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CHEBI:28876 - melphalan

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name melphalan
ChEBI ID CHEBI:28876
Definition A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:25815, CHEBI:6742
Supplier Information
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Formula C13H18Cl2N2O2
Net Charge 0
Average Mass 305.20000
Monoisotopic Mass 304.075
InChI 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
InChIKey SGDBTWWWUNNDEQ-LBPRGKRZSA-N
SMILES N[C@@H](Cc1ccc(cc1)N(CCCl)CCCl)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): drug allergen
Any drug which causes the onset of an allergic reaction.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
(via nitrogen mustard )
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
Application(s): drug allergen
Any drug which causes the onset of an allergic reaction.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing melphalan (CHEBI:28876) has role alkylating agent (CHEBI:22333)
melphalan (CHEBI:28876) has role antineoplastic agent (CHEBI:35610)
melphalan (CHEBI:28876) has role carcinogenic agent (CHEBI:50903)
melphalan (CHEBI:28876) has role drug allergen (CHEBI:88188)
melphalan (CHEBI:28876) has role immunosuppressive agent (CHEBI:35705)
melphalan (CHEBI:28876) is a L-phenylalanine derivative (CHEBI:84144)
melphalan (CHEBI:28876) is a nitrogen mustard (CHEBI:37598)
melphalan (CHEBI:28876) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
melphalan (CHEBI:28876) is a organochlorine compound (CHEBI:36683)
IUPAC Name
4-[bis(2-chloroethyl)amino]-L-phenylalanine
INNs Sources
melfalano ChemIDplus
melphalan KEGG DRUG
melphalanum ChemIDplus
Synonyms Sources
3-(p-(Bis(2-chloroethyl)amino)phenyl)-L-alanine ChemIDplus
3-p-(Di(2-chloroethyl)amino)-phenyl-L-alanine ChemIDplus
4-(Bis(2-chloroethyl)amino)-L-phenylalanine ChemIDplus
L-3-(p-(Bis(2-chloroethyl)amino)phenyl)alanine ChemIDplus
L-PAM ChemIDplus
L-Phenylalanine mustard ChemIDplus
L-Sarcolysine ChemIDplus
p-Bis(beta-chloroethyl)aminophenylalanine ChemIDplus
p-Di-(2-chloroethyl)amino-L-phenylalanine ChemIDplus
p-L-Sarcolysin ChemIDplus
p-N,N-bis(2-chloroethyl)amino-L-phenylalanine ChEBI
p-N-Bis(2-chloroethyl)amino-L-phenylalanine ChemIDplus
Phenylalanine mustard ChemIDplus
Phenylalanine nitrogen mustard ChemIDplus
Database Links Databases
D00369 KEGG DRUG
DB01042 DrugBank
Melphalan Wikipedia
US108552 Patent
US275057 Patent
US3032584 Patent
US3032585 Patent
View more database links
Registry Numbers Types Sources
148-82-3 CAS Registry Number KEGG DRUG
148-82-3 CAS Registry Number ChemIDplus
2816456 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10820424 PubMed citation Europe PMC
10937717 PubMed citation Europe PMC
11680815 PubMed citation Europe PMC
11914777 PubMed citation Europe PMC
18481314 PubMed citation Europe PMC
445303 PubMed citation Europe PMC
7494795 PubMed citation Europe PMC
7605343 PubMed citation Europe PMC
8552138 PubMed citation Europe PMC
8951232 PubMed citation Europe PMC
9218926 PubMed citation Europe PMC
9250538 PubMed citation Europe PMC
Last Modified
15 October 2015
General Comment
2011-02-10 A chemotherapy drug that is usually administered to treat multiple myeloma, melanoma, ovarian and breast cancer.