Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetate
Completing data — refresh the page later to see the latest
Basic information
- CAS
25990-37-8- Standard SMILES
COC(=O)CC1C2(C)C3=C(C)C(c4ccoc4)CC3OC2C2OC(=O)C3(C)C=CC(=O)C1(C)C23- InChIKey
JZIQWNPPBKFOPT-UHFFFAOYSA-N- Molecular formula
- C27H30O7
- Average molar mass
- 466.5 g/mol
- Monoisotopic mass
- 466.19915329
Names & identifiers
- Preferred name
- Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetate
- IUPAC
- methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetate
- English name
- nimbolide
- Molecular formula
- C27H30O7
- Molecular weight
- 466.52
Names & synonyms
methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetatemethyl 2-(6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo(9.6.1.02,9.04,8.015,18)octadeca-7,13-dien-10-yl)acetateRefChem:813580874-681-5NSC309909Methyl 2-[(1R,2S,4R,6R,9R,10S,11R,15R,18R)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadeca-7,13-dien-10-yl]acetateMEGxp0_001495CHEMBL1968854SCHEMBL16561839NCI60_002662XN164985F82256
Show more names
nimbolideNSC 309909Nimbolide (25 mg)Nimbolide, 10 mM in DMSONimbolide, CyclinA and ERK1/2 inhibitor(17R)-7α,15β:21,23-Diepoxy-6α-hydroxy-4,8-dimethyl-1-oxo-11-methoxycarbonyl-18,24-dinor-11,12-seco-5α-chola-2,13,20,22-tetrene-4α-carboxylic acid γ-lactonemethyl [(2aR,5aR,6S,6aR,8R,9aR,10aS,10bR,10cR)-8-furan-3-yl-2a,5a,6a,7-tetramethyl-2,5-dioxo-2a,5a,6,6a,8,9,9a,10a,10b,10c-decahydro-2H,5H-cyclopenta[d]naphtho[2,3-b:1,8-b''c'']difuran-6-yl]acetate
Properties
Computed structural propertiesFilling in
- XLogP
- 2.2
- Topological polar surface area
- 92 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 1,040
Physicochemical properties
- Melting point
- 223 °C · >223°C (dec.)
- Boiling point
- 608.6 · 608.6±55.0 °C(Predicted)
- Density
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform, Ethyl Acetate
- form
- powder
- color
- Light Beige to Yellow
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- KMTFKEPRKBPCJW-UHFFFAOYSA-N
- SMILES
- C12C3(C)C=CC(=O)C1(C)C(CC(=O)OC)C1(C)C4C(C(C=C4C)C4=COC=C4)OC1C2OC3=O
- FDA UNII
- 993 G4LGD6 · N993G4LGD6
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- rtecs
- GY2370000
- Toxicity
- hamster,LD50,intraperitoneal,> 500mg/kg (500mg/kg),Toxicology Letters. Vol. 30, Pg. 159, 1986.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Applications
UsesNimbolide, a natural triterpenoid present in the edible parts of the neem tree (Azadirachta indica), was found to be growth-inhibitory in human colon carcinoma HT-29 cells. Nimbolide treatment of cells at 2.5 - 10 μM resulted in moderate to very strong growth inhibition.
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