AFCDB: Galactinol (FDB001147)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:51 UTC

Update date

2020-09-17 15:39:19 UTC

Primary ID

FDB001147

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Galactinol

Description

Galactinol belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Galactinol is an extremely weak basic (essentially neutral) compound (based on its pKa). galactinol can be biosynthesized from D-galactose and myo-inositol; which is catalyzed by the enzyme Alpha-galactosidase a. In humans, galactinol is involved in galactose metabolism. Outside of the human body, Galactinol has been detected, but not quantified in, several different foods, such as welsh onions, boysenberries, common verbena, rowanberries, and common sages. This could make galactinol a potential biomarker for the consumption of these foods. An alpha-D-galactoside having a 1D-myo-inositol substituent at the anomeric position.

CAS Number

3687-64-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	490 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-5.6	ChemAxon
logS	0.16	ALOGPS
pKa (Strongest Acidic)	11.98	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	200.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.19 m³·mol⁻¹	ChemAxon
Polarizability	31.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H22O11

IUPAC name

(1S,2R,3R,4S,5S,6R)-6-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexane-1,2,3,4,5-pentol

InChI Identifier

InChI=1S/C12H22O11/c13-1-2-3(14)4(15)10(21)12(22-2)23-11-8(19)6(17)5(16)7(18)9(11)20/h2-21H,1H2/t2-,3+,4+,5-,6-,7+,8+,9+,10-,11-,12-/m1/s1

InChI Key

VCWMRQDBPZKXKG-DXNLKLAMSA-N

Isomeric SMILES

OC[C@H]1O[C@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Average Molecular Weight

342.2965

Monoisotopic Molecular Weight

342.116211546

Classification

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Cyclohexanol
Oxane
Monosaccharide
Cyclitol or derivatives
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:17505 )
alpha-D-galactoside (CHEBI:17505 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 42.11%; H 6.48%; O 51.42%	DFC
Melting Point	Mp 220-222° (open tube) (dihydrate)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +135.6 (c, 2.0 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Galactinol, TMS_4_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_5_22, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_5_23, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_5_25, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_5_26, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_5_31, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_5_56, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_21, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_28, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_29, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_31, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_32, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_36, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_51, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_6_52, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_21, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactinol, TMS_7_22, 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 32V, negative	splash10-0h4x-7904000000-ccaf9f6687f64152ff23	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-0006-0109000000-8102050f464d000d3639	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-0006-2609000000-e6624e0c1ee1a4dd5d1e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-002o-5904000000-4283a4fb4f8cf4f19d74	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-0m0l-7901000000-d5688e9378c34693bb5d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-0m50-9700000000-f5df8546e5822b05f22d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-0c09-9400000000-21b8d5b25d2288b75665	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0abi-9200000000-e11f19704a4d0757d5c6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, negative	splash10-0abi-9100000000-5df2f732d48fdb0b6b2e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 39V, negative	splash10-0abi-9000000000-98cab41297cfda142a65	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 43V, negative	splash10-0a4r-9000000000-6d734010a85dbe389e5b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-03fr-1900000000-0e5e88acb391a5362633	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-000j-9000000000-e7a410e700b0b77a74d1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-03di-1900000000-26f1961e559148ee1251	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-00di-0309000000-e9fad444fae1c2923781	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-00di-2809000000-f280939ea0cf3a8ee6c8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-0229-3904000000-a75f976ae237644aa4af	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-0hbl-4902000000-28dd3b4eef1ceda8406d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, negative	splash10-0gy9-7900000000-53a7af36249547a16c8f	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001l-0905000000-bc53a6d03ab9d8b02baa	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-7bbed0664c521fb4270e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-2900000000-f1a9e6f3f3bafcf97d45	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-1819000000-cde5898087ea6deed212	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1901000000-eafd7d1c6bedd75ea49b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-8900000000-50532db99265ea7eb896	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

388558

ChEMBL ID

Not Available

KEGG Compound ID

C01235

Pubchem Compound ID

439451

Pubchem Substance ID

Not Available

ChEBI ID

17505

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05826

CRC / DFC (Dictionary of Food Compounds) ID

BTX28-K:BTX28-K

EAFUS ID

Not Available

Dr. Duke ID

GALACTINOL|GLACTINOL

BIGG ID

Not Available

KNApSAcK ID

C00001162

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

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Alpha-galactosidase A	GLA	P06280

Pathways

Name	SMPDB Link	KEGG Link
Galactose Metabolism	SMP00043	map00052

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Galactinol (FDB001147)

Structure for FDB001147 (Galactinol)