N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}-4-{[4-(morpholin-4-ylmethyl)phenyl]ethynyl}benzamide

Identification

Generic Name
N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}-4-{[4-(morpholin-4-ylmethyl)phenyl]ethynyl}benzamide
DrugBank Accession Number
DB07536
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 437.4883
Monoisotopic: 437.195070989
Chemical Formula
C24H27N3O5
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylaseNot AvailableAquifex aeolicus (strain VF5)
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
Medicalerrors
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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 hippuric acids and derivatives. These are compounds containing a hippuric acid or a derivative, with a structure characterized the presence of a benzoyl group linked to the N-terminal of a glycine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Hippuric acids and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Phenylmethylamines / Benzoyl derivatives / Benzylamines / Aralkylamines / Morpholines / Trialkylamines / Secondary carboxylic acid amides / Secondary alcohols / Hydroxamic acids
show 7 more
Substituents
Alcohol / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzoyl / Benzylamine / Carbonyl group
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FQYBTYFKOHPWQT-VGSWGCGISA-N
InChI
InChI=1S/C24H27N3O5/c1-17(28)22(24(30)26-31)25-23(29)21-10-8-19(9-11-21)3-2-18-4-6-20(7-5-18)16-27-12-14-32-15-13-27/h4-11,17,22,28,31H,12-16H2,1H3,(H,25,29)(H,26,30)/t17-,22+/m1/s1
IUPAC Name
(2S,3R)-N,3-dihydroxy-2-[(4-{2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl}phenyl)formamido]butanamide
SMILES
[H][C@](C)(O)[C@]([H])(NC(=O)C1=CC=C(C=C1)C#CC1=CC=C(CN2CCOCC2)C=C1)C(=O)NO

References

General References
Not Available
PubChem Compound
11546620
PubChem Substance
99444007
ChemSpider
9721399
BindingDB
50200120
ChEBI
134107
ChEMBL
CHEMBL260091
ZINC
ZINC000029049396
PDBe Ligand
C90
PDB Entries
2jt2 / 3nzk / 5u39 / 5vwm

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 Solubility0.0159 mg/mLALOGPS
logP1.53ALOGPS
logP1.39ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.71ChemAxon
pKa (Strongest Basic)6.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area111.13 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.61 m3·mol-1ChemAxon
Polarizability47.75 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6583
Blood Brain Barrier-0.6853
Caco-2 permeable-0.6911
P-glycoprotein substrateSubstrate0.7665
P-glycoprotein inhibitor INon-inhibitor0.5328
P-glycoprotein inhibitor IINon-inhibitor0.968
Renal organic cation transporterNon-inhibitor0.8564
CYP450 2C9 substrateNon-substrate0.8648
CYP450 2D6 substrateNon-substrate0.8157
CYP450 3A4 substrateNon-substrate0.5149
CYP450 1A2 substrateNon-inhibitor0.8457
CYP450 2C9 inhibitorNon-inhibitor0.7563
CYP450 2D6 inhibitorNon-inhibitor0.8521
CYP450 2C19 inhibitorNon-inhibitor0.7477
CYP450 3A4 inhibitorNon-inhibitor0.8099
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9421
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.7826
BiodegradationNot ready biodegradable0.9846
Rat acute toxicity2.3857 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8025
hERG inhibition (predictor II)Inhibitor0.5244
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/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

Targets

Drugtargets
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Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
Udp-3-o-[3-hydroxymyristoyl] n-acetylglucosamine deacetylase activity
Specific Function
Involved in the biosynthesis of lipid A, a phosphorylated glycolipid that anchors the lipopolysaccharide to the outer membrane of the cell.
Gene Name
lpxC
Uniprot ID
O67648
Uniprot Name
UDP-3-O-[3-hydroxymyristoyl] N-acetylglucosamine deacetylase
Molecular Weight
32144.765 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 on September 15, 2010 21:23 / Updated on June 12, 2020 16:52