NAV

Cyclo(his-pro)

Identification

Generic Name
Cyclo(his-pro)
DrugBank Accession Number
DB02414
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 234.2545
Monoisotopic: 234.111675712
Chemical Formula
C11H14N4O2
Synonyms
  • (3S,8aS)-3-(1H-Imidazol-4-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
  • cyclo(histidyl-prolyl)
  • cyclo(L-His-L-Pro)
  • Histidyl-proline diketopiperazine
  • Histidyl-proline-diketopiperazine
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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 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 / Imidazoles / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds
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Substituents
1,4-diazinane / 2,5-dioxopiperazine / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Dioxopiperazine / Heteroaromatic compound
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
imidazoles, pyrrolopyrazine (CHEBI:41471)
Affected organisms
Not Available

Chemical Identifiers

UNII
Q10817UXVT
CAS number
53109-32-3
InChI Key
NAKUGCPAQTUSBE-IUCAKERBSA-N
InChI
InChI=1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1
IUPAC Name
(3S,8aS)-3-[(1H-imidazol-5-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dione
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O

References

General References
Not Available
PubChem Compound
449094
PubChem Substance
46506361
ChemSpider
395717
ChEBI
90039
ChEMBL
CHEMBL188225
ZINC
ZINC000004899569
PDBe Ligand
CHQ
PDB Entries
1w1t / 3n1a

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility11.8 mg/mLALOGPS
logP-0.64ALOGPS
logP-1.6Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.86Chemaxon
pKa (Strongest Basic)6.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area78.09 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity59.85 m3·mol-1Chemaxon
Polarizability23.46 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9825
Blood Brain Barrier+0.5574
Caco-2 permeable-0.6904
P-glycoprotein substrateSubstrate0.5956
P-glycoprotein inhibitor IInhibitor0.5226
P-glycoprotein inhibitor IIInhibitor0.5081
Renal organic cation transporterNon-inhibitor0.5747
CYP450 2C9 substrateNon-substrate0.8656
CYP450 2D6 substrateNon-substrate0.7071
CYP450 3A4 substrateNon-substrate0.5051
CYP450 1A2 substrateNon-inhibitor0.6703
CYP450 2C9 inhibitorNon-inhibitor0.6876
CYP450 2D6 inhibitorNon-inhibitor0.8719
CYP450 2C19 inhibitorNon-inhibitor0.7028
CYP450 3A4 inhibitorNon-inhibitor0.7232
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5392
Ames testNon AMES toxic0.8099
CarcinogenicityNon-carcinogens0.9574
BiodegradationNot ready biodegradable0.9937
Rat acute toxicity2.3170 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8749
hERG inhibition (predictor II)Non-inhibitor0.6996
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-MSsplash10-00kb-9120000000-c52cbaa093c30930bdbc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-f0f0620951f79c3a099c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-ba49fa3efaca5c30d946
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0290000000-46379bddc709172bfa39
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-1690000000-725cb05cb9d758174de1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9750000000-5e1c45f9fc63c5f0aeb9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0296-9620000000-4047b2d48c052ba68811
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]-143.488
predicted
DeepCCS 1.0 (2019)
[M+H]+145.88359
predicted
DeepCCS 1.0 (2019)
[M+Na]+151.89748
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 July 02, 2020 13:16