ChemFOnt: Showing chemical card for 3-Deoxyarabinohexonic acid (CFc000000247)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:35 UTC

Chemfont ID

CFc000000247

Molecule Identification

Common Name

3-Deoxyarabinohexonic acid

Definition

3-Deoxyarabinohexonic acid, also known as arabino-3-deoxyhexonate or D-2-keto-3-deoxygluconate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms. 3-deoxyarabinohexonic acid is a thermal decomposition product of plant-derived sugars such as nigerose (3-O-alpha-D-glucopyranosyl-D-glucose), turanose and 3-O-methyl glucose. 3-deoxyarabinohexonic acid is found in plants and plant products that have been heated. As a consequence, it can be detected in the biofluids of animals that have consumed plant foods (including humans).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoic acid	ChEBI
3-Deoxy-arabino-hexonic acid	ChEBI
3-Deoxyarabino-hexonic acid	ChEBI
(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoate	Generator
3-Deoxy-arabino-hexonate	Generator
3-Deoxyarabino-hexonate	Generator
3-Deoxyarabinohexonate	Generator
3-Deoxy-D-arabino-hexonic acid	HMDB
Arabino-3-deoxyhexonate	HMDB
Arabino-3-deoxyhexonic acid	HMDB
D-2-Keto-3-deoxygluconate	HMDB
3-Deoxy-arabino-hexonic acid, monosodium salt, (D)-isomer	HMDB
3-Deoxy-arabino-hexonic acid, (D)-isomer	HMDB
3-Deoxy-D-arabino-hexonate	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

(2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid

Traditional Name

3-deoxy-arabinohexonic acid

CAS Registry Number

29625-79-4

SMILES

OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O

InChI Identifier

InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1

InChI Key

YGMNHEPVTNXLLS-VAYJURFESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Alpha-hydroxy acid
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000346)

Source

Exogenous

Exogenous (HMDB: HMDB0000346)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000346)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000346)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	255 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.7	ChemAxon
logS	0.15	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	37.17 m³·mol⁻¹	ChemAxon
Polarizability	16.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000346

DrugBank ID

DB03303

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021969

KNApSAcK ID

Not Available

Chemspider ID

134838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Hanninen, Kari; Niemela, Klaus. Alkaline degradation of peat humic acids. Part II. Identification of hydrophilic products. Acta Chemica Scandinavica (1992), 46(5), 459-63.

Showing chemical card for 3-Deoxyarabinohexonic acid (CFc000000247)

MOL for CFc000000247 (3-Deoxyarabinohexonic acid)

3D MOL for CFc000000247 (3-Deoxyarabinohexonic acid)

3D SDF for CFc000000247 (3-Deoxyarabinohexonic acid)

3D-SDF for CFc000000247 (3-Deoxyarabinohexonic acid)

PDB for CFc000000247 (3-Deoxyarabinohexonic acid)

3D PDB for CFc000000247 (3-Deoxyarabinohexonic acid)

SMILES for CFc000000247 (3-Deoxyarabinohexonic acid)

INCHI for CFc000000247 (3-Deoxyarabinohexonic acid)

Structure for CFc000000247 (3-Deoxyarabinohexonic acid)

3D Structure for CFc000000247 (3-Deoxyarabinohexonic acid)