ChemFOnt: Showing chemical card for Didanosine (CFc000009348)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:27 UTC

Chemfont ID

CFc000009348

Molecule Identification

Common Name

Didanosine

Definition

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite. [PubChem]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,3-Dideoxyinosine	ChEBI
9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one	ChEBI
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one	ChEBI
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol	ChEBI
9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one	ChEBI
DDI	ChEBI
DdIno	ChEBI
Didanosina	ChEBI
Didanosinum	ChEBI
Dideoxyinosine	ChEBI
Videx	Kegg
ABBR ddi	Kegg
2',3' Dideoxyinosine	HMDB
Bristol-myers brand OF didanosine	HMDB
DdI (antiviral)	HMDB
Bristol myers squibb brand OF didanosine	HMDB
2',3'-Dideoxyinosine	HMDB
Bristol myers brand OF didanosine	HMDB
Bristol-myers squibb brand OF didanosine	HMDB

Chemical Formula

C₁₀H₁₂N₄O₃

Average Molecular Weight

236.2273

Monoisotopic Molecular Weight

236.09094027

IUPAC Name

9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

Traditional Name

didanosine

CAS Registry Number

69655-05-6

SMILES

OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O

InChI Identifier

InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1

InChI Key

BXZVVICBKDXVGW-NKWVEPMBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. Purine 2',3'-dideoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2',3'-dideoxyribonucleosides

Direct Parent

Purine 2',3'-dideoxyribonucleosides

Alternative Parents

Substituents

Purine 2',3'-dideoxyribonucleoside
6-oxopurine
Hypoxanthine
Purinone
Imidazopyrimidine
Purine
Pyrimidone
N-substituted imidazole
Pyrimidine
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Vinylogous amide
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2',3'-dideoxyribonucleoside (CHEBI:490877 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015037)
Extracellular (HMDB: HMDB0015037)

Source

Exogenous

Exogenous (HMDB: HMDB0015037)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Didanosine Action Pathway (PathBank: SMP0000739)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.58 g/L	ALOGPS
logP	-0.99	ALOGPS
logP	-0.35	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.59 m³·mol⁻¹	ChemAxon
Polarizability	22.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon