Details of the Drug

General Information of Drug (ID: DMVYNJZ)

Drug Name
BUTAPROST
Synonyms
Butaprost; (R)-Butaprost; 69648-38-0; UNII-HP16WVP23Y; TR-4979; HP16WVP23Y; NCGC00165753-01; Butaprostum; (1R,2R,3R)-3-Hydroxy-2-[(1E,4R)-4-hydroxy-4-(1-propylcyclobutyl)-1-butenyl]-5-oxo-cyclopentaneheptanoic acid methyl ester; Butaprostum [Latin]; Bay q 4218; Butaprost [USAN:INN:BAN]; Butaprost (free acid); AC1NSJVB; Butaprost (USAN/INN); DSSTox_RID_83186; DSSTox_CID_28919; SCHEMBL94764; DSSTox_GSID_48993; CHEMBL271896; GTPL3379; DTXSID8048993; BDBM85602; BAY-Q-4218; ZINC4215145; Tox21_113480; MFCD00867055; 1090AH; PDSP2_001674
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 408.6
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C24H40O5
IUPAC Name
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,4R)-4-hydroxy-4-(1-propylcyclobutyl)but-1-enyl]-5-oxocyclopentyl]heptanoate
Canonical SMILES
CCCC1(CCC1)[C@@H](C/C=C/[C@H]2[C@@H](CC(=O)[C@@H]2CCCCCCC(=O)OC)O)O
InChI
InChI=1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3/b11-8+/t18-,19-,21-,22-/m1/s1
InChIKey
XRISENIKJUKIHD-LHQZMKCDSA-N
Cross-matching ID
PubChem CID
5311035
CAS Number
69648-38-0
TTD ID
D0W2OT

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin E2 receptor EP1 (PTGER1) TTG1QMU PE2R1_HUMAN Antagonist [2]
Prostaglandin E2 receptor EP2 (PTGER2) TT1ZAVI PE2R2_HUMAN Antagonist [2]
Prostaglandin E2 receptor EP3 (PTGER3) TTPNGDE PE2R3_HUMAN Antagonist [2]
Prostaglandin E2 receptor EP4 (PTGER4) TT79WV3 PE2R4_HUMAN Antagonist [2]
Prostaglandin F2-alpha receptor (PTGFR) TTT2ZAR PF2R_HUMAN Antagonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
11-beta-hydroxysteroid dehydrogenase 1 (HSD11B1) OTO7FJA9 DHI1_HUMAN Gene/Protein Processing [3]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [4]
Cyclic AMP-dependent transcription factor ATF-3 (ATF3) OTC1UOHP ATF3_HUMAN Gene/Protein Processing [5]
Interleukin-23 subunit alpha (IL23A) OTYO99HC IL23A_HUMAN Gene/Protein Processing [6]
NAD-dependent protein deacetylase sirtuin-1 (SIRT1) OTAYZMOY SIR1_HUMAN Gene/Protein Processing [5]
Steroid hormone receptor ERR1 (ESRRA) OTTDTUSP ERR1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) 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
Prostaglandin F2-alpha receptor (PTGFR) DTT PTGFR 8.25E-02 -0.05 -0.14
Molecular Expression Atlas (MEA) 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: 3379).
2 Evaluation of WO 2012/177618 A1 and US-2014/0179750 A1: novel small molecule antagonists of prostaglandin-E2 receptor EP2.Expert Opin Ther Pat. 2015 Jul;25(7):837-44.
3 PTGER1 and PTGER2 receptors mediate regulation of progesterone synthesis and type 1 11beta-hydroxysteroid dehydrogenase activity by prostaglandin E2 in human granulosa lutein cells. J Endocrinol. 2007 Sep;194(3):595-602.
4 Dual regulation of 2-adrenoceptor messenger RNA expression in human lung fibroblasts by 2-cAMP signaling; delayed upregulated inhibitors oppose a rapid in onset, direct stimulation of gene expression. Naunyn Schmiedebergs Arch Pharmacol. 2014 Jul;387(7):649-57. doi: 10.1007/s00210-014-0971-7. Epub 2014 Apr 8.
5 Prostaglandin E2 down-regulates sirtuin 1 (SIRT1), leading to elevated levels of aromatase, providing insights into the obesity-breast cancer connection. J Biol Chem. 2019 Jan 4;294(1):361-371.
6 Prostaglandin E2 regulates Th17 cell differentiation and function through cyclic AMP and EP2/EP4 receptor signaling. J Exp Med. 2009 Mar 16;206(3):535-48. doi: 10.1084/jem.20082293. Epub 2009 Mar 9.
7 Estrogen receptor-related receptor alpha mediates up-regulation of aromatase expression by prostaglandin E2 in prostate stromal cells. Mol Endocrinol. 2010 Jun;24(6):1175-86.