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33570-04-6 molecular structure
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(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

ChemBase ID: 126153
Molecular Formular: C15H18O8
Molecular Mass: 326.29862
Monoisotopic Mass: 326.10016754
SMILES and InChIs

SMILES:
CC(C)(C)[C@@]1(C[C@H]2[C@@]3([C@@]41[C@H](C(=O)O[C@H]4OC3=O)O)CC(=O)O2)O
Canonical SMILES:
O=C1O[C@@H]2[C@@]3(C1)C(=O)O[C@H]1[C@]3([C@](C2)(O)C(C)(C)C)[C@@H](O)C(=O)O1
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

Cite this record

CBID:126153 http://www.chembase.cn/molecule-126153.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
bilobalide
Synonyms
(-)-Bilobalide from Ginkgo biloba leaves
Bilobalide
CAS Number
33570-04-6
MDL Number
MFCD00238547
PubChem SID
24892116
162220494
PubChem CID
73581
CHEMBL
133266
Chemspider ID
21106418
IUPHAR ligand ID
2366
Wikipedia Title
Bilobalide

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
B9031 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.97425  H Acceptors
H Donor LogD (pH = 5.5) -0.28442824 
LogD (pH = 7.4) -0.28443965  Log P -0.5177614 
Molar Refractivity 69.9879 cm3 Polarizability 29.278425 Å3
Polar Surface Area 119.36 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
oral expand Show data source
Legal Status
legal expand Show data source
Purity
≥93% (HPLC) expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B9031 external link
Biochem/physiol Actions
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-hydroxytryptamine type 3 (5-HT(3)) receptor antagonist, may be used to study the function of these receptors in brain processes such as cognition and memory. Bilobalide may also be used to study the function of platelet-activating factor receptors in cardiomyocytes.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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