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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL428647
CHEMBL428647
Compound Name PACLITAXEL
ChEMBL Synonyms BMS-181339-01 | PACITAXEL | PACLITAXEL | PAXENE | ABRAXANE | TAXOL | TAXOL 100
Max Phase 4 (Approved)
Trade Names PACLITAXEL | PACITAXEL | PAXENE | TAXOL 100 | ABRAXANE | TAXOL
Molecular Formula C47H51NO14

Additional synonyms for CHEMBL428647 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@H]3OC[C@@]3(OC(=O)C)[ ...
Download SMILES
Standard InChI InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11 ...
Download InChI
Standard InChI Key RCINICONZNJXQF-MZXODVADSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • HeCaToS Compounds
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL428647

Molecule Features

CHEMBL428647 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Tubulin inhibitor Tubulin DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Adrenocortical CarcinomaD018268EFO:0003093adrenocortical carcinoma2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma3ClinicalTrials
Carcinoma, Merkel CellD015266EFO:1001471Merkel cell skin cancer2ClinicalTrials
Keratosis, ActinicD055623EFO:0002496actinic keratosis2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Testicular NeoplasmsD013736EFO:0005088testicular carcinoma2ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma3ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma2ClinicalTrials
Adenocarcinoma, Bronchiolo-AlveolarD002282EFO:0000308bronchoalveolar adenocarcinoma2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000708squamous cell lung carcinoma3ClinicalTrials
Constriction, PathologicD003251EFO:0006818stricture2ClinicalTrials
Esophageal NeoplasmsD004938EFO:0005922esophageal squamous cell carcinoma3ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma3ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm3ClinicalTrials
Ovarian NeoplasmsD010051Orphanet:398934Malignant epithelial tumor of ovary3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0003860pancreatic neoplasm3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma3ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer1ClinicalTrials
Salivary Gland NeoplasmsD012468EFO:0003826salivary gland neoplasm2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
Sex Cord-Gonadal Stromal TumorsD018312EFO:0007483sex cord-gonadal stromal tumor2ClinicalTrials
Triple Negative Breast NeoplasmsD064726EFO:0005537triple-negative breast cancer3ClinicalTrials
Ureteral NeoplasmsD014516EFO:0003844ureteral neoplasm2ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001416cervical adenocarcinoma3ClinicalTrials
Anus NeoplasmsD001005EFO:0003835anal neoplasm1ClinicalTrials
Carcinoma, Large CellD018287EFO:0003050large cell lung carcinoma3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
Endometrial NeoplasmsD016889EFO:1001512endometrial carcinoma3ClinicalTrials
Gastrointestinal Stromal TumorsD046152Orphanet:44890Gastrointestinal stromal tumor2ClinicalTrials
HypersensitivityD006967EFO:0003785allergy3ClinicalTrials
Myocardial InfarctionD009203EFO:0000612myocardial infarction3ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma3ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma2ClinicalTrials
Fallopian Tube NeoplasmsD005185EFO:1000251Fallopian Tube Carcinoma2ClinicalTrials
Genital Neoplasms, FemaleD005833EFO:1001331Genital neoplasm, female2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
MelanomaD008545EFO:0000756melanoma3ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm3ClinicalTrials
Neuroendocrine TumorsD018358EFO:1001901neuroendocrine neoplasm2ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis2ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000294bladder tumor3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
Coronary RestenosisD023903EFO:0004224Coronary Restenosis2ClinicalTrials
Digestive System DiseasesD004066EFO:0000405digestive system disease2ClinicalTrials
Hereditary Breast and Ovarian Cancer SyndromeD061325Orphanet:145Hereditary breast and ovarian cancer syndrome2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0003897stomach neoplasm3ClinicalTrials
Urogenital NeoplasmsD014565EFO:0003863urogenital neoplasm3ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm3ClinicalTrials
Biliary Tract NeoplasmsD001661EFO:0003891biliary tract neoplasm2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma1ClinicalTrials
Carcinoma, Pancreatic DuctalD021441EFO:0002517pancreatic ductal adenocarcinoma3ClinicalTrials
Carcinoma, VerrucousD018289EFO:0007535verrucous carcinoma1ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma2ClinicalTrials
DiseaseD004194EFO:0000408disease1ClinicalTrials
Gestational Trophoblastic DiseaseD031901Orphanet:59305Gestational trophoblastic neoplasm3ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection3ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
Penile NeoplasmsD010412EFO:1001094penile neoplasm2ClinicalTrials
Sarcoma, KaposiD012514EFO:0000558Kaposi's sarcoma3ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm3ClinicalTrials
Uterine Cervical DysplasiaD002578EFO:1000910dysplasia of cervix2ClinicalTrials
Vulvar NeoplasmsD014846EFO:0002921vulvar carcinoma2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma3ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection3ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0004284upper aerodigestive tract neoplasm3ClinicalTrials
HemangiosarcomaD006394EFO:0003968angiosarcoma2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
Mouth NeoplasmsD009062EFO:0003868mouth neoplasm2ClinicalTrials
Peripheral Arterial DiseaseD058729EFO:0004265peripheral arterial disease3ClinicalTrials
Prostatic HyperplasiaD011470EFO:0000284benign prostatic hyperplasia2ClinicalTrials
Testicular NeoplasmsD013736EFO:0004281testicular neoplasm2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma2ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm3ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia3ClinicalTrials
Inflammatory Breast NeoplasmsD058922EFO:1000984inflammatory breast carcinoma3ClinicalTrials
IschemiaD007511EFO:0000556ischemia3ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma3ClinicalTrials
Peripheral Vascular DiseasesD016491EFO:0003875peripheral vascular disease2ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0000503gastric adenocarcinoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov PACLITAXEL
The Cochrane Collaboration PACLITAXEL

Metabolites for CHEMBL428647

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
853.9 853.331 3.74 10 221.29 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
14 4 2 15 4 2


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.9 - 3.95 3.95 3 62 0.13

Structural Alerts

There are 5 structural alerts for CHEMBL428647. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01C - PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS
L01CD - Taxanes
L01CD01 - paclitaxel

ChemSpider ChemSpider:RCINICONZNJXQF-MZXODVADSA-N
DailyMed paclitaxel
PubChem SID: 124893045 SID: 144205660 SID: 418145 SID: 56463361

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL428647



ACToR 33069-62-4
BindingDB 50001839
Brenda 69683 16457 8756 3120
ChEBI 45863
ChemicalBook CB3273425
DrugBank DB01229
DrugCentral 2044
eMolecules 506301 36754358 29541201
EPA CompTox Dashboard DTXSID9023413
FDA SRS P88XT4IS4D
Guide to Pharmacology 2770
Human Metabolome Database HMDB0015360
IBM Patent System 3459B429F32D5681BB382846E26EE895
LINCS LSM-6346
Metabolights MTBLC45863
MolPort MolPort-001-742-627
Nikkaji J17.834I
PDBe TA1
PharmGKB PA450761
PubChem 36314
PubChem: Drugs of the Future 12013494
PubChem: Thomson Pharma 14840887 14767269
Recon taxol
Rhea 45863
SureChEMBL SCHEMBL3976
ZINC ZINC000096006020

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