(1S,5S,7R)-N~7~-(BIPHENYL-4-YLMETHYL)-N~3~-HYDROXY-6,8-DIOXA-3-AZABICYCLO[3.2.1]OCTANE-3,7-DICARBOXAMIDE

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 Number
DB07026
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: 383.3978
Monoisotopic: 383.148120797
Chemical Formula
C20H21N3O5
InChI Key
PPLDARNGJSQINK-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][[email protected]]12CN(C[[email protected]]([H])(O1)[[email protected]@]([H])(O2)C(=O)NCC1=CC=C(C=C1)C1=CC=CC=C1)C(=O)NO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMacrophage metalloelastaseNot 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
PubChem Compound
11987860
PubChem Substance
99443497
ChemSpider
10160333
BindingDB
29018
HET
37A
PDB Entries
2hu6

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 Solubility0.458 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
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 biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Morpholine carboxylic acids and derivatives / 1,4-oxazepines / 1,3-dioxolanes / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Oxacyclic compounds / Azacyclic compounds / Acetals / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Biphenyl / Morpholine-4-carboxylic acid or derivatives / Para-oxazepine / Oxazinane / Morpholine / Meta-dioxolane / Carboxamide group / Secondary carboxylic acid amide / Carbonic acid derivative / Acetal
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not 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 hydropho...
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 December 01, 2017 15:45