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Showing Compound dihydrosphingosine (FDB030824)

Record Information
Version1.0
Creation date2015-05-07 20:12:42 UTC
Update date2019-11-26 03:21:54 UTC
Primary IDFDB030824
Secondary Accession Numbers
  • FDB021924
Chemical Information
FooDB Namedihydrosphingosine
DescriptionSphinganine, also known as c18-dihydrosphingosine or safingol, is a member of the class of compounds known as 1,2-aminoalcohols. 1,2-aminoalcohols 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 practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Sphinganine can be found in a number of food items such as agar, biscuit, herbs and spices, and pasta, which makes sphinganine a potential biomarker for the consumption of these food products. Sphinganine can be found primarily in blood, feces, and urine, as well as throughout most human tissues. Sphinganine exists in all eukaryotes, ranging from yeast to humans. In humans, sphinganine is involved in few metabolic pathways, which include globoid cell leukodystrophy, metachromatic leukodystrophy (MLD), and sphingolipid metabolism. Sphinganine is also involved in few metabolic disorders, which include fabry disease, gaucher disease, and krabbe disease. Moreover, sphinganine is found to be associated with pregnancy. Sphinganine is a lyso-sphingolipid protein kinase inhibitor. It has the molecular formula C18H39NO2 and is a colorless solid. Medicinally, safingol has demonstrated promising anticancer potential as a modulator of multi-drug resistance and as an inducer of necrosis. The administration of safingol alone has not been shown to exert a significant effect on tumor cell growth. However, preclinical and clinical studies have shown that combining safingol with conventional chemotherapy agents such as fenretinide, vinblastine, irinotecan and mitomycin C can dramatically potentiate their antitumor effects. Currently in Phase I clinical trials, it is believed to be safe to co-administer with cisplatin .
CAS Number764-22-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
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
Polarizability40.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H39NO2
IUPAC name(2S,3R)-2-aminooctadecane-1,3-diol
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO
Average Molecular Weight301.5078
Monoisotopic Molecular Weight301.298079497
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.
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 effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSphinganine, 3 TMS, GC-MS Spectrumsplash10-0udi-3980100000-87c0074f611dec416856Spectrum
GC-MSSphinganine, 3 TMS, GC-MS Spectrumsplash10-0udi-1690000000-8fed2f980c631302b97bSpectrum
GC-MSSphinganine, non-derivatized, GC-MS Spectrumsplash10-0udi-3980100000-87c0074f611dec416856Spectrum
GC-MSSphinganine, non-derivatized, GC-MS Spectrumsplash10-0udi-1690000000-8fed2f980c631302b97bSpectrum
Predicted GC-MSSphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-9120000000-0cfd71520376dffc3c78Spectrum
Predicted GC-MSSphinganine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uk9-4490200000-f4c4281643554b83dd43Spectrum
Predicted GC-MSSphinganine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSphinganine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0iml-3791000000-013fe5eb404ccb2873852012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-04469479cb6d836030932012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0bt9-9000000000-4f682b26d6efc16731412012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0009000000-4d5daf40edf51d7c5ce42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0f89-2196000000-86bd4d9593c5a53dfc942012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-01qa-9130000000-819bc3df8d7408799b9f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03xr-9000000000-0b47410c79f07946095a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03xr-9000000000-6dd6eb4c242974e7f7cc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ab9-3892000000-6d8fa67090a1cebaa6f32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0159-0092000000-6e15bf1516b938239cb52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0009000000-4d5daf40edf51d7c5ce42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f89-2196000000-86bd4d9593c5a53dfc942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01qa-9130000000-819bc3df8d7408799b9f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-9000000000-3157cbca45e3dce158e42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03xr-9000000000-6dd6eb4c242974e7f7cc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-2390000000-a002411e49400899cf3c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0gx0-5096000000-ad6ab79ab16fab02d6932021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9000000000-5afe9071156e7abc48f22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Negativesplash10-0159-0092000000-9c001535e8080ffe05e22021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-0092000000-4cad101913d628c296ba2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-2290000000-e693ddcd90fd9234c6692016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-9740000000-808c9a702fe97ec9078e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1089000000-00c77e7cc5d9f3475be72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-115c-5091000000-dc391e96a566caaa06022016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-a74567f0d047f0915ffc2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference