NP-MRD: Showing NP-Card for 5-methyl-tetrahydrofolate (NP0334852)

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Record Information

Version

2.0

Created at

2024-09-10 22:47:05 UTC

Updated at

2024-09-10 22:47:06 UTC

NP-MRD ID

NP0334852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-tetrahydrofolate

Description

5-methyl-tetrahydrofolate was first documented in 2023 (PMID: 38116318). Based on a literature review a significant number of articles have been published on 5-methyl-tetrahydrofolate (PMID: 37733056) (PMID: 37694554) (PMID: 37586674) (PMID: 37449444) (PMID: 37220602) (PMID: 37054966).

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv2104 05262301192D          

 33 35  0  0  0  0            999 V2000
    5.7158   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2  4  1  0  0  0  0
  2 10  2  0  0  0  0
  3  5  2  0  0  0  0
  3 10  1  0  0  0  0
  4 11  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 12  1  0  0  0  0
  8 22  1  0  0  0  0
  9 12  1  0  0  0  0
  9 23  1  0  0  0  0
 10 17  1  0  0  0  0
 11 22  1  0  0  0  0
 12 27  1  0  0  0  0
 13 19  1  0  0  0  0
 13 24  1  0  0  0  0
 14 28  2  0  0  0  0
 14 29  1  0  0  0  0
 15 16  2  0  0  0  0
 15 18  1  0  0  0  0
 15 27  1  0  0  0  0
 16 23  1  0  0  0  0
 16 25  1  0  0  0  0
 17 24  1  0  0  0  0
 17 30  2  0  0  0  0
 18 26  2  0  0  0  0
 18 31  1  0  0  0  0
 19 32  2  0  0  0  0
 19 33  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  0  0  0  0
M  END

Structure #1
  Mrv2104 05262301192D          

 33 35  0  0  0  0            999 V2000
    5.7158   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2  4  1  0  0  0  0
  2 10  2  0  0  0  0
  3  5  2  0  0  0  0
  3 10  1  0  0  0  0
  4 11  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 12  1  0  0  0  0
  8 22  1  0  0  0  0
  9 12  1  0  0  0  0
  9 23  1  0  0  0  0
 10 17  1  0  0  0  0
 11 22  1  0  0  0  0
 12 27  1  0  0  0  0
 13 19  1  0  0  0  0
 13 24  1  0  0  0  0
 14 28  2  0  0  0  0
 14 29  1  0  0  0  0
 15 16  2  0  0  0  0
 15 18  1  0  0  0  0
 15 27  1  0  0  0  0
 16 23  1  0  0  0  0
 16 25  1  0  0  0  0
 17 24  1  0  0  0  0
 17 30  2  0  0  0  0
 18 26  2  0  0  0  0
 18 31  1  0  0  0  0
 19 32  2  0  0  0  0
 19 33  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CNC2=CC=C(C=C2)C(=O)NC(CCC(O)=O)C(O)=O)CNC2=C1C(O)=NC(=N)N2

> <INCHI_IDENTIFIER>
InChI=1/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)

