Bilobalide - Moligand™, analytical standard , CAS No.33570-04-6

CAS: 33570-04-6 Cat. No.: B101648 Molecular Weight: 326.3 EC Number: 608-892-9

GRADE & PURITY Analytical standard, Moligand™

Synonyms

(-)-Bilobalide | HY-N0076 | AS-17551 | BILOBALIDE [WHO-DD] | 2,5 Dibromotoluene | 2,5-Dichloro-p-quinone | MFCD00238547 | Q418459 | CCG-208160 | DTXSID10873207 | SMR000232342 | Bilobalide | SCHEMBL285824 | CHEBI:3103 | 5-Methyl-2-chlorophenol | 2-Chlor-4-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(-)-Bilobalide | HY-N0076 | AS-17551 | BILOBALIDE [WHO-DD] | 2, 5 Dibromotoluene | 2, 5-Dichloro-p-quinone | MFCD00238547 | Q418459 | CCG-208160 | DTXSID10873207 | SMR000232342 | Bilobalide | SCHEMBL285824 | CHEBI:3103 | 5-Methyl-2-chlorophenol | 2-Chlor-4-

Specifications & Purity

Moligand™, analytical standard

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

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™

Note

Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

• Canonical Smiles: CC(C)(C)C1(CC2C3(C14C(C(=O)OC4OC3=O)O)CC(=O)O2)O
• 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
• InChIKey: MOLPUWBMSBJXER-YDGSQGCISA-N
• 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
• 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=

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 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.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GLRA2 Tchem Glycine receptor subunit alpha-2 (1 Activities)

Discover Target: GLRA2

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

HTR3A Tclin 5-hydroxytryptamine receptor 3A (1 Activities)

Discover Target: HTR3A

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

GLRA1 Tclin Glycine receptor subunit alpha-1 (1 Activities)

Discover Target: GLRA1

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

GLRB Tclin Glycine receptor subunit beta (2 Activities)

Discover Target: GLRB

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

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

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

NR1I2 Tchem Pregnane X receptor (6667 Activities)

Discover Target: NR1I2

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

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

Discover Target: ALOX15

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

HepG2 (196354 Activities)

Explore this target

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

GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

Discover Target: GNAS

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

NR1I3 Tchem Nuclear receptor subfamily 1 group I member 3 (655 Activities)

Discover Target: NR1I3

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

SMN1 Tchem Survival motor neuron protein (34246 Activities)

Discover Target: SMN1

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

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

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

Associated Targets(non-human)

PC-12 (7051 Activities)

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

Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

Discover Target: Nr1i2

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

Mechanisms of Action

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

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]

4. Jieying Zhou, Wei Luo, Lingxin Zeng, Shihao Xu, Ruohan Wu, Jiaqi Lu, Ying Li, Wei Xiong.  (2026)  A Bubble-Driven Drug Delivery System Enhances Oral Absorption and Antipyretic Efficacy of Poorly Water-Soluble Andrographolide.  International Journal of Nanomedicine,      [PMID:] [10.2147/IJN.S574265]