Nitrocefin

Identification

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Name
Nitrocefin
Accession Number
DB11592
Type
Small Molecule
Groups
Experimental
Description

Nitrocefin is a chromogenic cephalosporin substrate used to detect the presence of beta-lactamase enzymes, an important mediator of bacterial antibiotic resistance. While other detection methods exist, such as PCR, nitrocefin allows for rapid detection using few materials and inexpensive equipment.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
EWP54G0J8F
CAS number
41906-86-9
Weight
Average: 516.5
Monoisotopic: 516.040955839
Chemical Formula
C21H16N4O8S2
InChI Key
LHNIIDJCEODSHA-OQRUQETBSA-N
InChI
InChI=1S/C21H16N4O8S2/c26-16(9-14-2-1-7-34-14)22-17-19(27)23-18(21(28)29)12(10-35-20(17)23)4-3-11-5-6-13(24(30)31)8-15(11)25(32)33/h1-8,17,20H,9-10H2,(H,22,26)(H,28,29)/b4-3+/t17-,20-/m1/s1
IUPAC Name
(6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(\C=C\C3=CC=C(C=C3[N+]([O-])=O)[N+]([O-])=O)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CS1)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
6436140
PubChem Substance
347827999
ChemSpider
4940809
ChEMBL
CHEMBL480517
Wikipedia
Nitrocefin

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 Solubility0.0022 mg/mLALOGPS
logP2.52ALOGPS
logP2.48ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area172.99 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity125.92 m3·mol-1ChemAxon
Polarizability46.68 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

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 cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Nitrobenzenes / Styrenes / Nitroaromatic compounds / 1,3-thiazines / Thiophenes / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines
show 12 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Nitrobenzene / Nitroaromatic compound / Styrene / Monocyclic benzene moiety / Meta-thiazine / Benzenoid / Heteroaromatic compound
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on May 11, 2016 14:21 / Updated on June 04, 2019 07:24