Identification

Name
Degraded Cephaloridine
Accession Number
DB04133  (EXPT00884)
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: 340.418
Monoisotopic: 340.05514839
Chemical Formula
C14H16N2O4S2
InChI Key
SFVACKBZMIZHCK-ZWNOBZJWSA-N
InChI
InChI=1S/C14H16N2O4S2/c1-8-7-22-13(16-12(8)14(19)20)10(6-17)15-11(18)5-9-3-2-4-21-9/h2-4,6,10,13,16H,5,7H2,1H3,(H,15,18)(H,19,20)/t10-,13-/m1/s1
IUPAC Name
(2R)-5-methyl-2-[(1R)-2-oxo-1-[2-(thiophen-2-yl)acetamido]ethyl]-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
SMILES
[H][C@@](NC(=O)CC1=CC=CS1)(C=O)[C@]1([H])NC(C(O)=O)=C(C)CS1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot AvailableStaphylococcus aureus
APenicillin-binding protein 1A
inhibitor
Clostridium perfringens (strain 13 / Type A)
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
5287902
PubChem Substance
46507610
ChemSpider
4450179
HET
CED
PDB Entries
1ghm / 3sh8 / 4n9k / 5ghy / 5ghz

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 Solubility0.0411 mg/mLALOGPS
logP1.12ALOGPS
logP0.86ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-0.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.02 m3·mol-1ChemAxon
Polarizability33.42 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6262
Blood Brain Barrier-0.9406
Caco-2 permeable-0.7226
P-glycoprotein substrateSubstrate0.7319
P-glycoprotein inhibitor INon-inhibitor0.8802
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9406
CYP450 2C9 substrateNon-substrate0.7947
CYP450 2D6 substrateNon-substrate0.8108
CYP450 3A4 substrateNon-substrate0.5515
CYP450 1A2 substrateNon-inhibitor0.8225
CYP450 2C9 inhibitorNon-inhibitor0.7681
CYP450 2D6 inhibitorNon-inhibitor0.9287
CYP450 2C19 inhibitorNon-inhibitor0.7594
CYP450 3A4 inhibitorNon-inhibitor0.943
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8358
Ames testNon AMES toxic0.8111
CarcinogenicityNon-carcinogens0.9428
BiodegradationNot ready biodegradable0.777
Rat acute toxicity2.3269 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9897
hERG inhibition (predictor II)Non-inhibitor0.9612
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-MSNot Available
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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
1,3-thiazines / Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Thiohemiaminal derivatives / Azacyclic compounds / Carboxylic acids / Dialkylamines / Monocarboxylic acids and derivatives
show 6 more
Substituents
Alpha-amino acid or derivatives / Meta-thiazine / Thiophene / Heteroaromatic compound / Carboxamide group / Secondary carboxylic acid amide / Amino acid / Carboxylic acid / Secondary aliphatic amine / Enamine
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiophenes, thiazinemonocarboxylic acid, 1,3-thiazine (CHEBI:41453)

Targets

Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
Not Available
Gene Name
blaZ
Uniprot ID
P00807
Uniprot Name
Beta-lactamase
Molecular Weight
31348.98 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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]
Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring glycosyl groups
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
pbpA
Uniprot ID
Q8XJ01
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
75176.35 Da
References
  1. Powell JK, Young KD: Lysis of Escherichia coli by beta-lactams which bind penicillin-binding proteins 1a and 1b: inhibition by heat shock proteins. J Bacteriol. 1991 Jul;173(13):4021-6. [PubMed:2061284]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [PubMed:12650826]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [PubMed:12650826]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Khamdang S, Takeda M, Babu E, Noshiro R, Onozato ML, Tojo A, Enomoto A, Huang XL, Narikawa S, Anzai N, Piyachaturawat P, Endou H: Interaction of human and rat organic anion transporter 2 with various cephalosporin antibiotics. Eur J Pharmacol. 2003 Mar 28;465(1-2):1-7. [PubMed:12650826]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 05:16