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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:51 UTC
HMDB IDHMDB0015176
Secondary Accession Numbers
  • HMDB15176
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
4-(Bis(2-chloroethyl)amino)phenylalanineMeSH
MedphalanMeSH
MerphalanMeSH
SarcolysineMeSH
SarkolysinMeSH
AlkeranMeSH
Mustard, phenylalanineMeSH
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 KeySGDBTWWWUNNDEQ-LBPRGKRZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • Amphetamine or derivatives
  • L-alpha-amino acid
  • Nitrogen mustard
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Tertiary amine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Alkyl halide
  • Amine
  • Organic oxygen compound
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.36 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.23 m³·mol⁻¹ChemAxon
Polarizability31.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-3890000000-153ff87813e7a797c73bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01c3-8295000000-421b0e52574345db725fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000w-2930000000-b95beb5e9c3e61b7687fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000w-2930000000-b95beb5e9c3e61b7687fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0093000000-78045bae5e6c1e79e22dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1490000000-3b1f7009692b1139989bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-3930000000-b0f45ffda87388d4384aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-8c401366ace5d7fc1f08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v4i-1192000000-fd136d877921c8afed95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9530000000-511158435cb1ef063085View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01042 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01042 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
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. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [PubMed:19190342 ]