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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015122
Secondary Accession Numbers
  • HMDB0030167
  • HMDB15122
  • HMDB30167
Metabolite Identification
Common NameCytarabine
DescriptionCytarabine, or cytosine arabinoside, a pyrimidine nucleoside analog, is found in mushrooms. Cytarabine is isolated from the mushroom Xerocomus nigromaculatus of unknown palatability. Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle to stop normal cell development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle. Cytarabine is a chemotherapy agent used mainly in the treatment of hematological malignancies such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It is also known as ara C. Cytosine arabinoside is an antimetabolic agent with the chemical name of 1 -arabinofuranosylcytosine. Its mode of action is due to its rapid conversion into cytosine arabinoside triphosphate, which damages DNA when the cell cycle holds in the S phase (synthesis of DNA). Rapidly dividing cells, which require DNA replication for mitosis, are therefore most affected. Cytosine arabinoside also inhibits both DNA and RNA polymerases and nucleotide reductase enzymes needed for DNA synthesis
Structure
Data?1582753261
Synonyms
ValueSource
1-beta-D-ArabinofuranosylcytosineChEBI
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinoneChEBI
Ara-CChEBI
ArabinocytosineChEBI
Arabinoside CChEBI
CitarabinaChEBI
CytarabinumChEBI
Cytosine arabinosideChEBI
Cytosine-1-beta-D-arabinofuranosideChEBI
Cytosine-beta-D-arabinofuranosideChEBI
DepocytKegg
1-b-D-ArabinofuranosylcytosineGenerator
1-Β-D-arabinofuranosylcytosineGenerator
4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinoneGenerator
4-Amino-1-β-D-arabinofuranosyl-2(1H)-pyrimidinoneGenerator
Cytosine-1-b-D-arabinofuranosideGenerator
Cytosine-1-β-D-arabinofuranosideGenerator
Cytosine-b-D-arabinofuranosideGenerator
Cytosine-β-D-arabinofuranosideGenerator
(beta-D-Arabinofuranosyl)cytosineHMDB
1-ArabinofuranosylcytosineHMDB
1-beta -D-ArabinofaranosylcytosineHMDB
1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinoneHMDB
1-beta -D-ArabinofuranosylcytosineHMDB
1-beta-D-ArabinofaranosylcytosineHMDB
1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinoneHMDB
1-beta-D-Arabinofuranosyl-cytosineHMDB
1-beta-D-Arabinofuranosylcytosine, cytosine arabinosideHMDB
1-beta-D-Arabinosyl-cytosineHMDB
1-beta-D-ArabinosylcytosineHMDB
1beta -ArabinofuranasylcytosineHMDB
1beta -D-ArabinofuranosylcytosineHMDB
1beta -D-ArabinosylcytosineHMDB
1beta-ArabinofuranasylcytosineHMDB
1beta-D-ArabinofuranosylcytosineHMDB
1beta-D-ArabinosylcytosineHMDB
2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosylHMDB
4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidinHMDB
4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidineHMDB
4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinoneHMDB
4-Amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-oneHMDB
AlexanHMDB
ArabinocytidineHMDB
ArabinofuranosylcytosineHMDB
ArabinosylcytosineHMDB
ArabitinHMDB
AraCHMDB
AracytidineHMDB
AracytinHMDB
AracytineHMDB
ArafcytHMDB
beta -ArabinosylcytosineHMDB
beta -Cytosine arabinosideHMDB
beta -D-ArabinosylcytosineHMDB
beta-Ara cHMDB
beta-ArabinosylcytosineHMDB
beta-Cytosine arabinosideHMDB
beta-D-ArabinosylcytosineHMDB
CytarabinHMDB
CytarabinaHMDB
Cytarabine liposome injectionHMDB
CytarabinosideHMDB
CytonalHMDB
CytosarHMDB
Cytosar-uHMDB
Cytosine 1-beta-D-arabinofuranosideHMDB
Cytosine arabinofuranosideHMDB
Cytosine arabinoseHMDB
Cytosine beta-D-arabinofuranosideHMDB
Cytosine beta-D-arabinosideHMDB
Cytosine, beta -D-arabinosideHMDB
Cytosine, beta-D-arabinosideHMDB
Cytosine-1-beta-D-arabinofuranoside hydrochlorideHMDB
Cytosine-beta -arabinosideHMDB
Cytosine-beta -D-arabinofuranosideHMDB
Cytosine-beta-arabinosideHMDB
CytosinearabinosideHMDB
DepocyteHMDB
ErpalfaHMDB
IretinHMDB
SpongocytidineHMDB
TarabineHMDB
UdicilHMDB
Arabinoside, cytosineHMDB
CytosarUHMDB
Hydrochloride, cytarabineHMDB
Cytarabine hydrochlorideHMDB
Cytosar uHMDB
Ara CHMDB
beta Ara CHMDB
CytarabineMeSH
Chemical FormulaC9H13N3O5
Average Molecular Weight243.2166
Monoisotopic Molecular Weight243.085520541
IUPAC Name4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
Traditional Namecytarabine
CAS Registry Number147-94-4
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
InChI KeyUHDGCWIWMRVCDJ-CCXZUQQUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point212 - 213 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility43.8 g/LNot Available
LogP-2.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility43.8 g/LALOGPS
logP-2.2ALOGPS
logP-2.8ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)-0.062ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.61 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.54 m³·mol⁻¹ChemAxon
