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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:51 UTC
HMDB IDHMDB0015063
Secondary Accession Numbers
  • HMDB15063
Metabolite Identification
Common NameAzacitidine
DescriptionAzacitidine is only found in individuals that have used or taken this drug. It is a pyrimidine nucleoside analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. [PubChem]Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine is thought to induce antineoplastic activity via two mechanisms; inhibition of DNA methyltransferase at low doses, causing hypomethylation of DNA, and direct cytotoxicity in abnormal hematopoietic cells in the bone marrow through its incorporation into DNA and RNA at high doses, resulting in cell death. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein. Its incorporation into DNA leads to a covalent binding with DNA methyltransferases, which prevents DNA synthesis and subsequent cytotoxicity.
Structure
Data?1582753253
Synonyms
ValueSource
4-Amino-1-beta-D-ribofuranosyl-S-triazin-2(1H)-oneChEBI
AzacitidinaChEBI
AzacitidinumChEBI
VidazaKegg
4-Amino-1-b-D-ribofuranosyl-S-triazin-2(1H)-oneGenerator
4-Amino-1-β-D-ribofuranosyl-S-triazin-2(1H)-oneGenerator
5 AZCHMDB
AzacytidineHMDB
Pharmion brand OF azacitidineHMDB
5 AzacytidineHMDB
AzacitidineChEBI
Chemical FormulaC8H12N4O5
Average Molecular Weight244.2047
Monoisotopic Molecular Weight244.080769514
IUPAC Name4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
Traditional Nameazacitidine
CAS Registry Number320-67-2
SMILES
NC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
InChI KeyNMUSYJAQQFHJEW-KVTDHHQDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pentose monosaccharide
  • Amino-1,3,5-triazine
  • Aminotriazine
  • Triazinone
  • Monosaccharide
  • Triazine
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.1 g/LNot Available
LogP-3.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.1 g/LALOGPS
logP-2.4ALOGPS
logP-3.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-0.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area140.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.19 m³·mol⁻¹ChemAxon
Polarizability21.5 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.22331661259
DarkChem[M-H]-151.13231661259
DeepCCS[M+H]+151.96830932474
DeepCCS[M-H]-149.57330932474
DeepCCS[M-2H]-183.92930932474
DeepCCS[M+Na]+158.94330932474
AllCCS[M+H]+154.932859911
AllCCS[M+H-H2O]+151.132859911
AllCCS[M+NH4]+158.432859911
AllCCS[M+Na]+159.532859911
AllCCS[M-H]-151.732859911
AllCCS[M+Na-2H]-151.532859911
AllCCS[M+HCOO]-151.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AzacitidineNC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O3603.8Standard polar33892256
AzacitidineNC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O2219.0Standard non polar33892256
AzacitidineNC1=NC(=O)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O2597.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Azacitidine,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O2464.8Semi standard non polar33892256
Azacitidine,1TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O2458.3Semi standard non polar33892256
Azacitidine,1TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N)=NC1=O2450.4Semi standard non polar33892256
Azacitidine,1TMS,isomer #4C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N12500.8Semi standard non polar33892256
Azacitidine,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2383.4Semi standard non polar33892256
Azacitidine,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2379.6Semi standard non polar33892256
Azacitidine,2TMS,isomer #3C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C=N12431.0Semi standard non polar33892256
Azacitidine,2TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O[Si](C)(C)C2361.5Semi standard non polar33892256
Azacitidine,2TMS,isomer #5C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N12443.2Semi standard non polar33892256
Azacitidine,2TMS,isomer #6C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N12435.2Semi standard non polar33892256
Azacitidine,2TMS,isomer #7C[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)[Si](C)(C)C2427.3Semi standard non polar33892256
Azacitidine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2310.3Semi standard non polar33892256
Azacitidine,3TMS,isomer #2C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=N12409.9Semi standard non polar33892256
Azacitidine,3TMS,isomer #3C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=N12405.8Semi standard non polar33892256
Azacitidine,3TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O2409.3Semi standard non polar33892256
Azacitidine,3TMS,isomer #5C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N12401.8Semi standard non polar33892256
Azacitidine,3TMS,isomer #6C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O2400.3Semi standard non polar33892256
Azacitidine,3TMS,isomer #7C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O2395.1Semi standard non polar33892256
Azacitidine,4TMS,isomer #1C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N12420.8Semi standard non polar33892256
Azacitidine,4TMS,isomer #1C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N12545.8Standard non polar33892256
Azacitidine,4TMS,isomer #1C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N13284.6Standard polar33892256
Azacitidine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2432.9Semi standard non polar33892256
