D-norleucine
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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
Target Actions Organism UPhenylalanine-4-hydroxylase Not Available Humans UParathyroid hormone Not Available Humans UHepatocyte nuclear factor 1-alpha Not Available Humans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PDB Entries
- 1r9v / 1s1o / 1s4a / 5go7 / 5go8 / 5gob / 5goc / 5god / 5gog / 5goh … show 13 more
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 89.2 mg/mL ALOGPS logP -1.7 ALOGPS logP -1.4 Chemaxon logS -0.17 ALOGPS pKa (Strongest Acidic) 2.79 Chemaxon pKa (Strongest Basic) 9.53 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 34.22 m3·mol-1 Chemaxon Polarizability 14.43 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9769 Blood Brain Barrier + 0.7921 Caco-2 permeable - 0.7039 P-glycoprotein substrate Non-substrate 0.558 P-glycoprotein inhibitor I Non-inhibitor 0.9819 P-glycoprotein inhibitor II Non-inhibitor 0.9863 Renal organic cation transporter Non-inhibitor 0.9387 CYP450 2C9 substrate Non-substrate 0.7979 CYP450 2D6 substrate Non-substrate 0.7598 CYP450 3A4 substrate Non-substrate 0.7665 CYP450 1A2 substrate Non-inhibitor 0.5715 CYP450 2C9 inhibitor Non-inhibitor 0.9087 CYP450 2D6 inhibitor Non-inhibitor 0.9056 CYP450 2C19 inhibitor Non-inhibitor 0.9187 CYP450 3A4 inhibitor Non-inhibitor 0.9346 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.966 Ames test Non AMES toxic 0.8973 Carcinogenicity Non-carcinogens 0.8014 Biodegradation Ready biodegradable 0.8118 Rat acute toxicity 1.2754 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9819 hERG inhibition (predictor II) Non-inhibitor 0.9696
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00bl-9000000000-201d4196a590a77910e6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-9000000000-a7afdd4bb94757e8b1b8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0900000000-2cd1f32fe4a7641186f7 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-9000000000-45f93ae5fc614ca45ef7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-2900000000-0be4eef53f215d38ea28 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-9000000000-03b7d752fe633a117617 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05mo-9000000000-607b827173ddca0afea3 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 131.3259458 predictedDarkChem Lite v0.1.0 [M-H]- 125.61932 predictedDeepCCS 1.0 (2019) [M+H]+ 131.8692458 predictedDarkChem Lite v0.1.0 [M+H]+ 128.9224 predictedDeepCCS 1.0 (2019) [M+Na]+ 131.2395458 predictedDarkChem Lite v0.1.0 [M+Na]+ 137.53554 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsPhenylalanine-4-hydroxylase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the hydroxylation of L-phenylalanine to L-tyrosine
- Specific Function
- iron ion binding
- Gene Name
- PAH
- Uniprot ID
- P00439
- Uniprot Name
- Phenylalanine-4-hydroxylase
- Molecular Weight
- 51861.565 Da
References
2. DetailsParathyroid hormone
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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
- Specific Function
- hormone activity
- Gene Name
- PTH
- Uniprot ID
- P01270
- Uniprot Name
- Parathyroid hormone
- Molecular Weight
- 12861.0 Da
3. DetailsHepatocyte nuclear factor 1-alpha
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional activator that regulates the tissue specific expression of multiple genes, especially in pancreatic islet cells and in liver (By similarity). Binds to the inverted palindrome 5'-GTTAATNATTAAC-3' (PubMed:10966642, PubMed:12453420). Activates the transcription of CYP1A2, CYP2E1 and CYP3A11 (By similarity)
- Specific Function
- DNA binding
- Gene Name
- HNF1A
- Uniprot ID
- P20823
- Uniprot Name
- Hepatocyte nuclear factor 1-alpha
- Molecular Weight
- 67386.03 Da
References
- 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