MiMeDB: Showing metabocard for Sphingosine (MMDBc0000780)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:46 UTC

Update Date

2024-10-11 00:51:02 UTC

Metabolite ID

MMDBc0000780

Metabolite Identification

Common Name

Sphingosine

Description

Sphingosine, also known as (4E)-sphingenine or sphing-4-enine, 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. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids. Sphingolipids are a class of cell membrane lipids that include sphingomyelin. Thus, sphingosine is considered to be a sphingoid base lipid. Sphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingosine is found in all living organisms ranging from bacteria to plants to humans. Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine. Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine. Within humans and other mammals, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through its interaction with the enzyme sphingosine kinase 2. sphingosine 1-phosphate is an important signaling molecule. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. In humans, sphingosine is involved in globoid cell leukodystrophy.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3R)-(e)-2-Amino-1,3-dihydroxy-4-octadecene	ChEBI
(2S,3R,4E)-2-Amino-3-hydroxyoctadec-4-ene-1-ol	ChEBI
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol	ChEBI
(2S,3R,e)-2-Aminooctadec-4-ene-1,3-diol	ChEBI
(4E)-Sphing-4-enine	ChEBI
(4E)-Sphingenine	ChEBI
(e)-2-Amino-4-octadecan-1,3-diol	ChEBI
(e)-D-Erythro-4-octadecene-1,3-diol	ChEBI
2-Amino-4-octadecene-1,3-diol	ChEBI
C18 Sphingosine	ChEBI
D-(+)-Erythro-1,3-dihydroxy-2-amino-4-trans-octadecene	ChEBI
D-Erythro-sphingosine	ChEBI
Sph	ChEBI
Sphing-4-enine	ChEBI
Sphingenine	ChEBI
Sphingoid	ChEBI
Sphingosin	ChEBI
Sphingosine D18:1	ChEBI
trans-4-Sphingenine	ChEBI
trans-D-Erythro-2-amino-4-octadecene-1,3-diol	ChEBI
4-Sphingenine	MeSH, HMDB
4 Sphingenine	MeSH, HMDB
(-)-D-erythro-Sphingosine	HMDB
(-)-Sphingosine	HMDB
(2S,3R)-Sphingosine	HMDB
4-trans-Sphingenine	HMDB
C18-Sphingosine	HMDB
D-(+)-erythro-4-trans-Sphingenine	HMDB
D-Sphingosine	HMDB
D-erythro-C18-Sphingosine	HMDB
Erythrosphingosine	HMDB
Sphingosine	HMDB
erythro-4-Sphingenine	HMDB
erythro-C18-Sphingosine	HMDB
SP(d18:1)	HMDB

Molecular Formula

C₁₈H₃₇NO₂

Average Mass

299.4919

Monoisotopic Mass

299.282429433

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

InChI Key

WWUZIQQURGPMPG-KRWOKUGFSA-N

Chemical Taxonomy

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

sphing-4-enine (CHEBI:16393 )
Sphing-4-enines (Sphingosines) (C00319 )
Sphing-4-enines (Sphingosines) (LMSP01010001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Lysosome
Membrane

