1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
Basic information
- CAS
126-49-8- Standard SMILES
O=C(O)C(=O)CC1(C(=O)O)C=CC(O)C=C1- InChIKey
FPWMCUPFBRFMLH-UHFFFAOYSA-N- Molecular formula
- C10H10O6
- Average molar mass
- 226.18 g/mol
- Monoisotopic mass
- 226.04773803
Overview
Prephenic acid is an oxo dicarboxylic acid that consists of 4-hydroxycyclohexa-2,5-diene-1-carboxylic acid substituted by a 2-carboxy-2-oxoethyl group at position 1. It has a role as a plant metabolite and an Escherichia coli metabolite. It is a conjugate acid of a (1s,4s)-prephenate(2-) and a prephenate(2-).
Names & identifiers
- Preferred name
- 1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
- IUPAC
- 1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
- English name
- prephenic acid
- Molecular formula
- C10H10O6
- Molecular weight
- 226.18
Names & synonyms
prephenate126-49-81-carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acidRefChem:907541Prephenic acid1-Carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acidPrephenic acid, ciscis-prephenic acid1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid(1s,4s)-prephenic acid87664-40-2Z66B98Z97I
Show more names
α-Oxo-1-carboxy-4-hydroxy-2,5-cyclohexadiene-1β-propanoic acid2,5-Cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-α-oxo-
cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid2,5-Cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-alpha-oxo-(1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acidPREcis-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acidPrephenic acid [MI]UNII-Z66B98Z97Ibmse000108
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 378
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section155 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Boiling point
- 482.6 · 482.6±45.0 °C(Predicted)
- Density
- 1.543 · 1.543±0.06 g/cm3(Predicted)
- pka
- 2.48 · 2.48±0.54(Predicted)
- FDA UNII
- 66 B98Z97I · Z66B98Z97I
Chemistry & industry
Additional notes
DefinitionChEBI: An oxo dicarboxylic acid that consists of 4-hydroxycyclohexa-2,5-diene-1-carboxylic acid substituted by a 2-carboxy-2-oxoethyl group at position 1.
Related reactions
2 records
Compound notes
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