| Common Name |
Didymin
| Description |
Didymin is found in citrus. Didymin is from leaves of Monarda didyma (bergamot) and Citrus speciesDidymin has been shown to exhibit anti-proliferative function (PMID 19733932 ).Didymin belongs to the family of Flavonoid O-Glycosides. These are compounds containing a carbohydrate moiety which is o-glycosidically linked to one of the flavonoid backbones (2-phenylchromen-4-one, 3-phenylchromen-4-one or 4-phenylcoumarin).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29482 (Didymin)
| Synonyms |
| Value |
Source |
4'-Methoxy-5,7-dihydroxyflavanone-7-O-rutinosideHMDB
NeoponcirinHMDB
| Chemical Formlia |
C28H34O14
| Average Molecliar Weight |
594.5612
| Monoisotopic Molecliar Weight |
594.194855796
| IUPAC Name |
5-hydroxy-2-(4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-3,4-dihydro-2H-1-benzopyran-4-one
| Traditional Name |
5-hydroxy-2-(4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-2,3-dihydro-1-benzopyran-4-one
| CAS Registry Number |
14259-47-3
| SMILES |
COC1=CC=C(C=C1)C1CC(=O)C2=C(O1)C=C(OC1OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C1O)C=C2O
| InChI Identifier |
InChI=1S/C28H34O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-29,31-36H,9-10H2,1-2H3
| InChI Key |
RMCRQBAILCLJGU-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
| Kingdom |
Organic compounds
| Super Class |
Phenylpropanoids and polyketides
| Class |
Flavonoids
| Sub Class |
Flavonoid glycosides
| Direct Parent |
Flavonoid-7-O-glycosides
| Alternative Parents |
4-O-methylated flavonoids
Flavanones
5-hydroxyflavonoids
Phenolic glycosides
Alkyl glycosides
O-glycosyl compounds
Disaccharides
Chromones
Methoxybenzenes
Aryl alkyl ketones
Anisoles
Alkyl aryl ethers
Oxanes
Vinylogous acids
Secondary alcohols
1,2-diols
Oxacyclic compounds
Acetals
Hydrocarbon derivatives
| Substituents |
Flavonoid-7-o-glycoside
Methoxyflavonoid skeleton
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavanone
Fatty acyl glycoside
5-hydroxyflavonoid
Flavan
Phenolic glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Chromane
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Anisole
Alkyl aryl ether
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Polyol
Ketone
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
anti-proliferative
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point211 – 213 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility2.01 mg/mLALOGPS
logP-0.11ALOGPS
logP-0.011ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.84ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area214.06 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity138.79 m3·mol-1ChemAxon
Polarizability59.41 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-002s-0290260000-87e824e7ff71cf49eccfView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-000i-0390100000-e833b7ae36c4c6aabdb4View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0f79-0960000000-f3a1b2db7e551bbabb15View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-000f-3490380000-4d255fb7584ab3878105View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-000i-2590110000-49d0f437355f5323bdf9View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-00kr-2390000000-5e728be84d6bcb578e7dView in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
214
| FoodDB ID |
FDB000612
| KNApSAcK ID |
C00008223
| Chemspider ID |
77297
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29482
| Metagene Link |
HMDB29482
| METLIN ID |
Not Available
| PubChem Compound |
85705
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Bromfenac (sodium hydrate)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Hung JY, Hsu YL, Ko YC, Tsai YM, Yang CJ, Huang MS, Kuo PL: Didymin, a dietary flavonoid glycoside from citrus fruits, induces Fas-mediated apoptotic pathway in human non-small-cell lung cancer cells in vitro and in vivo. Lung Cancer. 2010 Jun;68(3):366-74. doi: 10.1016/j.lungcan.2009.08.013. Epub 2009 Sep 5. [PubMed:19733932 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 3045112