Azacitidine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O2560.6Standard non polar33892256
Azacitidine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3062.0Standard polar33892256
Azacitidine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2422.2Semi standard non polar33892256
Azacitidine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C2544.1Standard non polar33892256
Azacitidine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3019.2Standard polar33892256
Azacitidine,4TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C2420.3Semi standard non polar33892256
Azacitidine,4TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C2561.4Standard non polar33892256
Azacitidine,4TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C2991.6Standard polar33892256
Azacitidine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2471.4Semi standard non polar33892256
Azacitidine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2551.3Standard non polar33892256
Azacitidine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2819.9Standard polar33892256
Azacitidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O2702.5Semi standard non polar33892256
Azacitidine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O2701.2Semi standard non polar33892256
Azacitidine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N)=NC1=O2690.5Semi standard non polar33892256
Azacitidine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N12719.9Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2837.8Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2835.2Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=N12877.2Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C2806.8Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N12866.9Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N12850.9Semi standard non polar33892256
Azacitidine,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)[Si](C)(C)C(C)(C)C2869.6Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3014.4Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N13064.5Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N13059.1Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3039.2Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N13046.3Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O3053.5Semi standard non polar33892256
Azacitidine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O3038.2Semi standard non polar33892256
Azacitidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N13224.0Semi standard non polar33892256
Azacitidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N13310.6Standard non polar33892256
Azacitidine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N13523.2Standard polar33892256
Azacitidine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3249.2Semi standard non polar33892256
Azacitidine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3352.7Standard non polar33892256
Azacitidine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3338.7Standard polar33892256
Azacitidine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3237.2Semi standard non polar33892256
Azacitidine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3335.5Standard non polar33892256
Azacitidine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3306.1Standard polar33892256
Azacitidine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3240.2Semi standard non polar33892256
Azacitidine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3342.2Standard non polar33892256
Azacitidine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3285.6Standard polar33892256
Azacitidine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3423.9Semi standard non polar33892256
Azacitidine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3457.6Standard non polar33892256
Azacitidine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3241.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Azacitidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-08nc-9420000000-deb4c3c2e01ce611d8052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azacitidine GC-MS (3 TMS) - 70eV, Positivesplash10-0072-9783700000-4e1593dee5d4eee4fa532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Azacitidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 10V, Positive-QTOFsplash10-03di-0910000000-bf3b4f701f0a4e9f2cd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 20V, Positive-QTOFsplash10-03di-6900000000-5d329d9eaea6433ed7cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 40V, Positive-QTOFsplash10-03dm-9300000000-9df054033868819ef47c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 10V, Negative-QTOFsplash10-0udl-4690000000-2cfa5eaefe0d852fc7702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 20V, Negative-QTOFsplash10-01ox-9600000000-c47176436749bbaa62012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 40V, Negative-QTOFsplash10-00l6-9100000000-71ffe7618fd437f421312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 10V, Positive-QTOFsplash10-03di-0900000000-ad27e26e064f360f30062021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 20V, Positive-QTOFsplash10-03di-4900000000-5d9421c40d3f45d9dc692021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 40V, Positive-QTOFsplash10-03ka-9500000000-79a738f312e868981bd22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 10V, Negative-QTOFsplash10-01ox-1960000000-94c1bdd861f9dd5e7a9e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 20V, Negative-QTOFsplash10-0006-9500000000-0f6f7a947b16f6e8119a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Azacitidine 40V, Negative-QTOFsplash10-00kf-9000000000-6ba499348317121c0ac22021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00928 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00928 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 IDDB00928
