Showing Compound Sphinganine (FDB021924)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:15 UTC

Update date

2020-09-17 15:38:31 UTC

Primary ID

FDB021924

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sphinganine

Description

Sphinganine, also known as D18:0 or safingol, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Thus, sphinganine is considered to be a sphingoid base lipid molecule. Sphinganine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphinganine exists in all living species, ranging from bacteria to humans. Within humans, sphinganine participates in a number of enzymatic reactions. In particular, sphinganine can be converted into 3-dehydrosphinganine; which is mediated by the enzyme 3-ketodihydrosphingosine reductase. In addition, sphinganine can be converted into sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine kinase 2. In humans, sphinganine is involved in the metabolic disorder called the fabry disease pathway. Outside of the human body, Sphinganine has been detected, but not quantified in, several different foods, such as beech nuts, docks, citrus, watercress, and brazil nuts. This could make sphinganine a potential biomarker for the consumption of these foods. A Sphinganine having (2S,3R)-configuration.

CAS Number

764-22-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S,3R)-2-Amino-1,3-octadecanediol	ChEBI
(2S,3R)-2-Aminooctadecane-1,3-diol	ChEBI
(R-(R,s))-2-aminooctadecane-1,3-diol	ChEBI
2-Amino-1,3-dihydroxyoctadecane	ChEBI
C18-Dihydrosphingosine	ChEBI
C18-Sphinganine	ChEBI
D-Erythro-1,3-dihydroxy-2-aminooctadecane	ChEBI
D-Erythro-2-amino-1,3-octadecanediol	ChEBI
D-Erythro-C18-dihydrosphingosine	ChEBI
D18:0	ChEBI
Dihydrosphingosine	ChEBI
Octadecasphinganine	ChEBI
Safingol	ChEBI
Erythro-D-sphinganine	HMDB
2-Aminooctadecane-1,3-diol	HMDB
Threo-dihydrosphingosine	HMDB
2-Amino-D-erythro-1,3-octadecanediol	HMDB
C18-Dihydro-sphingosine	HMDB
D-Erythro-sphinganine	HMDB
Dihydro-C18-sphingosine	HMDB
Erythro-sphinganine	HMDB
[R-(R,s)]-2-amino-1,3-octadecanediol	HMDB
(2S,3R)-Sphinganine	HMDB
D-Erythro-dihydrosphingosine	HMDB
SP(D18:0)	HMDB
Sphinganine	HMDB
(2S,3R)-2-amino-1,3-Octadecanediol	ChEBI
[R-(R,S)]-2-amino-1,3-Octadecanediol	hmdb
2-amino-1,3-Dihydroxyoctadecane	ChEBI
2-amino-D-erythro-1,3-Octadecanediol	hmdb
C18-dihydro-Sphingosine	hmdb
D-erythro-1,3-Dihydroxy-2-aminooctadecane	hmdb
D-erythro-2-Amino-1,3-octadecanediol	hmdb
D-erythro-C18-Dihydrosphingosine	hmdb
D-erythro-Sphinganine	hmdb
erythro-Sphinganine	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	5.2	ALOGPS
logP	4.77	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	90.93 m³·mol⁻¹	ChemAxon
Polarizability	40.68 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

