LatanoprostAcid - Moligand™, ≥98% , Agonist of FP receptor, CAS No.41639-83-2, Agonist of FP receptor

CAS: 41639-83-2 Cat. No.: L133844 Molecular Weight: 390.51 EC Number: 682-021-0

GRADE & PURITY Moligand™, ≥98%

Synonyms

NCGC00165820-01 | ethynyitrimethylsilane | latanoprost (free acid form) | latanoprost-free acid | (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid | Latonoprost acid | Z-7-[(1R,2R,3R,5S)-3,5-bis(oxidanyl)-2

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Latanoprost (free acid) is a metabolite of Latanoprost, an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (free acid) by endogenous esterase enzymes. The free acid form is 200 times more potent than latanoprost as an FP receptor ligand for the human recombinant FP receptor. Latanoprost is the isopropyl ester of a PGF2α analog containing an aromatic group (17-phenyl) in the ω-chain. Lat-FA is the corresponding carboxylic acid of this analog. Lat-FA is a potent FP receptor agonist with an EC50 of 3.6 nM for human FP receptors, which is twice the potency of PGF2α. Therefore making Latanoprost (free acid) is an activator of PGF2αR.
An F-series prostaglandin (PG) analog.

Specifications

Synonyms

NCGC00165820-01 | ethynyitrimethylsilane | latanoprost (free acid form) | latanoprost-free acid | (Z)-7-[(1R, 2R, 3R, 5S)-3, 5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid | Latonoprost acid | Z-7-[(1R, 2R, 3R, 5S)-3, 5-bis(oxidanyl)-2

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Potent, selective FP prostanoid receptor agonist, F-series prostaglandin analog. 200 times as potent as isopropyl ester form.

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%

Names and Identifiers

• Canonical Smiles: C1C(C(C(C1O)CC=CCCCC(=O)O)CCC(CCC2=CC=CC=C2)O)O
• IUPAC Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid
• InChIKey: HNPFPERDNWXAGS-NFVOFSAMSA-N
• INCHI: 1S/C23H34O5/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/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@H]1O)C/C=C\CCCC(=O)O)CC[C@H](CCC2=CC=CC=C2)O)O
• WGK Germany: 3
• Alternate CAS: 41639-83-2
• MeSH Entry Terms: PhXa 85;PhXa-85;PhXa85
• Molecular Weight: 390.51
• Reaxy-Rn: 41200353
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=41200353&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 Falpha - hydroxy monocarboxylic acid

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)

SLCO2A1 Tchem Solute carrier organic anion transporter family member 2A1 (1 Activities)

Discover Target: SLCO2A1

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

PTGFR Tclin Prostaglandin F2-alpha receptor (1 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

Caco-2 (12174 Activities)

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

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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

Associated Targets(non-human)

Felis catus (3858 Activities)

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

Oryctolagus cuniculus (11301 Activities)

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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 water (>0.8 mg/ml at 25 °C), ethanol (~100 mg/ml), DMSO (~100 mg/ml), DMF (~100 mg/ml), and methanol.
• Molecular Weight: 390.500 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 390.241 Da
• Monoisotopic Mass: 390.241 Da
• Topological Polar Surface Area: 98.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 472.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1