NAV

Verpacamide A

Identification

Generic Name
Verpacamide A
DrugBank Accession Number
DB04433
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 253.3009
Monoisotopic: 253.153874877
Chemical Formula
C11H19N5O2
Synonyms
  • Cyclo-(L-arginine-L-proline) inhibitor
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UChitinase BNot AvailableSerratia marcescens
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 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
2,5-dioxopiperazines / N-alkylpiperazines / Tertiary carboxylic acid amides / Pyrrolidines / Secondary carboxylic acid amides / Lactams / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds
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Substituents
1,4-diazinane / 2,5-dioxopiperazine / Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Carboximidamide / Dioxopiperazine / Guanidine
show 16 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
guanidines, pyrrolopyrazine (CHEBI:40745)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZRJHYOXNWCMGMW-YUMQZZPRSA-N
InChI
InChI=1S/C11H19N5O2/c12-11(13)14-5-1-3-7-10(18)16-6-2-4-8(16)9(17)15-7/h7-8H,1-6H2,(H,15,17)(H4,12,13,14)/t7-,8-/m0/s1
IUPAC Name
N-{3-[(3S,8aS)-1,4-dioxo-octahydropyrrolo[1,2-a]pyrazin-3-yl]propyl}guanidine
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CCCNC(N)=N)NC2=O

References

General References
Not Available
PubChem Compound
449095
PubChem Substance
46505787
ChemSpider
395718
ZINC
ZINC000013584769
PDBe Ligand
ALJ
PDB Entries
1w1v

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 Solubility1.6 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.1Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.27Chemaxon
pKa (Strongest Basic)12.17Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area111.31 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity75.71 m3·mol-1Chemaxon
Polarizability26.68 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9519
Blood Brain Barrier+0.7097
Caco-2 permeable-0.6954
P-glycoprotein substrateSubstrate0.7339
P-glycoprotein inhibitor INon-inhibitor0.732
P-glycoprotein inhibitor IINon-inhibitor0.7704
Renal organic cation transporterInhibitor0.5772
CYP450 2C9 substrateNon-substrate0.8972
CYP450 2D6 substrateNon-substrate0.6812
CYP450 3A4 substrateNon-substrate0.5789
CYP450 1A2 substrateNon-inhibitor0.8073
CYP450 2C9 inhibitorNon-inhibitor0.8722
CYP450 2D6 inhibitorNon-inhibitor0.8805
CYP450 2C19 inhibitorNon-inhibitor0.832
CYP450 3A4 inhibitorNon-inhibitor0.9524
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9781
Ames testNon AMES toxic0.6619
CarcinogenicityNon-carcinogens0.9556
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5631 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8263
hERG inhibition (predictor II)Non-inhibitor0.8264
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-MSsplash10-002g-9110000000-51a30f457afcc1fbe116
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-bcddb096672609ce4b53
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-04f0e70db3e86934e2a9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6t-2970000000-1c5c2d35a937d7759ad0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-8090000000-f73d1e916a8a99518e9a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-9720000000-13819bdb954a7e1883fc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zor-3930000000-87fde5cb355cb7e20ecf
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]-175.1659667
predicted
DarkChem Lite v0.1.0
[M-H]-149.53923
predicted
DeepCCS 1.0 (2019)
[M+H]+175.9069667
predicted
DarkChem Lite v0.1.0
[M+H]+151.9348
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.9469667
predicted
DarkChem Lite v0.1.0
[M+Na]+157.97098
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Chitinase B
Kind
Protein
Organism
Serratia marcescens
Pharmacological action
Unknown
General Function
Chitinase activity
Specific Function
Not Available
Gene Name
chiB
Uniprot ID
P11797
Uniprot Name
Chitinase B
Molecular Weight
55463.97 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. [Article]
  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. [Article]

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