Delphinidin 3-O-glucoside (YMDB01665)

Identification

YMDB ID

YMDB01665

Name

Delphinidin 3-O-glucoside

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Delphinidin 3-O-glucoside is an anthocyanin, which is a class of polyphenol. Anthocyanins are plant pigments found in many red berries including grape and grape skin. The cell wall of S. cerevisiae is permeable to anthocyanins and as a consequence the anthocyanins can be retained by yeast during wine-making; this adsorption can have an influence on wine color. Anthocyanins can react with yeast metabolites to form pyranoanthocyanins, which are more stable pigments formed during wine ageing and are of great importance for the color of aged wines. [PMID: 12822951] [PMID: 17303275]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Delphinidin 3-glucoside
Delphinidin 3-O-beta-D-glucoside
Mirtillin
Delfinidin 3-O-beta-D-glucoside
Delphinidin 3-O-glucoside
Delfinidin 3-O-b-D-glucoside
Delfinidin 3-O-β-D-glucoside
Delphinidin 3-O-b-D-glucoside
Delphinidin 3-O-β-D-glucoside
Delphinidin 3-monoglucoside
Delphinidin 3-O-beta-D-glucopyranoside
Delphinidol 3-glucoside
Myrtillin
Myrtillin a
Delphinidin 3-O-glucopyranoside
Delphinidin 3-O-beta-glucoside
Delphinidin-3-glucoside

CAS number

6906-38-3

Weight

Average: 465.3842
Monoisotopic: 465.103301136

InChI Key

XENHPQQLDPAYIJ-PEVLUNPASA-O

InChI

InChI=1S/C21H20O12/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27)/p+1/t15-,17-,18+,19-,21-/m1/s1

IUPAC Name

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional IUPAC Name

5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

Chemical Formula

C₂₁H₂₁O₁₂

SMILES

OC[C@H]1O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

Chemical Taxonomy

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	213.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.24 m³·mol⁻¹	ChemAxon
Polarizability	43.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0feb-9602600000-45aed3fc2911f95c79eb	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-5510009000-d60ac3b75f44a32e605b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_54) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_71) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_81) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_87) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_88) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_76) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_82) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_83) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_87) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_88) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_91) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_6_58) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_6_59) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_6_62) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_6_63) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Delphinidin 3-glucoside,3TMS,#54" TMS) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0w29-0139400000-820d95dd9b931186bf3c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009100000-900e146ee03a33c5e31c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0091300000-9658b19c1d3c3ad88775	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0100900000-78712e7fc63bf2f6c41c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-1300900000-174d36b448e52a2ab4a1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-7902100000-1c91ff38e96e02e42e96	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2300900000-0ea3c4becf795cde3fa2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6800900000-cf4c9c44468a09663848	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9300000000-05d37d94d7cc9ad734d7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aos-0006900000-ff93644803a0dd8e09fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0039400000-bcb4b7e5729a0597c0af	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9i-5398200000-c60c5f9ebfd4dff713d0	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	31463
HMDB ID	HMDB0037997
Pubchem Compound ID	443650
Kegg ID	C12138
ChemSpider ID	24842325
FOODB ID	FDB017191
Wikipedia ID	Delphinidin-3-O-glucoside
BioCyc ID	Not Available

Structure for #<Compound:0xa351a5d8>