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Dimethylcurcumin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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Data Packages
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Identification

Generic Name
Dimethylcurcumin
DrugBank Accession Number
DB06133
Background

Dimethylcurcumin is a synthetic chemical compound that is loosely based on a compound found in curcumin. It is a novel anti-androgen that enhances androgen receptor degradation.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 396.439
Monoisotopic: 396.157288493
Chemical Formula
C23H24O6
Synonyms
Not Available
External IDs
  • ASC-J9
  • ASCJ-9
  • CHC-004
  • GO-Y-025
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Pharmacology

Indication

Investigated for use/treatment in acne and alopecia.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AAndrogen receptor
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
D60XLY608D
CAS number
52328-98-0
InChI Key
ZMGUKFHHNQMKJI-CIOHCNBKSA-N
InChI
InChI=1S/C23H24O6/c1-26-20-11-7-16(13-22(20)28-3)5-9-18(24)15-19(25)10-6-17-8-12-21(27-2)23(14-17)29-4/h5-15,24H,1-4H3/b9-5+,10-6+,18-15-
IUPAC Name
(1E,4Z,6E)-1,7-bis(3,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
SMILES
COC1=CC=C(\C=C\C(\O)=C\C(=O)\C=C\C2=CC(OC)=C(OC)C=C2)C=C1OC

References

General References
Not Available
ChemSpider
4978553
ChEMBL
CHEMBL128748
ZINC
ZINC000100007120
Wikipedia
Dimethylcurcumin

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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2CompletedTreatmentAcne1somestatusstop reasonjust information to hide
2CompletedTreatmentAcne Vulgaris1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00141 mg/mLALOGPS
logP4.38ALOGPS
logP4.05Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)9.04Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area74.22 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity115.09 m3·mol-1Chemaxon
Polarizability44.04 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0009000000-cfba69da9848ffe08230
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0119000000-394893e61989973e71bb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fr5-0229000000-b3e2a0a50030164b75c1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0hh9-2595000000-543f5d393b59683a3f07
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gvk-0917000000-81e00ef68ed1c93cc056
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0449000000-c49257964b14f2851cee
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-241.2665818
predicted
DarkChem Lite v0.1.0
[M+H]+241.9527818
predicted
DarkChem Lite v0.1.0
[M+Na]+241.4960818
predicted
DarkChem Lite v0.1.0

Targets

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Details1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues (PubMed:19022849). Transcription factor activity is modulated by bound coactivator and corepressor proteins like ZBTB7A that recruits NCOR1 and NCOR2 to the androgen response elements/ARE on target genes, negatively regulating androgen receptor signaling and androgen-induced cell proliferation (PubMed:20812024). Transcription activation is also down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3
Specific Function
androgen binding
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
99187.115 Da
References
  1. Lai KP, Huang CK, Chang YJ, Chung CY, Yamashita S, Li L, Lee SO, Yeh S, Chang C: New therapeutic approach to suppress castration-resistant prostate cancer using ASC-J9 via targeting androgen receptor in selective prostate cells. Am J Pathol. 2013 Feb;182(2):460-73. doi: 10.1016/j.ajpath.2012.10.029. Epub 2012 Dec 4. [Article]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at November 18, 2007 18:30 / Updated at June 12, 2020 16:52