S-9-(2-hydroxypropyl)adenine
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Identification
- Generic Name
- S-9-(2-hydroxypropyl)adenine
- DrugBank Accession Number
- DB03000
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 193.2058
Monoisotopic: 193.096359999 - Chemical Formula
- C8H11N5O
- Synonyms
- 9-Hydroxypropyladenine, S-Isomer
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UThymidine kinase inducerHuman herpesvirus 1 (strain KOS) UAdenosine deaminase inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- 6-aminopurines
- Alternative Parents
- Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Secondary alcohols / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 14047-27-9
- InChI Key
- MJZYTEBKXLVLMY-YFKPBYRVSA-N
- InChI
- InChI=1S/C8H11N5O/c1-5(14)2-13-4-12-6-7(9)10-3-11-8(6)13/h3-5,14H,2H2,1H3,(H2,9,10,11)/t5-/m0/s1
- IUPAC Name
- (2S)-1-(6-amino-9H-purin-9-yl)propan-2-ol
- SMILES
- [H][C@@](C)(O)CN1C=NC2=C(N)N=CN=C12
References
- General References
- Not Available
- External Links
- PubChem Compound
- 445210
- PubChem Substance
- 46508593
- ChemSpider
- 392913
- ZINC
- ZINC000002046907
- PDBe Ligand
- APS
- PDB Entries
- 1e2i
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 5.45 mg/mL ALOGPS logP -0.29 ALOGPS logP -0.58 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 15.15 Chemaxon pKa (Strongest Basic) 3.74 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 89.85 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 52.21 m3·mol-1 Chemaxon Polarizability 19.22 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0002-2900000000-a6cbe3f7c93b82b1f8fd Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0900000000-da367486af1072593d98 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-0900000000-7b644afbfededcaedfda Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0900000000-1716a8018012be88f78f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00l6-2900000000-bc195a790d390f8db74f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-1900000000-1cfd93ac8eae6275da15 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-053u-2900000000-5a3bbb7aeacd4fbdc6af Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 146.9475858 predictedDarkChem Lite v0.1.0 [M-H]- 142.7433 predictedDeepCCS 1.0 (2019) [M+H]+ 147.5067858 predictedDarkChem Lite v0.1.0 [M+H]+ 145.1202 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.2317858 predictedDarkChem Lite v0.1.0 [M+Na]+ 151.10701 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsThymidine kinase
- Kind
- Protein
- Organism
- Human herpesvirus 1 (strain KOS)
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Catalyzes the transfer of the gamma-phospho group of ATP to thymidine to generate dTMP in the salvage pathway of pyrimidine synthesis. The dTMP serves as a substrate for DNA polymerase during viral DNA replication. Allows the virus to be reactivated and to grow in non-proliferative cells lacking a high concentration of phosphorylated nucleic acid precursors.
- Specific Function
- Atp binding
- Gene Name
- TK
- Uniprot ID
- P17402
- Uniprot Name
- Thymidine kinase
- Molecular Weight
- 40926.565 Da
References
- Sharmila Tagore S, Swaminathan J, Manikandan D, Gomathi S, Sabarinathan N, Ramalingam M, Sethuraman V: Crystallographic investigation, Hirshfeld surface analysis, NLO characterization and experimental spectral (UV and NMR) studies with DFT probe on(R)-9-(2-hydroxy propyl)adenine. Heliyon. 2021 Apr 29;7(4):e06593. doi: 10.1016/j.heliyon.2021.e06593. eCollection 2021 Apr. [Article]
- DE Clercq E, Descamps J, DE Somer P, Holyacute A: (S)-9-(2,3-Dihydroxypropyl)adenine: An Aliphatic Nucleoside Analog with Broad-Spectrum Antiviral Activity. Science. 1978 May 5;200(4341):563-5. doi: 10.1126/science.200.4341.563. [Article]
2. DetailsAdenosine deaminase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
- Gene Name
- ADA
- Uniprot ID
- P00813
- Uniprot Name
- Adenosine deaminase
- Molecular Weight
- 40764.13 Da
References
- DE Clercq E, Descamps J, DE Somer P, Holyacute A: (S)-9-(2,3-Dihydroxypropyl)adenine: An Aliphatic Nucleoside Analog with Broad-Spectrum Antiviral Activity. Science. 1978 May 5;200(4341):563-5. doi: 10.1126/science.200.4341.563. [Article]
- Sharmila Tagore S, Swaminathan J, Manikandan D, Gomathi S, Sabarinathan N, Ramalingam M, Sethuraman V: Crystallographic investigation, Hirshfeld surface analysis, NLO characterization and experimental spectral (UV and NMR) studies with DFT probe on(R)-9-(2-hydroxy propyl)adenine. Heliyon. 2021 Apr 29;7(4):e06593. doi: 10.1016/j.heliyon.2021.e06593. eCollection 2021 Apr. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 30, 2023 10:33