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Bilobalide A
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| 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 |
| Formula | C15H18O8 |
| HBA | 8 |
| HBD | 2 |
| MW | 326.3 |
| Rotatable Bonds | 0 |
| TPSA | 119.36 |
| LogP | -0.74 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 326.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rosa canina | Rosaceae | Plantae | 74635 |
Showing of synonyms
Bilobalide A
Bilobalide
33570-04-6
Bilobalid
(-)-Bilobalide
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*,5aalpha,8beta,8aS*,9alpha,10aalpha))-
(3aS,8R,8aS,9R,10aS)-9-tert-butyl-8,9-dihydroxydihydro-9H-furo[2,3-b]furo[3',2':2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)-trione
(3aS,8R,8aS,9R,10aS)-9-tert-butyl-8,9-dihydroxydihydro-9H-furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione
DTXCID00820705
BILOBALIDE (CONSTITUENT OF GINKGO)
(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
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-, (3aS,5aR,8R,8aS,9R,10aS)-
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-, (3aS,5aR,8R,8aS,9R,10aS)-
Tert-butyl(dihydroxy)[?]trione
Bilobalide?
MFCD00132880
Bilobalide (Standard)
(-)-Bilobalide from Ginkgo biloba leaves
BILOBALIDE [MI]
BILOBALIDE [WHO-DD]
MLS000563448
SCHEMBL285824
GTPL2366
CHEMBL1318117
HY-N0076R
MOLPUWBMSBJXER-YDGSQGCISA-N
HMS2205O12
BCP28255
EX-A6793
HY-N0076
MFCD00238547
AKOS024282583
CCG-208160
CS-1517
FB65801
NCGC00142501-01
NCGC00142501-02
AS-17551
SMR000232342
BILOBALIDE (CONSTITUENT OF GINKGO) [DSC]
Q418459
SR-01000712074
SR-01000712074-4
(-)-Bilobalide from Ginkgo biloba leaves, >=93% (HPLC)
(1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.0^{1,11}.0^{4,8}]tetradecane-2,6,13-trione
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-,(3aS,5aR,8R,8aS,9R,10aS)-
- Fetni S, Bertella N, et al. (2020). Composition and biological activity of the Algerian plant Rosa canina L by HPLC-UV-MS. Arabian Journal of Chemistry, 2020, 13(1), 1105-1119. [View]
Pubchem:
73581
Cas:
33570-04-6
Gnps:
CCMSLIB00005771954
Zinc:
ZINC000008679998
Chebi:
3103
Nmrshiftdb2:
60022429
Chembl:
CHEMBL1318117
CPRiL:
62231
SMILES: C1C(=O)OC(OC2=O)C1(C234)CCC3OC(=O)C4
Level: 0
Mol. Weight: 326.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.74
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.75
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.88
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.38
- Plasma Protein Binding
- 47.38
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.71
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.66
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.79
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -0.31
- Rat (Acute)
- 3.46
- Rat (Chronic Oral)
- 2.52
- Fathead Minnow
- 3.89
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 347.77
- Hydration Free Energy
- -9.21
- Log(D) at pH=7.4
- 0.59
- Log(P)
- 0.3
- Log S
- -2.39
- Log(Vapor Pressure)
- -7.72
- Melting Point
- 227.93
- pKa Acid
- 4.84
- pKa Basic
- 2.19
No predicted protein targets found for this compound.