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9072
KEGG Compound IDC11262
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzacitidine
METLIN IDNot Available
PubChem Compound9444
PDB IDNot Available
ChEBI ID2038
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 References
  1. Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82. [PubMed:15793220 ]
  2. Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102. [PubMed:14585280 ]
  3. Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. [PubMed:17612710 ]
  4. Silverman LR, Demakos EP, Peterson BL, Kornblith AB, Holland JC, Odchimar-Reissig R, Stone RM, Nelson D, Powell BL, DeCastro CM, Ellerton J, Larson RA, Schiffer CA, Holland JF: Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: a study of the cancer and leukemia group B. J Clin Oncol. 2002 May 15;20(10):2429-40. [PubMed:12011120 ]
  5. Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. [PubMed:11700387 ]
  6. O'Dwyer K, Maslak P: Azacitidine and the beginnings of therapeutic epigenetic modulation. Expert Opin Pharmacother. 2008 Aug;9(11):1981-6. doi: 10.1517/14656566.9.11.1981 . [PubMed:18627335 ]
  7. Cihak A: Biological effects of 5-azacytidine in eukaryotes. Oncology. 1974;30(5):405-22. [PubMed:4142650 ]
  8. Issa JP, Kantarjian H: Azacitidine. Nat Rev Drug Discov. 2005 May;Suppl:S6-7. [PubMed:15962522 ]
  9. Sullivan M, Hahn K, Kolesar JM: Azacitidine: a novel agent for myelodysplastic syndromes. Am J Health Syst Pharm. 2005 Aug 1;62(15):1567-73. [PubMed:16030365 ]
  10. Siddiqui MA, Scott LJ: Azacitidine: in myelodysplastic syndromes. Drugs. 2005;65(13):1781-9; discussion 1790-1. [PubMed:16114977 ]
  11. Abdulhaq H, Rossetti JM: The role of azacitidine in the treatment of myelodysplastic syndromes. Expert Opin Investig Drugs. 2007 Dec;16(12):1967-75. [PubMed:18042004 ]
  12. Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;83(22):11950-8. doi: 10.1128/JVI.01406-09. Epub 2009 Sep 2. [PubMed:19726509 ]
  13. Keating GM: Azacitidine: a review of its use in higher-risk myelodysplastic syndromes/acute myeloid leukaemia. Drugs. 2009;69(17):2501-18. doi: 10.2165/11202840-000000000-00000. [PubMed:19911860 ]

Enzymes

General function:
Involved in zinc ion binding
Specific function:
This enzyme scavenge exogenous and endogenous cytidine and 2'-deoxycytidine for UMP synthesis.
Gene Name:
CDA
Uniprot ID:
P32320
Molecular weight:
16184.545
References
  1. Garcia-Manero G, Stoltz ML, Ward MR, Kantarjian H, Sharma S: A pilot pharmacokinetic study of oral azacitidine. Leukemia. 2008 Sep;22(9):1680-4. doi: 10.1038/leu.2008.145. Epub 2008 Jun 12. [PubMed:18548103 ]
General function:
Involved in DNA binding
Specific function:
Methylates CpG residues. Preferentially methylates hemimethylated DNA. Associates with DNA replication sites in S phase maintaining the methylation pattern in the newly synthesized strand, that is essential for epigenetic inheritance. Associates with chromatin during G2 and M phases to maintain DNA methylation independently of replication. It is responsible for maintaining methylation patterns established in development. DNA methylation is coordinated with methylation of histones. Mediates transcriptional repression by direct binding to HDAC2. In association with DNMT3B and via the recruitment of CTCFL/BORIS, involved in activation of BAG1 gene expression by modulating dimethylation of promoter histone H3 at H3K4 and H3K9.
Gene Name:
DNMT1
Uniprot ID:
P26358
Molecular weight:
184817.425
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82. [PubMed:15793220 ]
  3. Cataldo VD, Cortes J, Quintas-Cardama A: Azacitidine for the treatment of myelodysplastic syndrome. Expert Rev Anticancer Ther. 2009 Jul;9(7):875-84. doi: 10.1586/era.09.61. [PubMed:19589026 ]
  4. Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102. [PubMed:14585280 ]
  5. Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. [PubMed:17612710 ]
  6. Silverman LR, Demakos EP, Peterson BL, Kornblith AB, Holland JC, Odchimar-Reissig R, Stone RM, Nelson D, Powell BL, DeCastro CM, Ellerton J, Larson RA, Schiffer CA, Holland JF: Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: a study of the cancer and leukemia group B. J Clin Oncol. 2002 May 15;20(10):2429-40. [PubMed:12011120 ]
  7. Fenaux P: Inhibitors of DNA methylation: beyond myelodysplastic syndromes. Nat Clin Pract Oncol. 2005 Dec;2 Suppl 1:S36-44. [PubMed:16341239 ]
  8. Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. [PubMed:11700387 ]
  9. O'Dwyer K, Maslak P: Azacitidine and the beginnings of therapeutic epigenetic modulation. Expert Opin Pharmacother. 2008 Aug;9(11):1981-6. doi: 10.1517/14656566.9.11.1981 . [PubMed:18627335 ]
  10. Hollenbach PW, Nguyen AN, Brady H, Williams M, Ning Y, Richard N, Krushel L, Aukerman SL, Heise C, MacBeth KJ: A comparison of azacitidine and decitabine activities in acute myeloid leukemia cell lines. PLoS One. 2010 Feb 2;5(2):e9001. doi: 10.1371/journal.pone.0009001. [PubMed:20126405 ]
  11. Glover AB, Leyland-Jones B: Biochemistry of azacitidine: a review. Cancer Treat Rep. 1987 Oct;71(10):959-64. [PubMed:2443243 ]