Page last updated: 2024-09-25

2-(n-myristoylamino)-1-phenyl-1-propanol

Description

2-(N-myristoylamino)-1-phenyl-1-propanol: ceramidase inhibitor; RN given for ((R*,S*)-(+-))-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID124735
CHEMBL ID429926
CHEBI ID93338
SCHEMBL ID611869
MeSH IDM0261565

Synonyms (53)

Synonym
CBIOL_001751
BRD-K76274772-001-02-7
BIO1_000037
BIO1_000526
BIO1_001015
BIO2_000128
BIO2_000608
BSPBIO_001408
NCGC00161371-01
NCGC00161371-02
d-erythro-mapp
KBIO2_005264
KBIO3_000255
KBIO2_002696
KBIOGR_000128
KBIOSS_000128
KBIO2_000128
KBIO3_000256
IDI1_033878
NCGC00161371-03
HMS1989G10
60847-25-8
BML3-E01
mapp, d-erythro
HMS1361G10
HMS1791G10
CHEMBL429926 ,
n-[(1s,2r)-1-hydroxy-1-phenylpropan-2-yl]tetradecanamide
143492-38-0
(1s,2r-d-erythro-2-n-myristoylamino)-1-phenyl-1-propanol
bdbm50392473
2-(n-myristoylamino)-1-phenyl-1-propanol
(r*,s*)-(+-)-n-(2-hydroxy-1-methyl-2-phenylethyl)tetradecanamide
tetradecanamide, n-(2-hydroxy-1-methyl-2-phenylethyl)-, (r*,s*)-(+-)-
SCHEMBL611869
d-erythro-2-tetradecanoylamino-1-phenyl-1-propanol
143492-39-1
HMS3648G09
HMS3402G10
gtpl8817
d-e-mapp
CHEBI:93338
J-007821
n-(1-hydroxy-1-phenylpropan-2-yl)tetradecanimidic acid
DTXSID00931906
Q27077017
sr-01000946211
SR-01000946211-1
MS-25732
n-((1s,2r)-1-hydroxy-1-phenylpropan-2-yl)tetradecanamide
CS-0138591
HY-137422
AKOS040755605

Drug Classes (1)

