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Bilobalide - 10mM in DMSO, high purity , CAS No.33570-04-6
Non-competitive GABA, glycine and 5-HT3 receptor antagonist
Basic Description
Synonyms
Bilobalide | 33570-04-6 | Bilobalid | (-)-Bilobalide | Bilobalide A | UNII-M81D2O8H7U | CHEBI:3103 | M81D2O8H7U | DTXSID10873207 | 4H,5aH,9H-Furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-, (5aR-(3aS
Specifications & Purity
Moligand™, 10mM in DMSO
Biochemical and Physiological Mechanisms
Bioactive terpenoid found in Ginkgo biloba. Bilobalide, a biologically active terpenic trilactone (terpinoid), derived from geranylgeranyl pyrophosphate (GGPP) is an inducer of cytochrome P450 enzymes CYP3A1 and CYP1A2. Bilobalide, a GABAA, GABAA-rho, 5-h
Storage Temp
Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Grade
Moligand™
Taxonomic Classification
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 Acylals Gamma butyrolactones Tetrahydrofurans Tertiary alcohols Secondary alcohols Cyclic alcohols and derivatives Oxacyclic compounds Acetals Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework
Aliphatic heteropolycyclic compounds
Substituents
Bilobalide - Diterpenoid - Tricarboxylic acid or derivatives - Furofuran - Acylal - Gamma butyrolactone - Cyclic alcohol - Tetrahydrofuran - Tertiary alcohol - Carboxylic acid ester - Lactone - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Acetal - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Alcohol - 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
sesquiterpene lactone
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.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
(1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.01,11.04,8]tetradecane-2,6,13-trione
INCHI
InChI=1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1
InChIKey
MOLPUWBMSBJXER-YDGSQGCISA-N
Smiles
CC(C)(C)C1(CC2C3(C14C(C(=O)OC4OC3=O)O)CC(=O)O2)O
Isomeric SMILES
CC(C)(C)[C@@]1(C[C@H]2[C@@]3([C@]14[C@H](C(=O)O[C@H]4OC3=O)O)CC(=O)O2)O
WGK Germany
3
RTECS
LV1665000
Molecular Weight
326.3
Reaxy-Rn
9144268
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9144268&ln=
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Specific Rotation[α]
-60° (C=1,Acetone)
Molecular Weight
326.300 g/mol
XLogP3
-0.300
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
1
Exact Mass
326.1 Da
Monoisotopic Mass
326.1 Da
Topological Polar Surface Area
119.000 Ų
Heavy Atom Count
23
Formal Charge
0
Complexity
650.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
6
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
Citations of This Product
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).
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).
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).
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3 Citations