Biospecimen Locations

Blood
Epidermis
Feces
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle
Spleen
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Kidney
Leukocyte
Liver
Placenta
Platelet
Skeletal Muscle
Spleen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191901	Lipid phosphate phosphohydrolase 2	Unknown	O43688	Homo sapiens
MMDBp0191907	Lipid phosphate phosphohydrolase 1	Unknown	O14494	Homo sapiens
MMDBp0191912	Lipid phosphate phosphohydrolase 3	Unknown	O14495	Homo sapiens
MMDBp0192100	Globoside alpha-1,3-N-acetylgalactosaminyltransferase 1	Unknown	Q8N5D6	Homo sapiens
MMDBp0192203	N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase	Enzyme	Q9Y2B2	Homo sapiens
MMDBp0192558	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q	Enzyme	Q9BRB3	Homo sapiens
MMDBp0192559	Phosphatidylinositol N-acetylglucosaminyltransferase subunit A	Enzyme	P37287	Homo sapiens
MMDBp0192560	Phosphatidylinositol N-acetylglucosaminyltransferase subunit H	Enzyme	Q14442	Homo sapiens
MMDBp0192561	Phosphatidylinositol N-acetylglucosaminyltransferase subunit P	Enzyme	P57054	Homo sapiens
MMDBp0192562	Phosphatidylinositol N-acetylglucosaminyltransferase subunit C	Enzyme	Q92535	Homo sapiens
MMDBp0192688	Sphingosine kinase 1	Unknown	Q9NYA1	Homo sapiens
MMDBp0192689	Sphingosine kinase 2	Unknown	Q9NRA0	Homo sapiens
MMDBp0192690	Acid ceramidase	Enzyme	Q13510	Homo sapiens
MMDBp0193223	Ganglioside GM2 activator	Enzyme	P17900	Homo sapiens
MMDBp0193531	T-cell surface glycoprotein CD1e, membrane-associated	Enzyme	P15812	Homo sapiens
MMDBp0193582	Sphingosine 1-phosphate receptor 4	Enzyme	O95977	Homo sapiens
MMDBp0193602	Sphingosine 1-phosphate receptor 2	Enzyme	O95136	Homo sapiens
MMDBp0193636	Epididymal secretory protein E1	Enzyme	P61916	Homo sapiens
MMDBp0193638	Sphingosine 1-phosphate receptor 1	Enzyme	P21453	Homo sapiens
MMDBp0193667	Sphingosine 1-phosphate receptor 5	Enzyme	Q9H228	Homo sapiens
MMDBp0193670	Ceramide synthase 1	Enzyme	P27544	Homo sapiens
MMDBp0193673	Antigen-presenting glycoprotein CD1d	Enzyme	P15813	Homo sapiens
MMDBp0193742	GPI mannosyltransferase 1	Enzyme	Q9H3S5	Homo sapiens
MMDBp0193755	Phosphatidylinositol-glycan biosynthesis class W protein	Enzyme	Q7Z7B1	Homo sapiens
MMDBp0193805	Phosphatidylinositol-glycan biosynthesis class X protein	Enzyme	Q8TBF5	Homo sapiens
MMDBp0193806	GPI mannosyltransferase 4	Enzyme	Q86VD9	Homo sapiens
MMDBp0194033	Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase	Enzyme	Q9BYG0	Homo sapiens
MMDBp0194044	Beta-1,3-galactosyltransferase 5	Enzyme	Q9Y2C3	Homo sapiens
MMDBp0194119	GPI mannosyltransferase 3	Enzyme	Q92521	Homo sapiens
MMDBp0194120	Phosphatidylinositol-glycan biosynthesis class F protein	Enzyme	Q07326	Homo sapiens
MMDBp0194121	GPI ethanolamine phosphate transferase 2	Enzyme	Q5H8A4	Homo sapiens
MMDBp0194122	GPI ethanolamine phosphate transferase 1	Enzyme	O95427	Homo sapiens
MMDBp0194123	GPI ethanolamine phosphate transferase 3	Enzyme	Q8TEQ8	Homo sapiens
MMDBp0194124	GPI transamidase component PIG-S	Enzyme	Q96S52	Homo sapiens
MMDBp0194125	GPI transamidase component PIG-T	Enzyme	Q969N2	Homo sapiens
MMDBp0194126	Phosphatidylinositol glycan anchor biosynthesis class U protein	Enzyme	Q9H490	Homo sapiens
MMDBp0194127	GPI mannosyltransferase 2	Enzyme	Q9NUD9	Homo sapiens
MMDBp0194128	Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y	Enzyme	Q3MUY2	Homo sapiens
MMDBp0194133	Pleckstrin homology domain-containing family A member 8	Unknown	Q96JA3	Homo sapiens
MMDBp0194488	G-protein coupled receptor 6	Unknown	P46095	Homo sapiens
MMDBp0195879	Putative neutral ceramidase C	Enzyme	P0C7U2	Homo sapiens
MMDBp0195880	Alkaline ceramidase 2	Enzyme	Q5QJU3	Homo sapiens
MMDBp0195881	Neutral ceramidase	Enzyme	Q9NR71	Homo sapiens
MMDBp0195885	Non-lysosomal glucosylceramidase	Enzyme	Q9HCG7	Homo sapiens
MMDBp0196045	Sphingosine kinase 1	Enzyme	Q96GK1	Homo sapiens
MMDBp0196227	Alkaline ceramidase 1	Enzyme	Q8TDN7	Homo sapiens
MMDBp0196348	Sphingosine 1-phosphate receptor 3	Unknown	Q99500	Homo sapiens
MMDBp0196494	Ceramide synthase 5	Unknown	Q8N5B7	Homo sapiens
MMDBp0196528	GPI-anchor transamidase	Enzyme	Q92643	Homo sapiens
MMDBp0196556	Glycosylphosphatidylinositol anchor attachment 1 protein	Unknown	O43292	Homo sapiens
MMDBp0196557	Protein PLEKHA9	Unknown	O95397	Homo sapiens
MMDBp0196558	Glycolipid transfer protein domain-containing protein 2	Unknown	A6NH11	Homo sapiens
MMDBp0196559	Putative uncharacterized protein PLEKHA8	Unknown	B5MDU3	Homo sapiens
MMDBp0196560	T-cell surface glycoprotein CD1a	Unknown	P06126	Homo sapiens
MMDBp0196561	Glycolipid transfer protein domain-containing protein 1	Unknown	Q5TA50	Homo sapiens
MMDBp0196562	T-cell surface glycoprotein CD1c	Unknown	P29017	Homo sapiens
MMDBp0196563	Lipopolysaccharide-binding protein	Unknown	P18428	Homo sapiens
MMDBp0196564	Putative uncharacterized protein DKFZp434L0435	Unknown	Q9UFH6	Homo sapiens
MMDBp0196565	T-cell surface glycoprotein CD1b	Unknown	P29016	Homo sapiens
MMDBp0196566	Glycolipid transfer protein	Unknown	Q9NZD2	Homo sapiens
MMDBp0196637	Sphingosine-1-phosphate phosphatase 2	Enzyme	Q8IWX5	Homo sapiens
MMDBp0196705	Ceramide synthase 2	Unknown	Q96G23
MMDBp0196706	Ceramide synthase 3	Unknown	Q8IU89
MMDBp0196707	Ceramide synthase 4	Unknown	Q9HA82
MMDBp0196708	Ceramide synthase 6	Unknown	Q6ZMG9

