rutin (CHEBI:28527)

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CHEBI:28527 - rutin

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ChEBI Name	rutin

ChEBI ID	CHEBI:28527

Definition	A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45398, CHEBI:8923, CHEBI:26585

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

RUT - Ideal conformer

Mrv1927 05282121293D

starting HoverWatcher_5

Time for openFile(RUT - Ideal conformer

Mrv1927 05282121293D

73 77 0 0 0 0 999 V2000

-0.9390 -2.5430 1.1560 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.7410 -1.5460 0.7450 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9840 -1.3000 -0.5730 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8040 -0.2770 -0.9400 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.3810 -2.1220 -1.5590 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.5800 -1.9350 -2.7490 O 0 0 0 0 0 0 0 0 0 0 0 0

0.1390 -4.0630 -1.9970 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0380 -3.9020 -3.3330 O 0 0 0 0 0 0 0 0 0 0 0 0

0.9520 -5.0730 -1.5180 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1320 -5.2350 -0.1490 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9340 -6.2310 0.3100 O 0 0 0 0 0 0 0 0 0 0 0 0

0.5020 -4.3920 0.7520 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3180 -3.3720 0.2920 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5020 -3.2060 -1.0920 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3810 -0.6860 1.7580 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.6240 -0.1570 2.8070 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.2280 0.6530 3.7500 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4930 1.1730 4.7690 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.5910 0.9310 3.6600 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.1830 1.7220 4.5920 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.3440 0.4010 2.6220 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.7470 -0.4030 1.6740 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.9850 0.6940 -1.5950 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.8770 1.7430 -2.2620 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.7460 1.1050 -3.2010 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.9920 2.7610 -2.9900 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.8010 3.8270 -3.4920 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9650 3.3150 -1.9960 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.0370 4.1550 -2.6860 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.2160 2.1470 -1.3500 C 0 0 1 0 0 0 0 0 0 0 0 0

0.8360 2.6910 -0.3820 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.1350 1.3210 -0.6370 O 0 0 0 0 0 0 0 0 0 0 0 0

2.4880 2.1620 1.1210 C 0 0 1 0 0 0 0 0 0 0 0 0

1.6070 1.6070 0.1420 O 0 0 0 0 0 0 0 0 0 0 0 0

3.1330 1.0290 1.9220 C 0 0 2 0 0 0 0 0 0 0 0 0

4.0370 1.5780 2.8840 O 0 0 0 0 0 0 0 0 0 0 0 0

3.8980 0.1110 0.9620 C 0 0 2 0 0 0 0 0 0 0 0 0

4.6270 -0.8650 1.7100 O 0 0 0 0 0 0 0 0 0 0 0 0

4.8700 0.9640 0.1400 C 0 0 1 0 0 0 0 0 0 0 0 0

5.4870 0.1540 -0.8630 O 0 0 0 0 0 0 0 0 0 0 0 0

4.0930 2.1010 -0.5280 C 0 0 2 0 0 0 0 0 0 0 0 0

5.0480 2.9380 -1.3810 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4980 2.9290 0.4690 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8010 -4.4420 -3.5810 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4500 -5.7370 -2.2100 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3720 -7.0080 0.4320 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6490 -4.5280 1.8130 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5680 -0.3730 2.8750 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4620 0.5010 5.4630 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.4210 1.1500 5.3350 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.3990 0.6190 2.5560 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3360 -0.8130 0.8670 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3750 0.2020 -2.3530 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4710 2.2520 -1.5040 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.2780 0.4700 -2.7020 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4760 2.2730 -3.8170 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.4380 3.4310 -4.1020 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4770 3.8920 -1.2260 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5500 4.8710 -3.0830 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2740 1.5580 -2.1250 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3420 3.2130 0.4360 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4930 3.3810 -0.9100 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9220 2.8050 1.7940 H 0 0 0 0 0 0 0 0 0 0 0 0

2.3590 0.4570 2.4340 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5150 2.1520 3.4610 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1950 -0.3890 0.2960 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9780 -1.3680 2.2210 H 0 0 0 0 0 0 0 0 0 0 0 0

5.6350 1.3800 0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0890 0.7290 -1.3550 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3130 1.6820 -1.1640 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8290 3.3580 -0.7460 H 0 0 0 0 0 0 0 0 0 0 0 0

5.5020 2.3070 -2.1450 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4950 3.7470 -1.8590 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 13 1 0 0 0 0

