4'-PHOSPHOPANTETHEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H23N2O7PS
Molecular Weight	358.348
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)NCCS

InChI

InChIKey=JDMUPRLRUUMCTL-VIFPVBQESA-N

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)/t9-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C11H23N2O7PS
Molecular Weight	358.348
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Top-down mass spectrometry on low-resolution instruments: characterization of phosphopantetheinylated carrier domains in polyketide and non-ribosomal biosynthetic pathways.	2008-05-15	18006314
Genetic interaction between the Escherichia coli AcpT phosphopantetheinyl transferase and the YejM inner membrane protein.	2008-03	18245839
Inhibition kinetics and emodin cocrystal structure of a type II polyketide ketoreductase.	2008-02-19	18205400
Identification of a subunit of NADH-dehydrogenase as a p49/STRAP-binding protein.	2008-01-29	18230186
A mammalian type I fatty acid synthase acyl carrier protein domain does not sequester acyl chains.	2008-01-04	17971456
Structure-assisted discovery of an aminothiazole derivative as a lead molecule for inhibition of bacterial fatty-acid synthesis.	2007-12	18084068
Acyl carrier protein: structure-function relationships in a conserved multifunctional protein family.	2007-12	18059524
10-formyltetrahydrofolate dehydrogenase requires a 4'-phosphopantetheine prosthetic group for catalysis.	2007-11-23	17884809
SanT, a bidomain protein, is essential for nikkomycin biosynthesis of Streptomyces ansochromogenes.	2007-11-03	17825260
Mechanism and substrate recognition of human holo ACP synthase.	2007-11	18022563
An mRNA-protein fusion at N-terminus for evolutionary protein engineering.	2007-08-29	17848981
Electrospray ionization mass spectra of acyl carrier protein are insensitive to its solution phase conformation.	2007-08	17604643
High-throughput profiling of posttranslational modification enzymes by phage display.	2007-07	17695643
Isothermal unfolding studies on the apo and holo forms of Plasmodium falciparum acyl carrier protein. Role of the 4'-phosphopantetheine group in the stability of the holo form of Plasmodium falciparum acyl carrier protein.	2007-07	17555524
Functional characterization of the recombinant N-methyltransferase domain from the multienzyme enniatin synthetase.	2007-06-18	17471480
Phylogenetic analysis of condensation domains in NRPS sheds light on their functional evolution.	2007-05-16	17506888
Nonribosomal peptide synthesis in Aspergillus fumigatus and other fungi.	2007-05	17464044
Structural basis for substrate delivery by acyl carrier protein in the yeast fatty acid synthase.	2007-04-13	17431182
Aminoacyl-coenzyme A synthesis catalyzed by adenylation domains.	2007-03-06	17303131
Enzymatic and cellular study of a serotonin N-acetyltransferase phosphopantetheine-based prodrug.	2007-03-01	17258461
Structural studies of fatty acyl-(acyl carrier protein) thioesters reveal a hydrophobic binding cavity that can expand to fit longer substrates.	2007-01-05	17059829
Distribution patterns of small-molecule ligands in the protein universe and implications for origin of life and drug discovery.	2007	17727706
GliP, a multimodular nonribosomal peptide synthetase in Aspergillus fumigatus, makes the diketopiperazine scaffold of gliotoxin.	2006-12-19	17154540
Overexpression, crystallization and preliminary X-ray crystallographic analysis of phosphopantetheine adenylyltransferase from Enterococcus faecalis.	2006-11-01	17077496
Facile detection of acyl and peptidyl intermediates on thiotemplate carrier domains via phosphopantetheinyl elimination reactions during tandem mass spectrometry.	2006-10-24	17042494
A dedicated phosphopantetheinyl transferase for the fredericamycin polyketide synthase from Streptomyces griseus.	2006-10-06	16895912
Localized protein interaction surfaces on the EntB carrier protein revealed by combinatorial mutagenesis and selection.	2006-08-30	16925399
