Showing Compound Delphinidin 3-rutinoside (FDB017195)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:56 UTC

Update date

2019-11-26 03:14:24 UTC

Primary ID

FDB017195

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Delphinidin 3-rutinoside

Description

Delphinidin 3-rutinoside belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Delphinidin 3-rutinoside is found, on average, in the highest concentration within blackcurrants (Ribes nigrum). Delphinidin 3-rutinoside has also been detected, but not quantified in, several different foods, such as black elderberries (Sambucus nigra), ryes (Secale cereale), flaxseeds (Linum usitatissimum), gooseberries (Ribes uva-crispa), and cassavas (Manihot esculenta). This could make delphinidin 3-rutinoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Delphinidin 3-rutinoside.

CAS Number

15674-58-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.16 g/L	ALOGPS
logP	0.66	ALOGPS
logP	-0.93	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	272.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	149.11 m³·mol⁻¹	ChemAxon
Polarizability	57.86 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

C27H31O16

IUPAC name

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}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

InChI Identifier

InChI=1S/C27H30O16/c1-8-18(32)21(35)23(37)26(40-8)39-7-17-20(34)22(36)24(38)27(43-17)42-16-6-11-12(29)4-10(28)5-15(11)41-25(16)9-2-13(30)19(33)14(31)3-9/h2-6,8,17-18,20-24,26-27,32,34-38H,7H2,1H3,(H4-,28,29,30,31,33)/p+1/t8-,17+,18-,20+,21+,22-,23+,24+,26+,27+/m0/s1

InChI Key

PLKUTZNSKRWCCA-LTSKFBHWSA-O

Isomeric SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC4=C(O)C=C(O)C=C4[O+]=C3C3=CC(O)=C(O)C(O)=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Average Molecular Weight

611.5254

Monoisotopic Molecular Weight

611.161209944

Classification

Description

Belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Anthocyanidin
O-glycosyl compound
Glycosyl compound
Disaccharide
1-benzopyran
Benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin glycoside (CHEBI:80441 )
Anthocyanidins (C16315 )
Anthocyanidins and anthocyanins (C16315 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 53.03%; H 5.11%; O 41.86%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Delphinidin 3-rutinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-7290080000-389242df57a220b7e05d	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Delphinidin 3-rutinoside, TMS_2_14, 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 , negative	splash10-0pb9-0008009000-da50664ccc99574542b5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009000000-06dd4eb8d0b165f1f55f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0000009000-538b87e504fb98a67666	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0f6t-0008900000-dda365a62acf8edd9888	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-8d90d5a29443a5636f95	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0000309000-65470cb495e2f16536a9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-e46aea6d0ae527edf9f3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009100000-9f157dd28479031dbb5a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-6d7eb80c28d75c63d301	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-48d926ac2b7178822087	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-97c996a33fe11648d9b0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0002-0001902000-9efb8106152232e6b81d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009002000-ac2c38f3faa572f1dd75	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0201009000-9734edbe289475bf632c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-1911027000-05ad9f9052f97f6627b6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rb-6911000000-b9b1b75110d9d6127892	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-4421009000-bbb7510141a8a0be93f1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fs-5911002000-d560b616b894c71ffb4b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btd-9520000000-94c0f30ccb75b62cde32	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0cdi-0109736000-717e08b743f268a5acd6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0229332000-0b861b7b69daaf2b9d3c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg3-5579310000-53a53074798f69e7ecdf	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4590910

ChEMBL ID

Not Available

KEGG Compound ID

C16315

Pubchem Compound ID

5492231

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

DrugBank ID

Not Available

HMDB ID

HMDB38001

CRC / DFC (Dictionary of Food Compounds) ID

OJK30-N:KWN35-C

EAFUS ID

Not Available

Dr. Duke ID

DELPHINIDIN-3-RUTINOSIDE|DELPHINIDIN-3-O-BETA-D-RUTINOSIDE

BIGG ID

Not Available

KNApSAcK ID

C00006708

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

Tulipanin

Phenol-Explorer Metabolite ID

Duplicate IDS

Not Available

Old DFC IDS

CMR96-N:KWN35-C

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Eggplant	Expected but not quantified	Not Available	Keiko Azuma, Akio Ohyama, Katsunari Ippoushi, Takashi Ichiyanagi, Atsuko Takeuchi, Takeo Saito and Hiroyuki Fukuoka. Structures and Antioxidant Activity of Anthocyanins in Many Accessions of Eggplant and Its Related Species. J. Agric. Food Chem., 2008, 56 (21), pp 10154-10159. DOI: 10.1021/jf801322m, PHYTOHUB
Banana	Expected but not quantified	Not Available	KNAPSACK
Blackcurrant	0.000 - 304.917 mg/100 g	101.725 mg/100 g	PHENOL EXPLORER, DUKE, KNAPSACK
Cassava	Expected but not quantified	Not Available	KNAPSACK
Flaxseed	Expected but not quantified	Not Available	DUKE
Potato	Expected but not quantified	Not Available	DUKE
Rye	Expected but not quantified	Not Available	KNAPSACK