Compound

(4R)-hydroxysphinganine

A cationic sphingoid that is the conjugate acid of phytosphingosine, obtained by protonation of the primary amino function; major species at pH 7.3.

Definition from ChEBI (CHEBI:64124), read 2026-09-23. CC BY 4.0.

CHEBI:64124ChEBI

Open in the graph

Structure

2D depiction

No three-dimensional record for this entry.

Class: Organic compound, cation
Formula: C18H40NO3
Mass: 318.522 g/mol
Charge: +1
InChIKey: AERBNCYCJBRYDG-KSZLIROESA-O
SMILES: CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H]([NH3+])CO
Look it up: ChEBI By InChIKey

Identity from ChEBI. Not evidence.

What it touches on the way

Mechanistic reach

5 entities

5 entities reached.

0 reported hops5 assembled from the scaffold

What the reference databases state

Statements

9 statements

9 statements · 2 reference databases · Subject: (4R)-hydroxysphinganine · Sources: Human-GEM, Rhea

Order

(4R)-hydroxysphinganine is converted to (4R)-hydroxysphinganine 1-phosphateCompoundRhea RHEA:33563Inferred only
(4R)-hydroxysphinganine is converted to (4R)-hydroxysphinganine 1-phosphateCompoundHuman-GEM MAR12081Inferred only
(4R)-hydroxysphinganine 1-phosphate is converted to (4R)-hydroxysphinganineCompoundRhea RHEA:33067Inferred only
(4R)-hydroxysphinganine 1-phosphate is converted to (4R)-hydroxysphinganineCompoundRhea RHEA:33563Inferred only
(4R)-hydroxysphinganine is a substrate of ASAH1ProteinRhea RHEA:41303Inferred only
(4R)-hydroxysphinganine is a substrate of CERS5ProteinRhea RHEA:64008Inferred only
(4R)-hydroxysphinganine is a substrate of CERS6ProteinRhea RHEA:64008Inferred only
(4R)-hydroxysphinganine is a substrate of SPHK1ProteinHuman-GEM MAR12081Inferred only
(4R)-hydroxysphinganine is a substrate of SPHK2ProteinRhea RHEA:33563Inferred only

Reactions

32 reactions

water+an N-acyl-(4R)-4-hydroxysphinganine(4R)-hydroxysphinganine+fatty acid
Catalysed by ACER3 or ASAH1 or ACER1 or ACER2 or ASAH2
Reaction pageLeft to rightBalance undeterminableEC 3.5.1.23cytosol
Human-GEM MAR00716CC BY 4.0Reference data
ATP+(4R)-hydroxysphinganineADP+proton+(4R)-hydroxysphinganine 1-phosphate
Catalysed by SPHK1
Reaction pageLeft to rightBalancedEC 2.7.1.91cytosol
Human-GEM MAR12081CC BY 4.0Reference data
(4R)-hydroxysphinganine(4R)-hydroxysphinganine
Reaction pageLeft to rightBalancedGolgi apparatus, cytosol
Human-GEM MAR12109CC BY 4.0Reference data
(4R)-hydroxysphinganine(4R)-hydroxysphinganine
Reaction pageLeft to rightBalancedendoplasmic reticulum, cytosol
Human-GEM MAR12110CC BY 4.0Reference data
water+N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-(4R)-hydroxysphinganine(5Z,8Z,11Z,14Z)-eicosatetraenoate+(4R)-hydroxysphinganine
Catalysed by ACER3
Reaction pageLeft to rightBalancedEC 3.5.1.23endoplasmic reticulum
Human-GEM MAR20075CC BY 4.0Reference data
water+N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-(4R)-hydroxysphinganine(5Z,8Z,11Z,14Z)-eicosatetraenoate+(4R)-hydroxysphinganine
Catalysed by ACER3
Reaction pageLeft to rightBalancedEC 3.5.1.23Golgi apparatus
Human-GEM MAR20076CC BY 4.0Reference data
water+N-(11Z-eicosenoyl)-(4R)-hydroxysphinganine(11Z)-eicosenoate+(4R)-hydroxysphinganine
Catalysed by ACER3
Reaction pageLeft to rightBalancedEC 3.5.1.23endoplasmic reticulum
Human-GEM MAR20081CC BY 4.0Reference data
water+N-(11Z-eicosenoyl)-(4R)-hydroxysphinganine(11Z)-eicosenoate+(4R)-hydroxysphinganine
Catalysed by ACER3
Reaction pageLeft to rightBalancedEC 3.5.1.23Golgi apparatus
Human-GEM MAR20082CC BY 4.0Reference data
water+N-(9Z-octadecenoyl)-(4R)-hydroxysphinganine(9Z)-octadecenoate+(4R)-hydroxysphinganine
Catalysed by ACER3
Reaction pageLeft to rightBalancedEC 3.5.1.23endoplasmic reticulum
Human-GEM MAR20087CC BY 4.0Reference data
water+N-(9Z-octadecenoyl)-(4R)-hydroxysphinganineelaidic acid+(4R)-hydroxysphinganine
Catalysed by ACER3
Reaction pageLeft to rightBalancedEC 3.5.1.23Golgi apparatus
Human-GEM MAR20088CC BY 4.0Reference data
(4R)-hydroxysphinganine 1-phosphate+water(4R)-hydroxysphinganine+hydrogenphosphate
Catalysed by SGPP2
Reaction pageLeft to rightBalanced
Rhea RHEA:33067CC BY 4.0Reference data
hexacosanoyl-CoA+(4R)-hydroxysphinganineCHEBI:52980+coenzyme A(4-)+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:33339CC BY 4.0Reference data

Show the remaining 20

Other names

5 names

Resolves to: (4R)-hydroxysphinganine

Also called: 4-hydroxysphinganine4-hydroxysphinganine(1+)4-hydroxysphinganinium(1+)phytosphingosinium(1+)
Systematic name: (2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-aminium