Malabaricone C
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Basic information
- CAS
63335-25-1- Standard SMILES
O=C(CCCCCCCCc1ccc(O)c(O)c1)c1c(O)cccc1O- InChIKey
HCOZRFYGIFMIEX-UHFFFAOYSA-N- Molecular formula
- C21H26O5
- Average molar mass
- 358.4 g/mol
- Monoisotopic mass
- 358.17802393
Overview
Malabaricone C is a natural product found in Myristica cinnamomea. It has a role as a metabolite.
Names & identifiers
- Preferred name
- Malabaricone C
- IUPAC
- 1-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)nonan-1-one
- English name
- Malabaricone C
- Molecular formula
- C21H26O5
- Molecular weight
- 358.43
Names & synonyms
Malabaricone C63335-25-11-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)nonan-1-oneC9K53R3PRNDTXSID40212721NSC-2879681-Nonanone, 1-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)-RefChem:155351DTXCID701352121-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)-1-nonanoneCHEBI:69015UNII-C9K53R3PRN
Show more names
lipid metabolism,Inhibitor,sphingomyelin synthase,SMS 1,diet,obesity,inhibit,Malabaricone C,SMS 2
CHEMBL524100MEGxp0_000379orb1217787orb1296979SCHEMBL7784918Malabaricone C, 10 mM in DMSOGLXC-21346HY-N8518
Database identifiers
- CAS
63335-25-1- PubChem CID
- 100313
- DTXSID
DTXSID40212721- ChEMBL
CHEMBL524100- ChEBI
CHEBI:69015- UNII
- C9K53R3PRN
- Nikkaji
- J19.530H
Properties
Computed structural propertiesFilling in
- XLogP
- 5.7
- Topological polar surface area
- 98 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 10
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 403
Experimental & physicochemical properties
Melting Point119 - 121 °C
Physical DescriptionSolid
Physicochemical properties
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 25 mg/ml; · DMF: 25 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml
- form
- A crystalline solid
- color
- White to off-white
- InChI
- InChI=1S/C21H26O5/c22-16-13-12-15(14-20(16)26)8-5-3-1-2-4-6-9-17(23)21-18(24)10-7-11-19(21)25/h7,10-14,22,24-26H,1-6,8-9H2
- InChIKey
- HCOZRFYGIFMIEX-UHFFFAOYSA-N
- SMILES
- C(C1=C(O)C=CC=C1O)(=O)CCCCCCCCC1=CC=C(O)C(O)=C1
- FDA UNII
- 9 K53R3PRN · C9K53R3PRN
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
DescriptionMalabaricone C is a diarylnonanoid that has been found in Myristica and has diverse biological activities. It scavenges 59.9% of 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals when used at a concentration of 7 μg/ml. Malabaricone C is active against S. aureus, B. subtilis, and C. albicans in vitro (MICs = 2-32 μg/ml). It is cytotoxic to A549, HL-60, and MCF-7 cells (IC50s = 12.3, 46.1, and 10.8 μM, respectively). Malabaricone C inhibits sphingomyelin synthase 1 (SMS1) and SMS2 activity in cell lysates (IC50s = 3 and 1.5 μM, respectively). It decreases body weight gain, hepatic steatosis, and hepatic and plasma triglyceride levels in a mouse model of high-fat diet-induced obesity when administered at a dose of 0.1% in the diet.
UsesMalabaricone C is a useful research chemical compound from Myristica malabarica which exhibits antioxidant activity.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A natural product found in Myristica cinnamomea.
Related reactions
0 records
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Compound notes
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