Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015037
Secondary Accession Numbers
  • HMDB15037
Metabolite Identification
Common NameDidanosine
DescriptionA dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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
Data?1582753250
Synonyms
ValueSource
2,3-DideoxyinosineChEBI
9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-oneChEBI
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-oneChEBI
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-olChEBI
9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-oneChEBI
DDIChEBI
DdInoChEBI
DidanosinaChEBI
DidanosinumChEBI
DideoxyinosineChEBI
VidexKegg
ABBR ddiKegg
2',3' DideoxyinosineHMDB
Bristol-myers brand OF didanosineHMDB
DdI (antiviral)HMDB
Bristol myers squibb brand OF didanosineHMDB
2',3'-DideoxyinosineHMDB
Bristol myers brand OF didanosineHMDB
Bristol-myers squibb brand OF didanosineHMDB
Chemical FormulaC10H12N4O3
Average Molecular Weight236.2273
Monoisotopic Molecular Weight236.09094027
IUPAC Name9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional Namedidanosine
CAS Registry Number69655-05-6
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 KeyBXZVVICBKDXVGW-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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2',3'-dideoxyribonucleosides
Direct ParentPurine 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 - 163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.58 g/LNot Available
LogP-0.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.58 g/LALOGPS
logP-0.99ALOGPS
logP-0.35ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.59 m³·mol⁻¹ChemAxon
Polarizability22.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+153.3431661259
DarkChem[M-H]-153.73931661259
DeepCCS[M+H]+148.69830932474
DeepCCS[M-H]-146.30230932474
DeepCCS[M-2H]-179.6230932474
DeepCCS[M+Na]+154.6130932474
AllCCS[M+H]+152.932859911
AllCCS[M+H-H2O]+149.032859911
AllCCS[M+NH4]+156.532859911
AllCCS[M+Na]+157.532859911
AllCCS[M-H]-154.132859911
AllCCS[M+Na-2H]-153.832859911
AllCCS[M+HCOO]-153.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DidanosineOC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O3067.6Standard polar33892256
DidanosineOC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O2281.6Standard non polar33892256
DidanosineOC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O2618.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Didanosine,1TMS,isomer #1C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2[NH]C=NC3=O)O12317.4Semi standard non polar33892256
Didanosine,1TMS,isomer #2C[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1CC[C@@H](CO)O1)C=N22448.2Semi standard non polar33892256
Didanosine,2TMS,isomer #1C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O12428.1Semi standard non polar33892256
Didanosine,2TMS,isomer #1C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O12603.7Standard non polar33892256
Didanosine,2TMS,isomer #1C[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C)C=NC3=O)O13273.0Standard polar33892256
Didanosine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2[NH]C=NC3=O)O12542.5Semi standard non polar33892256
Didanosine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC(=O)C2=C1N([C@H]1CC[C@@H](CO)O1)C=N22665.6Semi standard non polar33892256
Didanosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O12818.3Semi standard non polar33892256
Didanosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O13019.2Standard non polar33892256
Didanosine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@@H]1CC[C@H](N2C=NC3=C2N([Si](C)(C)C(C)(C)C)C=NC3=O)O13321.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Didanosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9670000000-b8e1fdd18fda2c412cef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Didanosine GC-MS (1 TMS) - 70eV, Positivesplash10-005c-7090000000-ed6dc7eca7c11c73693a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Didanosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Didanosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOFsplash10-000i-0090000000-fed0a8ffc5839fe73fe12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOFsplash10-000i-0490000000-0ac04c4f4e817e6da3912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOFsplash10-000i-0920000000-14a23956c10d3f6e7e9a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOFsplash10-000i-0900000000-de4599cfceaa460892912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOFsplash10-000i-1900000000-10d07c81e3fc72fcfef22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , negative-QTOFsplash10-000i-1900000000-84e8bb1bea77e6b5bfca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOFsplash10-000i-0900000000-6a0516d1b3cec255e0502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOFsplash10-000i-0900000000-fd0dfb766f1c628d170d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOFsplash10-000i-0900000000-3d9e0ecfaf77d867a9d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOFsplash10-000i-0900000000-e0e7d0c808e14d842dbb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOFsplash10-000i-1900000000-9d4b77c3e99e9f9a2c2a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine LC-ESI-QFT , positive-QTOFsplash10-000i-1900000000-2bb63f71ec2e92ce075d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 90V, Negative-QTOFsplash10-000i-1900000000-1475736d859ee324d92e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 75V, Negative-QTOFsplash10-000i-0900000000-2cd1a2d12ed9691544152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 45V, Negative-QTOFsplash10-000i-0920000000-410013d0d67e872eea6b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 60V, Negative-QTOFsplash10-000i-0900000000-544cf7886920f267da7a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 45V, Positive-QTOFsplash10-000i-0900000000-74008fe84aaa4adb23ed2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 60V, Positive-QTOFsplash10-000i-0900000000-532725f06bed9d035dcf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Didanosine 90V, Positive-QTOFsplash10-000i-1900000000-7d5a4e68524522f15eca2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Didanosine 10V, Positive-QTOFsplash10-000i-0920000000-a89fd678ed8a8c16accc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Didanosine 20V, Positive-QTOFsplash10-000i-0900000000-a1a5b268d419fff836022016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Didanosine 40V, Positive-QTOFsplash10-03dr-1900000000-32bbc23c752210d7cd6f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Didanosine 10V, Negative-QTOFsplash10-000i-0190000000-383b44cf919dd28ff3bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Didanosine 20V, Negative-QTOFsplash10-000i-2940000000-309e7293be866f0e29aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Didanosine 40V, Negative-QTOFsplash10-052u-3900000000-0828603c96a200af867a2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00900 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00900 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00900
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID45864
KEGG Compound IDC06953
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDidanosine
METLIN IDNot Available
PubChem Compound50599
PDB ID2DI
ChEBI ID490877
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]