NAV

N-[4-([(2-Amino-4-oxo-1,4-dihydropyrido[3,2-d]pyrimidin-6-yl)methyl]{(2E)-3-[4-carbamoyl-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazol-5-yl]-2-propenoyl}amino)benzoyl]-L-glutamic acid

Identification

Generic Name
N-[4-([(2-Amino-4-oxo-1,4-dihydropyrido[3,2-d]pyrimidin-6-yl)methyl]{(2E)-3-[4-carbamoyl-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazol-5-yl]-2-propenoyl}amino)benzoyl]-L-glutamic acid
DrugBank Accession Number
DB04057
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 815.6374
Monoisotopic: 815.191197975
Chemical Formula
C32H34N9O15P
Synonyms
  • beta-DADF, MSA, multisubstrate adduct inhibitor
  • β-DADF, MSA, multisubstrate adduct inhibitor
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBifunctional purine biosynthesis protein PURHNot 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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Imidazole ribonucleosides and ribonucleotides
Sub Class
1-ribosyl-imidazolecarboxamides
Direct Parent
1-ribosyl-imidazolecarboxamides
Alternative Parents
Pentose phosphates / Glutamic acid and derivatives / Acylaminobenzoic acid and derivatives / Hippuric acids / N-acyl-alpha amino acids / Glycosylamines / Pyridopyrimidines / Monosaccharide phosphates / Anilides / 2-heteroaryl carboxamides
show 25 more
Substituents
1,2-diol / 1-ribosyl-imidazolecarboxamide / 2-heteroaryl carboxamide / Acylaminobenzoic acid or derivatives / Alcohol / Alkyl phosphate / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives
show 54 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyridopyrimidine, N-acyl-L-glutamic acid, 1-(phosphoribosyl)imidazole (CHEBI:44048)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XRZABKCMPVBQFX-UGTLBTQMSA-N
InChI
InChI=1S/C32H34N9O15P/c33-27(47)24-19(41(13-35-24)30-26(46)25(45)20(56-30)12-55-57(52,53)54)8-9-21(42)40(11-15-3-6-17-23(36-15)29(49)39-32(34)38-17)16-4-1-14(2-5-16)28(48)37-18(31(50)51)7-10-22(43)44/h1-6,8-9,13,18,20,25-26,30,45-46H,7,10-12H2,(H2,33,47)(H,37,48)(H,43,44)(H,50,51)(H2,52,53,54)(H3,34,38,39,49)/b9-8+/t18-,20+,25+,26+,30+/m0/s1
IUPAC Name
(2S)-2-({4-[(2E)-N-({2-amino-4-oxo-1H,4H-pyrido[3,2-d]pyrimidin-6-yl}methyl)-3-{4-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-5-yl}prop-2-enamido]phenyl}formamido)pentanedioic acid
SMILES
[H]N([H])C(=O)C1=C(\C=C\C(=O)N(CC2=NC3=C(C=C2)N([H])C(=NC3=O)N([H])[H])C2=CC=C(C=C2)C(=O)N([H])[C@@H](CCC(O)=O)C(O)=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

References

General References
Not Available
PubChem Compound
6323417
PubChem Substance
46507189
ChemSpider
4883412
ZINC
ZINC000098209190
PDBe Ligand
MS1
PDB Entries
1oz0

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
logP-3.8Chemaxon
pKa (Strongest Acidic)1.16Chemaxon
pKa (Strongest Basic)2.94Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count19Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area381.74 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity190.06 m3·mol-1Chemaxon
Polarizability74.45 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.864
Blood Brain Barrier-0.599
Caco-2 permeable-0.7137
P-glycoprotein substrateSubstrate0.7022
P-glycoprotein inhibitor INon-inhibitor0.78
P-glycoprotein inhibitor IINon-inhibitor0.9797
Renal organic cation transporterNon-inhibitor0.8788
CYP450 2C9 substrateNon-substrate0.8114
CYP450 2D6 substrateNon-substrate0.8283
CYP450 3A4 substrateSubstrate0.5433
CYP450 1A2 substrateNon-inhibitor0.7957
CYP450 2C9 inhibitorNon-inhibitor0.8217
CYP450 2D6 inhibitorNon-inhibitor0.8194
CYP450 2C19 inhibitorNon-inhibitor0.8225
CYP450 3A4 inhibitorNon-inhibitor0.5727
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8606
Ames testNon AMES toxic0.7164
CarcinogenicityNon-carcinogens0.9109
BiodegradationNot ready biodegradable0.9728
Rat acute toxicity2.5732 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9385
hERG inhibition (predictor II)Non-inhibitor0.5067
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000039210-1927886c1f03e7d30880
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0h6s-2000002910-f6bb6e0b17870f8cf950
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kmi-1000379700-6a09aab5606b655d4f57
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0umi-3400001900-cad23608db066ec8b004
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01bi-0100079100-de21ed78293225802326
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0201-5201012920-3cfd28216c4b2603efc9
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-243.84892
predicted
DeepCCS 1.0 (2019)
[M+H]+245.55043
predicted
DeepCCS 1.0 (2019)
[M+Na]+251.70729
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Bifunctional purine biosynthesis protein PURH
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.Promotes insulin receptor/INSR autophosphorylation and is involved in INSR internalization (PubMed:25687571).
Gene Name
ATIC
Uniprot ID
P31939
Uniprot Name
Bifunctional purine biosynthesis protein PURH
Molecular Weight
64615.255 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]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52