Isopenicillin N

Identification

Generic Name
Isopenicillin N
DrugBank Accession Number
DB03550
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 359.398
Monoisotopic: 359.115106109
Chemical Formula
C14H21N3O6S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

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
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 / 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
Aliphatic heteropolycyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Azacycle / Azetidine / Beta-lactam
show 31 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:18165)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
58678-43-6
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-carboxypentanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CCC[C@H](N)C(O)=O)C(O)=O

References

General References
Not Available
KEGG Compound
C05557
PubChem Compound
440723
PubChem Substance
46504620
ChemSpider
389596
ChEBI
18165
ZINC
ZINC000004096831
PDBe Ligand
IP1
PDB Entries
1qje / 6y0p / 6zao / 6zaq

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 Solubility8.96 mg/mLALOGPS
logP-1.4ALOGPS
logP-3.4Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.83Chemaxon
pKa (Strongest Basic)9.23Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area150.03 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity83.05 m3·mol-1Chemaxon
Polarizability35.64 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-MSsplash10-01ox-9225000000-979f250fa6dd5461f291
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-0952000000-08562930ce5ba1227584
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-71826aeb60faf831a6c8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0901000000-68828436b45415ceaf39
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-1394000000-cf618c9e4449e7092f85
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2910000000-9b55b4027f25708d71b6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9650000000-5021e546ba283933f08a
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]-191.0294001
predicted
DarkChem Lite v0.1.0
[M-H]-191.3192001
predicted
DarkChem Lite v0.1.0
[M-H]-176.70567
predicted
DeepCCS 1.0 (2019)
[M+H]+189.2174001
predicted
DarkChem Lite v0.1.0
[M+H]+190.0167001
predicted
DarkChem Lite v0.1.0
[M+H]+179.10124
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.0464001
predicted
DarkChem Lite v0.1.0
[M+Na]+190.7154001
predicted
DarkChem Lite v0.1.0
[M+Na]+185.01376
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52