Polarizability22.53 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]+155.4631661259
DarkChem[M-H]-147.65731661259
DeepCCS[M+H]+153.98430932474
DeepCCS[M+H]+152.79730932474
DeepCCS[M-H]-151.58830932474
DeepCCS[M-H]-150.43930932474
DeepCCS[M-2H]-185.95930932474
DeepCCS[M+Na]+160.96430932474
DeepCCS[M-2H]-184.13730932474
DeepCCS[M+Na]+159.23230932474
AllCCS[M+H]+155.532859911
AllCCS[M+H-H2O]+151.732859911
AllCCS[M+NH4]+159.032859911
AllCCS[M+Na]+160.032859911
AllCCS[M-H]-152.532859911
AllCCS[M+Na-2H]-152.532859911
AllCCS[M+HCOO]-152.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CytarabineNC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O3802.7Standard polar33892256
CytarabineNC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O2260.6Standard non polar33892256
CytarabineNC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O2622.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cytarabine,1TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O)[C@@H]1O2449.8Semi standard non polar33892256
Cytarabine,1TMS,isomer #2C[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=CC(N)=NC2=O)O[C@@H]1CO2447.9Semi standard non polar33892256
Cytarabine,1TMS,isomer #3C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CC(N)=NC1=O2442.5Semi standard non polar33892256
Cytarabine,1TMS,isomer #4C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=C12503.8Semi standard non polar33892256
Cytarabine,2TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O2410.6Semi standard non polar33892256
Cytarabine,2TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O)[C@@H]1O[Si](C)(C)C2406.7Semi standard non polar33892256
Cytarabine,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=C12468.4Semi standard non polar33892256
Cytarabine,2TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N)=NC1=O2395.5Semi standard non polar33892256
Cytarabine,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=C12475.9Semi standard non polar33892256
Cytarabine,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=C12470.8Semi standard non polar33892256
Cytarabine,2TMS,isomer #7C[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C=C1)[Si](C)(C)C2464.3Semi standard non polar33892256
Cytarabine,3TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2357.3Semi standard non polar33892256
Cytarabine,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=C12457.8Semi standard non polar33892256
Cytarabine,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=C12453.2Semi standard non polar33892256
Cytarabine,3TMS,isomer #4C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O)[C@@H]1O2420.4Semi standard non polar33892256
Cytarabine,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=C12451.9Semi standard non polar33892256
Cytarabine,3TMS,isomer #6C[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)O[C@@H]1CO2405.7Semi standard non polar33892256
Cytarabine,3TMS,isomer #7C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O2403.3Semi standard non polar33892256
Cytarabine,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=C12469.0Semi standard non polar33892256
Cytarabine,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=C12572.3Standard non polar33892256
Cytarabine,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=C12969.5Standard polar33892256
Cytarabine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O2441.6Semi standard non polar33892256
Cytarabine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O2581.5Standard non polar33892256
Cytarabine,4TMS,isomer #2C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O2890.7Standard polar33892256
Cytarabine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O)[C@@H]1O[Si](C)(C)C2428.3Semi standard non polar33892256
Cytarabine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O)[C@@H]1O[Si](C)(C)C2563.6Standard non polar33892256
Cytarabine,4TMS,isomer #3C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O)[C@@H]1O[Si](C)(C)C2847.2Standard polar33892256
Cytarabine,4TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O2428.4Semi standard non polar33892256
Cytarabine,4TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O2576.3Standard non polar33892256
Cytarabine,4TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC1=O2820.1Standard polar33892256
Cytarabine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2477.5Semi standard non polar33892256
Cytarabine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2558.6Standard non polar33892256
Cytarabine,5TMS,isomer #1C[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2669.6Standard polar33892256
