Showing Compound Diosmetin 7-rutinoside (FDB000693)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-02-24 19:10:12 UTC

Primary ID

FDB000693

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Diosmetin 7-rutinoside

Description

Diosmin 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. Diosmin is found, on average, in the highest concentration within a few different foods, such as hyssops (Hyssopus officinalis), peppermints (Mentha X piperita), and lemons (Citrus limon). Diosmin has also been detected, but not quantified in, several different foods, such as green vegetables, mandarin orange (clementine, tangerine), rosemaries (Rosmarinus officinalis), spearmints (Mentha spicata), and sweet oranges (Citrus sinensis). This could make diosmin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Diosmin.

CAS Number

520-27-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinoside	HMDB
Barosmin	HMDB
Daflon	HMDB
Diosmetin 7-O-rutinoside	HMDB
Diosmetin 7-rutinoside	HMDB
Diosmetin-7-O-rutinoside	HMDB
Diosmil	HMDB
Diosmin, ban, inn	HMDB
Diosmin, BAN, INN	db_source
Diosmine	HMDB

Showing 1 to 10 of 22 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.54 g/L	ALOGPS
logP	0.08	ALOGPS
logP	-0.44	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.39 m³·mol⁻¹	ChemAxon
Polarizability	59.9 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C28H32O15

IUPAC name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one

InChI Identifier

InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3

InChI Key

GZSOSUNBTXMUFQ-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(OC1OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C1O)C=C2O

Average Molecular Weight

608.5447

Monoisotopic Molecular Weight

608.174120354

Classification

Description

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

Substituents

Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Oxane
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Anti-inflammatory

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	0.14	PERRISSOUD,D & TESTA,B (1986)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 55.26%; H 5.30%; O 39.44%	DFC
Melting Point	Mp 280 dec. (in vacuo)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Diosmetin 7-rutinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-7432290000-d70f47a129b3142c35cb	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0900-6331019000-bde6242eed34a2bd808d	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diosmetin 7-rutinoside, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-0249000000-bd1d2df9c9ae8a17841f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0090000000-d4179a0eac71cee296c4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0090000000-2d58a9e098baf7884b31	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0001900000-cb8633696196ba8d631a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0001900000-0804b33b8df38a53f208	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0089-0009100000-02518ed6c111bd22a8f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0089-0009100000-33682b6050606a7b1811	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-0249000000-bd1d2df9c9ae8a17841f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0090000000-6c0964f69118a53d9c02	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0009403000-576343b0109027111529	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0bt9-0008903000-60aff456412fa112c030	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0091000000-7022821f0c4a5d745678	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-08fr-0004907000-5cb30d60fe09978a64b9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0091000000-12577c1dd4b5cfa80125	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0020009000-dfe53d41d78137fd25f7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0w29-0009400000-3bd7d8bfd41e0700368e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090001000-af1d868643550c0db6ab	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0020009000-93ef6149b97e092e4a5a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0020009000-ba94be76e265df4c7a26	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udl-0139153000-a5df8b8ace59185711f6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0149100000-745e0883625146afe113	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uei-1598000000-7d042cfcc8d7a6d00ffc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bta-3491236000-47db98d4ee7c0cbbd9d8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2490010000-590296c798c9902cd85c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000t-1190000000-3e769837d46cbf206b3d	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4510141

ChEMBL ID

Not Available

KEGG Compound ID

C10039

Pubchem Compound ID

5353588

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

232

DrugBank ID

Not Available

HMDB ID

HMDB29548

CRC / DFC (Dictionary of Food Compounds) ID

BKL03-G:BFP73-M

EAFUS ID

Not Available

Dr. Duke ID

DIOSMIN

BIGG ID

Not Available

KNApSAcK ID

C00004362

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

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti capillary-fragility			DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti clastogen			DUKE
anti CVI			DUKE
anti cytotoxic	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
anti edemic			DUKE
anti hemorrhoidal	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE