D-Methionine

Identification

Summary

D-Methionine is an amino acid found in mixture products used for nutrient supplementation.

Brand Names
Prosol
Generic Name
D-Methionine
DrugBank Accession Number
DB02893
Background

Not Available

Type
Small Molecule
Groups
Approved, Experimental, Investigational
Structure
Weight
Average: 149.211
Monoisotopic: 149.051049291
Chemical Formula
C5H11NO2S
Synonyms
Not Available
External IDs
  • MRX-1024
  • NSC-45689

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatMalnutrition; proteinCombination Product in combination with: Serine (DB00133), Alanine (DB00160), Phenylalanine (DB00120), Tryptophan (DB00150), Lactic acid (DB04398), Calcium chloride (DB01164), Histidine (DB00117), Lysine (DB00123), Valine (DB00161), Arginine (DB00125), Tyrosine (DB00135), Isoleucine (DB00167), Threonine (DB00156), Glycine (DB00145), Magnesium chloride (DB09407), Proline (DB00172), Sodium chloride (DB09153), Leucine (DB00149), Methionine (DB00134)•••••••••••••••••••• •••••••••••••
Used as adjunct in combination to treatNegative nitrogen balance••••••••••••••••••••• •• ••• •••••••••• •••••
Used as adjunct in combination to treatNegative nitrogen balance•••••••••••••••••••• •••••••••••••••• •••••••••• •• ••••• •••••
Used as adjunct in combination to treatNegative nitrogen balance••••••••••••••••••••• ••••••••• ••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMethionine aminopeptidase 2Not AvailableHumans
UTranscriptional regulator, HTH_3 familyNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
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
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
20% ProsolD-Methionine (0.76 g) + Alanine (2.76 g) + Arginine (1.96 g) + Aspartic acid (0.6 g) + Glutamic acid (1.02 g) + Glycine (2.06 g) + Histidine (1.18 g) + Isoleucine (1.08 g) + Leucine (1.08 g) + Lysine (1.35 g) + Methionine (0.76 g) + Phenylalanine (1 g) + Proline (1.34 g) + Serine (1.02 g) + Threonine (0.98 g) + Tryptophan (0.32 g) + Tyrosine (0.05 g) + Valine (1.44 g)LiquidIntravenousBaxter Laboratories1996-10-09Not applicableCanada flag
Nutrineal Pd4D-Methionine (85 mg) + Alanine (95.1 mg) + Arginine (107.1 mg) + Calcium chloride (18.4 mg) + Glycine (51 mg) + Histidine (71.4 mg) + Isoleucine (85 mg) + Sodium lactate (448 mg) + Leucine (102 mg) + Lysine (95.5 mg) + Magnesium chloride (5.1 mg) + Methionine (85 mg) + Phenylalanine (57 mg) + Proline (59.5 mg) + Serine (51 mg) + Sodium chloride (538 mg) + Threonine (64.6 mg) + Tryptophan (27 mg) + Tyrosine (30 mg) + Valine (139.3 mg)LiquidHemodialysisBaxter Laboratories1998-09-252021-11-02Canada flag
Nutrineal PD4 mit 1,1 % Aminosäuren - PeritonealdialyselösungD-Methionine (85 mg) + Alanine (95.1 mg) + Arginine (107.1 mg) + Calcium chloride (18.4 mg) + Glycine (51 mg) + Histidine (71.4 mg) + Isoleucine (85 mg) + Sodium lactate (448 mg) + Leucine (102 mg) + Lysine (95.5 mg) + Magnesium chloride (5.1 mg) + Methionine (85 mg) + Phenylalanine (57 mg) + Proline (59.5 mg) + Serine (51 mg) + Sodium chloride (538 mg) + Threonine (64.6 mg) + Tryptophan (27 mg) + Tyrosine (30 mg) + Valine (139.3 mg)SolutionParenteralBaxter Healthcare Gmb H2000-06-29Not applicableAustria flag

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as methionine and derivatives. These are compounds containing methionine or a derivative thereof resulting from reaction of methionine 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
Methionine and derivatives
Alternative Parents
D-alpha-amino acids / Thia fatty acids / Amino acids / Sulfenyl compounds / Monocarboxylic acids and derivatives / Dialkylthioethers / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Dialkylthioether / Fatty acid / Fatty acyl
show 15 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, methionine (CHEBI:16867) / Other amino acids (C00855)
Affected organisms
Not Available

