Basic information
- CAS
16816-67-4- Standard SMILES
CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)NCCSSCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)CO- InChIKey
DJWYOLJPSHDSAL-ROUUACIJSA-N- Molecular formula
- C22H42N4O8S2
- Average molar mass
- 554.7 g/mol
- Monoisotopic mass
- 554.2444063
Overview
Pantethine is an organic disulfide that consists of two molecules of pantothenic acid linked by amide bonds to a cysteamine disulfide bridging group. It has a role as a coenzyme and a nutraceutical. It is functionally related to a pantothenic acid.
Names & identifiers
- Preferred name
- Pantethine
- IUPAC
- (2R)-N-[3-[2-[2-[3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyldisulfanyl]ethylamino]-3-oxopropyl]-2,4-dihydroxy-3,3-dimethylbutanamide
- English name
- D-Pantethine
- Molecular formula
- C22H42N4O8S2
- Molecular weight
- 554.72
Names & synonyms
pantethineD-Pantethine16816-67-4PantominPantetinaPantosinBis(pantothenamidoethyl) disulfideD-Bis(N-pantothenyl-beta-aminoethyl) disulfideDTXSID9046815Bis(N-pantothenylamidoethyl) disulfide7K81IL792LD-Bis(N-pantothenyl-2-aminoethyl)-disulfide
Show more names
D-pantethine syrupPatethinePANTETHINLipodelPanthecinDermorizinLBF FACTOR
NSC-759269CHEBI:31959DTXCID901473899(2R)-N-[2-({2-[(2-{3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanamido}ethyl)disulfanyl]ethyl}carbamoyl)ethyl]-2,4-dihydroxy-3,3-dimethylbutanamideBUTANAMIDE, N,N'-(DITHIOBIS(2,1-ETHANEDIYLIMINO(3-OXO-3,1-PROPANEDIYL)))BIS(2,4-DIHYDROXY-3,3-DIMETHYL-, (2R,2'R)-Butanamide, N,N'-[dithiobis[2,1-ethanediylimino(3-oxo-3,1-propanediyl)]]bis[2,4-dihydroxy-3,3-dimethyl-, (2R,2'R)-(2R)-N-(2-((2-((2-(3-((2R)-2,4-dihydroxy-3,3-dimethylbutanamido)propanamido)ethyl)disulfanyl)ethyl)carbamoyl)ethyl)-2,4-dihydroxy-3,3-dimethylbutanamideRefChem:169900
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 248 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 19
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 652
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsHair conditioning; Emollient
Physical DescriptionSolid
Collision Cross Section
224.97 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
222.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- alpha
- 27 · D27 +13.5° (c = 3.75 in water)
- Boiling point
- 987.2 · 987.2±65.0 °C(Predicted)
- Density
- 1.1949 · 1.1949 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- syrup
- pka
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Warning
H400 (50%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Butanamide, N,N'-[dithiobis[2,1-ethanediylimino(3-oxo-3,1-propanediyl)]]bis[2,4-dihydroxy-3,3-dimethyl-, [R-(R*,R*)]-
Directive (EC) No 46/2002
Butanamide, N,N'-[dithiobis[2,1-ethanediylimino(3-oxo-3,1-propanediyl)]]bis[2,4-dihydroxy-3,3-dimethyl-, (2R,2'R)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAquatic Acute 1 (50%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- ES4392700
- Toxicity
- LD50 oral in rat: > 10gm/kg
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H400
- Precautionary statements
- P273-P391-P501
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Cellular LocationsCytoplasm
Uses & manufacturing
Household ProductsInformation on 4 consumer products that contain Pantethine in the following categories is provided:
Use ClassificationCosmetics -> Hair conditioning; Emollient
Applications
DescriptionD-Pantethine is a compound in which two molecules of D-pantetheine bind through an S-S linkage. D-Pantethine is available from commercial sources as well as from D-pantothenic acid. It is known that the sulfhydryl group is the metabolically active part of the molecule. Coenzyme A is an essential cofactor in over 70 biological pathways, such as fatty acid oxidation, carbohydrate metabolism, and amino acid catabolism. Studies conducted in vitro suggest that D-Pantethine inhibits the activity of aldehyde dehydrogenase; however, related metabolites of the compound, such as Taurine (sc-202354), D-pantetheine, Coenzyme A, and D-pantothenate activate this enzyme.
Usesantilipemic
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
4 records
Compound notes
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