Diosmin (CED0005094)

Record Information

Version

1.0

Creation Date

2016-05-22 05:24:17 UTC

Update Date

2026-05-14 19:01:32 UTC

Accession Number

CHEM018625

Identification

Common Name

Diosmin

Class

Small Molecule

Description

Diosmin is an organic compound with the chemical formula C28H32O15. Diosmin belongs to the flavonoid glycosides, a subclass of flavonoids within the organic compounds. With an average molecular weight of 608.54 g/mol, Diosmin is a heavy molecule. In industrial applications, it serves as an antioxidant. At the molecular level, it is recorded as an agonist of the Aryl hydrocarbon receptor (AHR). The compound is identified in four recorded sources. It is found in healthcare, pharmaceuticals, and veterinary products as a vasoprotective agent, and in food, food processing, and cookware specifically regarding molasses and the treatment of molasses. Additionally, it is present in indoor air as part of air, dust, and atmospheric transport, and in household cleaning and consumer products such as tobacco product cases. Exposure to Diosmin can occur through oral, inhalation, and topical routes.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3',5,7-Trihydroxy-4'-methoxyflavone 7-rhamnoglucoside	ChEBI
3',5,7-Trihydroxy-4'-methoxyflavone-7-rutinoside	ChEBI
Diosmetin 7-neohesperidoside	ChEBI
Diosmetin 7-O-rutinoside	ChEBI
Diosmine	ChEBI
Diosminum	ChEBI
Neodiosmin	ChEBI
Daflon	Kegg
Barosmin	MeSH
Buchu resin	MeSH
Resin, buchu	MeSH
Venosmine	MeSH

Chemical Formula

C₂₈H₃₂O₁₅

Average Molecular Mass

608.545 g/mol

Monoisotopic Mass

608.174 g/mol

CAS Registry Number

520-27-4

IUPAC Name

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

Traditional Name

diosmin

SMILES

COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O1

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/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1

InChI Key

GZSOSUNBTXMUFQ-YFAPSIMESA-N

Chemical Taxonomy

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

rutinoside (CHEBI:4631 )
disaccharide derivative (CHEBI:4631 )
monomethoxyflavone (CHEBI:4631 )
glycosyloxyflavone (CHEBI:4631 )
dihydroxyflavanone (CHEBI:4631 )
flavones (C10039 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	59.17 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-0159-0960010000-fe04b8935dfef822b8ba	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0000009000-afd1640b539ec58a4616	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0000009000-afd1640b539ec58a4616	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052b-0091007000-37f41b107b871f3ae8d4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0000009000-afd1640b539ec58a4616	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0091000000-a356b08129066c8cc235	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1249000000-89e125689ac3c8ab2522	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0090000000-5ba2996dd1e65cd9aef6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udj-0298000000-0bbbfc4f4a4f06eabd19	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-1249000000-89e125689ac3c8ab2522	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0pb9-0079000000-3ec59b6cb85bb16ee539	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0pb9-0059000000-23c28bc86f2cb99c8879	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-0119243000-f16c98edd9a3d904640f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0229100000-644d699dbc0150b95b36	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udr-2769000000-bb9bda7010517389263b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4j-4490237000-890bdf4e4d72059328ef	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-2490010000-f62cdd107e91feb48f5a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000t-1190000000-05c10c73e5b47ee49053	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
8564.0	Log mg/kg	[4800:15000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
292	Vasoprotectives	Healthcare, pharmaceuticals & veterinary products	Not Available
546	Molasses And Treatment Of Molasses	Food, food processing & cookware	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Predicted (SEA)	7.00643
Click to view 3D structure	Cytochrome P450 1A1	P04798	Humans	Predicted (SEA)	5.44945
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	39.1582
Click to view 3D structure	Nonstructural protein 5	V5TFZ2	Dengue virus	Predicted (SEA)	1.01204
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	16.3483
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	179.365
Click to view 3D structure	Beta-secretase 1	P56817	Humans	Predicted (SEA)	32.2296
Click to view 3D structure	Inositol hexakisphosphate kinase 2	Q9UHH9	Humans	Predicted (SEA)	3.42537
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P15121	Humans	Predicted (SEA)	10.8989
Click to view 3D structure	Xanthine dehydrogenase/oxidase	P47989	Humans	Predicted (SEA)	4.7488
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P07943	Rattus norvegicus	Predicted (SEA)	7.86277
Click to view 3D structure	Lysine-specific histone demethylase 1A	O60341	Humans	Predicted (SEA)	7.55137
Click to view 3D structure	DNA topoisomerase 1	Q9WUL0	Rattus norvegicus	Predicted (SEA)	3.19182
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	79.017
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	36.5113
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	54.8837
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	66.094
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	82.9873
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	29.7384
Click to view 3D structure	Multidrug resistance-associated protein 1	P33527	Humans	Predicted (SEA)	5.3716
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	78.472
Click to view 3D structure	MAP kinase-interacting serine/threonine-protein kinase 2	Q9HBH9	Humans	Predicted (SEA)	177.263
Click to view 3D structure	Arginase	O96394	Leishmania amazonensis	Predicted (SEA)	2.64687
Click to view 3D structure	Amyloid-beta precursor protein	P05067	Humans	Predicted (SEA)	45.0747
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	62.2015