Details of the Drug

General Information of Drug (ID: DM6HDKQ)

Drug Name

[3H]mibolerone

Synonyms

Mibolerone; MIBOLERONE; 3704/9/4; Miboleronum; Mibolerona; Cheque; U-10,997; UNII-9OGY4BOR8D; NSC 72260; 9OGY4BOR8D; U 10997; Matenon; Miboleron; 17-beta-Hydroxy-7-alpha,17-dimethylestr-4-en-3-one; CHEBI:34849; U-10997; 17beta-Hydroxy-7alpha,17-dimethylestr-4-en-3-one; (7alpha,17beta)-17-hydroxy-7,17-dimethylestr-4-en-3-one; 7alpha-17alpha-dimethyl-19-nortestosterone; CDB 904; Cheque (Veterinary)

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

302.5

Logarithm of the Partition Coefficient (xlogp)

3.2

Rotatable Bond Count (rotbonds)

0

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C20H30O2
IUPAC Name: (7R,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,13,17-trimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES: C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C)O
InChI: InChI=1S/C20H30O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h11-12,15-18,22H,4-10H2,1-3H3/t12-,15+,16-,17+,18-,19+,20+/m1/s1
InChIKey: PTQMMNYJKCSPET-OMHQDGTGSA-N

Cross-matching ID

PubChem CID: 251636
ChEBI ID: CHEBI:34849
CAS Number: 3704-09-4
UNII: 9OGY4BOR8D
DrugBank ID: DB11429
TTD ID: D06VZE

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Androgen receptor (AR)	TTS64P2	ANDR_HUMAN	Inhibitor	[2]
Androgen receptor messenger RNA (AR mRNA)	TTKPW01	ANDR_HUMAN	Agonist	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Acireductone dioxygenase (ADI1)	OT8IOD03	MTND_HUMAN	Gene/Protein Processing	[4]
Homeobox protein Nkx-3.1 (NKX3-1)	OT0DO6ZU	NKX31_HUMAN	Gene/Protein Processing	[5]
Kallikrein-2 (KLK2)	OT9RE37R	KLK2_HUMAN	Gene/Protein Processing	[6]
Matrilysin (MMP7)	OTVT3SEJ	MMP7_HUMAN	Gene/Protein Processing	[7]
Prostate-specific antigen (KLK3)	OTFGSBFJ	KLK3_HUMAN	Gene/Protein Processing	[6]
Vascular endothelial growth factor A, long form	OTIM9MZ3	VEGFA_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Androgen receptor (AR)	DTT	AR	2.13E-01	-0.07	-0.11

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3456).
2	Design, synthesis, and pharmacological characterization of 4-[4, 4-dimethyl-3-(4-hydroxybutyl)-5-oxo-2-thioxo-1-imidazolidinyl]- 2-iodobenzonitrile... J Med Chem. 2000 Aug 24;43(17):3344-7.
3	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 628).
4	Expression and function of the human androgen-responsive gene ADI1 in prostate cancer. Neoplasia. 2007 Aug;9(8):643-51. doi: 10.1593/neo.07415.
5	A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells. Endocrinology. 1999 Nov;140(11):5451-4. doi: 10.1210/endo.140.11.7246.
6	Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells. Cancer Res. 1999 Dec 1;59(23):5892-5.
7	Androgen receptor-Ets protein interaction is a novel mechanism for steroid hormone-mediated down-modulation of matrix metalloproteinase expression. J Biol Chem. 1996 Sep 27;271(39):23907-13. doi: 10.1074/jbc.271.39.23907.
8	Effects of treatment with androgen receptor ligands on microRNA expression of prostate cancer cells. Toxicology. 2015 Jul 3;333:45-52. doi: 10.1016/j.tox.2015.04.002. Epub 2015 Apr 3.