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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-20 20:29:27 UTC
HMDB IDHMDB0000269
Secondary Accession Numbers
  • HMDB00269
Metabolite Identification
Common NameSphinganine
DescriptionSphinganine is a blocker postlysosomal cholesterol transport by inhibition of low-density lipoprotein-induced esterification of cholesterol and cause unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested the possibility that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease. (PMID 1817037 ).
Structure
Thumb
Synonyms
ValueSource
(2S,3R)-2-amino-1,3-OctadecanediolChEBI
(2S,3R)-2-Aminooctadecane-1,3-diolChEBI
(R-(R*,s*))-2-aminooctadecane-1,3-diolChEBI
2-amino-1,3-DihydroxyoctadecaneChEBI
C18-DihydrosphingosineChEBI
C18-SphinganineChEBI
D-erythro-1,3-Dihydroxy-2-aminooctadecaneChEBI
D-erythro-2-amino-1,3-OctadecanediolChEBI
D-erythro-C18-DihydrosphingosineChEBI
D18:0ChEBI
DihydrosphingosineChEBI
OctadecasphinganineChEBI
SafingolChEBI
2-amino-D-erythro-1,3-OctadecanediolHMDB
C18-dihydro-SphingosineHMDB
D-erythro-SphinganineHMDB
dihydro-C18-SphingosineHMDB
erythro-SphinganineHMDB
[R-(R*,s*)]-2-amino-1,3-octadecanediolHMDB
Safingol, (R-(r*,r*))-isomerMeSH
Safingol, ((r*,s*)-(+-))-isomerMeSH
erythro-D-SphinganineMeSH
Safingol, (S-(r*,s*))-isomerMeSH
2-Aminooctadecane-1,3-diolMeSH
Safingol hydrochlorideMeSH
SaginfolMeSH
threo-DihydrosphingosineMeSH
Chemical FormulaC18H39NO2
Average Molecular Weight301.5078
Monoisotopic Molecular Weight301.298079497
IUPAC Name(2S,3R)-2-aminooctadecane-1,3-diol
Traditional Namesphinganine
CAS Registry Number764-22-7
SMILES
CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO
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 KeyOTKJDMGTUTTYMP-ZWKOTPCHSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0045 g/LALOGPS
logP5.2ALOGPS
logP4.77ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)9.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity90.93 m³·mol⁻¹ChemAxon
Polarizability40.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-3980100000-87c0074f611dec416856View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-1690000000-8fed2f980c631302b97bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3980100000-87c0074f611dec416856View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1690000000-8fed2f980c631302b97bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9120000000-0cfd71520376dffc3c78View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-4490200000-f4c4281643554b83dd43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0iml-3791000000-013fe5eb404ccb287385View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-04469479cb6d83603093View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bt9-9000000000-4f682b26d6efc1673141View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0009000000-4d5daf40edf51d7c5ce4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0f89-2196000000-86bd4d9593c5a53dfc94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-01qa-9130000000-819bc3df8d7408799b9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03xr-9000000000-0b47410c79f07946095aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03xr-9000000000-6dd6eb4c242974e7f7ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ab9-3892000000-6d8fa67090a1cebaa6f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0159-0092000000-6e15bf1516b938239cb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-4d5daf40edf51d7c5ce4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f89-2196000000-86bd4d9593c5a53dfc94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01qa-9130000000-819bc3df8d7408799b9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-9000000000-3157cbca45e3dce158e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-9000000000-6dd6eb4c242974e7f7ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-2390000000-a002411e49400899cf3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0092000000-4cad101913d628c296baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-2290000000-e693ddcd90fd9234c669View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-9740000000-808c9a702fe97ec9078eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1089000000-00c77e7cc5d9f3475be7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-115c-5091000000-dc391e96a566caaa0602View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-a74567f0d047f0915ffcView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Platelet
  • Spleen
  • Stratum Corneum
  • Thyroid Gland
Pathways
NameSMPDB/PathwhizKEGG
Fabry diseasePw000501Pw000501 greyscalePw000501 simpleNot Available
Gaucher DiseasePw000201Pw000201 greyscalePw000201 simpleNot Available
Globoid Cell LeukodystrophyPw000202Pw000202 greyscalePw000202 simpleNot Available
Krabbe diseasePw000502Pw000502 greyscalePw000502 simpleNot Available
Metachromatic Leukodystrophy (MLD)Pw000203Pw000203 greyscalePw000203 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 +/- 0.00033 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00023 +/- 0.00020 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000013 +/- 0.0000059 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
UrineDetected and Quantified0.00011 +/- 0.00015 umol/mmol creatinineAdult (>18 years old)FemalePregnancy details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Ribar S, Mesaric M, Sedic M: Sphingoid bases as possible diagnostic parameters. Croat Med J. 2003 Apr;44(2):165-70. [PubMed:12698507 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021924
