MiMeDB: Showing metabocard for (6S)-5,6,7,8-tetrahydropteroic acid (MMDBc0054979)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:03 UTC

Update Date

2022-08-12 20:09:10 UTC

MiMeDB ID

MMDBc0054979

Metabolite Identification

Common Name

(6S)-5,6,7,8-tetrahydropteroic acid

Description

(6S)-5,6,7,8-tetrahydropteroate belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. Based on a literature review very few articles have been published on (6S)-5,6,7,8-tetrahydropteroate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 24 26  0  0  1  0            999 V2000
   -4.2868    0.0000    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
   -3.5724   -0.4125    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
   -1.4289    0.0000    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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    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
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  6  0  0  0
  9  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16  5  1  0  0  0  0
 16  8  1  0  0  0  0
 17  6  1  0  0  0  0
 17 11  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 14  1  0  0  0  0
 20 12  2  0  0  0  0
 20 14  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 13  2  0  0  0  0
  9 24  1  1  0  0  0
M  CHG  1  21  -1
M  END
> <DATABASE_ID>
MMDBc0054979

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(CNC2=CC=C(C=C2)C(O)=O)CNC2=C(N1)C([O-])=NC(=N)N2

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,9,16,18H,5-6H2,(H,22,23)(H4,15,17,19,20,21)/p-1/t9-/m0/s1

> <INCHI_KEY>
OXIZGFYJYJOABB-VIFPVBQESA-M

> <FORMULA>
C14H15N6O3

> <MOLECULAR_WEIGHT>
315.314

> <EXACT_MASS>
315.121111947

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.528598255447655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-6-{[(4-carboxyphenyl)amino]methyl}-2-imino-1,2,5,6,7,8-hexahydropteridin-4-olate

> <JCHEM_LOGP>
-1.3534414809154716

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.923289963261674

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.691693265318858

> <JCHEM_PKA_STRONGEST_BASIC>
5.814317790180123

> <JCHEM_POLAR_SURFACE_AREA>
144.69

> <JCHEM_REFRACTIVITY>
114.8636

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-{[(4-carboxyphenyl)amino]methyl}-2-imino-5,6,7,8-tetrahydro-1H-pteridin-4-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -9.336   3.850   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2    8                                                       
CONECT    5    9   16                                                       
CONECT    6    9   17                                                       
CONECT    7    1    2   13                                                  
CONECT    8    3    4   16                                                  
CONECT    9    5    6   18   24                                             
CONECT   10   11   12   18                                                  
CONECT   11   10   17   19                                                  
CONECT   12   10   20   21                                                  
CONECT   13    7   22   23                                                  
CONECT   14   15   19   20                                                  
CONECT   15   14                                                            
CONECT   16    5    8                                                       
CONECT   17    6   11                                                       
CONECT   18    9   10                                                       
CONECT   19   11   14                                                       
CONECT   20   12   14                                                       
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   13                                                            
CONECT   24    9                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

Synonyms

Value	Source
(6S)-5,6,7,8-Tetrahydropteroic acid	Generator

Chemical Formula

C₁₄H₁₅N₆O₃

Average Molecular Weight

315.314

Monoisotopic Molecular Weight

315.121111947

IUPAC Name

(6S)-6-{[(4-carboxyphenyl)amino]methyl}-2-imino-1,2,5,6,7,8-hexahydropteridin-4-olate

Traditional Name

(6S)-6-{[(4-carboxyphenyl)amino]methyl}-2-imino-5,6,7,8-tetrahydro-1H-pteridin-4-olate

CAS Registry Number

Not Available

SMILES

[H][C@]1(CNC2=CC=C(C=C2)C(O)=O)CNC2=C(N1)C([O-])=NC(=N)N2

InChI Identifier

InChI=1S/C14H16N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,9,16,18H,5-6H2,(H,22,23)(H4,15,17,19,20,21)/p-1/t9-/m0/s1

InChI Key

OXIZGFYJYJOABB-VIFPVBQESA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Aminobenzoic acid
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Aniline or substituted anilines
Phenylalkylamine
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Azacycle
Secondary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pteroates (CHEBI:85414 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-1.4	ChemAxon
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	5.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	144.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.86 m³·mol⁻¹	ChemAxon
Polarizability	31.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34999690

KEGG Compound ID

Not Available

BioCyc ID

CPD-9020

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91820062

PDB ID

Not Available

ChEBI ID

85414

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (6S)-5,6,7,8-tetrahydropteroic acid (MMDBc0054979)

MOL for #<Metabolite:0x00007f09201cbcd8>

3D MOL for #<Metabolite:0x00007f09201cbcd8>

3D SDF for #<Metabolite:0x00007f09201cbcd8>

3D-SDF for #<Metabolite:0x00007f09201cbcd8>

PDB for #<Metabolite:0x00007f09201cbcd8>

3D PDB for #<Metabolite:0x00007f09201cbcd8>

SMILES for #<Metabolite:0x00007f09201cbcd8>

INCHI for #<Metabolite:0x00007f09201cbcd8>

Structure for #<Metabolite:0x00007f09201cbcd8>

3D Structure for #<Metabolite:0x00007f09201cbcd8>