(3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione

Identification

Name
(3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione
Accession Number
DB04520  (EXPT03139)
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: 260.2884
Monoisotopic: 260.116092388
Chemical Formula
C14H16N2O3
InChI Key
LSGOTAXPWMCUCK-RYUDHWBXSA-N
InChI
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
IUPAC Name
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione
SMILES
[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=C(O)C=C1)NC2=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UChitinase BNot AvailableSerratia marcescens
UChitinaseNot 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
KEGG Compound
C10605
PubChem Compound
119404
PubChem Substance
46507651
ChemSpider
106647
ChEBI
6631
ChEMBL
CHEMBL359788
ZINC
ZINC000001629943
PDBe Ligand
TYP
PDB Entries
1w1y

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 Solubility11.2 mg/mLALOGPS
logP0.44ALOGPS
logP0.55ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.49ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.64 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.88 m3·mol-1ChemAxon
Polarizability26.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9818
Blood Brain Barrier-0.6267
Caco-2 permeable-0.7219
P-glycoprotein substrateSubstrate0.7624
P-glycoprotein inhibitor INon-inhibitor0.6511
P-glycoprotein inhibitor IIInhibitor0.6391
Renal organic cation transporterNon-inhibitor0.6329
CYP450 2C9 substrateNon-substrate0.8569
CYP450 2D6 substrateNon-substrate0.6472
CYP450 3A4 substrateSubstrate0.5241
CYP450 1A2 substrateNon-inhibitor0.8801
CYP450 2C9 inhibitorNon-inhibitor0.8033
CYP450 2D6 inhibitorNon-inhibitor0.7185
CYP450 2C19 inhibitorNon-inhibitor0.6279
CYP450 3A4 inhibitorNon-inhibitor0.711
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6733
Ames testNon AMES toxic0.8383
CarcinogenicityNon-carcinogens0.9361
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4729 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8831
hERG inhibition (predictor II)Non-inhibitor0.6239
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-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Pyrrolidines / Cyclic carboximidic acids / Lactams / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
Alpha-amino acid or derivatives / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Benzenoid / Pyrrolidine / Tertiary carboxylic acid amide / Cyclic carboximidic acid / Carboxamide group / Lactam
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenols, dipeptide, homodetic cyclic peptide, pyrrolopyrazine (CHEBI:6631)

Targets

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. [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]
Kind
Protein
Organism
Serratia marcescens
Pharmacological action
Unknown
General Function
Chitinase activity
Specific Function
Not Available
Gene Name
chiB
Uniprot ID
Q54276
Uniprot Name
Chitinase
Molecular Weight
55468.96 Da
References
  1. 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]

Drug created on June 13, 2005 07:24 / Updated on March 01, 2020 19:24

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