Showing Compound Pteroyltriglutamic acid (FDB022730)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:36 UTC

Update date

2015-07-21 06:57:20 UTC

Primary ID

FDB022730

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pteroyltriglutamic acid

Description

A crystalline conjugate of folic acid containing three molecules of glutamic acid instead of one and having the general properties of a polypeptide. (http://medical-dictionary.thefreedictionary.com/pteropterin) As a measure of enterocyte function, the deconjugation of Pteroylpolyglutamic acid (pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid) to folic acid and subsequent active absorption was measured in 19 patients with progressive systemic sclerosis and compared with 14 controls. The absorption step of folic acid was identical in the two groups, while deconjugation of pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid was significantly decreased in the patients with progressive systemic sclerosis. This observation suggests a primary epithelial defect of the small intestine in patients with progressive systemic sclerosis. (PMID 3583071) Glutamyl hydrolase cleaves the poly-g-glutamate chain folate and antifolate poly-g-glutamates. Its cellular location is lysosomal with large amts. of the enzyme constitutively secreted. The highest levels of glutamyl hydrolase mRNA in humans is found in the liver and kidney. (PMID: 10598552) [HMDB]

CAS Number

89-38-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
2-{[4-carboxy-4-({4-carboxy-1-hydroxy-4-[(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butylidene}amino)-1-hydroxybutylidene]amino}pentanedioate	Generator, HMDB
Folic acid diglutamate	HMDB
N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acid	HMDB
N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-Glutamic acid	hmdb
N-[N-(N-Pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-glutamic acid	HMDB
N-[N-(N-pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-Glutamic acid	hmdb
N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-glutamic acid	HMDB
N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-Glutamic acid	hmdb
Pteropterin	HMDB, MeSH
Pteropterin, sodium salt	MeSH, HMDB

Showing 1 to 10 of 17 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	-2.6	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	2.08	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	341.79 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	167.19 m³·mol⁻¹	ChemAxon
Polarizability	67.38 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

Chemical Formula

C29H33N9O12

IUPAC name

2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid

InChI Identifier

InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)

InChI Key

WOLQREOUPKZMEX-UHFFFAOYSA-N

Isomeric SMILES

NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1

Average Molecular Weight

699.6254

Monoisotopic Molecular Weight

699.224867565

Classification

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha-amino acid
Glutamic acid or derivatives
Glutamine or derivatives
Tetracarboxylic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Pterin
Alpha-amino acid or derivatives
Pteridine
Aminobenzamide
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Pyrimidone
Aralkylamine
Secondary aliphatic/aromatic amine
Aminopyrimidine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
N-acyl-amine
Benzenoid
Pyrazine
Pyrimidine
Vinylogous amide
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxamide group
Secondary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

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	Pteroyltriglutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-0221229000-c23f869dc13b1d95272a	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pteroyltriglutamic acid, TMS_2_14, 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	splash10-001i-0330009000-e987962787f2029e2f08	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0960106000-21f9d9b3b6972db9bc7c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0941002000-891cdeb849daa1e9d839	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f8a-0000009000-bd7ecf2c2eeac6ea62e6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gws-0110019000-44f0bdd173f7125a9395	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f97-5941201000-3d500662a3c45848f410	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0290004200-8f2f396143788196bc73	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5a-0771391000-85c9b3b383e3d558e48b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-0951010000-28b5c68dcb7492d5286e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052s-0010009000-f025b4c029bb870e38f9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0nni-0311109000-18e4bbbd67edf5591bc5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0w4i-3924031000-85da69ca05ffb0871921	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

6702

ChEMBL ID

CHEMBL498845

KEGG Compound ID

Not Available

Pubchem Compound ID

6968

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01902

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

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

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 Pteroyltriglutamic acid (FDB022730)

Structure for FDB022730 (Pteroyltriglutamic acid)