NAV

methyl 4-bromo-N-[8-(hydroxyamino)-8-oxooctanoyl]-L-phenylalaninate

Identification

Generic Name
methyl 4-bromo-N-[8-(hydroxyamino)-8-oxooctanoyl]-L-phenylalaninate
DrugBank Accession Number
DB08505
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 429.306
Monoisotopic: 428.094684567
Chemical Formula
C18H25BrN2O5
Synonyms
Not Available
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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
UHistone deacetylase-like amidohydrolaseNot AvailableAlcaligenes sp. (strain DSM 11172)
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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Amphetamines and derivatives / Bromobenzenes / Fatty acid esters / Aryl bromides / N-acyl amines / Methyl esters / Secondary carboxylic acid amides / Hydroxamic acids
show 7 more
Substituents
Alpha-amino acid ester / Amphetamine or derivatives / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Benzenoid / Bromobenzene / Carbonyl group / Carboxamide group / Carboxylic acid ester
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
UPYGSQPRAHMDPD-HNNXBMFYSA-N
InChI
InChI=1S/C18H25BrN2O5/c1-26-18(24)15(12-13-8-10-14(19)11-9-13)20-16(22)6-4-2-3-5-7-17(23)21-25/h8-11,15,25H,2-7,12H2,1H3,(H,20,22)(H,21,23)/t15-/m0/s1
IUPAC Name
methyl (2S)-3-(4-bromophenyl)-2-[7-(hydroxycarbamoyl)heptanamido]propanoate
SMILES
[H][C@@](CC1=CC=C(Br)C=C1)(NC(=O)CCCCCCC(=O)NO)C(=O)OC

References

General References
Not Available
PubChem Compound
23640756
PubChem Substance
99444976
ChemSpider
23319843
BindingDB
50375546
ChEMBL
CHEMBL406734
ZINC
ZINC000016052595
PDBe Ligand
S17
PDB Entries
2vcg

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 Solubility0.00778 mg/mLALOGPS
logP2.44ALOGPS
logP2.6Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.91Chemaxon
pKa (Strongest Basic)-1.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area104.73 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity99.84 m3·mol-1Chemaxon
Polarizability40.87 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5894
Blood Brain Barrier+0.911
Caco-2 permeable-0.7295
P-glycoprotein substrateNon-substrate0.5495
P-glycoprotein inhibitor INon-inhibitor0.7545
P-glycoprotein inhibitor IINon-inhibitor0.871
Renal organic cation transporterNon-inhibitor0.9178
CYP450 2C9 substrateNon-substrate0.8437
CYP450 2D6 substrateNon-substrate0.8335
CYP450 3A4 substrateNon-substrate0.5381
CYP450 1A2 substrateNon-inhibitor0.7396
CYP450 2C9 inhibitorNon-inhibitor0.8244
CYP450 2D6 inhibitorNon-inhibitor0.8637
CYP450 2C19 inhibitorNon-inhibitor0.8105
CYP450 3A4 inhibitorNon-inhibitor0.8105
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8992
Ames testNon AMES toxic0.5482
CarcinogenicityNon-carcinogens0.8761
BiodegradationNot ready biodegradable0.9828
Rat acute toxicity2.3391 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9826
hERG inhibition (predictor II)Non-inhibitor0.7305
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/MSsplash10-00p1-0219100000-300dc2203a5a71b48620
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0019400000-1469e1e1042268985508
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-1829000000-d4b15b30a22811e34fde
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gxt-3139000000-a5ebdbbe8762af06887b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00l6-8922000000-fe986f026c92394f7d21
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01si-9762000000-0cc5def9e26804f264ff
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]-190.2423
predicted
DeepCCS 1.0 (2019)
[M+H]+192.6003
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.39816
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histone deacetylase-like amidohydrolase
Kind
Protein
Organism
Alcaligenes sp. (strain DSM 11172)
Pharmacological action
Unknown
General Function
Hydrolase activity
Specific Function
Exhibits significant levels of protein deacetylase activity comparable to those of eukaryotic HDACs in assays both with fluorogenic peptidic substrates and acetate-radiolabeled histones. Accepts pr...
Gene Name
hdaH
Uniprot ID
Q70I53
Uniprot Name
Histone deacetylase-like amidohydrolase
Molecular Weight
39423.38 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 21:32 / Updated at June 12, 2020 16:52