NAV

N-[(2S,4S,6R)-2-(dihydroxymethyl)-4-hydroxy-3,3-dimethyl-7-oxo-4lambda~4~-thia-1-azabicyclo[3.2.0]hept-6-yl]-2-phenylacetamide

Identification

Generic Name
N-[(2S,4S,6R)-2-(dihydroxymethyl)-4-hydroxy-3,3-dimethyl-7-oxo-4lambda~4~-thia-1-azabicyclo[3.2.0]hept-6-yl]-2-phenylacetamide
DrugBank Accession Number
DB08559
Background

N-[(2S,4S,6R)-2-(dihydroxymethyl)-4-hydroxy-3,3-dimethyl-7-oxo-4lambda~4~-thia-1-azabicyclo[3.2.0]hept-6-yl]-2-phenylacetamide is a solid. This compound belongs to the penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1]. This drug is known to target penicillin G acylase.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 352.405
Monoisotopic: 352.10929245
Chemical Formula
C16H20N2O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPenicillin G acylaseNot AvailableEscherichia coli
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Penicillins / N-acyl-alpha amino acids and derivatives / Phenylacetamides / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azetidines / Alkylthiols / Azacyclic compounds / Carboxylic acids
show 6 more
Substituents
Alkylthiol / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
WMPGEOZLAYOFHH-MBNYWOFBSA-N
InChI
InChI=1S/C16H20N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24(16)23)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14,23-24H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
IUPAC Name
(2S,5R,6R)-4-hydroxy-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@@]1(NC(=O)CC2=CC=CC=C2)C(=O)[N@]2[C@]1([H])[S@@]([H])(O)C(C)(C)[C@]2([H])C(O)=O

References

General References
Not Available
PubChem Compound
5289386
PubChem Substance
99445030
ChemSpider
25058322
PDBe Ligand
SOX
PDB Entries
1gm8 / 1gm9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility6.2 mg/mLALOGPS
logP0.75ALOGPS
logP0.068Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.35Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area106.94 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity85.85 m3·mol-1Chemaxon
Polarizability35.04 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9898
Blood Brain Barrier-0.9885
Caco-2 permeable-0.7254
P-glycoprotein substrateSubstrate0.5879
P-glycoprotein inhibitor INon-inhibitor0.9106
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9597
CYP450 2C9 substrateNon-substrate0.7773
CYP450 2D6 substrateNon-substrate0.8171
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.7736
CYP450 2C9 inhibitorNon-inhibitor0.8
CYP450 2D6 inhibitorNon-inhibitor0.8898
CYP450 2C19 inhibitorNon-inhibitor0.7797
CYP450 3A4 inhibitorNon-inhibitor0.8132
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9668
Ames testNon AMES toxic0.7465
CarcinogenicityCarcinogens 0.5485
BiodegradationNot ready biodegradable0.8801
Rat acute toxicity2.3082 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9983
hERG inhibition (predictor II)Non-inhibitor0.852
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-MSsplash10-0006-9314000000-a7ed903e6ea67e371211
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fi0-0904000000-b48c77f37e79408b7a26
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0896000000-baba8878ca66a6e84f4f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udv-4952000000-f16d7b7837c7fe1115b9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-1494000000-28e98d1d3829cb5ce391
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9521000000-6910eb960adbcf3f731b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9310000000-15da3d7a196fe7e44a3b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-159.84596
predicted
DeepCCS 1.0 (2019)
[M+H]+162.59016
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.73473
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Penicillin G acylase
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Penicillin amidase activity
Specific Function
Not Available
Gene Name
pac
Uniprot ID
P06875
Uniprot Name
Penicillin G acylase
Molecular Weight
94642.025 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. [Article]

Drug created at September 15, 2010 21:32 / Updated at June 12, 2020 16:52