You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:34 UTC
HMDB IDHMDB01416
Secondary Accession NumbersNone
Metabolite Identification
Common NamePantetheine 4'-phosphate
DescriptionPantetheine 4'-phosphate, or 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.
Structure
Thumb
Synonyms
ValueSource
4'-PhosphopantetheineChEBI
Pantotheine-4'-phosphateChEBI
PhosphopantetheineChEBI
PSH-4'-PChEBI
4'-PhosphopantotheineHMDB
D-Pantetheine 4'-phosphateHMDB
phospho-PantotheineHMDB
Chemical FormulaC11H23N2O7PS
Average Molecular Weight358.348
Monoisotopic Molecular Weight358.096358302
IUPAC Name[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid
Traditional Namepantetheine 4'-phosphate
CAS Registry Number2226-71-3
SMILES
CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS
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 KeyInChIKey=JDMUPRLRUUMCTL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pantothenate and CoA biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.38 mg/mLALOGPS
logP-0.71ALOGPS
logP-1.7ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area145.19 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.58 m3·mol-1ChemAxon
Polarizability34.28 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08ir-7695000000-0ee6ed099c01445060c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u0-9540000000-9e756a71b573d020fa6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03nc-9300000000-d292b023d1133331f546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-9225000000-72a847152c51b3a3daa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-f29815698df8b18a410aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-653db2061d8b7bf264f2View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pantothenate and CoA BiosynthesisSMP00027map00770
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022609
KNApSAcK IDNot Available
Chemspider ID962
KEGG Compound IDC01134
BioCyc IDPANTETHEINE-P
BiGG ID36886
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01416
Metagene LinkHMDB01416
METLIN IDNot Available
PubChem Compound987
PDB ID1H1T
ChEBI ID16858
References
Synthesis ReferenceMasuda, Toru; Fujii, Shoichiro; Takanohashi, Kunio. Pantetheine 4'-phosphate. Jpn. Tokkyo Koho (1971), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tahiliani AG, Beinlich CJ: Pantothenic acid in health and disease. Vitam Horm. 1991;46:165-228. [1746161 ]

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
Reactions
Dephospho-CoA + Water → Pantetheine 4'-phosphate + Adenosine monophosphatedetails
General function:
Involved in acyl carrier activity
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis in mitochondria. Accessory and non-catalytic subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), which functions in the transfer of electrons from NADH to the respiratory chain
Gene Name:
NDUFAB1
Uniprot ID:
O14561
Molecular weight:
17417.1
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
Reactions
Dephospho-CoA + Water → Pantetheine 4'-phosphate + Adenosine monophosphatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK4
Uniprot ID:
Q9NVE7
Molecular weight:
85990.12
Reactions
Adenosine triphosphate + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
May be the master regulator of the CoA biosynthesis (By similarity).
Gene Name:
PANK2
Uniprot ID:
Q9BZ23
Molecular weight:
30753.12
Reactions
Adenosine triphosphate + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK1
Uniprot ID:
Q8TE04
Molecular weight:
35578.965
Reactions
Adenosine triphosphate + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK3
Uniprot ID:
Q9H999
Molecular weight:
41093.695
Reactions
Adenosine triphosphate + Pantetheine → ADP + Pantetheine 4'-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes the fourth and fifth sequential steps of CoA biosynthetic pathway. The fourth reaction is catalyzed by the phosphopantetheine adenylyltransferase, coded by the coaD domain; the fifth reaction is catalyzed by the dephospho-CoA kinase, coded by the coaE domain. May act as a point of CoA biosynthesis regulation.
Gene Name:
COASY
Uniprot ID:
Q13057
Molecular weight:
62328.245
Reactions
Adenosine triphosphate + Pantetheine 4'-phosphate → Pyrophosphate + Dephospho-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Necessary for the biosynthesis of coenzyme A. Catalyzes the decarboxylation of 4-phosphopantothenoylcysteine to form 4'-phosphopantotheine.
Gene Name:
PPCDC
Uniprot ID:
Q96CD2
Molecular weight:
22394.965
Reactions
N-((R)-4'-phosphopantothenoyl)-L-cysteine → Pantetheine 4'-phosphate + CO(2)details
4-Phosphopantothenoylcysteine → Pantetheine 4'-phosphate + Carbon dioxidedetails
General function:
Involved in formyltetrahydrofolate dehydrogenase activity
Specific function:
Not Available
Gene Name:
ALDH1L2
Uniprot ID:
Q3SY69
Molecular weight:
101744.98
General function:
Involved in acyl carrier activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
A4UCS3
Molecular weight:
13714.9