Showing Compound 6-Lactoyltetrahydropterin (FDB022828)

Record Information

Version

1.0

Creation date

2011-09-21 00:20:14 UTC

Update date

2015-07-21 06:57:23 UTC

Primary ID

FDB022828

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

6-Lactoyltetrahydropterin

Description

6-Lactoyltetrahydropterin is a putative intermediate in the de novo synthesis of tetrahydrobiopterin (BH4) pathway, in a reaction involving the enzyme sepiapterin reductase (E.C. 1.1.1.153) in human liver. In brain, an enzyme distinct from sepiapterin reductase catalyzes the TPNH-dependent reduction of 6-pyruvoyl-tetrahydropterin to 6-lactoyl-tetrahydropterin. (PMID: 4004850) In brain, the expression of other enzymes involved in BH4 biosynthesis includes aldose reductase, carbonyl reductase, GTP-cyclohydrolase I, and 6-pyruvoyltetrahydrobiopterin. Sepiapterin reductase expression is increased in Parkinson's disease brain tissue. (PMID: 17270157) [HMDB]

CAS Number

33405-80-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1'-oxo-2'-Hydroxypropyl-tetrahydropterin	MeSH, HMDB
2-Amino-6-lactoyl-5,6,7,8-tetrahydropteridin-4(3H)-one	ChEBI
2-amino-6-Lactoyl-5,6,7,8-tetrahydropteridin-4(3H)-one	ChEBI
6-1'-oxo-2'-Hydroxypropyl tetrahydropterin	ChEBI
6-Lactoyl tetrahydropterin	HMDB
6-Lactoyl-5,6,7,8-tetrahydropterin	HMDB
6-lactoyl-5,6,7,8-tetrahydropterin	hmdb
Lactoyl-H4-pterin	HMDB
Lactoyl-PH4	HMDB

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.7	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	11.12	ChemAxon
pKa (Strongest Basic)	4.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.84 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.87 m³·mol⁻¹	ChemAxon
Polarizability	22.59 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

Chemical Formula

C9H13N5O3

IUPAC name

2-amino-6-(2-hydroxypropanoyl)-3,4,5,6,7,8-hexahydropteridin-4-one

InChI Identifier

InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,12,15H,2H2,1H3,(H4,10,11,13,14,17)

InChI Key

HKCYZTKHPLJZDR-UHFFFAOYSA-N

Isomeric SMILES

CC(O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2

Average Molecular Weight

239.2312

Monoisotopic Molecular Weight

239.101839307

Classification

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
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Acyloin
Pyrimidine
Alpha-aminoketone
Heteroaromatic compound
Vinylogous amide
Alpha-hydroxy ketone
1,3-aminoalcohol
Secondary alcohol
Ketone
Azacycle
Secondary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Carbonyl group
Organic nitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydropterin (CHEBI:17248 )
a small molecule (6-LACTOYL-5678-TETRAHYDROPTERIN )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	6-Lactoyltetrahydropterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2900000000-49dec0d6931d1e9bad0a	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2900000000-8f1d69e548d027d65a19	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Lactoyltetrahydropterin, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0090000000-a0f9d3c66da5b6d5f581	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0940000000-176c06edb35b9da14cbc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmi-4910000000-a4fc7ca72b4b46138d0f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-6c319e8337df67fc476d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1920000000-bfd50799ec0cb51b89fe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fdo-9200000000-fe4583b38b03564abe97	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0190000000-57a11b44e9df0fc1d6a5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-0690000000-b7a86bbaa7a707429283	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-7900000000-0cb0aca82f0fb03cb603	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kf-0910000000-77790fad0fe8dd8e8a4e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-0900000000-0d38a13d09e7cb8e4809	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-81ba6afc34a8818ef29d	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

148245

ChEMBL ID

Not Available

KEGG Compound ID

C04244

Pubchem Compound ID

169508

Pubchem Substance ID

Not Available

ChEBI ID

17248

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02065

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 6-Lactoyltetrahydropterin (FDB022828)

Structure for FDB022828 (6-Lactoyltetrahydropterin)