A genome rearrangement has orphaned the Escherichia coli K-12 AcpT phosphopantetheinyl transferase from its cognate Escherichia coli O157:H7 substrates.	2006-07	16824108
Solution structures of conformationally equilibrium forms of holo-acyl carrier protein (PfACP) from Plasmodium falciparum provides insight into the mechanism of activation of ACPs.	2006-06-06	16734426
Solution structure of Asl1650, an acyl carrier protein from Anabaena sp. PCC 7120 with a variant phosphopantetheinylation-site sequence.	2006-05	16597827
Solution structures of spinach acyl carrier protein with decanoate and stearate.	2006-04-25	16618110
Conformational switches modulate protein interactions in peptide antibiotic synthetases.	2006-04-14	16614225
4'-phosphopantetheine biosynthesis in Archaea.	2006-03-03	16371361
Gene cloning, expression and functional characterization of an acyl carrier protein AcpV from Vibrio anguillarum.	2006-03	16429280
An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment.	2006-03	16415216
Characterization of a nonspecific phosphopantetheinyl transferase from Pseudomonas syringae pv. syringae FF5.	2006-02-15	16423321
Protein function microarrays based on self-immobilizing and self-labeling fusion proteins.	2006-01	16342318
The enigmatic acyl carrier protein phosphodiesterase of Escherichia coli: genetic and enzymological characterization.	2005-10-14	16107329
Posttranslational modification of myxobacterial carrier protein domains in Pseudomonas sp. by an intrinsic phosphopantetheinyl transferase.	2005-07	15635461
Effect of modification of the length and flexibility of the acyl carrier protein-thioesterase interdomain linker on functionality of the animal fatty acid synthase.	2005-03-15	15751987
Modular synthesis of pantetheine and phosphopantetheine.	2004-12-23	15606070
Mechanistic studies on phosphopantothenoylcysteine decarboxylase: trapping of an enethiolate intermediate with a mechanism-based inactivating agent.	2004-12-14	15581364
Crystal structure of a dodecameric FMN-dependent UbiX-like decarboxylase (Pad1) from Escherichia coli O157: H7.	2004-11	15459342
Substrate-induced asymmetry and channel closure revealed by the apoenzyme structure of Mycobacterium tuberculosis phosphopantetheine adenylyltransferase.	2004-09	15322293
Specific labeling of cell surface proteins with chemically diverse compounds.	2004-07-28	15264811
Mutational analysis of peptidyl carrier protein and acyl carrier protein synthase unveils residues involved in protein-protein recognition.	2004-07-20	15248752
Crystal structure of the schiff base intermediate prior to decarboxylation in the catalytic cycle of aspartate alpha-decarboxylase.	2004-06-25	15184017
Structure-based mutational analysis of the 4'-phosphopantetheinyl transferases Sfp from Bacillus subtilis: carrier protein recognition and reaction mechanism.	2004-04-13	15065855
Chemo- and regioselective peptide cyclization triggered by the N-terminal fatty acid chain length: the recombinant cyclase of the calcium-dependent antibiotic from Streptomyces coelicolor.	2004-03-16	15005627
The ASRG database: identification and survey of Arabidopsis thaliana genes involved in pre-mRNA splicing.	2004	15575968

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:32:44 GMT 2025` Edited by `admin` on `Mon Mar 31 19:32:44 GMT 2025`
Record UNII	NM39WU8OFM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTYRAMIDE, 2,4-DIHYDROXY-N-(2-(2-MERCAPTOETHYLCARBAMOYL)ETHYL)-3,3-DIMETHYL-, 4-PHOSPHATE

Preferred Name

English

4'-PHOSPHOPANTETHEINE

Common Name

English

BUTANAMIDE, 2-HYDROXY-N-(3-((2-MERCAPTOETHYL)AMINO)-3-OXOPROPYL)-3,3-DIMETHYL-4-(PHOSPHONOOXY)-, (R)-

Systematic Name

English

BUTANAMIDE, 2-HYDROXY-N-(3-((2-MERCAPTOETHYL)AMINO)-3-OXOPROPYL)-3,3-DIMETHYL-4-(PHOSPHONOOXY)-, (2R)-

Systematic Name

English

PHOSPHOPANTETHEINE

Systematic Name

English

PANTETHEINE PHOSPHATE

Systematic Name

English

Code System Code Type Description

MESH

C003129