Didanosine - Moligand™, ≥98%(HPLC) , CAS No.69655-05-6

CAS: 69655-05-6 Cat. No.: D129790 Molecular Weight: 236.23 Beilstein Registry Number: 3619529 EC Number: 614-994-4

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

ddI | (-)-didanosine | DTXCID402927 | 9-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one | BRN 3619529 | CCRIS 805 | DIDANOSINE [HSDB] | Didanosine,(S) | Videx EC(TM)(slow-release capsules) | 9-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Didanosine is a reverse transcriptase inhibitor with an IC50 of 0.49 μM.
A potent anti-retroviral agent that acts by competing with natural dATP.

Specifications

Synonyms

ddI | (-)-didanosine | DTXCID402927 | 9-[(2R, 5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one | BRN 3619529 | CCRIS 805 | DIDANOSINE [HSDB] | Didanosine, (S) | Videx EC(TM)(slow-release capsules) | 9-[(2R, 5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

2′, 3′-Dideoxyinosine is a potent anti-retroviral agent. 2′, 3′-Dideoxyinosine is most effective in combination therapy for the treatment of HIV and related lymphoma.Potent anti-retroviral agent. HIV replication inhibitor. Inhibits reverse transcriptase. Cr

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Product Properties

• ALogP: -1.2

Names and Identifiers

• Canonical Smiles: C1CC(OC1CO)N2C=NC3=C2N=CNC3=O
• IUPAC Name: 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• InChIKey: BXZVVICBKDXVGW-NKWVEPMBSA-N
• 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
• Isomeric SMILES: C1C[C@@H](O[C@@H]1CO)N2C=NC3=C2N=CNC3=O
• RTECS: NM7460700
• Molecular Weight: 236.23
• Beilstein: 3619529
• Reaxy-Rn: 24723407
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24723407&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleosides
      • Subclass Purine 2',3'-dideoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleosides
• Subclass: Purine 2',3'-dideoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine 2',3'-dideoxyribonucleosides
• Alternative Parents: Hypoxanthines 6-oxopurines Pyrimidones N-substituted imidazoles Vinylogous amides Tetrahydrofurans Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.
• External Descriptors: purine 2',3'-dideoxyribonucleoside

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

Discover Target: HMGCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

Discover Target: INSR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

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HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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CALCR Tclin Calcitonin receptor (2215 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

Discover Target: OPRK1

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

Discover Target: HTR3A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR4 Tclin Serotonin 4 (5-HT4) receptor (2068 Activities)

Discover Target: HTR4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)

Discover Target: CACNA1C

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

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Mc4r Melanocortin receptor 4 (1205 Activities)

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Ltc4s Leukotriene C4 synthase (1 Activities)

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Sigmar1 Sigma opioid receptor (160 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

Discover Target: Pde4d

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Nos2 Nitric oxide synthase, inducible (3573 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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Hdac6 Histone deacetylase 6 (222 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Human alphaherpesvirus 2 (4932 Activities)

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Rattus norvegicus (775804 Activities)

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Cowpox virus (428 Activities)

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Vaccinia virus (4609 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Human T-cell leukemia virus type I (114 Activities)

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Vesicular stomatitis virus (4460 Activities)

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Human immunodeficiency virus 2 (5592 Activities)

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H9c2 (3506 Activities)

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Vero (26788 Activities)

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L cells (98 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Slc22a6 Solute carrier family 22 member 6 (141 Activities)

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Plasma (328 Activities)

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Glra2 Glycine receptor (1745 Activities)

Discover Target: Glra2

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (47 mg/mL at 25 °C), chloroform (<1 mg/mL at 23 °C), water (<1 mg/mL at 25 °C), ethanol (<1 mg/mL at 25 °C), and methanol (6 mg/mL at 23 °C).
• Sensitivity: Moisture sensitive
• Specific Rotation[α]: -28° (C=0.34,H2O)
• Melt Point(°C): 182°C
• Molecular Weight: 236.230 g/mol
• XLogP3: -1.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 236.091 Da
• Monoisotopic Mass: 236.091 Da
• Topological Polar Surface Area: 88.700 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 348.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Lei Xu, Jing Lu, Weiqi Meng, Fengjuan Cui.  (2021)  Determination of the Nucleoside Reverse Transcriptase Inhibitors Lamivudine, Stavudine, and Didanosine in Human Urine by Micellar Electrokinetic Chromatography Using the Ionic Liquid-Based Cationic Surfactant 1-Tetradecyl-3-Methylimidazolium Bromide.  ANALYTICAL LETTERS,      [PMID:] [10.1080/00032719.2021.1904970]