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002096	Sphingosine 1-phosphate	Sphingosine	sphingosine-1-phosphate phosphatase 1	VMH	12815058
MMDBr0002138	LysoSM(d18:1)	Phosphorylcholine	sphingomyelin phosphodiesterase 2, neutral membrane (neutral sphingomyelinase)	VMH	12069827 9972865
MMDBr0002150	Sphingosine	Sphingosine 1-phosphate	sphingosine kinase 1	VMH	10751414
MMDBr0004343	Galactosylsphingosine	D-Galactose	galactosylceramidase	VMH	8281145
MMDBr0009102	Sphingosine	Sphingosine 1-phosphate	sphingosine kinase 2	VMH	30371894
MMDBr0009374	Sphingosine 1-phosphate	Sphingosine	lipin 1	VMH	30371894
MMDBr0009375	Sphingosine 1-phosphate	Sphingosine	phosphatidic acid phosphatase type 2A	VMH	30371894
MMDBr0009377	Sphingosine	Galactosylsphingosine	Not Available	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	7	Human stool; Human ; Human feces; Human saliva; Human mucosa; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	2	Human ; Human feces; Human sputum; Human saliva; Human supragingival plaque; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Seed	Punica granatum	FooDB	31437929
Plant	Fruit	Phaseolus vulgaris	FooDB	31437929
Plant	Fruit	Ficus carica	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.000038485		0.0000375	0.00003947	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	11339295
Human Blood	Detected and Quantified	0.050	0.0013			uM	Adult (>18 years old)	Both	Normal	HMDB	17085324
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Leukocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000252

