ChemFOnt: Showing chemical card for Dihydroceramide (CFc000002903)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:53 UTC

Chemfont ID

CFc000002903

Molecule Identification

Common Name

Dihydroceramide

Definition

Dihydroceramide is an intermediate in sphingolipid metabolism. Dihydroceramide is the third to last step in the synthesis of beta-D-Galactosyl-1,4-beta-D glucosylceramide and is converted from sphinganine via the enzyme acyl-CoA-dependent ceramide synthase (EC 2.3.1.24). It is then converted to N-acylsphingosine via the enzyme fatty acid desaturase (EC 1.14.-.-).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acylsphinganine	HMDB
N-[(2S,3R)-1,3-Dihydroxyoctadecan-2-yl]formamide	HMDB

Chemical Formula

C₁₉H₃₉NO₃

Average Molecular Weight

329.5179

Monoisotopic Molecular Weight

329.292994119

IUPAC Name

N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]formamide

Traditional Name

N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]formamide

CAS Registry Number

None

SMILES

CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC=O

InChI Identifier

InChI=1S/C19H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(23)18(16-21)20-17-22/h17-19,21,23H,2-16H2,1H3,(H,20,22)/t18-,19+/m0/s1

InChI Key

XSDVOEIEBUGRQX-RBUKOAKNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Secondary carboxylic acid amides

Alternative Parents

Substituents

Secondary carboxylic acid amide
Secondary alcohol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0006752)

Exogenous

Food

Food (HMDB: HMDB0006752)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006752)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0006752)

Biochemical pathway

Metabolic pathway

Sphingolipid Metabolism (PathBank: SMP0002378)
Sphingolipid Metabolism (PathBank: SMP0063667)
Sphingolipid Metabolism (HMDB: HMDB0006752)

Disease pathway

Globoid Cell Leukodystrophy (PathBank: SMP0120702)
Metachromatic Leukodystrophy (MLD) (PathBank: SMP0120738)
Krabbe Disease (PathBank: SMP0120810)
Globoid Cell Leukodystrophy (HMDB: HMDB0006752)
Gaucher Disease (PathBank: SMP0120481)
Fabry Disease (PathBank: SMP0120809)

Role

Biological role

Energy source (HMDB: HMDB0006752)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006752)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0046 g/L	ALOGPS
logP	4.68	ALOGPS
logP	4.54	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.11	ChemAxon
pKa (Strongest Basic)	-0.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	95.88 m³·mol⁻¹	ChemAxon
Polarizability	42.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon