Phosphopantothenic acid
Basic information
- CAS
5875-50-3- Standard SMILES
CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)O- InChIKey
XHFVGHPGDLDEQO-ZETCQYMHSA-N- Molecular formula
- C9H18NO8P
- Average molar mass
- 299.21 g/mol
- Monoisotopic mass
- 299.07700353
Overview
(R)-4'-phosphopantothenic acid is an amidoalkyl phosphate that is the 4-phosphate derivative of (R)-pantothenic acid. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite and an Escherichia coli metabolite. It is functionally related to a (R)-pantothenic acid. It is a conjugate acid of a (R)-4'-phosphopantothenate(1-).
Names & identifiers
- Preferred name
- Phosphopantothenic acid
- IUPAC
- 3-[[(2R)-2-hydroxy-3,3-dimethyl-4-phosphonooxybutanoyl]amino]propanoic acid
- English name
- phosphopantothenic acid
- Molecular formula
- C9H18NO8P
- Molecular weight
- 299.22
Names & synonyms
Phosphopantothenic acid5875-50-34'-Phosphopantothenic acid4'-phosphopantothenatePhosphopantothenoate(R)-4'-phosphopantothenic acidD-Pantothenic acid 4'-phosphateUNII-1SCE5NG3E81SCE5NG3E8N-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-beta-alaninePANTOTHENATE PHOSPHATE3-[[(2R)-2-hydroxy-3,3-dimethyl-4-phosphonooxybutanoyl]amino]propanoic acid
Show more names
Vitamin B5 Impurity 2Calcium pantothenate Impurity 7β-Alanine, N-[(2R)-2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-3-[[(2R)-2-hydroxy-3,3-dimethyl-4-phosphonooxybutanoyl]amino]propanoicacid
CHEBI:15905(R)-N-(2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-beta-alanine3-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanamido]propanoic acidPANTOTHENIC ACID, 4'-(DIHYDROGEN PHOSPHATE)phosphopantothenate.BETA.-ALANINE, N-((2R)-2-HYDROXY-3,3-DIMETHYL-1-OXO-4-(PHOSPHONOOXY)BUTYL)-beta-Alanine, N-(2-hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl)-, (R)-3-((2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanamido)propanoic acid
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 153 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 376
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Density
- 1.488 · 1.488±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 1.894 · 1.894±0.10(predicted)
- FDA UNII
- 1 SCE5NG3E8 · 1SCE5NG3E8
Chemistry & industry
Pharmacology
Cellular LocationsMitochondria
Metabolite PathwaysPantothenate and CoA Biosynthesis
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: An amidoalkyl phosphate that is the 4-phosphate derivative of (R)-pantothenic acid.
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