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melphalan   Click here for help

GtoPdb Ligand ID: 7620

Synonyms: Alkeran® | CB-3025 | L-phenylalanine mustard (L-PAM) | L-sarcolysine | melfalan | Phelinun® | Sarcolysin®
Approved drug PDB Ligand
melphalan is an approved drug (FDA (1964), EMA (2020))
Compound class: Synthetic organic
Comment: Marketed formulations may contain melphalan hydrochloride.
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View more information in the IUPHAR Pharmacology Education Project: melphalan

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 66.56
Molecular weight 304.07
XLogP 0.36
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES ClCCN(c1ccc(cc1)CC(C(=O)O)N)CCCl
Isomeric SMILES ClCCN(c1ccc(cc1)C[C@@H](C(=O)O)N)CCCl
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
InChI Key SGDBTWWWUNNDEQ-LBPRGKRZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EU EMA (2020)  |  US FDA (1964)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Prodrug melphalan flufenamide
IUPAC Name Click here for help
(2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid
International Nonproprietary Names Click here for help
INN number INN
745 melphalan
Synonyms Click here for help
Alkeran® | CB-3025 | L-phenylalanine mustard (L-PAM) | L-sarcolysine | melfalan | Phelinun® | Sarcolysin®
Database Links Click here for help
CAS Registry No. 148-82-3
ChEBI CHEBI:28876
ChEMBL Ligand CHEMBL852
DrugBank Ligand DB01042
DrugCentral Ligand 1678
GtoPdb PubChem SID 223365955
PubChem CID 460612
RCSB PDB Ligand VUC
Search Google for chemical match using the InChIKey SGDBTWWWUNNDEQ-LBPRGKRZSA-N
Search Google for chemicals with the same backbone SGDBTWWWUNNDEQ
Search PubMed clinical trials melphalan
Search PubMed titles melphalan
Search PubMed titles/abstracts melphalan
UniChem Compound Search for chemical match using the InChIKey SGDBTWWWUNNDEQ-LBPRGKRZSA-N
UniChem Connectivity Search for chemical match using the InChIKey SGDBTWWWUNNDEQ-LBPRGKRZSA-N
Wikipedia Melphalan