2-[(Formyl-Hydroxy-Amino)-Methyl]-Heptanoic Acid [1-(2-Hydroxymethyl-Pyrrolidine-1-Carbonyl)-2-Methyl-Propyl]-Amide

Identification

Name
2-[(Formyl-Hydroxy-Amino)-Methyl]-Heptanoic Acid [1-(2-Hydroxymethyl-Pyrrolidine-1-Carbonyl)-2-Methyl-Propyl]-Amide
Accession Number
DB04310  (EXPT00630)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
P18SPA8N0K
CAS number
13434-13-4
Weight
Average: 385.4983
Monoisotopic: 385.257671245
Chemical Formula
C19H35N3O5
InChI Key
XJLATMLVMSFZBN-VYDXJSESSA-N
InChI
InChI=1S/C19H35N3O5/c1-4-5-6-8-14(11-16(24)21-27)18(25)20-17(13(2)3)19(26)22-10-7-9-15(22)12-23/h13-15,17,23,27H,4-12H2,1-3H3,(H,20,25)(H,21,24)/t14-,15+,17+/m1/s1
IUPAC Name
(2R)-N'-hydroxy-N-[(2S)-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-pentylbutanediamide
SMILES
[H][C@@](CCCCC)(CC(=O)NO)C(=O)N[C@@]([H])(C(C)C)C(=O)N1CCC[C@@]1([H])CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPeptide deformylase 2Not AvailableGeobacillus stearothermophilus
UPeptide deformylaseNot AvailableStaphylococcus aureus (strain MW2)
UPeptide deformylaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UPeptide deformylaseNot AvailableEscherichia coli (strain K12)
UPeptide deformylaseNot AvailableStaphylococcus aureus
UPeptide deformylaseNot AvailableLeptospira interrogans serogroup Icterohaemorrhagiae serovar Lai (strain 56601)
UPeptide deformylase 1Not AvailableBacillus cereus (strain ATCC 14579 / DSM 31)
UPeptide deformylase 2Not AvailableBacillus cereus (strain ATCC 14579 / DSM 31)
UPeptide deformylaseNot AvailableEnterococcus faecalis (strain ATCC 700802 / V583)
UPeptide deformylaseNot AvailableStreptococcus pyogenes serotype M1
UPeptide deformylase, mitochondrialNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C12056
PubChem Compound
443600
PubChem Substance
46505294
ChemSpider
391756
BindingDB
50089194
ChEMBL
CHEMBL308333
HET
BB2
PDB Entries
1g2a / 1ix1 / 1lqy / 1lru / 1lry / 1q1y / 1szz / 1ws1 / 2kmn / 2okl
show 25 more

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 Solubility3.03 mg/mLALOGPS
logP1.33ALOGPS
logP0.88ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.9ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.97 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity101.51 m3·mol-1ChemAxon
Polarizability42.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9742
Blood Brain Barrier-0.7393
Caco-2 permeable-0.7103
P-glycoprotein substrateSubstrate0.7332
P-glycoprotein inhibitor INon-inhibitor0.5178
P-glycoprotein inhibitor IINon-inhibitor0.7607
Renal organic cation transporterNon-inhibitor0.9352
CYP450 2C9 substrateNon-substrate0.8908
CYP450 2D6 substrateNon-substrate0.792
CYP450 3A4 substrateSubstrate0.5133
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9856
Ames testNon AMES toxic0.7229
CarcinogenicityNon-carcinogens0.6721
BiodegradationNot ready biodegradable0.9075
Rat acute toxicity2.3864 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9825
hERG inhibition (predictor II)Non-inhibitor0.7946
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Valine and derivatives / Alpha amino acid amides / N-acylpyrrolidines / N-acyl amines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Hydroxamic acids / Azacyclic compounds / Primary alcohols / Organopnictogen compounds
show 4 more
Substituents
Valine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-acylpyrrolidine / Fatty amide / N-acyl-amine / Fatty acyl / Tertiary carboxylic acid amide / Pyrrolidine / Carboxamide group
show 15 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
Not Available
Uniprot ID
O31410
Uniprot Name
Peptide deformylase 2
Molecular Weight
20382.365 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]
  3. 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]
Kind
Protein
Organism
Staphylococcus aureus (strain MW2)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q8NX78
Uniprot Name
Peptide deformylase
Molecular Weight
20559.37 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
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q9I7A8
Uniprot Name
Peptide deformylase
Molecular Weight
19364.995 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]
  3. 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]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
P0A6K3
Uniprot Name
Peptide deformylase
Molecular Weight
19328.23 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]
  3. 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]
Details
5. Peptide deformylase
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
P68826
Uniprot Name
Peptide deformylase
Molecular Weight
20558.39 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]
Kind
Protein
Organism
Leptospira interrogans serogroup Icterohaemorrhagiae serovar Lai (strain 56601)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q93LE9
Uniprot Name
Peptide deformylase
Molecular Weight
20379.185 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]
Kind
Protein
Organism
Bacillus cereus (strain ATCC 14579 / DSM 31)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def1
Uniprot ID
Q819U0
Uniprot Name
Peptide deformylase 1
Molecular Weight
17479.995 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]
Kind
Protein
Organism
Bacillus cereus (strain ATCC 14579 / DSM 31)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def2
Uniprot ID
Q819K2
Uniprot Name
Peptide deformylase 2
Molecular Weight
20474.205 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]
Kind
Protein
Organism
Enterococcus faecalis (strain ATCC 700802 / V583)
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins. Requires at least a dipeptide for an efficient rate of reaction. N-terminal L-methionine is a prerequisite for activi...
Gene Name
def
Uniprot ID
Q82ZJ0
Uniprot Name
Peptide deformylase
Molecular Weight
20911.76 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]
Kind
Protein
Organism
Streptococcus pyogenes serotype M1
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
def
Uniprot ID
P68771
Uniprot Name
Peptide deformylase
Molecular Weight
22862.095 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Peptide deformylase activity
Specific Function
Removes the formyl group from the N-terminal Met of newly synthesized proteins.
Gene Name
PDF
Uniprot ID
Q9HBH1
Uniprot Name
Peptide deformylase, mitochondrial
Molecular Weight
27013.25 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 November 02, 2018 05:55