Identification
NameN4-HYDROXY-2-ISOBUTYL-N1-(9-OXO-1,8-DIAZA-TRICYCLO[10.6.1.013,18]NONADECA-12(19),13,15,17-TETRAEN-10-YL)-SUCCINAMIDE
Accession NumberDB08489
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 456.5777
Monoisotopic: 456.27365566
Chemical FormulaC25H36N4O4
InChI KeyGCBPAPVOMPJQHK-NQIIRXRSSA-N
InChI
InChI=1S/C25H36N4O4/c1-17(2)13-18(15-23(30)28-33)24(31)27-21-14-19-16-29(22-10-6-5-9-20(19)22)12-8-4-3-7-11-26-25(21)32/h5-6,9-10,16-18,21,33H,3-4,7-8,11-15H2,1-2H3,(H,26,32)(H,27,31)(H,28,30)/t18-,21+/m1/s1
IUPAC Name
(2R)-N'-hydroxy-2-(2-methylpropyl)-N-[(10S)-9-oxo-1,8-diazatricyclo[10.6.1.0¹³,¹⁸]nonadeca-12(19),13(18),14,16-tetraen-10-yl]butanediamide
SMILES
[H][C@@](CC(C)C)(CC(=O)NO)C(=O)N[C@@]1([H])CC2=CN(CCCCCCNC1=O)C1=C2C=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
MatrilysinProteinunknownNot AvailableHumanP09237 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0139 mg/mLALOGPS
logP2.93ALOGPS
logP2.66ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.9ChemAxon
pKa (Strongest Basic)-0.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area112.46 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity126.81 m3·mol-1ChemAxon
Polarizability50.08 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9198
Blood Brain Barrier-0.7888
Caco-2 permeable-0.7742
P-glycoprotein substrateSubstrate0.7436
P-glycoprotein inhibitor INon-inhibitor0.8036
P-glycoprotein inhibitor IINon-inhibitor0.8682
Renal organic cation transporterNon-inhibitor0.9166
CYP450 2C9 substrateNon-substrate0.8694
CYP450 2D6 substrateNon-substrate0.7928
CYP450 3A4 substrateSubstrate0.6274
CYP450 1A2 substrateNon-inhibitor0.8924
CYP450 2C9 inhibitorNon-inhibitor0.7989
CYP450 2D6 inhibitorNon-inhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.7486
CYP450 3A4 inhibitorNon-inhibitor0.8695
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9442
Ames testNon AMES toxic0.5945
CarcinogenicityNon-carcinogens0.7613
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5118 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9439
hERG inhibition (predictor II)Non-inhibitor0.6616
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassMacrolactams
Direct ParentMacrolactams
Alternative ParentsN-acyl-alpha amino acids and derivatives / 3-alkylindoles / N-acyl amines / Benzenoids / Pyrroles / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Hydroxamic acids / Azacyclic compounds
SubstituentsMacrolactam / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 3-alkylindole / Indole / Indole or derivatives / Fatty amide / Fatty acyl / Benzenoid / N-acyl-amine
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Degrades casein, gelatins of types I, III, IV, and V, and fibronectin. Activates procollagenase.
Gene Name:
MMP7
Uniprot ID:
P09237
Uniprot Name:
Matrilysin
Molecular Weight:
29676.62 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 15:32 / Updated on June 11, 2017 21:18