CHEBI:31959 - pantethine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name pantethine
ChEBI ID CHEBI:31959
Definition An organic disulfide that consists of two molecules of pantothenic acid linked by amide bonds to a cysteamine disulfide bridging group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB7155114, eMolecules:593322, MolPort-003-959-185, ZINC000003874604
Download Molfile XML SDF
Wikipedia License
Pantethine (bis-pantethine or co-enzyme pantethine) is a dimeric form of pantetheine, which is produced from pantothenic acid (vitamin B5) by the addition of cysteamine. Pantethine was discovered by Gene Brown, a PhD student at the time. Pantethine is two molecules of pantetheine linked by a disulfide bridge. Pantetheine is an intermediate in the production of coenzyme A by the body. Most vitamin B5 supplements are in the form of calcium pantothenate, a salt of pantothenic acid, with doses in the range of 5 to 10 mg/day. In contrast, pantethine is sold as a dietary supplement for lowering blood cholesterol and triglycerides at doses of 500 to 1200 mg/day.
Read full article at Wikipedia
Formula C22H42N4O8S2
Net Charge 0
Average Mass 554.72100
Monoisotopic Mass 554.24441
InChI InChI=1S/C22H42N4O8S2/c1-21(2,13-27)17(31)19(33)25-7-5-15(29)23-9-11-35-36-12-10-24-16(30)6-8-26-20(34)18(32)22(3,4)14-28/h17-18,27-28,31-32H,5-14H2,1-4H3,(H,23,29)(H,24,30)(H,25,33)(H,26,34)/t17-,18-/m0/s1
InChIKey DJWYOLJPSHDSAL-ROUUACIJSA-N
SMILES CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)NCCSSCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO
Roles Classification
Biological Role(s): coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pantethine (CHEBI:31959) has functional parent pantothenic acid (CHEBI:7916)
pantethine (CHEBI:31959) has role coenzyme (CHEBI:23354)
pantethine (CHEBI:31959) has role nutraceutical (CHEBI:50733)
pantethine (CHEBI:31959) is a organic disulfide (CHEBI:35489)
IUPAC Name
(2R,2'R)-N,N'-{disulfanediylbis[ethane-2,1-diylimino(3-oxopropane-3,1-diyl)]}bis(2,4-dihydroxy-3,3-dimethylbutanamide)
Synonyms Sources
(R-(R*,R*))-N,N'-(Dithiobis(ethyleneimino(3-oxopropane-3,1-diyl)))bis(2,4-dihydroxy-3,3-dimethylbutyramide) ChemIDplus
Bis(pantothenamidoethyl) disulfide ChemIDplus
D-Bis(N-pantothenyl-beta-aminoethyl) disulfide ChemIDplus
D-pantethine ChEBI
N-[2-[2-[2-[3-[(2,4-dihydroxy-3,3-dimethyl-butanoyl)amino]propanoylamino]ethyldisulfanyl]ethylcarbamoyl]ethyl]-2,4-dihydroxy-3,3-dimethyl-butanamide HMDB
Pantetina ChemIDplus
Pantomin ChemIDplus
Manual Xrefs Databases
3417 DrugCentral
C12661 KEGG COMPOUND
D01234 KEGG DRUG
HMDB0003828 HMDB
Pantethine Wikipedia
View more database links
Registry Numbers Types Sources
16816-67-4 CAS Registry Number KEGG COMPOUND
16816-67-4 CAS Registry Number ChemIDplus
1718252 Reaxys Registry Number Reaxys
Citations
Suzuki Y, Itoh H, Abe T, Nishimura F, Sato Y, Takeyama M (2011)
Comparison of the effects of pantethine and fursultiamine on plasma gastrointestinal peptide levels in healthy volunteers.
Biological & pharmaceutical bulletin 34, 1640-1643 [PubMed:21963510]
[show Abstract]
Balibar CJ, Hollis-Symynkywicz MF, Tao J (2011)
Pantethine rescues phosphopantothenoylcysteine synthetase and phosphopantothenoylcysteine decarboxylase deficiency in Escherichia coli but not in Pseudomonas aeruginosa.
Journal of bacteriology 193, 3304-3312 [PubMed:21551303]
[show Abstract]
Rumberger JA, Napolitano J, Azumano I, Kamiya T, Evans M (2011)
Pantethine, a derivative of vitamin B(5) used as a nutritional supplement, favorably alters low-density lipoprotein cholesterol metabolism in low- to moderate-cardiovascular risk North American subjects: a triple-blinded placebo and diet-controlled investigation.
Nutrition research (New York, N.Y.) 31, 608-615 [PubMed:21925346]
[show Abstract]
(2010)
Pantethine. Monograph.
Alternative medicine review : a journal of clinical therapeutic 15, 279-282 [PubMed:21155629]
Cornille E, Abou-Hamdan M, Khrestchatisky M, Nieoullon A, de Reggi M, Gharib B (2010)
Enhancement of L-3-hydroxybutyryl-CoA dehydrogenase activity and circulating ketone body levels by pantethine. Relevance to dopaminergic injury.
BMC neuroscience 11, 51 [PubMed:20416081]
[show Abstract]
Rana A, Seinen E, Siudeja K, Muntendam R, Srinivasan B, van der Want JJ, Hayflick S, Reijngoud DJ, Kayser O, Sibon OC (2010)
Pantethine rescues a Drosophila model for pantothenate kinase-associated neurodegeneration.
Proceedings of the National Academy of Sciences of the United States of America 107, 6988-6993 [PubMed:20351285]
[show Abstract]
Last Modified
22 February 2017