MiMeDB: Showing metabocard for Tetrahydropteridine (MMDBc0029593)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:33:37 UTC

Update Date

2024-04-30 19:38:40 UTC

Metabolite ID

MMDBc0029593

Metabolite Identification

Common Name

Tetrahydropteridine

Description

Tetrahydropteridine is a member of the chemical class known as Pteridines and Derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. In a reversible reaction catalyzed by a nitroreductase / dihydropteridine reductase (EC 1.5.1.34), tetrahydropteridine can be converted to dihydropteridine while reducing NAD(P)+ to NAD(P)H. (KEGG)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
5,6,7,8-Tetrahydropteridine	Kegg
5,6,7,8-Tetrahydro-pteridine	HMDB
H4-Biopterin	HMDB
THP	HMDB
Tetrahydropteridine	ChEBI

Molecular Formula

C₆H₈N₄

Average Mass

136.1545

Monoisotopic Mass

136.074896276

IUPAC Name

5,6,7,8-tetrahydropteridine

Traditional Name

5,6,7,8-tetrahydropteridine

CAS Registry Number

10593-78-9

SMILES

C1CNC2=C(N1)C=NC=N2

InChI Identifier

InChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10)

InChI Key

IDAICLIJTRXNER-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Not Available

Direct Parent

Pteridines and derivatives

Alternative Parents

Substituents

Pteridine
Secondary aliphatic/aromatic amine
Imidolactam
Pyrimidine
Heteroaromatic compound
Azacycle
Secondary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pteridines (CHEBI:28889 )
a small molecule (5678-TETRAHYDROPTERIDINE )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.43 g/L	ALOGPS
logP	0.29	ALOGPS
logP	-0.58	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	19.35	ChemAxon
pKa (Strongest Basic)	5.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.45 m³·mol⁻¹	ChemAxon
Polarizability	13.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-f10ca50f06250e5030d3	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-9a1ed9296c96ac152018	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-63f9acde2a431bff2488	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-9100000000-9987b7952a5c983f7c8e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-93507d1f946deac8a074	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-36867a49c6c36342b032	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9800000000-c2d528a7546845512953	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-278b0289a2d1c7916e5b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-7f4a76469d170f8d43f9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05nf-7900000000-e829877fe8774c9c13f9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-06cd9080747456c7643d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c5f7233447b8e475f5c6	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500000000-a22ac8b5a57e8c2437f7	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192192	Dihydropteridine reductase	Unknown	P09417	Homo sapiens
MMDBp0194175	Inositol-tetrakisphosphate 1-kinase	Unknown	Q13572	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0001216

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022495

KNApSAcK ID

Not Available

Chemspider ID

151

KEGG Compound ID

C05650

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6086

PubChem Compound

156

PDB ID

Not Available

ChEBI ID

28889

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hoffman DR, Hoffman LH, Snyder F: Cytotoxicity and metabolism of alkyl phospholipid analogues in neoplastic cells. Cancer Res. 1986 Nov;46(11):5803-9. [PubMed:3756924 ]
Rao GN, Cotlier E: The enzymatic activities of GTP cyclohydrolase, sepiapterin reductase, dihydropteridine reductase and dihydrofolate reductase; and tetrahydrobiopterin content in mammalian ocular tissues and in human senile cataracts. Comp Biochem Physiol B. 1985;80(1):61-6. doi: 10.1016/0305-0491(85)90423-7. [PubMed:3881214 ]
Thoeni G, Werner ER, Werner-Felmayer G: Tetrahydropteridines suppress gene expression and induce apoptosis of activated RAW264.7 cells via formation of hydrogen peroxide. Free Radic Biol Med. 2004 Aug 1;37(3):375-85. doi: 10.1016/j.freeradbiomed.2004.05.010. [PubMed:15223071 ]
Werner ER, Hermetter A, Prast H, Golderer G, Werner-Felmayer G: Widespread occurrence of glyceryl ether monooxygenase activity in rat tissues detected by a novel assay. J Lipid Res. 2007 Jun;48(6):1422-7. doi: 10.1194/jlr.D600042-JLR200. Epub 2007 Feb 15. [PubMed:17303893 ]

Showing metabocard for Tetrahydropteridine (MMDBc0029593)

MOL for #<Metabolite:0x00007fdb7197eee8>

3D MOL for #<Metabolite:0x00007fdb7197eee8>

3D SDF for #<Metabolite:0x00007fdb7197eee8>

3D-SDF for #<Metabolite:0x00007fdb7197eee8>

PDB for #<Metabolite:0x00007fdb7197eee8>

3D PDB for #<Metabolite:0x00007fdb7197eee8>

SMILES for #<Metabolite:0x00007fdb7197eee8>

INCHI for #<Metabolite:0x00007fdb7197eee8>

Structure for #<Metabolite:0x00007fdb7197eee8>

3D Structure for #<Metabolite:0x00007fdb7197eee8>