Chemical Formula

C18H39NO2

IUPAC name

(2S,3R)-2-aminooctadecane-1,3-diol

InChI Identifier

InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1

InChI Key

OTKJDMGTUTTYMP-ZWKOTPCHSA-N

Isomeric SMILES

CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO

Average Molecular Weight

301.5078

Monoisotopic Molecular Weight

301.298079497

Classification

Description

Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents

Secondary alcohol
1,2-aminoalcohol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Primary aliphatic amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-aminooctadecane-1,3-diol (CHEBI:16566 )
Sphinganines (C00836 )
Sphinganines (LMSP01020001 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Sphinganine, 3 TMS, GC-MS Spectrum	splash10-0udi-3980100000-87c0074f611dec416856	Spectrum
GC-MS	Sphinganine, 3 TMS, GC-MS Spectrum	splash10-0udi-1690000000-8fed2f980c631302b97b	Spectrum
GC-MS	Sphinganine, non-derivatized, GC-MS Spectrum	splash10-0udi-3980100000-87c0074f611dec416856	Spectrum
GC-MS	Sphinganine, non-derivatized, GC-MS Spectrum	splash10-0udi-1690000000-8fed2f980c631302b97b	Spectrum
Predicted GC-MS	Sphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-9120000000-0cfd71520376dffc3c78	Spectrum
Predicted GC-MS	Sphinganine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uk9-4490200000-f4c4281643554b83dd43	Spectrum
Predicted GC-MS	Sphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sphinganine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0iml-3791000000-013fe5eb404ccb287385	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-9000000000-04469479cb6d83603093	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bt9-9000000000-4f682b26d6efc1673141	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0009000000-4d5daf40edf51d7c5ce4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0f89-2196000000-86bd4d9593c5a53dfc94	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-01qa-9130000000-819bc3df8d7408799b9f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-03xr-9000000000-0b47410c79f07946095a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03xr-9000000000-6dd6eb4c242974e7f7cc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0ab9-3892000000-6d8fa67090a1cebaa6f3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0159-0092000000-6e15bf1516b938239cb5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0009000000-4d5daf40edf51d7c5ce4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0f89-2196000000-86bd4d9593c5a53dfc94	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01qa-9130000000-819bc3df8d7408799b9f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03xr-9000000000-3157cbca45e3dce158e4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03xr-9000000000-6dd6eb4c242974e7f7cc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-2390000000-a002411e49400899cf3c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0gx0-5096000000-ad6ab79ab16fab02d693	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-9000000000-5afe9071156e7abc48f2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 25V, Negative	splash10-0159-0092000000-9c001535e8080ffe05e2	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fsi-0092000000-4cad101913d628c296ba	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-2290000000-e693ddcd90fd9234c669	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06r7-9740000000-808c9a702fe97ec9078e	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1089000000-00c77e7cc5d9f3475be7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-115c-5091000000-dc391e96a566caaa0602	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9030000000-a74567f0d047f0915ffc	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16566

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00269

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

36159

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Acid ceramidase	ASAH1	Q13510
Alkaline ceramidase 2	ACER2	Q5QJU3
Alkaline ceramidase 1	ACER1	Q8TDN7
Ganglioside GM2 activator	GM2A	P17900
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	PIGL	Q9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q	PIGQ	Q9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit A	PIGA	P37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit H	PIGH	Q14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit P	PIGP	P57054
Phosphatidylinositol N-acetylglucosaminyltransferase subunit C	PIGC	Q92535
T-cell surface glycoprotein CD1e, membrane-associated	CD1E	P15812
Epididymal secretory protein E1	NPC2	P61916
Ceramide synthase 1	CERS1	P27544
Antigen-presenting glycoprotein CD1d	CD1D	P15813
GPI mannosyltransferase 1	PIGM	Q9H3S5
Phosphatidylinositol-glycan biosynthesis class W protein	PIGW	Q7Z7B1
Phosphatidylinositol-glycan biosynthesis class X protein	PIGX	Q8TBF5
GPI mannosyltransferase 4	PIGZ	Q86VD9
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase	B3GNT5	Q9BYG0
Beta-1,3-galactosyltransferase 5	B3GALT5	Q9Y2C3
GPI mannosyltransferase 3	PIGB	Q92521
Phosphatidylinositol-glycan biosynthesis class F protein	PIGF	Q07326
GPI ethanolamine phosphate transferase 2	PIGG	Q5H8A4
GPI ethanolamine phosphate transferase 1	PIGN	O95427
GPI ethanolamine phosphate transferase 3	PIGO	Q8TEQ8
GPI transamidase component PIG-S	PIGS	Q96S52
GPI transamidase component PIG-T	PIGT	Q969N2
Phosphatidylinositol glycan anchor biosynthesis class U protein	PIGU	Q9H490
GPI mannosyltransferase 2	PIGV	Q9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y	PIGY	Q3MUY2
Non-lysosomal glucosylceramidase	GBA2	Q9HCG7
GPI-anchor transamidase	PIGK	Q92643
Sphingosine-1-phosphate phosphatase 2	SGPP2	Q8IWX5
Alkaline ceramidase 3	ACER3	Q9NUN7
Sphingosine kinase 1	SPHK1	Q96GK1
3-ketodihydrosphingosine reductase	KDSR	Q06136