Identification
Name(1S,5S,7R)-N~7~-(BIPHENYL-4-YLMETHYL)-N~3~-HYDROXY-6,8-DIOXA-3-AZABICYCLO[3.2.1]OCTANE-3,7-DICARBOXAMIDE
Accession NumberDB07026
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: 383.3978
Monoisotopic: 383.148120797
Chemical FormulaC20H21N3O5
InChI KeyPPLDARNGJSQINK-OKZBNKHCSA-N
InChI
InChI=1S/C20H21N3O5/c24-19(18-16-11-23(20(25)22-26)12-17(27-16)28-18)21-10-13-6-8-15(9-7-13)14-4-2-1-3-5-14/h1-9,16-18,26H,10-12H2,(H,21,24)(H,22,25)/t16-,17-,18+/m0/s1
IUPAC Name
(1S,5S,7R)-N3-hydroxy-N7-[(4-phenylphenyl)methyl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-3,7-dicarboxamide
SMILES
[H][C@]12CN(C[C@]([H])(O1)[C@@]([H])(O2)C(=O)NCC1=CC=C(C=C1)C1=CC=CC=C1)C(=O)NO
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Macrophage metalloelastaseProteinunknownNot AvailableHumanP39900 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 Solubility0.458 mg/mLALOGPS
logP1.34ALOGPS
logP1.51ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.04ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.13 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.56 m3·mol-1ChemAxon
Polarizability39.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9709
Blood Brain Barrier+0.8417
Caco-2 permeable-0.6685
P-glycoprotein substrateNon-substrate0.5548
P-glycoprotein inhibitor INon-inhibitor0.7543
P-glycoprotein inhibitor IINon-inhibitor0.9602
Renal organic cation transporterNon-inhibitor0.8647
CYP450 2C9 substrateNon-substrate0.8304
CYP450 2D6 substrateNon-substrate0.8136
CYP450 3A4 substrateNon-substrate0.5622
CYP450 1A2 substrateNon-inhibitor0.8043
CYP450 2C9 inhibitorNon-inhibitor0.748
CYP450 2D6 inhibitorNon-inhibitor0.8618
CYP450 2C19 inhibitorNon-inhibitor0.6286
CYP450 3A4 inhibitorNon-inhibitor0.7907
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8539
Ames testAMES toxic0.5515
CarcinogenicityNon-carcinogens0.7753
BiodegradationNot ready biodegradable0.5076
Rat acute toxicity2.5093 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9103
hERG inhibition (predictor II)Non-inhibitor0.6299
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBiphenyls and derivatives
Alternative ParentsMorpholine carboxylic acids and derivatives / 1,4-oxazepines / 1,3-dioxolanes / Secondary carboxylic acid amides / Oxacyclic compounds / Azacyclic compounds / Acetals / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
SubstituentsBiphenyl / Morpholine-4-carboxylic acid or derivatives / Para-oxazepine / Oxazinane / Morpholine / Meta-dioxolane / Carboxamide group / Secondary carboxylic acid amide / Acetal / Oxacycle
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
May be involved in tissue injury and remodeling. Has significant elastolytic activity. Can accept large and small amino acids at the P1' site, but has a preference for leucine. Aromatic or hydrophobic residues are preferred at the P1 site, with small hydrophobic residues (preferably alanine) occupying P3.
Gene Name:
MMP12
Uniprot ID:
P39900
Uniprot Name:
Macrophage metalloelastase
Molecular Weight:
54001.175 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 15:18 / Updated on June 11, 2017 21:04