Ginkgolide C - Moligand™, analytical standard, ≥99% , Antagonist of PAF receptor, CAS No.15291-76-6, Antagonist of PAF receptor

CAS: 15291-76-6 Cat. No.: G101972 Molecular Weight: 440.4 EC Number: 604-875-5

GRADE & PURITY Analytical standard, Moligand™, ≥99%

Synonyms

1,7-Dihydroxy-ginkgolide A | AS-56372 | SCHEMBL16452771 | Q-100179 | AKOS025311463 | MFCD06642603 | (1R,3R,6R,7S,8S,9R,10S,11R,12S,13S,16S,17R)-8-Tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadec

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

1, 7-Dihydroxy-ginkgolide A | AS-56372 | SCHEMBL16452771 | Q-100179 | AKOS025311463 | MFCD06642603 | (1R, 3R, 6R, 7S, 8S, 9R, 10S, 11R, 12S, 13S, 16S, 17R)-8-Tert-butyl-6, 9, 12, 17-tetrahydroxy-16-methyl-2, 4, 14, 19-tetraoxahexacyclo[8.7.2.01, 11.03, 7.07, 11.013, 17]nonadec

Specifications & Purity

Moligand™, analytical standard, ≥99%

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

Analytical standard, Moligand™

Action Type

ANTAGONIST

Mechanism of action

Antagonist of PAF receptor

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1C(=O)OC2C1(C34C(=O)OC5C3(C2O)C6(C(C5O)C(C)(C)C)C(C(=O)OC6O4)O)O
• IUPAC Name: (1R,3R,6R,7S,8S,9R,10S,11R,12S,13S,16S,17R)-8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione
• InChIKey: AMOGMTLMADGEOQ-PYLUGNSCSA-N
• INCHI: 1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6-,7+,8-,9+,10-,11+,15+,17+,18-,19-,20-/m1/s1
• Isomeric SMILES: C[C@@H]1C(=O)O[C@@H]2[C@]1([C@@]34C(=O)O[C@H]5[C@]3([C@@H]2O)[C@@]6([C@@H]([C@H]5O)C(C)(C)C)[C@H](C(=O)O[C@H]6O4)O)O
• WGK Germany: 3
• Molecular Weight: 440.4
• Reaxy-Rn: 25434485
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25434485&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene lactones
        • Level5 Diterpene lactones
          • Level6 Ginkgolides and bilobalides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Diterpene lactones
• Direct Parent: Ginkgolides and bilobalides
• Alternative Parents: Diterpenoids Tricarboxylic acids and derivatives Furofurans Gamma butyrolactones Tetrahydrofurans Tertiary alcohols Secondary alcohols Cyclic alcohols and derivatives Carboxylic acid esters Polyols Oxacyclic compounds Acetals Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Ginkgolide-skeleton - Diterpenoid - Tricarboxylic acid or derivatives - Furofuran - Gamma butyrolactone - Cyclic alcohol - Tetrahydrofuran - Tertiary alcohol - Carboxylic acid ester - Lactone - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Acetal - Carboxylic acid derivative - Polyol - Alcohol - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Organooxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as ginkgolides and bilobalides. These are diterpene lactones with a structure based either on the gingkolide or the bilobalide skeleton. The ginkgolide skeleton is a very rigid structure consisting of hexacyclic C20 trilactone. The cis-fused F/A/D/C ring junction forms an empty semi-ball hole, the D ring contains a cage form tetrahydrofuran ring which occupies the center of the empty hole, and the oxygen atoms of the D,C and F ring and 10-hydroxyl group consist of an analogous crown ether structure.
• External Descriptors: Not available

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)

PTAFR Tchem Platelet-activating factor receptor (1 Activities)

Discover Target: PTAFR

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

Chemical and Physical Properties

• Molecular Weight: 440.400 g/mol
• XLogP3: -1.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 1
• Exact Mass: 440.132 Da
• Monoisotopic Mass: 440.132 Da
• Topological Polar Surface Area: 169.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 957.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 12
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Lingling Wang, Xiuhua Zhao, Fengjian Yang, Weiwei Wu, Yanjie Liu, Li Wang, Lu Wang, Zijian Wang.  (2019)  Enhanced bioaccessibility in vitro and bioavailability of Ginkgo biloba extract nanoparticles prepared by liquid anti-solvent precipitation.  INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY,  54  (6): (2266-2276).  [PMID:] [10.1111/ijfs.14141]

2. Lingling Wang, Xiuhua Zhao, Yuangang Zu, Weiwei Wu, Yuanyuan Li, Chang Zu, Yin Zhang.  (2016)  Enhanced dissolution rate and oral bioavailability of ginkgo biloba extract by preparing nanoparticles via emulsion solvent evaporation combined with freeze drying (ESE-FR).  RSC Advances,  6  (81): (77346-77357).  [PMID:] [10.1039/C6RA14771B]

3. Yuan Gang Zu, Lingling Wang, Xiuhua Zhao, Yuanyuan Li, Weiwei Wu, Chang Zu, Yannian Huang, Mingfang Wu, Ziqi Feng.  (2016)  Purification of Ginkgo biloba Extract by Antisolvent Recrystallization.  CHEMICAL ENGINEERING & TECHNOLOGY,  39  (7): (1301-1308).  [PMID:] [10.1002/ceat.201500691]