2 3 2 0 0 0 0

2 15 1 0 0 0 0

3 4 1 0 0 0 0

3 5 1 0 0 0 0

4 23 1 0 0 0 0

5 6 2 0 0 0 0

5 14 1 0 0 0 0

7 8 1 0 0 0 0

7 9 1 0 0 0 0

7 14 2 0 0 0 0

8 44 1 0 0 0 0

9 10 2 0 0 0 0

9 45 1 0 0 0 0

10 11 1 0 0 0 0

10 12 1 0 0 0 0

11 46 1 0 0 0 0

12 13 2 0 0 0 0

12 47 1 0 0 0 0

13 14 1 0 0 0 0

15 16 2 0 0 0 0

15 22 1 0 0 0 0

16 17 1 0 0 0 0

16 48 1 0 0 0 0

17 18 1 0 0 0 0

17 19 2 0 0 0 0

18 49 1 0 0 0 0

19 20 1 0 0 0 0

19 21 1 0 0 0 0

20 50 1 0 0 0 0

21 22 2 0 0 0 0

21 51 1 0 0 0 0

22 52 1 0 0 0 0

23 24 1 0 0 0 0

23 32 1 0 0 0 0

23 53 1 6 0 0 0

24 25 1 0 0 0 0

24 26 1 0 0 0 0

24 54 1 1 0 0 0

25 55 1 0 0 0 0

26 27 1 0 0 0 0

26 28 1 0 0 0 0

26 56 1 6 0 0 0

27 57 1 0 0 0 0

28 29 1 0 0 0 0

28 30 1 0 0 0 0

28 58 1 1 0 0 0

29 59 1 0 0 0 0

30 31 1 0 0 0 0

30 32 1 0 0 0 0

30 60 1 6 0 0 0

31 34 1 0 0 0 0

31 61 1 0 0 0 0

31 62 1 0 0 0 0

33 34 1 0 0 0 0

33 35 1 0 0 0 0

33 43 1 0 0 0 0

33 63 1 1 0 0 0

35 36 1 0 0 0 0

35 37 1 0 0 0 0

35 64 1 1 0 0 0

36 65 1 0 0 0 0

37 38 1 0 0 0 0

37 39 1 0 0 0 0

37 66 1 6 0 0 0

38 67 1 0 0 0 0

39 40 1 0 0 0 0

39 41 1 0 0 0 0

39 68 1 1 0 0 0

40 69 1 0 0 0 0

41 42 1 0 0 0 0

41 43 1 0 0 0 0

41 70 1 6 0 0 0

42 71 1 0 0 0 0

42 72 1 0 0 0 0

42 73 1 0 0 0 0

M END): 24 ms

reading 73 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

73 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
In biochemistry, medicine, and related sciences, inositol generally refers to myo-inositol (formerly meso-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its formula is C6H12O6; the molecule has a ring of six carbon atoms, each with an hydrogen atom and a hydroxyl group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring. The compound is a carbohydrate, specifically a sugar alcohol (as distinct from aldoses like glucose) with half the sweetness of sucrose (table sugar). It is one of the most ancient components of living beings with multiple functions in eukaryotes, including structural lipids and secondary messengers. A human kidney makes about two grams per day from glucose, but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other neurotransmitters and some steroid hormones bind to their receptors. In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them. A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of polycystic ovary syndrome (PCOS). However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS. The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are scyllo-, muco-, D-chiro-, L-chiro-, and neo-inositol, although they occur in minimal quantities compared to myo-inositol. The other possible isomers are allo-, epi-, and cis-inositol.
Read full article at Wikipedia

Formula

C27H30O16

Net Charge

Average Mass

610.521

Monoisotopic Mass

610.15338

InChI

InChI=1S/C27H30O16/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/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1

InChIKey

IKGXIBQEEMLURG-NVPNHPEKSA-N

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C(O)=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Metabolite of Species	Details
Physalis longifolia (NCBI:txid161495)	Found in aerial part (BTO:0001658). CH2Cl2-MeOH(1:1) extract of the air-dried aerial parts See: PubMed

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	rutin (CHEBI:28527) has role antioxidant (CHEBI:22586) rutin (CHEBI:28527) has role metabolite (CHEBI:25212) rutin (CHEBI:28527) is a disaccharide derivative (CHEBI:63353) rutin (CHEBI:28527) is a quercetin O-glucoside (CHEBI:64621) rutin (CHEBI:28527) is a rutinoside (CHEBI:26587) rutin (CHEBI:28527) is a tetrahydroxyflavone (CHEBI:38684)

Incoming	rutin hydrate (CHEBI:232410) has part rutin (CHEBI:28527)

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside

Synonyms	Sources
3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	KEGG COMPOUND
3-Rhamnoglucosylquercetin	ChemIDplus
3-Rutinosyl quercetin	ChemIDplus
Phytomelin	KEGG COMPOUND
Quercetin 3-rutinoside	KEGG COMPOUND
Quercetin-3-rutinoside	KEGG COMPOUND
Rutin	KEGG COMPOUND
Rutoside	KEGG COMPOUND

Manual Xrefs	Databases
3535	DrugCentral
C00005413	KNApSAcK
C05625	KEGG COMPOUND
D00190	KEGG DRUG
D08499	KEGG DRUG
DB01698	DrugBank
HMDB0003249	HMDB
LSM-2457	LINCS
RUT	PDBeChem
Rutin	Wikipedia
RUTIN	MetaCyc
View more database links

Registry Numbers	Types	Sources
153-18-4	CAS Registry Number	KEGG COMPOUND
153-18-4	CAS Registry Number	ChemIDplus
75455	Reaxys Registry Number	Reaxys

Citations	Types	Sources
14979715	PubMed citation	Europe PMC
15601236	PubMed citation	Europe PMC
20701244	PubMed citation	Europe PMC
30307940	PubMed citation	Europe PMC
31382673	PubMed citation	Europe PMC
33917795	PubMed citation	Europe PMC

Last Modified

28 May 2021

CHEBI:28527 - rutin

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