Showing Compound Biflorin (FDB001390)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:57 UTC

Update date

2019-11-26 02:56:26 UTC

Primary ID

FDB001390

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Biflorin

Description

Constituent of Eugenia caryophyllata (clove) Biflorin is an o-naphthoquinone isolated from Capraria biflora L. (Scrophulariaceae, a perennial shrub widely distributed in several countries of tropical America). Biflorin has cytotoxic and antioxidant potential, strongly inhibiting the growth of five tested tumor cell lines, especially the skin, breast and colon cancer cells with IC50 of 0.40, 0.43 and 0.88 micro/ml for B16, MCF-7 and HCT-8, respectively, while the antioxidant activity was assayed against autoxidation of oleic acid in a water/alcohol system. (PMID: 16042338). Biflorin is found in herbs and spices and cloves.

CAS Number

89701-85-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
6-b-D-Glucopyranosyl-5,7-dihydroxy-2-methyl-4H-1-benzopyran-4-one, 9CI	db_source
6beta-C-Glucopyranosyl-5,7-dihydroxy-2-methylchromone	biospider

Predicted Properties

Property	Value	Source
Water Solubility	13.1 g/L	ALOGPS
logP	-0.72	ALOGPS
logP	-0.84	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	6.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.19 m³·mol⁻¹	ChemAxon
Polarizability	33.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H18O9

IUPAC name

5,7-dihydroxy-2-methyl-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

InChI Identifier

InChI=1S/C16H18O9/c1-5-2-6(18)10-8(24-5)3-7(19)11(13(10)21)16-15(23)14(22)12(20)9(4-17)25-16/h2-3,9,12,14-17,19-23H,4H2,1H3

InChI Key

XTZWWMZDVUKEDJ-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC(=O)C2=C(O1)C=C(O)C(C1OC(CO)C(O)C(O)C1O)=C2O

Average Molecular Weight

354.3087

Monoisotopic Molecular Weight

354.095082174

Classification

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Monosaccharide
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 54.24%; H 5.12%; O 40.64%	DFC
Melting Point	Mp 300-303° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]28D +24.4 (c, 0.34 in Py)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0009000000-1a02b48834390ce8c6fd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06ri-2329000000-ebc76c4a88ef0fd2305f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lfu-4391000000-cd8add8440ed63e25129	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0119000000-25b771ff671cbb7d2a26	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fdx-8598000000-1163327bad8734380b1b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9660000000-28a9f069e391f5cf5208	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02336

CRC / DFC (Dictionary of Food Compounds) ID

BZW64-D:BZW64-D

EAFUS ID

Not Available

Dr. Duke ID

BIFLORIN

BIGG ID

Not Available

KNApSAcK ID

C00002417

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-gingivitic	52217	An agent that reduces gingivitis symptoms, commonly used in managing plaque, inflammation, and gum disease, promoting oral health by preventing bacterial growth and infection.	DUKE
Anti periodontic		An agent that prevents or treats periodontal disease, reducing inflammation and infection in the gums and supporting tissues of the teeth, commonly used in managing periodontitis, gingivitis, and promoting oral health.	DUKE
Anti-plaque		An agent that removes or prevents the formation of dental plaque, a biofilm of bacteria, to prevent tooth decay and gum disease, commonly used in oral care products and therapeutic applications for periodontal health.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Phosphodiesterase inhibitor	23924	An agent that blocks phosphodiesterase enzymes, increasing cyclic nucleotide levels, and enhancing cellular signaling. Therapeutically, it treats respiratory, cardiovascular, and neurological disorders, with key medical uses including managing erectile dysfunction, pulmonary hypertension, and chronic obstructive pulmonary disease (COPD).	DUKE