D-norleucine

Identification

Generic Name
D-norleucine
DrugBank Accession Number
DB04419
Background

An unnatural amino acid that is used experimentally to study protein structure and function. It is structurally similar to METHIONINE, however it does not contain SULFUR.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 131.1729
Monoisotopic: 131.094628665
Chemical Formula
C6H13NO2
Synonyms
  • D-(−)-norleucine
  • D-2-aminohexanoic acid

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhenylalanine-4-hydroxylaseNot AvailableHumans
UParathyroid hormoneNot AvailableHumans
UHepatocyte nuclear factor 1-alphaNot AvailableHumans
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 d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
D-alpha-amino acids
Alternative Parents
Medium-chain fatty acids / Amino fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Fatty acid / Fatty acyl / Hydrocarbon derivative
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
2-aminohexanoic acid (CHEBI:42101)
Affected organisms
Not Available

Chemical Identifiers

UNII
VP8G7LX265
CAS number
327-56-0
InChI Key
LRQKBLKVPFOOQJ-RXMQYKEDSA-N
InChI
InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m1/s1
IUPAC Name
(2R)-2-aminohexanoic acid
SMILES
CCCC[C@@H](N)C(O)=O

References

Synthesis Reference

Erich Wunsch, Gerhard Wendlberger, Ernst Jaeger, Regine Scharf, Karl-Heinz Deimer, Hans Stocker, "13-Norleucine-14-desamido motilin, a method for preparing it and an agent containing it." U.S. Patent US3978035, issued August 31, 1976.

US3978035
General References
Not Available
PubChem Compound
456468
PubChem Substance
46507238
ChemSpider
401917
ChEBI
42101
ZINC
ZINC000002034415
PDBe Ligand
DNE
PDB Entries
1r9v / 1s1o / 1s4a / 5go7 / 5go8 / 5gob / 5goc / 5god / 5gog / 5goh
show 13 more

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 Solubility89.2 mg/mLALOGPS
logP-1.7ALOGPS
logP-1.4Chemaxon
logS-0.17ALOGPS
pKa (Strongest Acidic)2.79Chemaxon
pKa (Strongest Basic)9.53Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity34.22 m3·mol-1Chemaxon
Polarizability14.43 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9769
Blood Brain Barrier+0.7921
Caco-2 permeable-0.7039
P-glycoprotein substrateNon-substrate0.558
P-glycoprotein inhibitor INon-inhibitor0.9819
P-glycoprotein inhibitor IINon-inhibitor0.9863
Renal organic cation transporterNon-inhibitor0.9387
CYP450 2C9 substrateNon-substrate0.7979
CYP450 2D6 substrateNon-substrate0.7598
CYP450 3A4 substrateNon-substrate0.7665
CYP450 1A2 substrateNon-inhibitor0.5715
CYP450 2C9 inhibitorNon-inhibitor0.9087
CYP450 2D6 inhibitorNon-inhibitor0.9056
CYP450 2C19 inhibitorNon-inhibitor0.9187
CYP450 3A4 inhibitorNon-inhibitor0.9346
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.966
Ames testNon AMES toxic0.8973
CarcinogenicityNon-carcinogens0.8014
BiodegradationReady biodegradable0.8118
Rat acute toxicity1.2754 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9819
hERG inhibition (predictor II)Non-inhibitor0.9696
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-MSsplash10-00bl-9000000000-201d4196a590a77910e6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-9000000000-a7afdd4bb94757e8b1b8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-2cd1f32fe4a7641186f7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-45f93ae5fc614ca45ef7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2900000000-0be4eef53f215d38ea28
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-9000000000-03b7d752fe633a117617
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mo-9000000000-607b827173ddca0afea3
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]-131.3259458
predicted
DarkChem Lite v0.1.0
[M-H]-125.61932
predicted
DeepCCS 1.0 (2019)
[M+H]+131.8692458
predicted
DarkChem Lite v0.1.0
[M+H]+128.9224
predicted
DeepCCS 1.0 (2019)
[M+Na]+131.2395458
predicted
DarkChem Lite v0.1.0
[M+Na]+137.53554
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phenylalanine 4-monooxygenase activity
Specific Function
Not Available
Gene Name
PAH
Uniprot ID
P00439
Uniprot Name
Phenylalanine-4-hydroxylase
Molecular Weight
51861.565 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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor activity, rna polymerase ii distal enhancer sequence-specific binding
Specific Function
PTH elevates calcium level by dissolving the salts in bone and preventing their renal excretion. Stimulates [1-14C]-2-deoxy-D-glucose (2DG) transport and glycogen synthesis in osteoblastic cells.
Gene Name
PTH
Uniprot ID
P01270
Uniprot Name
Parathyroid hormone
Molecular Weight
12861.0 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
Transcriptional activator that regulates the tissue specific expression of multiple genes, especially in pancreatic islet cells and in liver. Required for the expression of several liver specific g...
Gene Name
HNF1A
Uniprot ID
P20823
Uniprot Name
Hepatocyte nuclear factor 1-alpha
Molecular Weight
67356.01 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52