AFCDB: Stachyose (FDB012320)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:06 UTC

Update date

2019-11-26 03:06:34 UTC

Primary ID

FDB012320

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Stachyose

Description

Isolated from soybean meal (Glycine max), tubers of Japanese artichoke (Stachys tubifera) and lentils Stachyose is a tetrasaccharide consisting of two D-galactose units, one D-glucose unit, and one D-fructose unit sequentially linked. Stachyose is a normal human metabolite present in human milk and is naturally found in many vegetables (e.g. green beans, soybeans and other beans) and plants. The glycosylation of serum transferrin from galactosemic patients with a deficiency of galactose-1-phosphate uridyl transferase (EC 2. 7.7 12) is abnormal but becomes normal after treatment with a galactose-free diet. Adhering to a galactose-free diet by strictly avoiding dairy products and known hidden sources of galactose does not completely normalize galactose-1-phosphate (gal-1-P) in erythrocytes from patients with galactosemia, since galactose released from stachyose may be absorbed and contribute to elevated gal-1-P values in erythrocytes of galactosemic patients. (PMID: 7671975, 9499382); Stachyose is a tetrasaccharide consisting of two ?-D-galactose units, one ?-D-glucose unit, and one ?-D-fructose unit sequentially linked as gal(?1?6)gal(?1?6)glc(?1?2?)fru. Stachyose is naturally found in numerous vegetables (e.g. green beans, soybeans and other beans) and plants.

CAS Number

470-55-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	411 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-8.1	ChemAxon
logS	-0.21	ALOGPS
pKa (Strongest Acidic)	11.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	347.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	133.6 m³·mol⁻¹	ChemAxon
Polarizability	62.55 Å³	ChemAxon
Number of Rings	4	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

C24H42O21

IUPAC name

2-({6-[(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

InChI Identifier

InChI=1S/C24H42O21/c25-1-6-10(28)14(32)17(35)21(41-6)39-3-8-11(29)15(33)18(36)22(42-8)40-4-9-12(30)16(34)19(37)23(43-9)45-24(5-27)20(38)13(31)7(2-26)44-24/h6-23,25-38H,1-5H2

InChI Key

UQZIYBXSHAGNOE-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(CO)(OC2OC(COC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O)C(O)C(O)C2O)C(O)C1O

Average Molecular Weight

666.5777

Monoisotopic Molecular Weight

666.221858406

Classification

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a tetrasaccharide (CPD-170 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 43.25%; H 6.35%; O 50.40%	DFC
Melting Point	Mp 167-170° (anhyd.)	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]23D +131.3 (c, 4.5 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-9051231e83f301a09a0e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ei-0902300000-1d2431079f0fcf16f362	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9800000000-9f5834420ffbcf1d03e5	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900001000-1b21dc3904103d99d080	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1900000000-92c5416ad039dfd6ec6b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-6911000000-f2c6489ad24930392c3e	2015-05-27	View Spectrum