> <INCHI_KEY>
ZNOVTXRBGFNYRX-UHFFFAOYNA-N

> <FORMULA>
C20H25N7O6

> <MOLECULAR_WEIGHT>
459.463

> <EXACT_MASS>
459.186631553

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.373490292929304

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-5.048991967647108

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2322116388828013

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.099451411166736

> <JCHEM_PKA_STRONGEST_BASIC>
20.746726416958037

> <JCHEM_POLAR_SURFACE_AREA>
199.46999999999997

> <JCHEM_REFRACTIVITY>
137.69580000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      10.669 -15.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667 -15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.671 -11.550   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      16.004 -10.780   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       6.668 -13.090   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      10.669 -10.780   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       0.000 -15.400   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      13.337 -10.780   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      14.671 -13.090   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      10.669 -13.860   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.334 -17.710   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.337 -15.400   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000 -18.480   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667 -18.480   0.000  0.00  0.00           O+0
CONECT    1   27                                                            
CONECT    2    4   10                                                       
CONECT    3    5   10                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    7   13                                                       
CONECT    7    6   14                                                       
CONECT    8   12   22                                                       
CONECT    9   12   23                                                       
CONECT   10    2    3   17                                                  
CONECT   11    4    5   22                                                  
CONECT   12    8    9   27                                                  
CONECT   13    6   19   24                                                  
CONECT   14    7   28   29                                                  
CONECT   15   16   18   27                                                  
CONECT   16   15   23   25                                                  
CONECT   17   10   24   30                                                  
CONECT   18   15   26   31                                                  
CONECT   19   13   32   33                                                  
CONECT   20   21   25   26                                                  
CONECT   21   20                                                            
CONECT   22    8   11                                                       
CONECT   23    9   16                                                       
CONECT   24   13   17                                                       
CONECT   25   16   20                                                       
CONECT   26   18   20                                                       
CONECT   27    1   12   15                                                  
CONECT   28   14                                                            
CONECT   29   14                                                            
CONECT   30   17                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
5-Methyl-tetrahydrofolic acid	Generator

Chemical Formula

C₂₀H₂₅N₇O₆

Average Mass

459.4630 Da

Monoisotopic Mass

459.18663 Da

IUPAC Name

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

Traditional Name

2-[(4-{[(4-hydroxy-2-imino-5-methyl-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

CAS Registry Number

Not Available

SMILES

CN1C(CNC2=CC=C(C=C2)C(=O)NC(CCC(O)=O)C(O)=O)CNC2=C1C(O)=NC(=N)N2

InChI Identifier

InChI=1/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)

InChI Key

ZNOVTXRBGFNYRX-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	-5	ChemAxon
pKa (Strongest Acidic)	-3.1	ChemAxon
pKa (Strongest Basic)	20.75	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.47 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.7 m³·mol⁻¹	ChemAxon
Polarizability	46.37 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wen J, Fei Y, Yuan L, Li K, Xu Q, Cao X, Su J, Zhu Y, Zhang Z: Analysis of the mediating role of BMI in associations of different folate forms with hepatic steatosis and liver fibrosis in adolescents in the USA: results from the NHANES 2017-2018. Front Endocrinol (Lausanne). 2023 Dec 5;14:1273580. doi: 10.3389/fendo.2023.1273580. eCollection 2023. [PubMed:38116318 ]
Chen Y, Xiang L, Luo L, Qin H, Tong S: Correlation of Nonalcoholic Fatty Liver Disease with Dietary Folate and Serum Folate in U.S. Adults: Cross-Sectional Analyses from National Health and Nutrition Examination Survey 2009-2018. Metab Syndr Relat Disord. 2023 Sep;21(7):389-396. doi: 10.1089/met.2023.0024. [PubMed:37733056 ]
Hetherington-Rauth M, Johnson E, Migliavacca E, Parimi N, Langsetmo L, Hepple RT, Grzywinski Y, Corthesy J, Ryan TE, Ferrucci L, Feige JN, Orwoll ES, Cawthon PM: Nutrient Metabolites Associated With Low D3Cr Muscle Mass, Strength, and Physical Performance in Older Men. J Gerontol A Biol Sci Med Sci. 2024 Feb 1;79(2):glad217. doi: 10.1093/gerona/glad217. [PubMed:37694554 ]
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Showing NP-Card for 5-methyl-tetrahydrofolate (NP0334852)

MOL for NP0334852 (5-methyl-tetrahydrofolate)

3D MOL for NP0334852 (5-methyl-tetrahydrofolate)

3D SDF for NP0334852 (5-methyl-tetrahydrofolate)

3D-SDF for NP0334852 (5-methyl-tetrahydrofolate)

PDB for NP0334852 (5-methyl-tetrahydrofolate)

3D PDB for NP0334852 (5-methyl-tetrahydrofolate)

SMILES for NP0334852 (5-methyl-tetrahydrofolate)

INCHI for NP0334852 (5-methyl-tetrahydrofolate)

Structure for NP0334852 (5-methyl-tetrahydrofolate)

3D Structure for NP0334852 (5-methyl-tetrahydrofolate)