Cytarabine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O)[C@@H]1O2692.2Semi standard non polar33892256
Cytarabine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=CC(N)=NC2=O)O[C@@H]1CO2697.4Semi standard non polar33892256
Cytarabine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CC(N)=NC1=O2685.9Semi standard non polar33892256
Cytarabine,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=C12782.1Semi standard non polar33892256
Cytarabine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2869.2Semi standard non polar33892256
Cytarabine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2870.8Semi standard non polar33892256
Cytarabine,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=C12940.9Semi standard non polar33892256
Cytarabine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N)=NC1=O2854.9Semi standard non polar33892256
Cytarabine,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=C12934.4Semi standard non polar33892256
Cytarabine,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=C12918.1Semi standard non polar33892256
Cytarabine,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=C1)[Si](C)(C)C(C)(C)C2911.3Semi standard non polar33892256
Cytarabine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3063.3Semi standard non polar33892256
Cytarabine,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=C13137.1Semi standard non polar33892256
Cytarabine,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=C13128.6Semi standard non polar33892256
Cytarabine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H](O)[C@@H]1O3081.4Semi standard non polar33892256
Cytarabine,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=C13115.8Semi standard non polar33892256
Cytarabine,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)O[C@@H]1CO3096.2Semi standard non polar33892256
Cytarabine,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O3076.5Semi standard non polar33892256
Cytarabine,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=C13299.2Semi standard non polar33892256
Cytarabine,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=C13333.6Standard non polar33892256
Cytarabine,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=C13318.5Standard polar33892256
Cytarabine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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]1O3281.9Semi standard non polar33892256
Cytarabine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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]1O3368.3Standard non polar33892256
Cytarabine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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]1O3209.7Standard polar33892256
Cytarabine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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)C3272.0Semi standard non polar33892256
Cytarabine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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)C3355.4Standard non polar33892256
Cytarabine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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)C3174.4Standard polar33892256
Cytarabine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O3274.3Semi standard non polar33892256
Cytarabine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O3358.3Standard non polar33892256
Cytarabine,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O3156.0Standard polar33892256
Cytarabine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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)C3460.3Semi standard non polar33892256
Cytarabine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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)C3469.5Standard non polar33892256
Cytarabine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=CC(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)C3133.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cytarabine GC-MS (5 TMS)splash10-0zfr-2951000000-7baf0e1ea8b1a34362e22018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cytarabine GC-MS (4 TMS)splash10-0g4j-2980000000-9337623aef7fec22dd972018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cytarabine GC-MS (Non-derivatized)splash10-0zfr-2951000000-7baf0e1ea8b1a34362e22018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cytarabine GC-MS (Non-derivatized)splash10-0g4j-2980000000-9337623aef7fec22dd972018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytarabine GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ml-9320000000-b032ad2c3dbed3face552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytarabine GC-MS (3 TMS) - 70eV, Positivesplash10-0fuu-3934200000-7c3baaaffddf6aacd0f32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytarabine 