Isopenicillin N

Identification

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Name
Isopenicillin N
Accession Number
DB03550  (EXPT01909)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 359.398
Monoisotopic: 359.115106109
Chemical Formula
C14H21N3O6S
InChI Key
MIFYHUACUWQUKT-GTQWGBSQSA-N
InChI
InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8+,9-,11+/m0/s1
IUPAC Name
(2S,5R,6R)-6-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@](N)(CCCC(O)=N[C@]1([H])C(=O)N2[C@]1([H])SC(C)(C)[C@]2([H])C(O)=O)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
KEGG Compound
C05557
PubChem Compound
440723
PubChem Substance
46504620
ChemSpider
389596
ChEBI
18165
HET
IP1
PDB Entries
1qje

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 Solubility0.791 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.6ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area153.52 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity83.57 m3·mol-1ChemAxon
Polarizability35.26 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9895
Blood Brain Barrier-0.9909
Caco-2 permeable-0.8304
P-glycoprotein substrateSubstrate0.6689
P-glycoprotein inhibitor INon-inhibitor0.9162
P-glycoprotein inhibitor IINon-inhibitor0.9974
Renal organic cation transporterNon-inhibitor0.9571
CYP450 2C9 substrateNon-substrate0.8432
CYP450 2D6 substrateNon-substrate0.8214
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8868
CYP450 2C9 inhibitorNon-inhibitor0.9069
CYP450 2D6 inhibitorNon-inhibitor0.9253
CYP450 2C19 inhibitorNon-inhibitor0.8939
CYP450 3A4 inhibitorNon-inhibitor0.8408
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.986
Ames testNon AMES toxic0.8601
CarcinogenicityNon-carcinogens0.8387
BiodegradationNot ready biodegradable0.9571
Rat acute toxicity1.9690 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9995
hERG inhibition (predictor II)Non-inhibitor0.9066
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 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 / L-alpha-amino acids / Medium-chain fatty acids / Heterocyclic fatty acids / Dicarboxylic acids and derivatives / N-acyl amines / Thiazolidines / Tertiary carboxylic acid amides / Amino acids
show 11 more
Substituents
Alpha-dipeptide / Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid / Penam / Medium-chain fatty acid / Heterocyclic fatty acid / Dicarboxylic acid or derivatives
show 31 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:18165)

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:52