ChemFOnt: Showing chemical card for Ribonolactone (CFc000001266)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:51 UTC

Chemfont ID

CFc000001266

Molecule Identification

Common Name

Ribonolactone

Definition

Ribonolactone, also known as D-ribono-1,4-lactone is a five-membered form of ribonolactone having D-configuration. It has a role as a metabolite. It is a ribonolactone and a butan-4-olide. It derives from a D-ribonic acid. Ribonolactone belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Ribonolactone is a metabolite normally not detectable in human biofluids; however, it has been found in the urine of patients with neuroblastoma.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-(+)-Ribonic acid gamma-lactone	ChEBI
D-Ribonic acid-1,4-lactone	ChEBI
D-Ribono-gamma-lactone	ChEBI
D-Ribonolactone	ChEBI
D-Ribopentono-1,4-lactone	ChEBI
Ribono-gamma-lactone	ChEBI
D-(+)-Ribonate g-lactone	Generator
D-(+)-Ribonate gamma-lactone	Generator
D-(+)-Ribonate γ-lactone	Generator
D-(+)-Ribonic acid g-lactone	Generator
D-(+)-Ribonic acid γ-lactone	Generator
D-Ribonate-1,4-lactone	Generator
D-Ribono-g-lactone	Generator
D-Ribono-γ-lactone	Generator
Ribono-g-lactone	Generator
Ribono-γ-lactone	Generator
D(+)-Ribonic acid gamma-lactone	HMDB
D-(+)-Ribonone-1.4-lactone	HMDB
D-ribono-1,4-Lactone	HMDB
delta-(+)-Ribonic acid g-lactone	HMDB
delta-(+)-Ribonic acid gamma-lactone	HMDB
delta-(+)-Ribonone-1.4-lactone	HMDB
delta-ribono-1,4-Lactone	HMDB
delta-ribono-gamma-Lactone	HMDB
delta-Ribonolactone	HMDB
delta-ribopentono-1,4-Lactone	HMDB
Deoxyribonolactone	HMDB
gamma-Lactone OF ribonate	HMDB
gamma-Lactone OF ribonic acid	HMDB
gamma-Lactone-ribonate	HMDB
gamma-Lactone-ribonic acid	HMDB
Ribonolactone	ChEBI

Chemical Formula

C₅H₈O₅

Average Molecular Weight

148.114

Monoisotopic Molecular Weight

148.037173366

IUPAC Name

(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

Traditional Name

D-ribosone

CAS Registry Number

5336-08-3

SMILES

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

InChI Identifier

InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1

InChI Key

CUOKHACJLGPRHD-BXXZVTAOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butan-4-olide (CHEBI:74168 )
ribonolactone (CHEBI:74168 )

Functional Ontology

Physiological effect

Health effect

Nervous system disorder

Peripheral nervous system disorder

Neuroblastoma (HMDB: HMDB0001900)

Urine (PMID: 699273)

Cellular substructure

Cytoplasm (HMDB: HMDB0001900)

Source

Endogenous

Endogenous (HMDB: HMDB0001900)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	847 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.1	ChemAxon
logS	0.76	ALOGPS
pKa (Strongest Acidic)	11.63	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.82 m³·mol⁻¹	ChemAxon
Polarizability	12.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon