zealexin A1 (CHEBI:142278)

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ChEBI Name	zealexin A1

ChEBI ID	CHEBI:142278

Definition	A sesquiterpene phytoalexin that is (S)-β-macrocarpene in which the methyl group that is attached to a double bond has undergone formal oxidation to give the corresponding carboxylic acid. It is produced by maize (Zea mays) to provide biochemical protection against fungal infection.

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

Supplier Information

Download	Molfile XML SDF

Formula

C15H22O2

Net Charge

Average Mass

234.335

Monoisotopic Mass

234.16198

InChI

InChI=1S/C15H22O2/c1-15(2)9-3-4-13(10-15)11-5-7-12(8-6-11)14(16)17/h4,7,11H,3,5-6,8-10H2,1-2H3,(H,16,17)/t11-/m1/s1

InChIKey

IQKSHFZTCNUYOT-LLVKDONJSA-N

SMILES

C1(C(O)=O)=CC[C@@](C=2CC(CCC2)(C)C)(CC1)[H]

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	phytoalexin A toxin made by a plant that acts against an organism attacking it. (via terpenoid phytoalexin )

ChEBI Ontology
Outgoing	zealexin A1 (CHEBI:142278) has functional parent (S)-β-macrocarpen-15-ol (CHEBI:141850) zealexin A1 (CHEBI:142278) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) zealexin A1 (CHEBI:142278) is a sesquiterpene phytoalexin (CHEBI:142279) zealexin A1 (CHEBI:142278) is conjugate acid of zealexin A1(1−) (CHEBI:141852)

Incoming	zealexin A1(1−) (CHEBI:141852) is conjugate base of zealexin A1 (CHEBI:142278)

IUPAC Name

(1S)-5',5'-dimethyl[1,1'-bi(cyclohexane)-1',3-diene]-4-carboxylic acid

Synonym	Source
(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-ene-1-carboxylic acid	MetaCyc

Registry Number	Type	Source
28861710	Reaxys Registry Number	Reaxys

Last Modified

02 October 2018