NAV

(3S,6S)-3,6-bis(4-hydroxybenzyl)piperazine-2,5-dione

Identification

Generic Name
(3S,6S)-3,6-bis(4-hydroxybenzyl)piperazine-2,5-dione
DrugBank Accession Number
DB08761
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 326.3465
Monoisotopic: 326.126657074
Chemical Formula
C18H18N2O4
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMycocyclosin synthaseNot AvailableMycobacterium tuberculosis
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Secondary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
1,4-diazinane / 1-hydroxy-2-unsubstituted benzenoid / 2,5-dioxopiperazine / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Dioxopiperazine
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
cyclo(tyrosyl-tyrosyl) (CHEBI:65063)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NGPCLOGFGKJCBP-HOTGVXAUSA-N
InChI
InChI=1S/C18H18N2O4/c21-13-5-1-11(2-6-13)9-15-17(23)20-16(18(24)19-15)10-12-3-7-14(22)8-4-12/h1-8,15-16,21-22H,9-10H2,(H,19,24)(H,20,23)/t15-,16-/m0/s1
IUPAC Name
(3S,6S)-3,6-bis[(4-hydroxyphenyl)methyl]piperazine-2,5-dione
SMILES
[H][C@@]1(CC2=CC=C(O)C=C2)NC(=O)[C@]([H])(CC2=CC=C(O)C=C2)NC1=O

References

General References
Not Available
PubChem Compound
11267350
PubChem Substance
99445232
ChemSpider
9442361
ChEBI
65063
ChEMBL
CHEMBL189558
PDBe Ligand
YTT
PDB Entries
3g5h / 5wp2 / 8tdp / 8tdq

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 Solubility0.147 mg/mLALOGPS
logP1.25ALOGPS
logP1.63Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.19Chemaxon
pKa (Strongest Basic)-4.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area98.66 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity87.79 m3·mol-1Chemaxon
Polarizability32.23 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7675
Blood Brain Barrier-0.5523
Caco-2 permeable-0.7828
P-glycoprotein substrateSubstrate0.6429
P-glycoprotein inhibitor INon-inhibitor0.9389
P-glycoprotein inhibitor IINon-inhibitor0.9888
Renal organic cation transporterNon-inhibitor0.9157
CYP450 2C9 substrateNon-substrate0.8553
CYP450 2D6 substrateNon-substrate0.8
CYP450 3A4 substrateNon-substrate0.6364
CYP450 1A2 substrateNon-inhibitor0.9119
CYP450 2C9 inhibitorNon-inhibitor0.9196
CYP450 2D6 inhibitorNon-inhibitor0.9079
CYP450 2C19 inhibitorNon-inhibitor0.9201
CYP450 3A4 inhibitorNon-inhibitor0.8907
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.956
Ames testNon AMES toxic0.9397
CarcinogenicityNon-carcinogens0.9238
BiodegradationNot ready biodegradable0.9548
Rat acute toxicity2.3063 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9773
hERG inhibition (predictor II)Non-inhibitor0.9327
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-b6cbbed031c1f3c93ad6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-4ec7ef56183c071166fb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0059-0689000000-dfb6ae311947f544fc86
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2149000000-dd3d59376f87a4828a61
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ed-3961000000-b3ce5405e5d30feecb63
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03k9-0920000000-175a7e59cbdbf633ac09
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]-193.212433
predicted
DarkChem Lite v0.1.0
[M-H]-184.85863
predicted
DeepCCS 1.0 (2019)
[M+H]+193.124433
predicted
DarkChem Lite v0.1.0
[M+H]+187.25421
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.344433
predicted
DarkChem Lite v0.1.0
[M+Na]+193.2837
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Mycocyclosin synthase
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes C-C bond formation between the carbons ortho to the phenolic hydroxyl of cyclo(L-tyr-L-tyr) (cYY) producing mycocyclosin. Can also use cyclo(L-Tyr-L-Phe) (cYF), cyclo(L-Tyr-L-Trp) (cYW) and cyclo(L-Tyr-L-3,4-dihydroxyphenylalanine) (cY-DOPA) as substrate.
Specific Function
Carbon monoxide binding
Gene Name
cyp121
Uniprot ID
P9WPP7
Uniprot Name
Mycocyclosin synthase
Molecular Weight
43255.455 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. [Article]

Drug created at September 15, 2010 21:34 / Updated at June 12, 2020 16:52