Chemical Identifiers

UNII
868496F25R
CAS number
348-67-4
InChI Key
FFEARJCKVFRZRR-SCSAIBSYSA-N
InChI
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1
IUPAC Name
(2R)-2-amino-4-(methylsulfanyl)butanoic acid
SMILES
CSCC[C@@H](N)C(O)=O

References

Synthesis Reference

Maria-Regina Kula, Matthias Kittelmann, "Method of using N-acetyl-2,3-Didehydroleucine acylase for the preparation of D- or L-tryptophyl glycine, D- or L-tryptophyl-D-methionine or L-tryptophyl-D-cysteine." U.S. Patent US5212069, issued July, 1992.

US5212069
General References
Not Available
KEGG Compound
C00855
PubChem Compound
84815
PubChem Substance
46505884
ChemSpider
76512
ChEBI
57932
ChEMBL
CHEMBL1234268
ZINC
ZINC000001532766
PDBe Ligand
MED
PDB Entries
1kq0 / 1tkj / 1y9q / 1zue / 2q33 / 3gp4 / 3tjw / 3trv / 3try / 4gls
show 29 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedPreventionHearing Loss, Noise-Induced2
1TerminatedTreatmentHead And Neck Cancer / Mucositis / Resected Head and Neck Cancer / Squamous Cell Carcinoma (SCC)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidIntravenous
Injection, solutionIntraperitoneal
LiquidHemodialysis
SolutionParenteral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)213 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.9 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.2Chemaxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.53Chemaxon
pKa (Strongest Basic)9.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity37.59 m3·mol-1Chemaxon
Polarizability15.46 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9797
Blood Brain Barrier+0.8447
Caco-2 permeable-0.6698
P-glycoprotein substrateNon-substrate0.5351
P-glycoprotein inhibitor INon-inhibitor0.9802
P-glycoprotein inhibitor IINon-inhibitor0.9919
Renal organic cation transporterNon-inhibitor0.8913
CYP450 2C9 substrateNon-substrate0.7875
CYP450 2D6 substrateNon-substrate0.7323
CYP450 3A4 substrateNon-substrate0.7008
CYP450 1A2 substrateNon-inhibitor0.8295
CYP450 2C9 inhibitorNon-inhibitor0.9489
CYP450 2D6 inhibitorNon-inhibitor0.9567
CYP450 2C19 inhibitorNon-inhibitor0.951
CYP450 3A4 inhibitorNon-inhibitor0.9758
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9938
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9224
BiodegradationReady biodegradable0.5613
Rat acute toxicity0.6483 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9725
hERG inhibition (predictor II)Non-inhibitor0.9655
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-MSsplash10-0mbd-9200000000-77e5cfb78936ad02d71c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-4900000000-88fffa573fcc1c98f185
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9100000000-564d61cb00638e9786b9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-fab730e138c77b66ffd0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0nmi-9200000000-06067d9ebf927500ebee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-b4b027dc132b4805d8e3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-fab730e138c77b66ffd0
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
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]-127.8572456
predicted
DarkChem Lite v0.1.0
[M-H]-125.97034
predicted
DeepCCS 1.0 (2019)
[M+H]+128.4227456
predicted
DarkChem Lite v0.1.0
[M+H]+129.2884
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.0686456
predicted
DarkChem Lite v0.1.0
[M+Na]+137.87843
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala...
Gene Name
METAP2
Uniprot ID
P50579
Uniprot Name
Methionine aminopeptidase 2
Molecular Weight
52891.145 Da
References
  1. Nonato MC, Widom J, Clardy J: Human methionine aminopeptidase type 2 in complex with L- and D-methionine. Bioorg Med Chem Lett. 2006 May 15;16(10):2580-3. Epub 2006 Mar 15. [Article]
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9KQN0
Uniprot Name
Transcriptional regulator, HTH_3 family
Molecular Weight
20353.97 Da

Drug created at June 13, 2005 13:24 / Updated at October 20, 2021 17:29