3-isobutyl-1-methyl-7H-xanthine

Identification

Name
3-isobutyl-1-methyl-7H-xanthine
Accession Number
DB07954
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
  • 1-methyl-3-isobutylxanthine
  • 3-isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione
  • 3-isobutyl-1-methylxanthine
  • 3-Isobutyl-1-methyxanthine
  • IBMX
External IDs
NSC-165960 / SC 2964 / SC-2964
Categories
UNII
TBT296U68M
CAS number
28822-58-4
Weight
Average: 222.2438
Monoisotopic: 222.111675712
Chemical Formula
C10H14N4O2
InChI Key
APIXJSLKIYYUKG-UHFFFAOYSA-N
InChI
InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
IUPAC Name
1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione
SMILES
CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcGMP-specific 3',5'-cyclic phosphodiesteraseNot AvailableHuman
UcGMP-inhibited 3',5'-cyclic phosphodiesterase BNot AvailableHuman
UHigh affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7ANot AvailableHuman
UcAMP-specific 3',5'-cyclic phosphodiesterase 4DNot AvailableHuman
UHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9ANot AvailableHuman
UHigh affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8ANot AvailableHuman
UcGMP-dependent 3',5'-cyclic phosphodiesteraseNot AvailableHuman
URetinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C13708
PubChem Compound
3758
PubChem Substance
99444425
ChemSpider
3627
BindingDB
50027176
ChEBI
34795
ChEMBL
CHEMBL275084
IUPHAR
388
Guide to Pharmacology
GtP Drug Page
HET
IBM
Wikipedia
IBMX
PDB Entries
1rkp / 1soj / 1zkl / 1zkn / 2hd1 / 2r8q / 2yy2 / 3dy8 / 3dyl / 3dyn
show 8 more

Clinical Trials

Clinical Trials
Not Available

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 Solubility5.44 mg/mLALOGPS
logP0.84ALOGPS
logP0.44ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)11.41ChemAxon
pKa (Strongest Basic)2.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.37 m3·mol-1ChemAxon
Polarizability22.52 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.989
Caco-2 permeable-0.5131
P-glycoprotein substrateNon-substrate0.5833
P-glycoprotein inhibitor INon-inhibitor0.7453
P-glycoprotein inhibitor IIInhibitor0.5777
Renal organic cation transporterNon-inhibitor0.8472
CYP450 2C9 substrateNon-substrate0.816
CYP450 2D6 substrateNon-substrate0.8375
CYP450 3A4 substrateSubstrate0.5588
CYP450 1A2 substrateInhibitor0.8472
CYP450 2C9 inhibitorNon-inhibitor0.9159
CYP450 2D6 inhibitorNon-inhibitor0.9667
CYP450 2C19 inhibitorNon-inhibitor0.9664
CYP450 3A4 inhibitorNon-inhibitor0.8583
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.955
Ames testNon AMES toxic0.7455
CarcinogenicityNon-carcinogens0.9232
BiodegradationNot ready biodegradable0.6337
Rat acute toxicity3.3966 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8844
hERG inhibition (predictor II)Non-inhibitor0.6887
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-3900100000-d4f10d08f06745544691

Taxonomy

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 / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
3-isobutyl-1-methylxanthine (CHEBI:43253) / a small molecule (CPD-5461)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase b binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. May play a role in fat metab...
Gene Name
PDE3B
Uniprot ID
Q13370
Uniprot Name
cGMP-inhibited 3',5'-cyclic phosphodiesterase B
Molecular Weight
124332.145 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name
PDE7A
Uniprot ID
Q13946
Uniprot Name
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
Molecular Weight
55504.475 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4D
Uniprot ID
Q08499
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Molecular Weight
91114.1 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Specifically hydrolyzes the second messenger cGMP, which is a key regulator of many important physiological processes. Highly specific: compared to other members of the cyclic nucleotide phosphodie...
Gene Name
PDE9A
Uniprot ID
O76083
Uniprot Name
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A
Molecular Weight
68491.95 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in maintaining basal levels of the cyclic nucleotide and/or in the cAMP reg...
Gene Name
PDE8A
Uniprot ID
O60658
Uniprot Name
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A
Molecular Weight
93303.05 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tpr domain binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.Isoform PDE2A2: Regulates Mit...
Gene Name
PDE2A
Uniprot ID
O00408
Uniprot Name
cGMP-dependent 3',5'-cyclic phosphodiesterase
Molecular Weight
105715.85 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Enzyme inhibitor activity
Specific Function
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name
PDE6G
Uniprot ID
P18545
Uniprot Name
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma
Molecular Weight
9643.09 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. [PubMed:10592235]

Drug created on September 15, 2010 15:27 / Updated on December 01, 2017 15:58