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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000269
Secondary Accession Numbers
  • HMDB00269
Metabolite Identification
Common NameSphinganine
DescriptionSphinganine 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 through its interaction with the enzyme 3-ketodihydrosphingosine reductase. In addition, sphinganine can be converted into sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine kinase 2. Outside of the human body, sphinganine has been detected, but not quantified in, several different foods, such as Mexican oregano, jostaberries, winter squash, angelica, and epazotes. This could make sphinganine a potential biomarker for the consumption of these foods. Sphinganine blocks postlysosomal cholesterol transport by inhibiting low-density lipoprotein-induced esterification of cholesterol and causing unesterified cholesterol to accumulate in perinuclear vesicles. It has been suggested that endogenous sphinganine may inhibit cholesterol transport in Niemann-Pick Type C (NPC) disease (PMID: 1817037 ).
Structure
Data?1582752119
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
Erythro-D-sphinganineHMDB
2-Aminooctadecane-1,3-diolHMDB
Threo-dihydrosphingosineHMDB
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
(2S,3R)-SphinganineHMDB
D-Erythro-dihydrosphingosineHMDB
SP(D18:0)HMDB
SphinganineHMDB
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
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.
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
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos188.00230932474
[M+H]+Not Available188.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000533
Predicted Molecular 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
Polarizability40.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.8931661259
DarkChem[M-H]-178.21631661259
AllCCS[M+H]+187.7832859911
AllCCS[M-H]-181.74132859911
DeepCCS[M+H]+186.72430932474
DeepCCS[M-H]-184.17330932474
DeepCCS[M-2H]-217.65930932474
DeepCCS[M+Na]+194.28130932474
AllCCS[M+H]+187.832859911
AllCCS[M+H-H2O]+185.032859911
AllCCS[M+NH4]+190.432859911
AllCCS[M+Na]+191.132859911
AllCCS[M-H]-181.732859911
AllCCS[M+Na-2H]-182.832859911
AllCCS[M+HCOO]-184.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SphinganineCCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO3334.4Standard polar33892256
SphinganineCCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO2465.1Standard non polar33892256
SphinganineCCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO2494.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sphinganine,1TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@@H](N)CO2451.1Semi standard non polar33892256
Sphinganine,1TMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO[Si](C)(C)C2450.2Semi standard non polar33892256
Sphinganine,1TMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N[Si](C)(C)C2521.2Semi standard non polar33892256
Sphinganine,2TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@@H](N)CO[Si](C)(C)C2505.8Semi standard non polar33892256
Sphinganine,2TMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)N[Si](C)(C)C2548.6Semi standard non polar33892256
Sphinganine,2TMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2538.8Semi standard non polar33892256
Sphinganine,2TMS,isomer #4CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2669.9Semi standard non polar33892256
Sphinganine,3TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2568.5Semi standard non polar33892256
Sphinganine,3TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2647.3Standard non polar33892256
Sphinganine,3TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N[Si](C)(C)C2524.8Standard polar33892256
Sphinganine,3TMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2769.6Semi standard non polar33892256
Sphinganine,3TMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2680.2Standard non polar33892256
Sphinganine,3TMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)N([Si](C)(C)C)[Si](C)(C)C2625.0Standard polar33892256
Sphinganine,3TMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2755.7Semi standard non polar33892256
Sphinganine,3TMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2717.1Standard non polar33892256
Sphinganine,3TMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2713.9Standard polar33892256
Sphinganine,4TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2825.5Semi standard non polar33892256
Sphinganine,4TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2735.7Standard non polar33892256
Sphinganine,4TMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2471.7Standard polar33892256
Sphinganine,1TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)CO2685.6Semi standard non polar33892256
Sphinganine,1TBDMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO[Si](C)(C)C(C)(C)C2688.5Semi standard non polar33892256
Sphinganine,1TBDMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N[Si](C)(C)C(C)(C)C2763.6Semi standard non polar33892256
Sphinganine,2TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)CO[Si](C)(C)C(C)(C)C2956.5Semi standard non polar33892256
Sphinganine,2TBDMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N[Si](C)(C)C(C)(C)C3015.0Semi standard non polar33892256
Sphinganine,2TBDMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2983.5Semi standard non polar33892256
Sphinganine,2TBDMS,isomer #4CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3111.9Semi standard non polar33892256
