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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL852
CHEMBL852
Compound Name MELPHALAN
ChEMBL Synonyms L-SARCOLYSIN | MELPHALAN | MELFALAN | AIKERAN | Melphalan hydrochloride | ALKERAN | EVOMELA | PHENYLALANINE MUSTARD | ALANINE NITROGEN MUSTARD | CB 3025
Max Phase 4 (Approved)
Trade Names MELPHALAN HYDROCHLORIDE | AIKERAN | ALKERAN | EVOMELA
Molecular Formula C13H18Cl2N2O2

Additional synonyms for CHEMBL852 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES N[C@@H](Cc1ccc(cc1)N(CCCl)CCCl)C(=O)O
Standard InChI InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9- ...
Download InChI
Standard InChI Key SGDBTWWWUNNDEQ-LBPRGKRZSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL852

Molecule Features

CHEMBL852 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AmyloidosisD000686Orphanet:314701Primary systemic amyloidosis3ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia3ClinicalTrials
Leukemia, Myelomonocytic, JuvenileD054429EFO:1000309Juvenile Myelomonocytic Leukemia2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma2ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia2ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma4DailyMed
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma2ClinicalTrials
ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
MelanomaD008545EFO:0000756melanoma3ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm2ClinicalTrials
Testicular NeoplasmsD013736EFO:0005088testicular carcinoma2ClinicalTrials
AnemiaD000740EFO:0004272anemia1ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease1ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer1ClinicalTrials
ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma3ClinicalTrials
beta-ThalassemiaD017086Orphanet:848Beta-thalassemia1ClinicalTrials
Autoimmune DiseasesD001327EFO:0005140autoimmune disease2ClinicalTrials
HistiocytosisD015614HP:0100727Histiocytosis2ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma4ClinicalTrials
DailyMed
ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
ThalassemiaD013789EFO:1001996Thalassemia2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Sarcoma, EwingD012512EFO:0000174Ewing sarcoma3ClinicalTrials
Smoldering Multiple MyelomaD000075122EFO:0003073asymptomatic myeloma3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm2ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease1ClinicalTrials
Leukemia, Erythroblastic, AcuteD004915EFO:1001257acute erythroblastic leukemia2ClinicalTrials
AmyloidosisD000686EFO:1001875amyloidosis2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma2ClinicalTrials
Hematologic DiseasesD006402EFO:0005803hematological system disease2ClinicalTrials
Inflammatory Breast NeoplasmsD058922EFO:1000984inflammatory breast carcinoma2ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma2ClinicalTrials
Metabolic DiseasesD008659EFO:0000589metabolic disease1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma3ClinicalTrials
Primary MyelofibrosisD055728EFO:0002430primary myelofibrosis2ClinicalTrials
Adenoma, Islet CellD007516EFO:0007331islet cell tumor2ClinicalTrials
Amyloidosis, FamilialD028226Orphanet:85443AL amyloidosis3ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia2ClinicalTrials
Leukemia, Plasma CellD007952EFO:0006475plasma cell leukemia2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer2ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma3ClinicalTrials
RetinoblastomaD012175Orphanet:790Retinoblastoma2ClinicalTrials
ClinicalTrials
Wiskott-Aldrich SyndromeD014923Orphanet:906Wiskott-Aldrich syndrome1ClinicalTrials

Clinical Data

ClinicalTrials.gov MELPHALAN
The Cochrane Collaboration MELPHALAN

Metabolites for CHEMBL852

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL852. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL5689 Tryptophan 5-hydroxylase 1 Homo sapiens 1.000
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.995
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.984
CHEMBL2009 Glutamate receptor ionotropic, AMPA 1 Homo sapiens 0.910

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5689 Tryptophan 5-hydroxylase 1 Homo sapiens 1.000
CHEMBL2919 Glutamate receptor ionotropic kainate 1 Rattus norvegicus 0.999
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.998
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.995
CHEMBL2009 Glutamate receptor ionotropic, AMPA 1 Homo sapiens 0.959
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.585
CHEMBL4354 Mu opioid receptor Cavia porcellus 0.401
CHEMBL1907 Aminopeptidase N Homo sapiens 0.311
CHEMBL4581 Kinesin-like protein 1 Homo sapiens 0.254

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
305.2 304.0745 1.93 8 66.56 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 2 0 4 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.12 9.54 .54 -1.97 1 19 0.72

Structural Alerts

There are 11 structural alerts for CHEMBL852. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01A - ALKYLATING AGENTS
L01AA - Nitrogen mustard analogues
L01AA03 - melphalan

ChemSpider ChemSpider:SGDBTWWWUNNDEQ-LBPRGKRZSA-N
DailyMed melphalan melphalan hydrochloride
PubChem SID: 144204561 SID: 144209720 SID: 170464727 SID: 17389837 SID: 26752787 SID: 56463160
Wikipedia Melphalan

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL852



ACToR 148-82-3
BindingDB 50025837
Brenda 135393
ChEBI 28876
ChemicalBook CB2492687
DrugBank DB01042
DrugCentral 1678
eMolecules 525665
EPA CompTox Dashboard DTXSID6020804
FDA SRS Q41OR9510P
Guide to Pharmacology 7620
Human Metabolome Database HMDB0015176
IBM Patent System A8B6BE210EE9F134FCBF770F3B7EFEF2
KEGG Ligand C07122
Mcule MCULE-8007157187
Metabolights MTBLC28876
MolPort MolPort-003-665-535
Nikkaji J2.962I
PubChem 460612 6918992
PubChem: Thomson Pharma 14898602 14874007
SureChEMBL SCHEMBL5872
ZINC ZINC000000001673

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/SGDBTWWWUNNDEQ-LBPRGKRZSA-N spacer
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