1-((1R)-1-(HYDROXYMETHYL)-3-{6-[(3-PHENYLPROPANOYL)AMINO]-1H-INDOL-1-YL}PROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE

Identification

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Name
1-((1R)-1-(HYDROXYMETHYL)-3-{6-[(3-PHENYLPROPANOYL)AMINO]-1H-INDOL-1-YL}PROPYL)-1H-IMIDAZOLE-4-CARBOXAMIDE
Accession Number
DB07783
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 445.5136
Monoisotopic: 445.211389755
Chemical Formula
C25H27N5O3
InChI Key
GUYYFMCFEPDDFL-OAQYLSRUSA-N
InChI
InChI=1S/C25H27N5O3/c26-25(33)22-15-30(17-27-22)21(16-31)11-13-29-12-10-19-7-8-20(14-23(19)29)28-24(32)9-6-18-4-2-1-3-5-18/h1-5,7-8,10,12,14-15,17,21,31H,6,9,11,13,16H2,(H2,26,33)(H,28,32)/t21-/m1/s1
IUPAC Name
1-[(2R)-1-hydroxy-4-[6-(3-phenylpropanamido)-1H-indol-1-yl]butan-2-yl]-1H-imidazole-4-carboxamide
SMILES
[H][C@](CO)(CCN1C=CC2=C1C=C(NC(=O)CCC1=CC=CC=C1)C=C2)N1C=NC(=C1)C(N)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAdenosine deaminaseNot 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
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
PubChem Compound
448903
PubChem Substance
99444254
ChemSpider
395565
BindingDB
22929
ChEMBL
CHEMBL338076
HET
FR4
PDB Entries
1uml

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 Solubility0.032 mg/mLALOGPS
logP2.88ALOGPS
logP2.39ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)3.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area115.17 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity127.7 m3·mol-1ChemAxon
Polarizability48.16 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9608
Blood Brain Barrier+0.7661
Caco-2 permeable-0.8362
P-glycoprotein substrateSubstrate0.6218
P-glycoprotein inhibitor INon-inhibitor0.8296
P-glycoprotein inhibitor IINon-inhibitor0.703
Renal organic cation transporterNon-inhibitor0.7335
CYP450 2C9 substrateNon-substrate0.8113
CYP450 2D6 substrateNon-substrate0.7604
CYP450 3A4 substrateNon-substrate0.6386
CYP450 1A2 substrateNon-inhibitor0.8528
CYP450 2C9 inhibitorNon-inhibitor0.7015
CYP450 2D6 inhibitorNon-inhibitor0.8712
CYP450 2C19 inhibitorNon-inhibitor0.713
CYP450 3A4 inhibitorNon-inhibitor0.5688
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6645
Ames testNon AMES toxic0.5569
CarcinogenicityNon-carcinogens0.8638
BiodegradationNot ready biodegradable0.9464
Rat acute toxicity2.1194 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9599
hERG inhibition (predictor II)Inhibitor0.6527
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/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

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
Indoles / 2-heteroaryl carboxamides / N-arylamides / Carbonylimidazoles / N-substituted imidazoles / Substituted pyrroles / Fatty amides / Benzene and substituted derivatives / Heteroaromatic compounds / Vinylogous amides
show 8 more
Substituents
N-alkylindole / Indole / 2-heteroaryl carboxamide / N-arylamide / Imidazole-4-carbonyl group / Monocyclic benzene moiety / Fatty amide / N-substituted imidazole / Substituted pyrrole / Fatty acyl
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Adenosine deaminase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 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 15:25 / Updated on June 04, 2019 06:46