1-deoxy-1-{2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl}-D-arabinitol

Identification

Generic Name
1-deoxy-1-{2,6,8-trioxo-7-[4-(phosphonooxy)butyl]-1,2,3,6,7,8-hexahydro-9H-purin-9-yl}-D-arabinitol
DrugBank Accession Number
DB02135
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 454.3264
Monoisotopic: 454.11009411
Chemical Formula
C14H23N4O11P
Synonyms
  • 4-[2,6,8-trioxo-9-[(2R,3S,4R)-2,3,4,5-tetrahydroxypentyl]-3H-purin-7-yl]butyl dihydrogen phosphate

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U6,7-dimethyl-8-ribityllumazine synthaseNot AvailableMycobacterium tuberculosis
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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / Monoalkyl phosphates / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas / Secondary alcohols / Lactams
show 7 more
Substituents
6-oxopurine / Alcohol / Alkaloid or derivatives / Alkyl phosphate / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VBXZSBKAJFXURR-MRTMQBJTSA-N
InChI
InChI=1S/C14H23N4O11P/c19-6-8(21)10(22)7(20)5-18-11-9(12(23)16-13(24)15-11)17(14(18)25)3-1-2-4-29-30(26,27)28/h7-8,10,19-22H,1-6H2,(H2,26,27,28)(H2,15,16,23,24)/t7-,8-,10+/m1/s1
IUPAC Name
(4-{2,6,8-trioxo-9-[(2R,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2,3,6,7,8,9-hexahydro-1H-purin-7-yl}butoxy)phosphonic acid
SMILES
[H]N1C2=C(N(CCCCOP(O)(O)=O)C(=O)N2C[C@@H](O)[C@H](O)[C@H](O)CO)C(=O)N([H])C1=O

References

General References
Not Available
PubChem Compound
657027
PubChem Substance
46506635
ChemSpider
571249
ZINC
ZINC000032304142
PDBe Ligand
TS1
PDB Entries
1w29

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 Solubility3.41 mg/mLALOGPS
logP-1.4ALOGPS
logP-3.9Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.81Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area229.43 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity106.28 m3·mol-1Chemaxon
Polarizability40.86 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000900000-0babca5a4be3f112f10f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0004900000-8a1bb86cf9384479a164
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05n0-0025900000-e9e045cba685d8398183
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kbb-2009200000-3aa3121b5b7636e73197
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-0495100000-f8d29d2a8b53894e80df
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-2962000000-c8ef29fc975a1495007c
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]-180.91634
predicted
DeepCCS 1.0 (2019)
[M+H]+183.3119
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.22444
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Specific Function
6,7-dimethyl-8-ribityllumazine synthase activity
Gene Name
ribH
Uniprot ID
P9WHE9
Uniprot Name
6,7-dimethyl-8-ribityllumazine synthase
Molecular Weight
16370.415 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52