Bimatoprost, free acid - Moligand™, ≥98% , Agonist of FP receptor, CAS No.38344-08-0, Agonist of FP receptor

CAS: 38344-08-0 Cat. No.: B347977 Molecular Weight: 388.5 EC Number: 806-621-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

17-phenyl trinor PGF2a | 5-HEPTENOIC ACID, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-5-PHENYL-1- PENTENYL)CYCLOPENTYL)-, (1R- (1.ALPHA.(Z),2.BETA.(1E,3S*),3.ALPHA.,5.ALPHA.))- | AC-30204 | SCHEMBL2472056 | (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-ph

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Bimatoprost, free acid is a metabolically stable analog of PGF|2α|and is a potent agonist for the PGF|2α|(FP receptor). It binds to the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF|2α|. Bimatoprost inhibits PGF|2α|binding with a K|i|of 1.1 nM at the rat recombinant FP receptor expressed in CHO cells. The isopropyl ester of bimatoprost is slightly better than PGF|2α|isopropyl ester in reducing the intraocular pressure in the cat eye with no irritation.

Specifications

Synonyms

17-phenyl trinor PGF2a | 5-HEPTENOIC ACID, 7-(3, 5-DIHYDROXY-2-(3-HYDROXY-5-PHENYL-1- PENTENYL)CYCLOPENTYL)-, (1R- (1.ALPHA.(Z), 2.BETA.(1E, 3S*), 3.ALPHA., 5.ALPHA.))- | AC-30204 | SCHEMBL2472056 | (5Z)-7-{(1R, 2R, 3R, 5S)-3, 5-dihydroxy-2-[(1E, 3S)-3-hydroxy-5-ph

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of FP receptor

Purity

≥98%

Product Properties

• Ki Data: PGF2α: Ki= 1.1 nM

Names and Identifiers

• Canonical Smiles: C1C(C(C(C1O)C=CC(CCC2=CC=CC=C2)O)CC=CCCCC(=O)O)O
• IUPAC Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoic acid
• InChIKey: YFHHIZGZVLHBQZ-KDACTHKWSA-N
• INCHI: 1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](CCC2=CC=CC=C2)O)C/C=C\CCCC(=O)O)O
• Molecular Weight: 388.5
• Reaxy-Rn: 41277337
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=41277337&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Eicosanoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Eicosanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Prostaglandins and related compounds
• Alternative Parents: Long-chain fatty acids Hydroxy fatty acids Unsaturated fatty acids Cyclopentanols Benzene and substituted derivatives Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Prostaglandin skeleton - Long-chain fatty acid - Hydroxy fatty acid - Monocyclic benzene moiety - Cyclopentanol - Fatty acid - Benzenoid - Unsaturated fatty acid - Cyclic alcohol - Secondary alcohol - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic oxide - Alcohol - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
• External Descriptors: Prostaglandins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PTGFR Tclin Prostaglandin F2-alpha receptor (2 Activities)

Discover Target: PTGFR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PTGFR Tclin Prostanoid FP receptor (687 Activities)

Discover Target: PTGFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGIR Tclin Prostanoid IP receptor (1280 Activities)

Discover Target: PTGIR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in PBS (pH 7.2) (~800 g/ml), ethanol (~100 mg/ml), DMF (~100 mg/ml), and DMSO (~100 mg/ml).
• Refractive Index: n20D1.62 (Predicted)
• Boil Point(°C): 597.38° C at 760 mmHg (Predicted)
• Melt Point(°C): 244.30° C (Predicted)
• Molecular Weight: 388.500 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 388.225 Da
• Monoisotopic Mass: 388.225 Da
• Topological Polar Surface Area: 98.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 509.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1