NAV

5-Benzylacyclouridine

Identification

Generic Name
5-Benzylacyclouridine
DrugBank Accession Number
DB07437
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 276.2878
Monoisotopic: 276.11100701
Chemical Formula
C14H16N2O4
Synonyms
  • 5-Bacu
  • 5-benzyl-1-(2-hydroxyethoxymethyl)uracil
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUridine phosphorylaseNot AvailableEscherichia coli (strain K12)
UUridine phosphorylase 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Hydropyrimidines / Benzene and substituted derivatives / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds
show 2 more
Substituents
Alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Monocyclic benzene moiety / Organic nitrogen compound
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidone, primary alcohol, hydroxyether (CHEBI:41037)
Affected organisms
Not Available

Chemical Identifiers

UNII
0H851I3O9D
CAS number
82857-69-0
InChI Key
SPJAGILXQBHHSZ-UHFFFAOYSA-N
InChI
InChI=1S/C14H16N2O4/c17-6-7-20-10-16-9-12(13(18)15-14(16)19)8-11-4-2-1-3-5-11/h1-5,9,17H,6-8,10H2,(H,15,18,19)
IUPAC Name
5-benzyl-1-[(2-hydroxyethoxy)methyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
OCCOCN1C=C(CC2=CC=CC=C2)C(=O)NC1=O

References

General References
Not Available
PubChem Compound
54929
PubChem Substance
99443908
ChemSpider
49600
BindingDB
50026387
ChEBI
41037
ChEMBL
CHEMBL17432
PDBe Ligand
BAU
PDB Entries
1u1c / 3euf / 3p0e / 3p0f

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.818 mg/mLALOGPS
logP0.48ALOGPS
logP0.72Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.95Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area78.87 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity72.06 m3·mol-1Chemaxon
Polarizability28.25 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8002
Blood Brain Barrier+0.7103
Caco-2 permeable-0.7155
P-glycoprotein substrateSubstrate0.6242
P-glycoprotein inhibitor IInhibitor0.5629
P-glycoprotein inhibitor IINon-inhibitor0.7124
Renal organic cation transporterNon-inhibitor0.7563
CYP450 2C9 substrateNon-substrate0.8173
CYP450 2D6 substrateNon-substrate0.8718
CYP450 3A4 substrateNon-substrate0.5832
CYP450 1A2 substrateNon-inhibitor0.8604
CYP450 2C9 inhibitorNon-inhibitor0.7931
CYP450 2D6 inhibitorNon-inhibitor0.8892
CYP450 2C19 inhibitorNon-inhibitor0.8779
CYP450 3A4 inhibitorInhibitor0.5065
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.881
Ames testNon AMES toxic0.6811
CarcinogenicityNon-carcinogens0.8505
BiodegradationNot ready biodegradable0.7
Rat acute toxicity1.8989 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8188
hERG inhibition (predictor II)Inhibitor0.6292
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0gb9-2090000000-590008fedbcf235fd9b7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-6877fadf52e004730f02
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05r0-0090000000-d199fd2f67345fd2fd0c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1590000000-162098c7e8a1b1fb0940
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pc0-0190000000-04a532fcff5d42c89f42
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ou-6910000000-d91925c289ccb903d247
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-3970000000-64f963dc8878eae4c513
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.8394446
predicted
DarkChem Lite v0.1.0
[M-H]-156.52312
predicted
DeepCCS 1.0 (2019)
[M+H]+176.8081446
predicted
DarkChem Lite v0.1.0
[M+H]+158.88115
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.1533446
predicted
DarkChem Lite v0.1.0
[M+Na]+164.97441
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Uridine phosphorylase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Uridine phosphorylase activity
Specific Function
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources ...
Gene Name
udp
Uniprot ID
P12758
Uniprot Name
Uridine phosphorylase
Molecular Weight
27158.88 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Uridine phosphorylase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Uridine phosphorylase activity
Specific Function
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate (PubMed:7488099). The produced molecules are then utilized as carbon an...
Gene Name
UPP1
Uniprot ID
Q16831
Uniprot Name
Uridine phosphorylase 1
Molecular Weight
33934.005 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 16:52