ClassDescription
alkylbenzeneA monocyclic arene that is benzene substituted with one or more alkyl groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency44.66840.011212.4002100.0000AID1030
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Acid ceramidaseHomo sapiens (human)IC50 (µMol)333.66670.02070.49251.0000AID1707269; AID1707270; AID691433
Alkaline ceramidase 2Homo sapiens (human)IC50 (µMol)1.00001.00001.00001.0000AID734964
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
fatty acid metabolic processAcid ceramidaseHomo sapiens (human)
keratinocyte differentiationAcid ceramidaseHomo sapiens (human)
sphingosine biosynthetic processAcid ceramidaseHomo sapiens (human)
ceramide biosynthetic processAcid ceramidaseHomo sapiens (human)
ceramide catabolic processAcid ceramidaseHomo sapiens (human)
regulation of steroid biosynthetic processAcid ceramidaseHomo sapiens (human)
regulation of programmed necrotic cell deathAcid ceramidaseHomo sapiens (human)
cellular response to tumor necrosis factorAcid ceramidaseHomo sapiens (human)
negative regulation of cell-matrix adhesionAlkaline ceramidase 2Homo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processAlkaline ceramidase 2Homo sapiens (human)
DNA damage responseAlkaline ceramidase 2Homo sapiens (human)
positive regulation of cell population proliferationAlkaline ceramidase 2Homo sapiens (human)
regulation of autophagyAlkaline ceramidase 2Homo sapiens (human)
sphingolipid catabolic processAlkaline ceramidase 2Homo sapiens (human)
DNA damage response, signal transduction by p53 class mediatorAlkaline ceramidase 2Homo sapiens (human)
response to retinoic acidAlkaline ceramidase 2Homo sapiens (human)
negative regulation of cell adhesion mediated by integrinAlkaline ceramidase 2Homo sapiens (human)
regulation of apoptotic processAlkaline ceramidase 2Homo sapiens (human)
sphingosine biosynthetic processAlkaline ceramidase 2Homo sapiens (human)
ceramide catabolic processAlkaline ceramidase 2Homo sapiens (human)
regulation of protein glycosylationAlkaline ceramidase 2Homo sapiens (human)
cellular response to xenobiotic stimulusAlkaline ceramidase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein bindingAcid ceramidaseHomo sapiens (human)
hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidesAcid ceramidaseHomo sapiens (human)
N-acylsphingosine amidohydrolase activityAcid ceramidaseHomo sapiens (human)
fatty acid amide hydrolase activityAcid ceramidaseHomo sapiens (human)
ceramidase activityAcid ceramidaseHomo sapiens (human)
N-acylsphingosine amidohydrolase activityAlkaline ceramidase 2Homo sapiens (human)
metal ion bindingAlkaline ceramidase 2Homo sapiens (human)
dihydroceramidase activityAlkaline ceramidase 2Homo sapiens (human)
ceramidase activityAlkaline ceramidase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
early endosomeAcid ceramidaseHomo sapiens (human)
endoplasmic reticulumAcid ceramidaseHomo sapiens (human)
extracellular regionAcid ceramidaseHomo sapiens (human)
extracellular spaceAcid ceramidaseHomo sapiens (human)
nucleusAcid ceramidaseHomo sapiens (human)
lysosomeAcid ceramidaseHomo sapiens (human)
lysosomal lumenAcid ceramidaseHomo sapiens (human)
extracellular exosomeAcid ceramidaseHomo sapiens (human)
tertiary granule lumenAcid ceramidaseHomo sapiens (human)
ficolin-1-rich granule lumenAcid ceramidaseHomo sapiens (human)
Golgi membraneAlkaline ceramidase 2Homo sapiens (human)
Golgi apparatusAlkaline ceramidase 2Homo sapiens (human)
Golgi membraneAlkaline ceramidase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID1707269Inhibition of acid ceramidase in human HL-60 cell lysates2020Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24
Design, Synthesis, and Biological Evaluation of a Series of Oxazolone Carboxamides as a Novel Class of Acid Ceramidase Inhibitors.
AID320186Decrease in endogenous sphingosine level in human MCF7 cells upto 50 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID1707270Inhibition of acid ceramidase in human HaCaT cell lysates2020Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24
Design, Synthesis, and Biological Evaluation of a Series of Oxazolone Carboxamides as a Novel Class of Acid Ceramidase Inhibitors.
AID320173Increase in endogenous ceramide level in human MCF7 cells at >25 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID691433Inhibition of aCDase expressed in human HL60 cell extract2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Novel amide- and sulfonamide-based aromatic ethanolamines: effects of various substituents on the inhibition of acid and neutral ceramidases.
AID320185Increase in endogenous C24:1-ceramide level in human MCF7 cells upto 5 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID691427Inhibition of recombinant human aCDase expressed in Sf9 cells using fluorescently-labeled acyl-NBD-C12-ceramide as substrate at 80 uM after 8 hrs by fluorescence assay2012Bioorganic & medicinal chemistry, Oct-15, Volume: 20, Issue:20
Novel amide- and sulfonamide-based aromatic ethanolamines: effects of various substituents on the inhibition of acid and neutral ceramidases.
AID320259Increase in endogenous C24-ceramide level in human MCF7 cells at 50 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID320174Decrease in endogenous sphingosine level in human MCF7 cells at >2.5 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID320188Decrease in endogenous C24-ceramide level in human MCF7 cells at 10 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID734977Inhibition of human recombinant neutral ceramidase using Acyl-NBD-C12-cer as substrate at 80 uM after 2 hrs by fluorescence assay2013Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4
Effective inhibition of acid and neutral ceramidases by novel B-13 and LCL-464 analogues.
AID734964Inhibition of alkaline ceramidase 2 in human HL-60 cells using 3H]C16-ceramide as substrate after 1 hr by liquid scintillation counting analysis2013Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4
Effective inhibition of acid and neutral ceramidases by novel B-13 and LCL-464 analogues.
AID320183Decrease in endogenous C24-ceramide level in human MCF7 cells upto 5 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID320184Decrease in endogenous sphingosine level in human MCF7 cells upto 5 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID734976Inhibition of human recombinant acid ceramidase using Acyl-NBD-C12-cer as substrate at 80 uM after 8 hrs by fluorescence assay2013Bioorganic & medicinal chemistry, Feb-15, Volume: 21, Issue:4
Effective inhibition of acid and neutral ceramidases by novel B-13 and LCL-464 analogues.
AID320182Decrease in endogenous C16-ceramide level in human MCF7 cells upto 5 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID320113Antiproliferative activity against human MCF7 cells after 48 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 1: synthesis and evaluation as potential anticancer agents.
AID320189Decrease in endogenous C24:1-ceramide level in human MCF7 cells at 10 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
AID320187Decrease in endogenous C16-ceramide level in human MCF7 cells at 10 uM after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (9.09)18.2507
2000's11 (50.00)29.6817
2010's6 (27.27)24.3611
2020's3 (13.64)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Dosage (1)

ArticleYear
Novel analogs of D-e-MAPP and B13. Part 2: signature effects on bioactive sphingolipids.
Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue: 2
2008
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]