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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:46 UTC
HMDB IDHMDB15176
Secondary Accession NumbersNone
Metabolite Identification
Common NameMelphalan
DescriptionAn alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - melphalan, the racemic mixture - merphalan, and the dextro isomer - medphalan; toxic to bone marrow, but little vesicant action; potential carcinogen. [PubChem]
Structure
Thumb
Synonyms
ValueSource
3-(P-(Bis(2-chloroethyl)amino)phenyl)-L-alanineChEBI
3-P-(Di(2-chloroethyl)amino)-phenyl-L-alanineChEBI
4-(Bis(2-chloroethyl)amino)-L-phenylalanineChEBI
L-3-(P-(Bis(2-chloroethyl)amino)phenyl)alanineChEBI
L-PAMChEBI
L-Phenylalanine mustardChEBI
L-SarcolysineChEBI
MelfalanoChEBI
MelphalanumChEBI
P-Bis(beta-chloroethyl)aminophenylalanineChEBI
P-Di-(2-chloroethyl)amino-L-phenylalanineChEBI
P-L-SarcolysinChEBI
P-N,N-Bis(2-chloroethyl)amino-L-phenylalanineChEBI
P-N-Bis(2-chloroethyl)amino-L-phenylalanineChEBI
Phenylalanine mustardChEBI
Phenylalanine nitrogen mustardChEBI
P-Bis(b-chloroethyl)aminophenylalanineGenerator
P-Bis(β-chloroethyl)aminophenylalanineGenerator
Chemical FormulaC13H18Cl2N2O2
Average Molecular Weight305.2
Monoisotopic Molecular Weight304.074533244
IUPAC Name(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
Traditional Namemelphalan
CAS Registry Number148-82-3
SMILES
N[C@@H](CC1=CC=C(C=C1)N(CCCl)CCCl)C(O)=O
InChI Identifier
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
InChI KeyInChIKey=SGDBTWWWUNNDEQ-LBPRGKRZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Substituted aniline
  • Dialkylarylamine
  • Nitrogen mustard
  • Aralkylamine
  • Aniline
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antineoplastic Agents, Alkylating
  • Myeloablative Agonists
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.58e-01 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 mg/mLALOGPS
logP-0.22ALOGPS
logP0.25ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.56 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.23 m3·mol-1ChemAxon
Polarizability31.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01042
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01042
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01042
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID405297
KEGG Compound IDC07122
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMelphalan
NuGOwiki LinkHMDB15176
Metagene LinkHMDB15176
METLIN IDNot Available
PubChem Compound460612
PDB IDNot Available
ChEBI ID28876
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Moscow JA, Swanson CA, Cowan KH: Decreased melphalan accumulation in a human breast cancer cell line selected for resistance to melphalan. Br J Cancer. 1993 Oct;68(4):732-7. [8398701 ]
  2. Souliotis VL, Dimopoulos MA, Episkopou HG, Kyrtopoulos SA, Sfikakis PP: Preferential in vivo DNA repair of melphalan-induced damage in human genes is greatly affected by the local chromatin structure. DNA Repair (Amst). 2006 Aug 13;5(8):972-85. Epub 2006 Jun 15. [16781199 ]
  3. Loeber R, Michaelson E, Fang Q, Campbell C, Pegg AE, Tretyakova N: Cross-linking of the DNA repair protein Omicron6-alkylguanine DNA alkyltransferase to DNA in the presence of antitumor nitrogen mustards. Chem Res Toxicol. 2008 Apr;21(4):787-95. doi: 10.1021/tx7004508. Epub 2008 Feb 14. [18324787 ]

Transporters

General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. Epub 2009 Feb 3. [19190342 ]