IMH

1,4-DIDEOXY-4-AZA-1-(S)-(9-DEAZAHYPOXANTHIN-9-YL)-D-RIBITOL

Created:	1999-07-08
Last modified:	2022-09-26

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21 entries where IMH is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	33
Chiral Atom Count	4
Bond Count	35
Aromatic Bond Count	5

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Chemical Component Summary
Name	1,4-DIDEOXY-4-AZA-1-(S)-(9-DEAZAHYPOXANTHIN-9-YL)-D-RIBITOL
Synonyms	Forodesine; Immucillin H
Systematic Name (OpenEye OEToolkits)	7-[(2~{S},3~{S},4~{R},5~{R})-5-(hydroxymethyl)-3,4-bis(oxidanyl)pyrrolidin-2-yl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
Formula	C₁₁ H₁₄ N₄ O₄
Molecular Weight	266.253
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	OC1C(NC(CO)C1O)c1c[NH]c2c1N=CNC2=O
SMILES	CACTVS	3.385	OC[CH]1N[CH]([CH](O)[CH]1O)c2c[nH]c3C(=O)NC=Nc23
SMILES	OpenEye OEToolkits	2.0.7	c1c(c2c([nH]1)C(=O)NC=N2)C3C(C(C(N3)CO)O)O
Canonical SMILES	CACTVS	3.385	OC[C@H]1N[C@H]([C@H](O)[C@@H]1O)c2c[nH]c3C(=O)NC=Nc23
Canonical SMILES	OpenEye OEToolkits	2.0.7	c1c(c2c([nH]1)C(=O)NC=N2)[C@H]3[C@@H]([C@@H]([C@H](N3)CO)O)O
InChI	InChI	1.06	InChI=1S/C11H14N4O4/c16-2-5-9(17)10(18)7(15-5)4-1-12-8-6(4)13-3-14-11(8)19/h1,3,5,7,9-10,12,15-18H,2H2,(H,13,14,19)/t5-,7+,9-,10+/m1/s1
InChIKey	InChI	1.06	IWKXDMQDITUYRK-KUBHLMPHSA-N

Drug Info: DrugBank

DrugBank ID	DB06185
Name	Forodesine
Groups	investigational
Description	Forodesine is a highly potent, orally active, rationally designed PNP inhibitor that has shown activity in preclinical studies with malignant cells and clinical utility against T-cell acute lymphoblastic leukemia and cutaneous T-cell lymphoma. Additional preliminary findings support its use for the management of some B-cell malignancies.
Synonyms	1,4-Dideoxy-4-aza-1-(S)-(9-deazahypoxanthin-9-yl)-D-ribitol Immucillin-H (1S)-1,4-dideoxy-4-imino-(9-deazahypoxanthin-9-yl)-D-ribitol Forodesine hydrochloride Immucillin H Forodesine
Indication	Investigated for use/treatment in lymphoma (non-hodgkin's) and leukemia (lymphoid).
Categories	Heterocyclic Compounds, Fused-Ring Nucleic Acids, Nucleotides, and Nucleosides Nucleosides Purine-Nucleoside Phosphorylase, antagonists & inhibitors Purines Pyrimidines
CAS number	209799-67-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Purine nucleoside phosphorylase	MENGYTYEDYKNTAEWLLSHTKHRPQVAIICGSGLGGLTDKLTQAQIFDY...	unknown

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682