Sphinganine,3TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3244.7Semi standard non polar33892256
Sphinganine,3TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C3156.5Standard non polar33892256
Sphinganine,3TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C2889.1Standard polar33892256
Sphinganine,3TBDMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3404.5Semi standard non polar33892256
Sphinganine,3TBDMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3180.3Standard non polar33892256
Sphinganine,3TBDMS,isomer #2CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2909.7Standard polar33892256
Sphinganine,3TBDMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3392.1Semi standard non polar33892256
Sphinganine,3TBDMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3200.2Standard non polar33892256
Sphinganine,3TBDMS,isomer #3CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2983.4Standard polar33892256
Sphinganine,4TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3656.7Semi standard non polar33892256
Sphinganine,4TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3346.7Standard non polar33892256
Sphinganine,4TBDMS,isomer #1CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2886.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sphinganine GC-MS (3 TMS)splash10-0udi-3980100000-87c0074f611dec4168562014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sphinganine GC-MS (3 TMS)splash10-0udi-1690000000-8fed2f980c631302b97b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sphinganine GC-MS (Non-derivatized)splash10-0udi-3980100000-87c0074f611dec4168562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sphinganine GC-MS (Non-derivatized)splash10-0udi-1690000000-8fed2f980c631302b97b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9120000000-0cfd71520376dffc3c782016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (2 TMS) - 70eV, Positivesplash10-0uk9-4490200000-f4c4281643554b83dd432017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sphinganine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-ITFT , negative-QTOFsplash10-0159-0092000000-6e15bf1516b938239cb52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 25V, Negative-QTOFsplash10-0159-0092000000-9c001535e8080ffe05e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0iml-3791000000-013fe5eb404ccb2873852012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03di-9000000000-04469479cb6d836030932012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0bt9-9000000000-4f682b26d6efc16731412012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0udi-0009000000-4d5daf40edf51d7c5ce42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0f89-2196000000-86bd4d9593c5a53dfc942012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-01qa-9130000000-819bc3df8d7408799b9f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-03xr-9000000000-0b47410c79f07946095a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-03xr-9000000000-6dd6eb4c242974e7f7cc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-qTof , Positive-QTOFsplash10-0ab9-3892000000-6d8fa67090a1cebaa6f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ , positive-QTOFsplash10-0udi-0009000000-4d5daf40edf51d7c5ce42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ , positive-QTOFsplash10-0f89-2196000000-86bd4d9593c5a53dfc942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ , positive-QTOFsplash10-01qa-9130000000-819bc3df8d7408799b9f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ , positive-QTOFsplash10-03xr-9000000000-3157cbca45e3dce158e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine LC-ESI-QQ , positive-QTOFsplash10-03xr-9000000000-6dd6eb4c242974e7f7cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine , positive-QTOFsplash10-0udi-2390000000-a002411e49400899cf3c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 10V, Positive-QTOFsplash10-0gx0-5096000000-ad6ab79ab16fab02d6932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 40V, Positive-QTOFsplash10-08fr-9000000000-5afe9071156e7abc48f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 20V, Positive-QTOFsplash10-03e9-9040000000-8a6a0ab6b7747fee43d62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 40V, Positive-QTOFsplash10-08fr-9000000000-666ced30bce6b3bc18192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 20V, Positive-QTOFsplash10-03e9-9030000000-2256d1f455c1953799fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 20V, Positive-QTOFsplash10-0f89-4095000000-742eb2c9ed03a93559fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 35V, Positive-QTOFsplash10-08gi-4590000000-6dc187f1b434d586c78f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sphinganine 20V, Positive-QTOFsplash10-0f89-4096000000-3411dcd7c276cabc4ff92021-09-20HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Placenta
  • Platelet
  • Spleen
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 +/- 0.00033 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  4. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030824
KNApSAcK IDC00007540
Chemspider ID82609
KEGG Compound IDC00836
BioCyc IDCPD-13612
BiGG IDNot Available
Wikipedia LinkSafingol
METLIN IDNot Available
PubChem Compound91486
PDB IDNot Available
ChEBI ID16566
Food Biomarker OntologyNot Available
VMH IDSPHGN
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  17. 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 ]

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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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.