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 - Cytarabine LC-ESI-QQ , negative-QTOFsplash10-0006-0190000000-eff861edb69ddab2c1952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , negative-QTOFsplash10-0a4i-0900000000-4b5b14f0a5467db173b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , negative-QTOFsplash10-0a4i-3900000000-d85ae6c771dd9206c4c22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , negative-QTOFsplash10-06sl-9600000000-b154ca170372bcbf8a4a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , negative-QTOFsplash10-00lu-9200000000-840df44a2d1149f4a7f72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , positive-QTOFsplash10-01ox-0790000000-270551529aa609aa9ce82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , positive-QTOFsplash10-03di-0900000000-855a7f8775ed4351b2902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , positive-QTOFsplash10-03di-0900000000-50671582f88f6b4d8cee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , positive-QTOFsplash10-03di-1900000000-54269291900f80d353c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-QQ , positive-QTOFsplash10-03di-7900000000-ae3ff52581cbe61410642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine LC-ESI-IT , positive-QTOFsplash10-03di-0900000000-9f3ae8e87da22e4e2e822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine 35V, Negative-QTOFsplash10-0btc-3910000000-0c7172b1308a7ac699d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytarabine 35V, Positive-QTOFsplash10-03di-0900000000-204e273853aa2d8e09ab2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 10V, Positive-QTOFsplash10-03di-0910000000-9575881412c4c94a7eae2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 20V, Positive-QTOFsplash10-03di-5900000000-2cb5f7e3dbd7baa35b562016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 40V, Positive-QTOFsplash10-03dj-9600000000-7d281b2b2d57c8786e112016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 10V, Negative-QTOFsplash10-01ox-0960000000-db9207082a1fabf42dae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 20V, Negative-QTOFsplash10-03xs-4910000000-c89de30dd376cbcb3b662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 40V, Negative-QTOFsplash10-00kf-9200000000-5715839499753b91f8452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 10V, Positive-QTOFsplash10-03di-0900000000-61fe3ac4032a2baf1b892021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 20V, Positive-QTOFsplash10-03di-2900000000-230b224d4d0dd71d0a492021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 40V, Positive-QTOFsplash10-02t9-9200000000-7262e80c4fe078b890fc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 10V, Negative-QTOFsplash10-03di-2900000000-66dec45988a096cc34832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 20V, Negative-QTOFsplash10-01ox-9500000000-bc463e76fd8ac42ac1d02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytarabine 40V, Negative-QTOFsplash10-0006-9100000000-98e1626c7f485521a57f2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2018-05-25Wishart LabView Spectrum
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
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2018-05-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00987 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00987 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00987
Phenol Explorer Compound IDNot Available
FooDB IDFDB001216
KNApSAcK IDNot Available
Chemspider ID6017
KEGG Compound IDC02961
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCytarabine
METLIN IDNot Available
PubChem Compound6253
PDB IDNot Available
ChEBI ID28680
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zaky DA, Betts RF, Douglas RG Jr, Bengali K, Neil GL: Varicella-zoster virus and subcutaneous cytarabine: correlation of in vitro sensitivities to blood levels. Antimicrob Agents Chemother. 1975 Mar;7(3):229-32. [PubMed:166610 ]
  2. Relling MV, Mulhern RK, Fairclough D, Baker D, Pui CH: Chlorpromazine with and without lorazepam as antiemetic therapy in children receiving uniform chemotherapy. J Pediatr. 1993 Nov;123(5):811-6. [PubMed:8229497 ]
  3. Mallick KS, Hajek AS, Parrish RK 2nd: Fluorouracil (5-FU) and cytarabine (ara-C) inhibition of corneal epithelial cell and conjunctival fibroblast proliferation. Arch Ophthalmol. 1985 Sep;103(9):1398-402. [PubMed:4038134 ]
  4. Bursztyn J, Boccara JF, Paillassou B, Bavoux F: [Corneal toxicity of cytarabine. Apropos of a case]. Ophtalmologie. 1989 Jun-Aug;3(3):229-30. [PubMed:2641118 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
References
  1. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]
General function:
Involved in zinc ion binding
Specific function:
Supplies the nucleotide substrate for thymidylate synthetase.
