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D-Leucine

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Identification

Generic Name
D-Leucine
DrugBank Accession Number
DB01746
Background

An essential branched-chain amino acid important for hemoglobin formation. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 131.1729
Monoisotopic: 131.094628665
Chemical Formula
C6H13NO2
Synonyms
  • (2R)-2-amino-4-methylpentanoic acid
  • (R)-(−)-leucine
  • (R)-leucine
  • D-2-Amino-4-methylvaleric acid
  • D-Leucin
  • D-Leuzin
External IDs
  • NSC-77687
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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
Leucine and derivatives
Alternative Parents
D-alpha-amino acids / Methyl-branched fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Branched fatty acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Fatty acid / Fatty acyl
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, leucine (CHEBI:28225) / Other amino acids (C01570)
Affected organisms
Not Available

Chemical Identifiers

UNII
965COD96YA
CAS number
328-38-1
InChI Key
ROHFNLRQFUQHCH-RXMQYKEDSA-N
InChI
InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m1/s1
IUPAC Name
(2R)-2-amino-4-methylpentanoic acid
SMILES
CC(C)C[C@@H](N)C(O)=O

References

General References
  1. Yanagida O, Kanai Y, Chairoungdua A, Kim DK, Segawa H, Nii T, Cha SH, Matsuo H, Fukushima J, Fukasawa Y, Tani Y, Taketani Y, Uchino H, Kim JY, Inatomi J, Okayasu I, Miyamoto K, Takeda E, Goya T, Endou H: Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. Biochim Biophys Acta. 2001 Oct 1;1514(2):291-302. [Article]
Human Metabolome Database
HMDB0013773
KEGG Compound
C01570
PubChem Compound
439524
PubChem Substance
46507999
ChemSpider
388617
ChEBI
28225
ChEMBL
CHEMBL1232258
ZINC
ZINC000000388396
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
DLE
PDB Entries
1al4 / 1alx / 1alz / 1av2 / 1bdw / 1bfw / 1c4b / 1c4d / 1czq / 1gmk …
show 160 more

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
PropertyValueSource
melting point (°C)293 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility69.8 mg/mLALOGPS
logP-1.8ALOGPS
logP-1.6Chemaxon
logS-0.27ALOGPS
pKa (Strongest Acidic)2.79Chemaxon
pKa (Strongest Basic)9.52Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity34.17 m3·mol-1Chemaxon
Polarizability14.25 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9785
Blood Brain Barrier+0.6686
Caco-2 permeable-0.8958
P-glycoprotein substrateNon-substrate0.6833
P-glycoprotein inhibitor INon-inhibitor0.9767
P-glycoprotein inhibitor IINon-inhibitor0.9875
Renal organic cation transporterNon-inhibitor0.9617
CYP450 2C9 substrateNon-substrate0.8483
CYP450 2D6 substrateNon-substrate0.7693
CYP450 3A4 substrateNon-substrate0.7389
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9543
CYP450 2D6 inhibitorNon-inhibitor0.9336
CYP450 2C19 inhibitorNon-inhibitor0.9608
CYP450 3A4 inhibitorNon-inhibitor0.9558
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.991
Ames testNon AMES toxic0.8892
CarcinogenicityNon-carcinogens0.7139
BiodegradationReady biodegradable0.7417
Rat acute toxicity1.5061 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9929
hERG inhibition (predictor II)Non-inhibitor0.976
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-MSsplash10-0006-9000000000-70cdb961a0819be4318a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-fec5e4f750925f07095c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-7018f8c9efcfd1d52fe5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9000000000-5b7d73ad382c1161f251
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3900000000-33b7e9a4c51fcc97e322
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-52d65f4aa677860e8908
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-c583a756caa5b0e00396
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]-130.3895458
predicted
DarkChem Lite v0.1.0
[M-H]-127.9447458
predicted
DarkChem Lite v0.1.0
[M-H]-130.2856458
predicted
DarkChem Lite v0.1.0
[M-H]-128.3536458
predicted
DarkChem Lite v0.1.0
[M-H]-126.722786
predicted
DeepCCS 1.0 (2019)
[M+H]+130.7971458
predicted
DarkChem Lite v0.1.0
[M+H]+129.1192458
predicted
DarkChem Lite v0.1.0
[M+H]+130.8682458
predicted
DarkChem Lite v0.1.0
[M+H]+129.3231458
predicted
DarkChem Lite v0.1.0
[M+H]+130.40718
predicted
DeepCCS 1.0 (2019)
[M+Na]+130.1429458
predicted
DarkChem Lite v0.1.0
[M+Na]+128.2040458
predicted
DarkChem Lite v0.1.0
[M+Na]+130.3042458
predicted
DarkChem Lite v0.1.0
[M+Na]+128.7443458
predicted
DarkChem Lite v0.1.0
[M+Na]+139.20018
predicted
DeepCCS 1.0 (2019)

