Showing Compound Pantetheine 4'-phosphate (FDB022609)

Record Information

Version

1.0

Creation date

2011-09-21 00:16:49 UTC

Update date

2015-07-21 06:57:16 UTC

Primary ID

FDB022609

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pantetheine 4'-phosphate

Description

4'-phosphopantetheine is a metabolite in the pantothenate and coenzyme A biosynthesis pathway. It can be generated from Pantatheine (via pantothenate kinase 1) or R-4'-Phospho-pantothenoyl-L-cysteine (via phosphopantothenoylcysteine decarboxylase) or Dephospho-CoA (via 4'-phosphopantetheine adenylyl-transferase and ectonucleotide pyrophosphatase). In most mammals, coenzyme A can be hydrolyzed to pantetheine and pantothenate in the intestinal lumen via the following series of reactions: coenzyme A leads to phosphopantetheine leads to pantetheine leads to pantothenate. The conversion of 4'-phosphopantetheine (4'-PP) to dephospho-CoA, is catalyzed by 4'-phosphopantetheine adenylyl-transferase. In mammalian systems, this step may occur in the mitochondria or in the cytosol. (PMID: 1746161) It has been identified as an essential cofactor in in the biosynthesis of fatty acids, polyketides, depsipeptides, peptides, and compounds derived from both carboxylic and amino acid precursors. In particular it is a key prosthetic group of acyl carrier protein (ACP) and peptidyl carrier proteins (PCP) and aryl carrier proteins (ArCP) derived from Coenzyme A. Phosphopantetheine fulfils two demands. Firstly, the intermediates remain covalently linked to the synthases (or synthetases) in an energy-rich thiol ester linkage. Secondly, the flexibility and length of phosphopantetheine chain (approximately 2 nm) allows the covalently tethered intermediates to have access to spatially distinct enzyme active sites. [HMDB]

CAS Number

2226-71-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
4'-Opantetheine	ChEBI
4'-Opantotheine	HMDB
4'-Phosphopantetheine	ChEBI
4'-Phosphopantotheine	HMDB
4'-phosphopantotheine	hmdb
D-Pantetheine 4'-ate	HMDB
D-Pantetheine 4'-phosphate	HMDB
O-Pantotheine	HMDB
Opantetheine	ChEBI
Pantetheine 4'-ate	ChEBI

Showing 1 to 10 of 25 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-1.7	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	145.19 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	81.58 m³·mol⁻¹	ChemAxon
Polarizability	34.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H23N2O7PS

IUPAC name

[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid

InChI Identifier

InChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19)

InChI Key

JDMUPRLRUUMCTL-UHFFFAOYSA-N

Isomeric SMILES

CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS

Average Molecular Weight

358.348

Monoisotopic Molecular Weight

358.096358302

Classification

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Secondary alcohol
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphopantetheine (CHEBI:16858 )

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	Pantetheine 4'-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-7921000000-38919c105245ede94f57	Spectrum
Predicted GC-MS	Pantetheine 4'-phosphate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9633000000-e3c273cefb49d43405b0	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08ir-7695000000-0ee6ed099c01445060c3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01u0-9540000000-9e756a71b573d020fa6e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03nc-9300000000-d292b023d1133331f546	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-054k-9225000000-72a847152c51b3a3daa2	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9200000000-f29815698df8b18a410a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-653db2061d8b7bf264f2	2015-09-15	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

962

ChEMBL ID

Not Available

KEGG Compound ID

C01134

Pubchem Compound ID

987

Pubchem Substance ID

Not Available

ChEBI ID

16858

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01416

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

36886

KNApSAcK ID

Not Available

HET ID

1H1T

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

Show entries

Search:

Name	Gene Name	UniProt ID
Acyl carrier protein, mitochondrial	NDUFAB1	O14561
Bifunctional coenzyme A synthase	COASY	Q13057
Fatty acid synthase	FASN	P49327
Mitochondrial 10-formyltetrahydrofolate dehydrogenase	ALDH1L2	Q3SY69
Pantothenate kinase 1	PANK1	Q8TE04
Pantothenate kinase 3	PANK3	Q9H999
Pantothenate kinase 4	PANK4	Q9NVE7