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(Rac) -Beraprost

CAT: 0804-HY-167091Size: 1 EachDry Ice: NoHazardous: No
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Description
(Rac) -Beraprost ((Rac) -ML 1229) is an orally active prostacyclin analog that inhibits the release of Ca2+ from intracellular storage sites by binding to prostacyclin membrane receptors (Prostaglandin Receptor), leading to relaxation of smooth muscle cells and vasodilation. Beraprost has vasodilatory, antiplatelet, and cytoprotective effects, making it promising for research in the field of cardiovascular diseases, such as thromboangiitis obliterans and atherosclerosis[1].
CAS Number
88430-50-6
Product Name Alternative
(Rac) -TRK-100 (free acid) ; (Rac) -ML 1229
UNSPSC
12352211
Target
Prostaglandin Receptor
Type
Reference compound
Related Pathways
GPCR/G Protein
Applications
Neuroscience-Neuromodulation
Field of Research
Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/beraprost.html
Smiles
O=C(CCCC1=CC=CC2=C1OC3CC(C(C23)/C=C/C(C(CC#CC)C)O)O)O
Molecular Formula
C24H30O5
Molecular Weight
398.49
References & Citations
[1]Li S, et al. Beraprost sodium mitigates renal interstitial fibrosis through repairing renal microvessels. J Mol Med (Berl) . 2019 Jun;97 (6) :777-791.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Beraprost

Beraprost is an organic heterotricyclic compound that is (3aS,8bS)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan in which the hydrogens at positions 1R, 2R and 5 are replaced by (3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl, hydroxy and 3-carboxypropyl groups, respectively. It is a prostaglandin receptor agonist which is approved to treat pulmonary arterial hypertension in Asia. It has a role as a vasodilator agent, an antihypertensive agent, a platelet aggregation inhibitor, a prostaglandin receptor agonist and an anti-inflammatory agent. It is a secondary allylic alcohol, a monocarboxylic acid, an organic heterotricyclic compound, a secondary alcohol and an enyne. It is a conjugate acid of a beraprost(1-).

CAS Number88430-50-6
PubChem CID6917951
IUPAC Name4-[(1R,2R,3aS,8bS)-2-hydroxy-1-[(E,3S)-3-hydroxy-4-methyloct-1-en-6-ynyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-5-yl]butanoic acid
Molecular FormulaC24H30O5
Molecular Weight398.5
XLogP3.2
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Heavy Atom Count29
Formal Charge0
Complexity659
SMILES
CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C3=CC=CC(=C3O2)CCCC(=O)O)O)O
InChI
InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1
InChIKey
CTPOHARTNNSRSR-APJZLKAGSA-N
Chemical Structure
2D Structure
2D structure of Beraprost
CAS: 88430-50-6
CID: 6917951
Formula: C24H30O5
MW: 398.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight398.5
XLogP33.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass398.20932405
Monoisotopic Mass398.20932405
Topological Polar Surface Area87 Ų
Heavy Atom Count29
Formal Charge0
Complexity659
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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