DrugBank ID

DB03203

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005463

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00319

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sphingosine

METLIN ID

Not Available

PubChem Compound

5280335

PDB ID

Not Available

ChEBI ID

16393

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Khan WA, Mascarella SW, Lewin AH, Wyrick CD, Carroll FI, Hannun YA: Use of D-erythro-sphingosine as a pharmacological inhibitor of protein kinase C in human platelets. Biochem J. 1991 Sep 1;278 ( Pt 2):387-92. doi: 10.1042/bj2780387. [PubMed:1898331 ]
Wertz PW, Downing DT: Free sphingosine in human epidermis. J Invest Dermatol. 1990 Feb;94(2):159-61. doi: 10.1111/1523-1747.ep12874122. [PubMed:2299191 ]
Rusakov SA, Filippova GN, Pushkareva MIu, Korobko VG, Alesenko AV: [The effect of tumor necrosis factor on the free sphingosine level and sphingomyelinase in murine liver cells and nuclei]. Biokhimiia. 1993 May;58(5):724-32. [PubMed:8338884 ]
Wong K, Kwan-Yeung L: Sphingosine mobilizes intracellular calcium in human neutrophils. Cell Calcium. 1993 Jun;14(6):493-505. doi: 10.1016/0143-4160(93)90008-t. [PubMed:8358772 ]
Sweeney EA, Sakakura C, Shirahama T, Masamune A, Ohta H, Hakomori S, Igarashi Y: Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines. Int J Cancer. 1996 May 3;66(3):358-66. doi: 10.1002/(SICI)1097-0215(19960503)66:3<358::AID-IJC16>3.0.CO;2-7. [PubMed:8621258 ]
Cuvillier O, Pirianov G, Kleuser B, Vanek PG, Coso OA, Gutkind S, Spiegel S: Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature. 1996 Jun 27;381(6585):800-3. doi: 10.1038/381800a0. [PubMed:8657285 ]
Alessenko AV, Korobko VG, Khrenov AV, Rozhnova UA, Soloviev AS, Shingarova LN: Relation of biological activity of mutant forms of recombinant human tumor necrosis factor alpha and accumulation of sphingosine in murine liver. Biochem Mol Biol Int. 1997 Jun;42(1):143-54. doi: 10.1080/15216549700202521. [PubMed:9192094 ]
Hisano N, Yatomi Y, Fujino MA, Igarashi Y, Kume S, Ozaki Y: Quantification of sphingosine derivatives in human platelets: inducible formation of free sphingosine. J Biochem. 1998 Feb;123(2):263-8. doi: 10.1093/oxfordjournals.jbchem.a021931. [PubMed:9538201 ]
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. doi: 10.1016/s0278-6915(99)00113-1. [PubMed:10654591 ]
Shin Y, Daly JW, Choi OH: Diverse effects of sphingosine on calcium mobilization and influx in differentiated HL-60 cells. Cell Calcium. 2000 May;27(5):269-80. doi: 10.1054/ceca.2000.0118. [PubMed:10859593 ]
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. doi: 10.1016/s0041-0101(00)00235-x. [PubMed:11223085 ]
Qiu M, Liu X: Determination of sphinganine, sphingosine and Sa/So ratio in urine of humans exposed to dietary fumonisin B1. Food Addit Contam. 2001 Mar;18(3):263-9. doi: 10.1080/02652030117470. [PubMed:11304035 ]
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. doi: 10.1016/s0378-4347(01)00041-x. [PubMed:11339295 ]
Authors unspecified: Toxicology and carcinogenesis studies of fumonisin B1 (cas no. 116355-83-0) in F344/N rats and B6C3F1 mice (feed studies). Natl Toxicol Program Tech Rep Ser. 2001 Dec;(496):1-352. [PubMed:11852482 ]
Arikawa J, Ishibashi M, Kawashima M, Takagi Y, Ichikawa Y, Imokawa G: Decreased levels of sphingosine, a natural antimicrobial agent, may be associated with vulnerability of the stratum corneum from patients with atopic dermatitis to colonization by Staphylococcus aureus. J Invest Dermatol. 2002 Aug;119(2):433-9. doi: 10.1046/j.1523-1747.2002.01846.x. [PubMed:12190867 ]
Gorska M, Dobrzyn A, Baranowski M: Concentrations of sphingosine and sphinganine in plasma of patients with type 2 diabetes. Med Sci Monit. 2005 Jan;11(1):CR35-8. [PubMed:15614193 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Sphingosine (MMDBc0000780)

MOL for #<Metabolite:0x00007f46e022fb18>

3D MOL for #<Metabolite:0x00007f46e022fb18>

3D SDF for #<Metabolite:0x00007f46e022fb18>

3D-SDF for #<Metabolite:0x00007f46e022fb18>

PDB for #<Metabolite:0x00007f46e022fb18>

3D PDB for #<Metabolite:0x00007f46e022fb18>

SMILES for #<Metabolite:0x00007f46e022fb18>

INCHI for #<Metabolite:0x00007f46e022fb18>

Structure for #<Metabolite:0x00007f46e022fb18>

3D Structure for #<Metabolite:0x00007f46e022fb18>