Transporters

Details1. Monocarboxylate transporter 10
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium- and proton-independent thyroid hormones and aromatic acids transporter (PubMed:11827462, PubMed:18337592, PubMed:28754537). Mediates both uptake and efflux of 3,5,3'-triiodothyronine (T3) and 3,5,3',5'-tetraiodothyronine (T4) with high affinity, suggesting a role in the homeostasis of thyroid hormone levels (PubMed:18337592). Responsible for low affinity bidirectional transport of the aromatic amino acids, such as phenylalanine, tyrosine, tryptophan and L-3,4-dihydroxyphenylalanine (L-dopa) (PubMed:11827462, PubMed:28754537). Plays an important role in homeostasis of aromatic amino acids (By similarity)
Specific Function
Amino acid transmembrane transporter activity
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [Article]
Details2. Large neutral amino acids transporter small subunit 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
The heterodimer with SLC3A2 functions as a sodium-independent, high-affinity transporter that mediates uptake of large neutral amino acids such as phenylalanine, tyrosine, leucine, histidine, methionine, tryptophan, valine, isoleucine and alanine (PubMed:10049700, PubMed:10574970, PubMed:11557028, PubMed:11564694, PubMed:12117417, PubMed:12225859, PubMed:15769744, PubMed:18262359, PubMed:25998567, PubMed:30867591, PubMed:9751058). The heterodimer with SLC3A2 mediates the uptake of L-DOPA (By similarity). Functions as an amino acid exchanger (PubMed:11557028, PubMed:12117417, PubMed:12225859, PubMed:30867591). May play a role in the transport of L-DOPA across the blood-brain barrier (By similarity). May act as the major transporter of tyrosine in fibroblasts (Probable). May mediate blood-to-retina L-leucine transport across the inner blood-retinal barrier (By similarity). Can mediate the transport of thyroid hormones diiodothyronine (T2), triiodothyronine (T3) and thyroxine (T4) across the cell membrane (PubMed:11564694). When associated with LAPTM4B, the heterodimer formed by SLC3A2 and SLC7A5 is recruited to lysosomes to promote leucine uptake into these organelles, and thereby mediates mTORC1 activation (PubMed:25998567). Involved in the uptake of toxic methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes (PubMed:12117417). Involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L-nitrosocysteine (L-CNSO) across the membrane (PubMed:15769744)
Specific Function
Amino acid transmembrane transporter activity
Gene Name
SLC7A5
Uniprot ID
Q01650
Uniprot Name
Large neutral amino acids transporter small subunit 1
Molecular Weight
55009.62 Da
References
  1. Yanagida O, Kanai Y, Chairoungdua A, Kim DK, Segawa H, Nii T, Cha SH, Matsuo H, Fukushima J, Fukasawa Y, Tani Y, Taketani Y, Uchino H, Kim JY, Inatomi J, Okayasu I, Miyamoto K, Takeda E, Goya T, Endou H: Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines. Biochim Biophys Acta. 2001 Oct 1;1514(2):291-302. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51