PABA/NO (CHEBI:195533)

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ChEBI Name	PABA/NO

ChEBI ID	CHEBI:195533

Definition	A C-nitro compound that is benzene substituted by [4-(methylamino)benzoyl]oxy, nitro, nitro, and (3,3-dimethyl-2-oxido-2λ⁵-triaz-1-en-1-yl)oxy groups at positions 1, 2, 4, and 5, respectively. It is an anti-cancer compound that is designed to release NO upon activation by glutathione.

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

Submitter	Doug Howe

Supplier Information

Download	Molfile XML SDF

Formula

C16H16N6O8

Net Charge

Average Mass

420.338

Monoisotopic Mass

420.10296

InChI

InChI=1S/C16H16N6O8/c1-17-11-6-4-10(5-7-11)16(23)29-14-9-15(30-18-22(28)19(2)3)13(21(26)27)8-12(14)20(24)25/h4-9,17H,1-3H3

InChIKey

DZJYJYAXGBNEMK-UHFFFAOYSA-N

SMILES

CNC1=CC=C(C=C1)C(=O)OC1=C(C=C(C(ON=[N+]([O-])N(C)C)=C1)[N+]([O-])=O)[N+]([O-])=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. 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.

ChEBI Ontology
Outgoing	PABA/NO (CHEBI:195533) has role antineoplastic agent (CHEBI:35610) PABA/NO (CHEBI:195533) has role apoptosis inducer (CHEBI:68495) PABA/NO (CHEBI:195533) has role prodrug (CHEBI:50266) PABA/NO (CHEBI:195533) is a C-nitro compound (CHEBI:35716) PABA/NO (CHEBI:195533) is a azoxy compound (CHEBI:37390) PABA/NO (CHEBI:195533) is a benzoate ester (CHEBI:36054) PABA/NO (CHEBI:195533) is a secondary amino compound (CHEBI:50995) PABA/NO (CHEBI:195533) is a triazene derivative (CHEBI:72573) PABA/NO (CHEBI:195533) is a zwitterion (CHEBI:27369)

IUPAC Name

5-[(3,3-dimethyl-2-oxido-2λ⁵-triaz-1-en-1-yl)oxy]-2,4-dinitrophenyl 4-(methylamino)benzoate

Synonyms	Sources
5-[(3,3-dimethyl-2-oxido-1-triazen-1-yl)oxy]-2,4-dinitrophenyl 4-(methylamino)benzoate	ChEBI
O²-(2,4-dinitro-5-(4-(N-methylamino)benzoyloxy)phenyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate	ChEBI
PABA/NO	SUBMITTER

Registry Number	Type	Source
875769-11-2	CAS Registry Number	SUBMITTER

Last Modified

11 August 2023