Diosmin

Details

• Internal ID: 8a4b6e1f-6924-4500-988e-9d851158ec9a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• 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]oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• InChI: 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
• Popularity: 1,257 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.50 g/mol
• Exact Mass: 608.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 520-27-4
• Barosmin
• Diosimin
• Venosmine
• Diosmil
• Flebosten
• Diosmine
• Daflon
• Tovene
• Ven-Detrex
• Diovenor
• Buchu Resin
• Litosmil
• Veno-V
• flebosmil
• Diosminum
• Rioven
• Diosmetin 7-O-rutinoside
• Diosven
• Flebaven
• Flebavena
• Hemerven
• Insuven
• Varinon
• Dioven
• Diosmetin-7-O-rutinoside
• Diosmetin 7-rutinoside
• UNII-7QM776WJ5N
• Diosmin [INN]
• 7QM776WJ5N
• CCRIS 7915
• CHEBI:4631
• DTXSID4045892
• Diosmin [INN:BAN]
• Diosmin [INN-Spanish]
• Diosmine [INN-French]
• Diosminum [INN-Latin]
• EINECS 208-289-7
• 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]oxymethyl]oxan-2-yl]oxychromen-4-one
• NSC-758417
• 3',5,7-trihydroxy-4'-methoxyflavone-7-rutinoside
• SE 4601
• DTXCID2025892
• 3',5,7-Trihydroxy-4'-methoxyflavone 7-rutinoside
• Diosmin (INN)
• NSC 758417
• 3',5,7-trihydroxy-4'-methoxyflavone 7-rhamnoglucoside
• 3',5,7-Trihydroxy-4'-methoxyflavone-7-(6-O-(-deoxy-alpha-L-mannopyraonsyl)-beta-D-glucopyranoside
• 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-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 3',5-Dihydroxy-4'-methoxy-4-oxo-4H-chromen-7-ylrutosid
• DIOSMIN (MART.)
• DIOSMIN [MART.]
• DIOSMIN (USP-RS)
• DIOSMIN [USP-RS]
• Diosmin, analytical standard
• 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-
• 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
• 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-((6-O-alpha-L-rhamnopyranosyl-beta-D-glycopyranosyl)oxy)-4-chromenon
• DIOSMIN (EP MONOGRAPH)
• DIOSMIN [EP MONOGRAPH]
• 3',5-Dihydroxy-4'-methoxy-4-oxo-4H-chromen-7-ylrutosid [IUPAC]
• Resin, Buchu
• 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• 7-((6-O-(6-Deoxy-ga-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
• CAS-520-27-4
• SR-01000799147
• C28H32O15
• Diosmina
• 3',5-Dihydroxy-4'-methoxy-4-oxo-4H-chromen-7-ylrutosid (IUPAC)
• NCGC00095022-01
• 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-
• 4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-
• Daflon (TN)
• MFCD00009772
• Diosmin (8)
• DIOSMINE [INCI]
• DIOSMIN [DSC]
• DIOSMIN [MI]
• DIOSMIN [WHO-DD]
• MLS001304032
• SCHEMBL120870
• CHEMBL231884
• C05CA03
• BDBM153267
• GLXC-13353
• HMS2233P16
• HMS3713L08
• Tox21_111392
• s2292
• AKOS015969767
• Tox21_111392_1
• BCP9000612
• CCG-208570
• DB08995
• SMP1_000183
• NCGC00344564-01
• 4H-1-Benzopyran-4-one,7-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-
• AS-13224
• BP-12422
• SMR000718616
• BCP0726000067
• LS-193056
• C10039
• D07858
• EN300-18388399
• 3',5,7-trihydroxy-4'-methoxy flavone-7-rutinoside
• Q2607865
• SR-01000799147-4
• SR-01000799147-5
• SR-01000799147-6
• Diosmin, European Pharmacopoeia (EP) Reference Standard
• Diosmin, United States Pharmacopeia (USP) Reference Standard
• Diosmin for system suitability, European Pharmacopoeia (EP) Reference Standard
• 4h-1-benzopiran-4-ona, 7-[[6-o-(6-deoxi-?-l-mannopiranosil)-?-d-glucopiranosil]oxi]-5-hidroxi-2-(3-hidroxi-4-metoxifenil)-
• 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-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one
• 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(O6-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)chromen-4-one
• 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• 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
• 7-((6-O-(6-DEOXY-GA-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-HYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.8881	88.81%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.5715	57.15%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7322	73.22%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.8632	86.32%
CYP3A4 substrate	+	0.5252	52.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7828	78.28%
CYP inhibitory promiscuity	-	0.6670	66.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9213	92.13%
Skin irritation	-	0.8249	82.49%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.8128	81.28%
Micronuclear	+	0.7492	74.92%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9101	91.01%
Acute Oral Toxicity (c)	III	0.6904	69.04%
Estrogen receptor binding	+	0.7726	77.26%
Androgen receptor binding	-	0.5498	54.98%
Thyroid receptor binding	+	0.5465	54.65%
Glucocorticoid receptor binding	+	0.5871	58.71%
Aromatase binding	-	0.4896	48.96%
PPAR gamma	+	0.7040	70.40%
Honey bee toxicity	-	0.7151	71.51%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	+	0.8477	84.77%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2392	P06746	DNA polymerase beta	25118.9 nM	Potency	via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.84%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.11%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	98.02%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.59%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.34%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.27%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.91%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.42%	96.09%
CHEMBL3194	P02766	Transthyretin	90.63%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.51%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.41%	97.36%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.33%	95.78%
CHEMBL3401	O75469	Pregnane X receptor	88.45%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.23%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.95%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.08%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.50%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.37%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.73%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.48%	90.71%
CHEMBL1907	P15144	Aminopeptidase N	83.47%	93.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.49%	96.00%

Plants that contains it

• Abies nephrolepis
• Aesculus turbinata
• Agathosma betulina
• Alnus alnobetula
• Angelica gigas
• Argyreia nervosa
• Artocarpus styracifolius
• Asyneuma campanuloides
• Campanula patula
• Campanula persicifolia
• Citrus × aurantium
• Citrus deliciosa
• Citrus maxima
• Citrus medica
• Dorstenia mannii
• Forsythia giraldiana
• Grona styracifolia
• Hedysarum setigerum
• Helichrysum arenarium
• Hyssopus officinalis
• Krameria erecta
• Lobelia chinensis
• Lobelia nummularia
• Meehania urticifolia
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Mentha spicata
• Nicotiana tabacum
• Rosmarinus officinalis
• Sicyos edulis
• Swertia diluta
• Tetradium ruticarpum
• Toddalia asiatica
• Zanthoxylum nitidum

Cross-Links

• PubChem: 5281613
• NPASS: NPC209296
• ChEMBL: CHEMBL231884
• LOTUS: LTS0240372
• wikiData: Q2607865