Compound

(E)-4-hydroxynon-2-enal

The E (trans) stereoisomer of 4-hydroxynon-2-enal; it is the primary α,β-unsaturated hydroxyalkenal produced by lipid peroxidation in cells.

Definition from ChEBI (CHEBI:58968), read 2026-09-23. CC BY 4.0.

CHEBI:58968ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (E)-4-hydroxynon-2-enal — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C9H16O2
Mass: 156.225 g/mol
Charge: 0
InChIKey: JVJFIQYAHPMBBX-FNORWQNLSA-N
SMILES: [H]C(=O)/C=C/C(O)CCCCC
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

3 entities

3 entities reached.

0 reported hops3 assembled from the scaffold

What the reference databases state

Statements

4 statements

4 statements · 2 reference databases · Subject: (E)-4-hydroxynon-2-enal · Sources: Human-GEM, Rhea

Order

(E)-4-hydroxynon-2-enal is converted to (E)-4-hydroxynon-2-enoateCompoundHuman-GEM MAR20041Inferred only
(E)-4-hydroxynon-2-enal is metabolised by ALDH3B1ProteinHuman-GEM MAR20041Inferred only
(E)-4-hydroxynon-2-enal is metabolised by GSTP1ProteinRhea RHEA:85343Inferred only
(E)-4-hydroxynon-2-enal is transported by ABCC1ProteinHuman-GEM MAR11778Inferred only

Reactions

12 reactions

16alpha-hydroxyestrone+16alpha-hydroxyestrone+MAM00432r+MAM00604c+MAM00624c+MAM00641c+MAM00641m+MAM00641r+MAM00641x+MAM00642c+MAM00642m+MAM00642r+MAM00642x+MAM00644c+MAM00645c+2-hydroxy-17beta-estradiol+2-hydroxy-17beta-estradiol+MAM00651c+MAM00651m+MAM00651r+MAM00651x+MAM00652c+MAM00652m+MAM00652r+MAM00652x+2-methoxy-17beta-estradiol+2-methoxyestrone+2-methoxyestrone+MAM00747r+MAM00828r+MAM00830c+MAM00925c+MAM00927c+MAM00945c+MAM00947c+MAM00949c+MAM00987c+MAM00987m+MAM00987r+MAM00987x+(E)-4-hydroxynon-2-enal+MAM01001c+MAM01001m+MAM01001r+MAM01001x+MAM01011c+4-methoxyestrone+3alpha-hydroxy-5alpha-pregnan-20-one+MAM01792r+MAM01794r+MAM02469cMAM10001e
Reaction pageLeft to rightBalance undeterminableGO:0005829, GO:0005783, GO:0005759, GO:0005777, GO:0005764, GO:0005615
Human-GEM MAR00037CC BY 4.0Reference data
MAM00731c(E)-4-hydroxynon-2-enal
Reaction pageReversibleBalancedGO:0005829
Human-GEM MAR02454CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal+ATP+water(E)-4-hydroxynon-2-enal+ADP+proton+phosphate(3-)
Transported by ABCC1
Reaction pageLeft to rightBalancedEC 7.6.2.2GO:0005829, GO:0005615
Human-GEM MAR11778CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR11912CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal+water+NADP(3-)2proton+NADPH(4-)+(E)-4-hydroxynon-2-enoate
Catalysed by ALDH3B1
Reaction pageLeft to rightBalancedEC 1.2.1.-GO:0005829
Human-GEM MAR20041CC BY 4.0Reference data
CHEBI:142617+NADP(3-)(E)-4-hydroxynon-2-enal+NADPH(4-)+hydron
Catalysed by AKR1B15 or AKR1B10
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:58416CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal+dioxygen+water(E)-4-hydroxynon-2-enoate+hydrogen peroxide+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:58988CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal+NADP(3-)+water(E)-4-hydroxynon-2-enoate+NADPH(4-)+2hydron
Catalysed by ALDH3B1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:59912CC BY 4.0Reference data
CHEBI:142617+NAD(1-)(E)-4-hydroxynon-2-enal+NADH(2-)+hydron
Catalysed by ADH7
Reaction pageRight to leftBalance undeterminable
Rhea RHEA:60976CC BY 4.0Reference data
CHEBI:156112+NADP(3-)(E)-4-hydroxynon-2-enal+NADPH(4-)+hydron
Catalysed by PTGR1
Reaction pageRight to leftBalance undeterminable
Rhea RHEA:64736CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal+NAD(1-)+water(E)-4-hydroxynon-2-enoate+NADH(2-)+2hydron
Catalysed by ALDH1A1 or ALDH1B1 or ALDH3B1 or ALDH7A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:67248CC BY 4.0Reference data
(E)-4-hydroxynon-2-enal+glutathione3-(glutathion-S-yl)-4-hydroxynonanal
Catalysed by GSTP1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:85343CC BY 4.0Reference data

Other names

9 names

Resolves to: (E)-4-hydroxynon-2-enal

Also called: (E)-4-hydroxy-2-nonenal4-HNE4-Hydroxy-2,3-trans-nonenal4-hydroxy-2E-nonenal4-hydroxynonenalFAL 9:1;OHNEtrans-4-Hydroxy-2-nonenal
Systematic name: (2E)-4-hydroxynon-2-enal