KNApSAcK IDC00007540
Chemspider ID82609
KEGG Compound IDC00836
BioCyc IDCPD-13612
BiGG ID36159
Wikipedia LinkSafingol
METLIN ID5268
PubChem Compound91486
PDB IDNot Available
ChEBI ID16566
References
Synthesis ReferenceRoush, William R.; Adam, Michael A. Directed openings of 2,3-epoxy alcohols via reactions with isocyanates: synthesis of (+)-erythro-dihydrosphingosine. Journal of Organic Chemistry (1985), 50(20), 3752-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ribar S, Mesaric M, Bauman M: High-performance liquid chromatographic determination of sphinganine and sphingosine in serum and urine of subjects from an endemic nephropathy area in Croatia. J Chromatogr B Biomed Sci Appl. 2001 Apr 25;754(2):511-9. [PubMed:11339295 ]
  2. van der Westhuizen L, Shephard GS, van Schalkwyk DJ: The effect of repeated gavage doses of fumonisin B1 on the sphinganine and sphingosine levels in vervet monkeys. Toxicon. 2001 Jul;39(7):969-72. [PubMed:11223085 ]
  3. van der Westhuizen L, Brown NL, Marasas WF, Swanevelder S, Shephard GS: Sphinganine/sphingosine ratio in plasma and urine as a possible biomarker for fumonisin exposure in humans in rural areas of Africa. Food Chem Toxicol. 1999 Dec;37(12):1153-8. [PubMed:10654591 ]
  4. Deguchi H, Yegneswaran S, Griffin JH: Sphingolipids as bioactive regulators of thrombin generation. J Biol Chem. 2004 Mar 26;279(13):12036-42. Epub 2004 Jan 13. [PubMed:14722105 ]
  5. Flamand N, Justine P, Bernaud F, Rougier A, Gaetani Q: In vivo distribution of free long-chain sphingoid bases in the human stratum corneum by high-performance liquid chromatographic analysis of strippings. J Chromatogr B Biomed Appl. 1994 Jun 3;656(1):65-71. [PubMed:7952048 ]
  6. Martinez G, Jimenez-Sanchez G, Divry P, Vianey-Saban C, Riudor E, Rodes M, Briones P, Ribes A: Plasma free fatty acids in mitochondrial fatty acid oxidation defects. Clin Chim Acta. 1997 Nov 28;267(2):143-54. [PubMed:9469249 ]
  7. Berg C, Trofast C, Bengtsson T: Platelets induce reactive oxygen species-dependent growth of human skin fibroblasts. Eur J Cell Biol. 2003 Nov;82(11):565-71. [PubMed:14703013 ]
  8. Voss KA, Plattner RD, Riley RT, Meredith FI, Norred WP: In vivo effects of fumonisin B1-producing and fumonisin B1-nonproducing Fusarium moniliforme isolates are similar: fumonisins B2 and B3 cause hepato- and nephrotoxicity in rats. Mycopathologia. 1998;141(1):45-58. [PubMed:9725030 ]
  9. Bouchon B, Portoukalian J, Orgiazzi J, Bornet H: Selective enrichment of phytosphingosine in glycosphingolipids of isolated human thyrocytes as compared to the whole thyroid. Biochem Biophys Res Commun. 1987 Mar 30;143(3):827-31. [PubMed:3566758 ]
  10. Dragusin M, Gurgui C, Schwarzmann G, Hoernschemeyer J, van Echten-Deckert G: Metabolism of the unnatural anticancer lipid safingol, L-threo-dihydrosphingosine, in cultured cells. J Lipid Res. 2003 Sep;44(9):1772-9. Epub 2003 Jun 1. [PubMed:12777464 ]
  11. Sharma N, He Q, Sharma RP: Sphingosine kinase activity confers resistance to apoptosis by fumonisin B1 in human embryonic kidney (HEK-293) cells. Chem Biol Interact. 2004 Dec 30;151(1):33-42. [PubMed:15607760 ]
  12. Bibel DJ, Aly R, Shinefield HR: Topical sphingolipids in antisepsis and antifungal therapy. Clin Exp Dermatol. 1995 Sep;20(5):395-400. [PubMed:8593716 ]
  13. Dyatlovitskaya EV, Kandyba AG, Kozlov AM, Somova OG: Sphinganine in sphingomyelins of tumors and mouse regenerating liver. Biochemistry (Mosc). 2001 May;66(5):502-4. [PubMed:11405884 ]
  14. Zimber A, Chedeville A, Gespach C, Abita JP: Inhibition of proliferation and induction of monocytic differentiation on HL60 human promyelocytic leukemia cells treated with bile acids in vitro. Int J Cancer. 1994 Oct 1;59(1):71-7. [PubMed:7927907 ]
  15. Rodriguez-Lafrasse C, Rousson R, Pentchev PG, Louisot P, Vanier MT: Free sphingoid bases in tissues from patients with type C Niemann-Pick disease and other lysosomal storage disorders. Biochim Biophys Acta. 1994 May 25;1226(2):138-44. [PubMed:8204660 ]
  16. Roff CF, Goldin E, Comly ME, Cooney A, Brown A, Vanier MT, Miller SP, Brady RO, Pentchev PG: Type C Niemann-Pick disease: use of hydrophobic amines to study defective cholesterol transport. Dev Neurosci. 1991;13(4-5):315-9. [PubMed:1817037 ]

Only showing the first 10 proteins. There are 60 proteins in total.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
Reactions
Sphinganine 1-phosphate + Water → Sphinganine + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
Reactions
Sphinganine 1-phosphate + Water → Sphinganine + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61
Reactions
Sphinganine 1-phosphate + Water → Sphinganine + Phosphoric aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the formation of some glycolipid via the addition of N-acetylgalactosamine (GalNAc) in alpha-1,3-linkage to some substrate. Glycolipids probably serve for adherence of some pathogens
Gene Name:
GBGT1
Uniprot ID:
Q8N5D6
Molecular weight:
40126.9
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGH
Uniprot ID:
Q14442
Molecular weight:
21080.415
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGP
Uniprot ID:
P57054
Molecular weight:
18089.055
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGC
Uniprot ID:
Q92535
Molecular weight:
33582.18

Only showing the first 10 proteins. There are 60 proteins in total.