672  -0.352   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.339  -0.342   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.345  -1.882   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.003   0.423   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.662   2.758   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.670   0.433   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.674  -0.322   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.656   4.298   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   31                                                            
CONECT    5   32                                                            
CONECT    6   32                                                            
CONECT    7   14   17                                                       
CONECT    8   15   18                                                       
CONECT    9   16   19                                                       
CONECT   10   18   21                                                       
CONECT   11   20   21                                                       
CONECT   12   22   30                                                       
CONECT   13   21                                                            
CONECT   14    7   15   16                                                  
CONECT   15    8   14                                                       
CONECT   16    9   14                                                       
CONECT   17    7   18   20                                                  
CONECT   18    8   10   17                                                  
CONECT   19    9   24   25                                                  
CONECT   20    1   11   17                                                  
CONECT   21   10   11   13                                                  
CONECT   22   12   23   31                                                  
CONECT   23   22   29                                                       
CONECT   24   19   27                                                       
CONECT   25   19   28                                                       
CONECT   26   27   28   30                                                  
CONECT   27   24   26                                                       
CONECT   28   25   26                                                       
CONECT   29   23   32                                                       
CONECT   30    2   12   26                                                  
CONECT   31    3    4   22                                                  
CONECT   32    5    6   29                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(6S)-Tetrahydrofolate	ChEBI
(6S)-Tetrahydrofolic acid	ChEBI
(6S)-THFA	ChEBI
5,6,7,8-Tetrahydrofolate	ChEBI
Tetrahydrofolate	ChEBI
THF	ChEBI
5,6,7,8-Tetrahydrofolic acid	Generator
5,6,7,8-Tetrahydrofolic acid, (D-(-))-isomer	MeSH
5,6,7,8-Tetrahydrofolic acid, (L)-isomer	MeSH
5,6,7,8-Tetrahydrofolic acid, ion (2-)-isomer	MeSH
Tetrahydropteroylglutamate	MeSH
Tetrahydrofolic acid	ChEBI, KEGG

Chemical Formula

C₁₉H₂₃N₇O₆

Average Mass

445.4292 Da

Monoisotopic Mass

445.17098 Da

IUPAC Name

(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Traditional Name

tetrahydrofolic acid

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

InChI Identifier

InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1

InChI Key

MSTNYGQPCMXVAQ-KIYNQFGBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Pterin
Aminobenzamide
Aminobenzoic acid or derivatives
Pteridine
Benzamide
Benzoic acid or derivatives
Aniline or substituted anilines
Benzoyl
Phenylalkylamine
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Heteroaromatic compound
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Carboxylic acid
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydrofolic acid (CHEBI:20506 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.96	ALOGPS
logP	-4.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	3.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	207.27 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	121.39 m³·mol⁻¹	ChemAxon
Polarizability	42.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon