ancitabine (CHEBI:74838)

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ChEBI Name	ancitabine

ChEBI ID	CHEBI:74838

Definition	An organic heterotricyclic compound resulting from the formal condensation of the oxo group of cytidine to the 2' position with loss of water to give the corresponding cyclic ether. A prodrug, it is metabolised to the antineoplastic agent cytarabine, so is used to maintain a more constant antineoplastic action.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C9H11N3O4

Net Charge

Average Mass

225.20130

Monoisotopic Mass

225.07496

InChI

InChI=1S/C9H11N3O4/c10-5-1-2-12-8-7(16-9(12)11-5)6(14)4(3-13)15-8/h1-2,4,6-8,10,13-14H,3H2/t4-,6-,7+,8-/m1/s1

InChIKey

BBDAGFIXKZCXAH-CCXZUQQUSA-N

SMILES

OC[C@H]1O[C@@H]2[C@@H](Oc3nc(=N)ccn23)[C@@H]1O

Roles Classification
Biological Role(s):	antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.

Application(s):	prodrug A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	ancitabine (CHEBI:74838) has role antimetabolite (CHEBI:35221) ancitabine (CHEBI:74838) has role antineoplastic agent (CHEBI:35610) ancitabine (CHEBI:74838) has role prodrug (CHEBI:50266) ancitabine (CHEBI:74838) is a diol (CHEBI:23824) ancitabine (CHEBI:74838) is a organic heterotricyclic compound (CHEBI:26979) ancitabine (CHEBI:74838) is conjugate base of ancitabine(1+) (CHEBI:74842)

Incoming	ancitabine(1+) (CHEBI:74842) is conjugate acid of ancitabine (CHEBI:74838)

IUPAC Name

(2R,3R,3aS,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol

Synonyms	Sources
2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine	ChEBI
2,2'-anhydro-AraC	ChEBI
2,2'-anhydroarabinosylcytosine	ChemIDplus
2,2'-anhydrocytidine	ChemIDplus
2,2'-cyclocytidine	ChemIDplus
2,2'-O-cyclocytidine	ChemIDplus
[2R-(2α,3β,3aβ,9aβ)]-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6H-furo[2',3':4,5]pxazolo[3,2-a]pyrimidine-2-methanol	ChEBI
anhydrocytidine	ChemIDplus
cyclocytidine	ChEBI
O^2,2'-cyclocytidine	ChEBI

Last Modified

22 February 2017