Gene Name:
DCTD
Uniprot ID:
P32321
Molecular weight:
21013.96
References
  1. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]
General function:
Involved in ATP binding
Specific function:
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DCK
Uniprot ID:
P27707
Molecular weight:
30518.315
References
  1. Ohta T, Hori H, Ogawa M, Miyahara M, Kawasaki H, Taniguchi N, Komada Y: Impact of cytidine deaminase activity on intrinsic resistance to cytarabine in carcinoma cells. Oncol Rep. 2004 Nov;12(5):1115-20. [PubMed:15492802 ]
  2. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]
General function:
Involved in DNA binding
Specific function:
Repair polymerase that plays a key role in base-excision repair. Has 5'-deoxyribose-5-phosphate lyase (dRP lyase) activity that removes the 5' sugar phosphate and also acts as a DNA polymerase that adds one nucleotide to the 3' end of the arising single-nucleotide gap. Conducts 'gap-filling' DNA synthesis in a stepwise distributive fashion rather than in a processive fashion as for other DNA polymerases.
Gene Name:
POLB
Uniprot ID:
P06746
Molecular weight:
38177.34
References
  1. Angeli JP, Ribeiro LR, Bellini MF, Mantovanil: Anti-clastogenic effect of beta-glucan extracted from barley towards chemically induced DNA damage in rodent cells. Hum Exp Toxicol. 2006 Jun;25(6):319-24. [PubMed:16866189 ]
  2. Miura S, Izuta S: DNA polymerases as targets of anticancer nucleosides. Curr Drug Targets. 2004 Feb;5(2):191-5. [PubMed:15011952 ]
  3. Krynetskaia NF, Phadke MS, Jadhav SH, Krynetskiy EY: Chromatin-associated proteins HMGB1/2 and PDIA3 trigger cellular response to chemotherapy-induced DNA damage. Mol Cancer Ther. 2009 Apr;8(4):864-72. doi: 10.1158/1535-7163.MCT-08-0695. [PubMed:19372559 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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. Ohta T, Hori H, Ogawa M, Miyahara M, Kawasaki H, Taniguchi N, Komada Y: Impact of cytidine deaminase activity on intrinsic resistance to cytarabine in carcinoma cells. Oncol Rep. 2004 Nov;12(5):1115-20. [PubMed:15492802 ]
  2. Lamba JK: Genetic factors influencing cytarabine therapy. Pharmacogenomics. 2009 Oct;10(10):1657-74. doi: 10.2217/pgs.09.118. [PubMed:19842938 ]

Transporters

General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs)
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Molecular weight:
50218.8
References
  1. Santini D, Vincenzi B, Fratto ME, Perrone G, Lai R, Catalano V, Cass C, Ruffini PA, Spoto C, Muretto P, Rizzo S, Muda AO, Mackey JR, Russo A, Tonini G, Graziano F: Prognostic role of human equilibrative transporter 1 (hENT1) in patients with resected gastric cancer. J Cell Physiol. 2010 May;223(2):384-8. doi: 10.1002/jcp.22045. [PubMed:20082300 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Chen R, Nelson JA: Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol. 2000 Jul 15;60(2):215-9. [PubMed:10825466 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
References
  1. Chen R, Nelson JA: Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol. 2000 Jul 15;60(2):215-9. [PubMed:10825466 ]