Natural Product (NP) Details

General Information of the NP (ID: NP5545)
Name
Misoprostol
Synonyms
misoprostol; 59122-46-2; Cytotec; Isprelor; Misoprostolum [INN-Latin]; SC-29333; Misodel; SC 29333; UNII-0E43V0BB57; CCRIS 6859; HSDB 3573; BRN 4155643; methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate; 0E43V0BB57; NCGC00162445-02; Misoprostolum; Misoprost; Misotol; Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester,(11a,13E)-; Misogon; Misopess; Misotac; GyMiso; methyl (11alpha,13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate; methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate; Cytotec (TN); misoprostol (methyl ester); SR-01000695425; XP-16J; MVI 200; 103601-27-0; methyl 7-((1R,2R,3R)-3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)heptanoate; 11; A-Misoprostol; CAS_59122-46-2; Misoprostol [USAN:USP:INN:BAN:JAN]; DSSTox_CID_897; Methyl (+-)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate; CHEMBL606; SCHEMBL7787; (11-alpha,13E)-(+-)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester; DSSTox_RID_75852; DSSTox_GSID_20897; MLS000028863; Misoprostol (JAN/USP/INN); GTPL1936; DTXSID7020897; BDBM85606; CHEBI:94387; Misoprostol, >=99% (HPLC); REGID_for_CID_5282381; HMS2090L10; HMS3648F03; HMS3715K08; EX-A1774; HY-B0610; Tox21_112010; MFCD00274550; (+/-)-15-Deoxy-(16RS)-16-hydroxy-16-methylprostaglandin E1 methyl ester; AKOS015899652; CCG-221093; DB00929; Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11alpha,13E)-; SMP1_000193; NCGC00162445-01; NCGC00162445-03; (+-)-Methyl (1R,2R,3R)-3-hydroxy-2-((E)-(4RS)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate; SMR000058558; CAS-59122-46-2; D00419; AB00513745-05; 122M462; A832173; Q416025; Q-201409; SR-01000695425-2; SR-01000695425-4; BRD-A50310035-001-01-6; Misoprostol, European Pharmacopoeia (EP) Reference Standard; UNII-0E43V0BB57 component OJLOPKGSLYJEMD-URPKTTJQSA-N; Misoprostol, United States Pharmacopeia (USP) Reference Standard; (+/-) methyl 11alpha, 16-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oate; (+/-) methyl 11alpha,16-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oate; (+/-) methyl-11alpha,16-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oate; (+/-) methyl-11alpha,16-dihydroxy-16-methyl-9-oxoprost13E-en-1-oate; (+/-)-(11a,13E)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oic acid methyl ester; (11alpha,13E)-11,16-Dihydroxy-16-methyl-9-oxoprosta-13-ene-1-oic acid methyl ester; Misoprostol for system suitability, European Pharmacopoeia (EP) Reference Standard; 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoic acid methyl ester; methyl 7-[(1R,2R,3R)-2-[(E)-4-methyl-4-oxidanyl-oct-1-enyl]-3-oxidanyl-5-oxidanylidene-cyclopentyl]heptanoate; Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11alpha,13E)-(+-)-
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Abortion [ICD-11: JA00] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.189
 
MDCK Permeability
 -4.875
 
PAMPA
 -
 
HIA
 - - -
 
Distribution
VDss
 -0.044
 
PPB
 70.9%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 ++
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - -
CYP2C9 substrate
 +
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 ++
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 ++
 
Excretion
CLplasma
 4.218
 
T1/2
 0.758
Toxicity
DILI
 - -
 
Rat Oral Acute Toxicity
 ++
 
FDAMDD
 +++
 
Respiratory
 +++
 
Human Hepatotoxicity
 +++
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 +
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C22H38O5
PubChem CID
5282381
Canonical SMILES
CCCCC(C)(CC=CC1C(CC(=O)C1CCCCCCC(=O)OC)O)O
InChI
1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1
InChIKey
OJLOPKGSLYJEMD-URPKTTJQSA-N
CAS Number
CAS 59122-46-2
ChEBI ID
CHEBI:94387
TTD Drug ID
D09ANG
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Mifepristone      Cushing syndrome     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Retrospective clinical study
                    Experimental
                    Result(s)		 The addition of mifepristone to medical treatment regimens for first trimester miscarriage significantly decreased the need for repeat medical dosing and surgical curettage.
Target and Pathway
Target(s) Prostacyclin receptor (PTGIR)  Molecule Info  [3]
KEGG Pathway Neuroactive ligand-receptor interaction Click to Show/Hide
2 Vascular smooth muscle contraction
3 Platelet activation
Pathwhiz Pathway Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin Click to Show/Hide
Pathway Interaction Database Thromboxane A2 receptor signaling Click to Show/Hide
Reactome Prostanoid ligand receptors Click to Show/Hide
2 G alpha (s) signalling events
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 GPCRs, Class A Rhodopsin-like
3 Small Ligand GPCRs
4 Endothelin Pathways
5 Platelet homeostasis
6 GPCR ligand binding
7 GPCR downstream signaling
References
Reference 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: 1936).
Reference 2 Combination therapy with mifepristone and misoprostol for the management of first trimester miscarriage: Improved success. Aust N Z J Obstet Gynaecol. 2018 Aug;58(4):438-442.
Reference 3 Palmitoylation of the human prostacyclin receptor. Functional implications of palmitoylation and isoprenylation. J Biol Chem. 2003 Feb 28;278(9):6947-58.
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