Rutin trihydrate

Details

• Internal ID: 5f4d7929-395e-423a-a659-d872f70aa9e7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(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;trihydrate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)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=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O.O.O.O
• InChI: InChI=1S/C27H30O16.3H2O/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9;;;/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3;3*1H2/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-;;;/m0.../s1
• InChI Key: NLLBWFFSGHKUSY-JPRRWYCFSA-N
• Popularity: 255 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₉
• Molecular Weight: 664.60 g/mol
• Exact Mass: 664.18507891 g/mol
• Topological Polar Surface Area (TPSA): 269.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -4.16
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 250249-75-3
• Rutoside trihydrate
• Rutoside trihydrate [EP]
• RF4N03853G
• DTXSID50179735
• RUTOSIDE TRIHYDRATE [WHO-DD]
• RUTOSIDE TRIHYDRATE [EP MONOGRAPH]
• 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-l-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, trihydrate
• 4H-1-BENZOPYRAN-4-ONE, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-, TRIHYDRATE
• RUTOSIDE TRIHYDRATE (EP MONOGRAPH)
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,4R,5S)-3,4,5-trihydroxy-6-(((2R,4R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,4R,5S)-3,4,5-trihydroxy-6-[[(2R,4R,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• RefChem:884059
• DTXCID10102226
• 684-230-2
• Rutin hydrate
• (+)-Rutin trihydrate
• Rutin (hydrate)
• 207671-50-9
• Rutin (trihydrate)
• Quercetin-3-rutinoside trihydrate
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(((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 trihydrate
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(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;trihydrate
• Rutin hydrate (JAN)
• MFCD00149490
• RUTIN HYDRATE [JAN]
• UNII-RF4N03853G
• C27H36O19
• Rutin (trihydrate) (Standard)
• (+)-Rutin trihydrate, 95%
• orb1980254
• SCHEMBL1096921
• SCHEMBL31128180
• NLLBWFFSGHKUSY-JPRRWYCFSA-N
• HY-W013075R
• Rutin trihydrate, >=90% (HPLC)
• Rutin trihydrate, analytical standard
• AKOS025310161
• CS-W013791
• GS-3606
• HY-W013075
• OR03679
• DA-77592
• DA-77593
• D00190
• D96045
• Rutin trihydrate 1000 microg/mL in Acetonitrile
• F869664
• Q27288087
• Rutin trihydrate, primary pharmaceutical reference standard
• Rutin hydrate (Rutoside hydrate; Quercetin 3-O-rutinoside hydrate)
• Rutoside trihydrate, European Pharmacopoeia (EP) Reference Standard
• Rutin trihydrate, United States Pharmacopeia (USP) Reference Standard
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(((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-
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(((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-onetrihydrate
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(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;trihydrate
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(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 trihydrate
• Quercetin-3-rutinoside hydrate;3-[[6-O-(6-Deoxy-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-4H-1 -benzopyran-4-one;Vitamin P hydrate;(+)-Rutin trihydrate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5679	56.79%
Caco-2	-	0.9269	92.69%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.5616	56.16%
OATP1B1 inhibitior	+	0.9117	91.17%
OATP1B3 inhibitior	+	0.9151	91.51%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6681	66.81%
P-glycoprotein inhibitior	-	0.6165	61.65%
P-glycoprotein substrate	-	0.5075	50.75%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.8737	87.37%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8973	89.73%
Skin irritation	-	0.8025	80.25%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3823	38.23%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.9233	92.33%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8983	89.83%
Acute Oral Toxicity (c)	III	0.5971	59.71%
Estrogen receptor binding	+	0.7901	79.01%
Androgen receptor binding	+	0.6176	61.76%
Thyroid receptor binding	+	0.5312	53.12%
Glucocorticoid receptor binding	+	0.6215	62.15%
Aromatase binding	+	0.6273	62.73%
PPAR gamma	+	0.7234	72.34%
Honey bee toxicity	-	0.7514	75.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9005	90.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.58%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.60%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.80%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.69%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.54%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	94.22%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.65%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.68%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.47%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.04%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.29%	99.17%
CHEMBL3194	P02766	Transthyretin	84.94%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.30%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.73%	93.65%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.53%	94.80%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.54%	95.78%
CHEMBL4208	P20618	Proteasome component C5	81.49%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.10%	97.36%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.33%	80.78%

Plants that contains it

• Gardenia jasminoides
• Ginkgo biloba

Cross-Links

• PubChem: 16218542
• NPASS: NPC155865