Basic information
- Standard SMILES
O=c1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1- InChIKey
DRTQHJPVMGBUCF-XVFCMESISA-N- Molecular formula
- C9H12N2O6
- Average molar mass
- 244.2 g/mol
- Monoisotopic mass
- 244.0695361
Overview
Uridine is a ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a betaN1-glycosidic bond. It has a role as a drug metabolite, a human metabolite and a fundamental metabolite. It is functionally related to a uracil.
Names & identifiers
- Preferred name
- Uridine
- IUPAC
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
- English name
- Uridine
- Molecular formula
- C9H12N2O6
- Molecular weight
- 244.2
Names & synonyms
uridine58-96-8UridinUracil riboside1-beta-D-RibofuranosyluracilCHEBI:16704WHI7HQ7H85DTXSID40891555NSC-20256NSC202561-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Show more names
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dioneURURDbeta-UridineURACIL-1-BETA-D-RIBOFURANOSIDED-URIDINEβ-Uridine
1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dioneAllo UridineAllo-Uridine1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidine-2,4-dione1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneRefChem:6340DTXCID001030648200-407-5
Database identifiers
- CAS
58-96-8、69-75-0- PubChem CID
- 6029
- DTXSID
DTXSID40891555- ChEMBL
CHEMBL100259- ChEBI
CHEBI:16704- UNII
- WHI7HQ7H85
- EC Number
- 200-407-5
- Nikkaji
- J4.593D
Properties
Computed structural properties
- XLogP
- -2
- Topological polar surface area
- 119 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 370
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure
LogP-1.98
Solubility34.9 [ug/mL] (The mean of the results at pH 7.4)
Melting Point163 °C
Optical Rotation(c = 2, H2O) [a]20 D = 9.4 ± 2°
Physical Description
Solid; [Merck Index] White powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section
160.1 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
152 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
150.7 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
166 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
152 Ų [M-H]-
Physicochemical properties
- Melting point
- 163 · 163-167 °C(lit.)
- alpha
- 8.4 · 8.4 º (c=2,water)
- Boiling point
- 387.12 °C · 387.12°C (rough estimate)
- Density
- 1.4221 · 1.4221 (rough estimate)
- refractive index
- 9 ° · 9 ° (C=2, H2O)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- powder
- pka
- 9.39 · 9.39±0.10(Predicted)
- color
- White to almost white
- PH
- 9.05 · 9.05
- biological source
- synthetic (organic)
- Water Solubility
- Soluble in water, dimethylsulfoxide, and methanol.
- λmax
- 262 · 262 (pH 7)；262 (pH 12)
- Merck
- 14 · 14,9877
- BRN
- 754904 · 754904
- Cosmetics Ingredients Functions
- SKIN PROTECTINGSKIN CONDITIONING
- InChI
- 1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
- InChIKey
- DRTQHJPVMGBUCF-XVFCMESISA-N
- SMILES
- OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=CC(=O)NC2=O
- LogP
- -1.581 · -1.581 (est)
- CAS DataBase Reference
- 58 · 58-96-8(CAS DataBase Reference)
- FDA UNII
- 7 HQ7H85 · WHI7HQ7H85
- NIST Chemistry Reference
- Uridine(58-96-8)
- EPA Substance Registry System
- Uridine (58-96-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 75 · NA.75
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P271-P280
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 24 · 24/25-36-26
- WGK Germany
- 3 · 3
- RTECS
- 1450000 · YR1450000
- F
- 10 · 10
- Hazard Note
- Keep Cold
- TSCA
- TSCA listed
- HS Code
- 29335990 · 29335990
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 85.7% (12 of 14) of all reports.
Warning
H315 (14.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 14 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Uridine
Status: Active Update: 12-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31621
Uridine: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryCauses somnolence, other liver changes, effects on transaminases, and inflammation in acute intraperitoneal studies of mice and rats; [RTECS] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (14.3%)
Toxicology
Toxicity DataMouse(ip): LD50 4335 mg/kg
Safety data
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YR1450000
- hs_code
- 29335990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Keep Cold
- safety_code
- 24/25-36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
WHI7HQ7H85
URIDINE
Established Pharmacologic Class [EPC] - Pyrimidine Analog
Chemical/Ingredient structural concept [Chemical/Ingredient] - Pyrimidines
Chemical/Ingredient structural concept [Chemical/Ingredient] - Analogs/Derivatives
Uridine is a Pyrimidine Analog. The chemical classification of uridine is Pyrimidines and Analogs/Derivatives.
Tissue LocationsPlacenta
Cellular LocationsExtracellular
Metabolite PathwaysBeta Ureidopropionase Deficiency
Uses & manufacturing
UsesNucleoside found throughout nature; [Merck Index]
General Manufacturing InformationUridine: ACTIVE
Applications
UsesUridine is a nucleoside, contains a uracil attached to a ribose ring via a β-N1-glycosidic bond
UsesUridine is a nucleoside; widely distributed in nature. Uridine is one of the four basic components of ribonucleic acid (RNA)
General DescriptionUridine is a pyrimidine nucleoside which is crucial for the synthesis of RNA and membranes. It helps in normal cell function and growth by forming pyrimidine nucleotide -lipid conjugates. Uridine has been studied as a rescue agent to reduce the toxicities associated with 5-fluorouracil (5-FU), thereby allowing the administration of higher doses of 5-FU in chemotherapy regimens. (NCI04)
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Uridine is a ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a fundamental metabolite and a drug metabolite. It is functionally related to a uracil.
Related reactions
108 records
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