Uridine diphosphate galactose (UDP-galactose)

Identification

Molecular formula

C₁₅H₂₄N₂O₁₇P₂

CAS number

2956-16-3

IUPAC name

(2S,3S,4S,5R,6R)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

State

State at room temperature: UDP-galactose is typically solid at room temperature, existing as a stable powder that is readily used in biochemical analysis and enzymatic reactions.

Melting point (Celsius)

210.00

Melting point (Kelvin)

483.00

Boiling point (Celsius)

150.00

Boiling point (Kelvin)

423.00

General information

Molecular weight

566.30g/mol

Molar mass

566.2980g/mol

Density

1.6000g/cm³

Appearence

Uridine diphosphate galactose (UDP-galactose) generally appears as a white crystalline powder. It is soluble in water, where it forms a colorless aqueous solution.

Comment on solubility

Solubility of (2S,3S,4S,5R,6R)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

The solubility of this complex compound is influenced by its multifaceted structure, which contains multiple hydroxyl groups and the presence of phosphate moieties. Here are some key points to consider regarding its solubility:

Polarity: The numerous hydroxyl (-OH) groups present enhance its polarity, likely resulting in high solubility in polar solvents, particularly water.
Hydrogen Bonding: The ability to form hydrogen bonds with water molecules can significantly increase solubility. Compounds with more functional groups capable of engaging in hydrogen bonding typically exhibit improved solubility.
Effects of pH: The presence of a carboxylic acid group suggests that the solubility may be pH-dependent. At lower pH values, the carboxylic acid can remain protonated, whereas at higher pH levels it may deprotonate, enhancing its ionization and resultant solubility.
Interactions with Solvents: In addition to water, solubility may vary with organic solvents. For instance, polar aprotic solvents could facilitate solubilization due to their capacity to stabilize charged species.
Cytotoxicity Considerations: Biological applications of this compound may also consider how solubility affects bioavailability and potential cytotoxic effects in aqueous environments.

In summary, the solubility of (2S,3S,4S,5R,6R)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid is anticipated to be high in water and polar solvents, primarily due to its polar functional groups and potential for hydrogen bonding. However, the specific conditions and interactions with the solvent system will ultimately dictate its solubility performance.

Interesting facts

Interesting Facts about (2S,3S,4S,5R,6R)-6-[[[[2R,3S,4R,5R]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

This complex compound is a fascinating example of the intricate relationships within organic chemistry and biochemistry. Here are some notable facts:

Pharmacological Potential: Due to its unique structure, this compound is studied for its potential therapeutic applications, particularly in the fields of anticancer and antiviral drug development.
Structural Complexity: The compound features multiple chiral centers, indicating its stereochemistry is crucial for its biological activity. Each stereocenter can influence how the compound interacts with biological systems, emphasizing the importance of structure-activity relationships in drug design.
Role of Phosphorylation: The presence of phosphoryl groups in the molecule is significant, as these groups are known to play essential roles in cellular signaling and metabolism. They can influence the compound's reactivity and affinity towards target proteins.
Nucleotide Mimicry: The dioxopyrimidine moiety suggests that the compound may mimic natural nucleotide structures, providing insights into its ability to interact with nucleic acids, which is essential for many biological processes.
Natural Product Inspiration: Compounds of similar architecture often draw inspiration from natural products, showcasing how nature can guide the development of synthetically derived compounds with enhanced biological properties.

This compound's intricate design embodies the complexity of life at the molecular level, serving as a reminder of how small changes in structure can lead to significant differences in function.

Synonyms

Udp-glucuronic acid

uridine diphosphate glucuronic acid

UDPGA

Udp glucuronic acid

UDPglucuronate

UDP-alpha-D-glucuronic acid

Uridine diphosphoglucuronic acid

2616-64-0

Uridinediphosphoglucuronic acid

Uridine 5'-diphospho-glucuronic acid

URIDINE-5'-DIPHOSPHATE-GLUCURONIC ACID

04SZC4MEFQ

CHEBI:17200

(2S,3S,4S,5R,6R)-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

alpha-D-Glucopyranuronic acid, 1-P'-ester with uridine 5'-(trihydrogen diphosphate)

DTXSID00903961

UDP-.ALPHA.-D-GLUCURONIC ACID

Uridine 5'-diphosphate alpha-D-Glucopyranuronic acid

URIDINE 5'-DIPHOSPHO-.ALPHA.-D-GLUCURONIC ACID

uridine 5'-[3-(alpha-D-glucopyranuronosyl) dihydrogen diphosphate]

.ALPHA.-D-GLUCOPYRANURONIC ACID, 1->P'-ESTER WITH URIDINE 5'-(TRIHYDROGEN DIPHOSPHATE)

Acid, UDP Glucuronic

Glucuronic Acid, UDP

uridine 5'-(3-(alpha-D-glucopyranuronosyl) dihydrogen diphosphate)

Acid, Uridine Diphosphoglucuronic

Diphosphoglucuronic Acid, Uridine

UDPglucuronic acid

(2S,3S,4S,5R,6R)-6-(((((((2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

(2S,3S,4S,5R,6R)-6-((((2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

DTXCID501331900

Uridine 5'diphosphoglucuronic acid

URIDINE 5'-DIPHOSPHO-ALPHA-D-GLUCURONIC ACID

ALPHA-D-GLUCOPYRANURONIC ACID, 1->P'-ESTER WITH URIDINE 5'-(TRIHYDROGEN DIPHOSPHATE)

alphaDGlucopyranuronic acid, 1P'ester with uridine 5'(trihydrogen diphosphate)

UDP-glucuronate

UDP-D-glucuronate

UDP-alpha-D-glucuronate

Uridine 5'-diphosphoglucuronic acid

UDP-D-glucuronic acid

udp-glcua

CHEMBL228057

UGA

Uridine-5'-Diphosphoglucuronic Acid

UNII-04SZC4MEFQ

UDP glucuronate

uridine diphosphate glucuronate

UDP-delta-glucuronate

udp-?-D-glucuronic acid

UDP-delta-glucuronic acid

bmse000292

UDP-|A-D-glucuronic acid

UDP-?-D-galacturonic acid

UDP-alpha-delta-glucuronate

Uridine pyrophosphoglucuronate

Uridine diphosphate-glucuronate

Uridine diphospho-D-glucuronate

GTPL1784

Uridine 5'-diphosphoglucuronate

Uridine pyrophosphoglucuronic acid

HDYANYHVCAPMJV-LXQIFKJMSA-N

Uridine diphospho-delta-glucuronate

Uridine diphospho-D-glucuronic acid

BDBM50209665

Uridine 5'-diphospho-a-D-glucuronate

DB03041

MU07657

Uridine diphospho-delta-glucuronic acid

DA-58863

Uridine 5'-diphospho-a-D-glucuronic acid

NS00015194

Uridine 5'-diphospho-alpha-delta-glucuronate

C00167

Uridine 5'-diphospho-alpha-delta-glucuronic acid

Q277638

Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate

Uridine[5']diphospho-?-D-galacturonopyranoside;UDP-GlcUA

a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphate

alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphate

uridine 5''-[3-(alpha-D-glucopyranuronosyl) dihydrogen diphosphate]

uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]

a-D-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)

alpha-D-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)

alpha-delta-Glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate)

alpha-delta-Glucopyranuronic acid 1-P'-ester with uridine 5'-(trihydrogen diphosphate)

(2S,3S,4S,5R,6R)-6-{[(S)-{[(R)-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]oxy}-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid (non-preferred name)