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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL90593
CHEMBL90593
Compound Name PRASTERONE
ChEMBL Synonyms PRASTERONE | DEHYDROANDROSTERONE | DHEA | NATROL DHEA | EM-760 | ENZYMATIC THERAPY | INTRAROSA
Max Phase 4 (Approved)
Trade Names DHEA | NATROL DHEA | ENZYMATIC THERAPY | INTRAROSA
Molecular Formula C19H28O2

Additional synonyms for CHEMBL90593 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=O
Standard InChI InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17( ...
Download InChI
Standard InChI Key FMGSKLZLMKYGDP-USOAJAOKSA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • 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


CHEMBL90593

Molecule Features

CHEMBL90593 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:N Topical:Y Black Box:N Availability Type:Prescription-only

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Myotonic DystrophyD009223Orphanet:206647Myotonic dystrophy2ClinicalTrials
AgingD000375GO:0007568aging3ClinicalTrials
Addison DiseaseD0002243ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus0ClinicalTrials
InfertilityD007246EFO:0000545infertility3ClinicalTrials
MenopauseD008593EFO:0003922menopause3ClinicalTrials
Sarcoma, SynovialD013584EFO:0001376synovial sarcoma1ClinicalTrials
Skin AgingD015595EFO:0005422skin aging3ClinicalTrials
Substance Withdrawal SyndromeD013375EFO:0005800substance withdrawal syndrome2ClinicalTrials
Anorexia NervosaD000856EFO:0004215anorexia nervosa3ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease2ClinicalTrials
MalariaD008288EFO:0001068malaria3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Sexual Dysfunction, PhysiologicalD012735EFO:0004714sexual dysfunction3ClinicalTrials
Atrophic VaginitisD059268EFO:1001271Atrophic Vaginitis3ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression2ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection2ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus3ClinicalTrials
Primary Ovarian InsufficiencyD016649EFO:0004266primary ovarian insufficiency2ClinicalTrials
Adrenal InsufficiencyD0003093ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov PRASTERONE
The Cochrane Collaboration PRASTERONE

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 CHEMBL90593. 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
CHEMBL1978 Cytochrome P450 19A1 Homo sapiens 1.000
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 1.000
CHEMBL4430 Cytochrome P450 17A1 Rattus norvegicus 1.000
CHEMBL1856 Steroid 5-alpha-reductase 2 Homo sapiens 1.000
CHEMBL3559 Steryl-sulfatase Homo sapiens 1.000
CHEMBL1871 Androgen Receptor Homo sapiens 1.000
CHEMBL1787 Steroid 5-alpha-reductase 1 Homo sapiens 1.000
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 1.000
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 1.000
CHEMBL242 Estrogen receptor beta Homo sapiens 1.000
CHEMBL4234 Estradiol 17-beta-dehydrogenase 3 Homo sapiens 1.000
CHEMBL3368 Glucocorticoid receptor Rattus norvegicus 1.000
CHEMBL3072 Androgen Receptor Rattus norvegicus 1.000
CHEMBL3056 Androgen Receptor Mus musculus 1.000
CHEMBL206 Estrogen receptor alpha Homo sapiens 0.999
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.996
CHEMBL5373 Cannabinoid CB2 receptor Mus musculus 0.993
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.988
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 0.955
CHEMBL2808 LXR-alpha Homo sapiens 0.943



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1978 Cytochrome P450 19A1 Homo sapiens 1.000
CHEMBL1856 Steroid 5-alpha-reductase 2 Homo sapiens 1.000
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 1.000
CHEMBL4430 Cytochrome P450 17A1 Rattus norvegicus 1.000
CHEMBL2027 Niemann-Pick C1-like protein 1 Homo sapiens 1.000
CHEMBL1787 Steroid 5-alpha-reductase 1 Homo sapiens 1.000
CHEMBL1871 Androgen Receptor Homo sapiens 1.000
CHEMBL3559 Steryl-sulfatase Homo sapiens 1.000
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 1.000
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 1.000
CHEMBL3072 Androgen Receptor Rattus norvegicus 1.000
CHEMBL242 Estrogen receptor beta Homo sapiens 1.000
CHEMBL206 Estrogen receptor alpha Homo sapiens 1.000
CHEMBL5409 G-protein coupled bile acid receptor 1 Homo sapiens 1.000
CHEMBL3368 Glucocorticoid receptor Rattus norvegicus 1.000
CHEMBL4234 Estradiol 17-beta-dehydrogenase 3 Homo sapiens 1.000
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 0.998
CHEMBL3056 Androgen Receptor Mus musculus 0.997
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.995
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.990

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
288.4 288.2089 3.88 0 37.3 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 0 2 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- - 3.31 3.31 0 21 0.69

Structural Alerts

There are 2 structural alerts for CHEMBL90593. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A14 - ANABOLIC AGENTS FOR SYSTEMIC USE
A14A - ANABOLIC STEROIDS
A14AA - Androstan derivatives
A14AA07 - prasterone

ChemSpider ChemSpider:FMGSKLZLMKYGDP-USOAJAOKSA-N
DailyMed prasterone
PubChem SID: 144204773 SID: 144209194 SID: 144213078 SID: 170465614 SID: 26753548 SID: 29215152 SID: 50106135 SID: 50106136 SID: 56320669 SID: 75250
Wikipedia Dehydroepiandrosterone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL90593



ACToR 53-43-0 105597-37-3
BindingDB 50223368
Brenda 9047 8810 114950 8270 114949 32591 4633 145360 123727 19993 194807 15722 11888 56467 275 44017 8089 43769
ChEBI 28689
ChemicalBook CB1475670
DrugBank DB01708
DrugCentral 795
eMolecules 35862385 29549852 496736
EPA CompTox Dashboard DTXSID4020379
FDA SRS 459AG36T1B
Guide to Pharmacology 2370
Human Metabolome Database HMDB0000077
IBM Patent System 7CF317B094A070BC5ECB2918E193FC86
KEGG Ligand C01227
LipidMaps LMST02020021
Metabolights MTBLC28689
MolPort MolPort-003-929-763
NIH Clinical Collection SAM001246922
Nikkaji J4.147E
PDBe AND
PharmGKB PA451993
PubChem 5881
PubChem: Drugs of the Future 12014907
PubChem: Thomson Pharma 14775640 14751238
Recon dhea
Rhea 28689
Selleck Dehydroepiandrosterone(DHEA)
SureChEMBL SCHEMBL24156
ZINC ZINC000003807917

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