Page last updated: 2024-11-07

b 581

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Description

B 581: blocks farnesylated but not geranylgeranylated or myristylated, oncogenic Ras signaling & transformation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

B 581 : A dipeptide obtained from the tetrapeptide Cys-Val-Phe-Met by reduction of the amide carbonyl groups of the Cys and Val residues. [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]

Cross-References

ID SourceID
PubMed CID132887
CHEMBL ID91722
CHEBI ID83620
SCHEMBL ID2723960
MeSH IDM0234135

Synonyms (51)

Synonym
CBIOL_001875 ,
CHEMBL91722 ,
chebi:83620 ,
(s-(r*,s*))-n-(n-(2-((2-amino-3-mercaptopropyl)amino)-3-methylbutyl)-l-phenylalanyl)-l-methionine
l-methionine, n-(n-(2-((2-amino-3-mercaptopropyl)amino)-3-methylbutyl)-l-phenylalanyl)-, (s-(r*,s*))-
BRD-K04877770-001-03-4
b 581
BIO2_000186
BIO1_001139
BIO2_000666
BIO1_000161
BIO1_000650
SMP2_000242
BSPBIO_001466
IDI1_033936
b581, >95% (hplc), solid
NCGC00163425-02
ftase inhibitor i
b581
NCGC00163425-01
n-[2(s)-[2(r)-amino-3-mercaptopropylamino]-3-methylbutyl]-phe-met-oh
KBIO2_000186
KBIO2_002754
KBIOGR_000186
KBIO3_000371
KBIOSS_000186
KBIO3_000372
KBIO2_005322
NCGC00163425-03
b-581
149759-96-6
HMS1989J08
HMS1361J08
HMS1791J08
bdbm50059852
(s)-2-{(s)-2-[(s)-2-((r)-2-amino-3-mercapto-propylamino)-3-methyl-butylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid
(s)-2-((s)-2-((s)-2-((r)-2-amino-3-mercaptopropylamino)-3-methylbutylamino)-3-phenylpropanamido)-4-(methylthio)butanoic acid
(2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropyl]amino]-3-methylbutyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
SCHEMBL2723960
n-[(2s)-2-{[(2r)-2-amino-3-sulfanylpropyl]amino}-3-methylbutyl]-l-phenylalanyl-l-methionine
HMS3402J08
DTXSID30164381
J-008620
n-[2(s)-[2(r)-amino-3-mercaptopropylamino]-3-methyl-butyl]-phe-met
Q27157026
(2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-azaniumyl-3-sulfanylpropyl]amino]-3-methylbutyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoate
l-methionine, n-[(2s)-2-[[(2r)-2-amino-3-mercaptopropyl]amino]-3-methylbutyl]-l-phenylalanyl-
HY-128044
CS-0095096
n-[(2s)-((2r)-2-amino-3-mercaptopropylamino)-3-methylbutyl]-l-phenylalanyl-l-methionine
AKOS040744436
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
peptidomimeticA small protein-like chain designed to mimic a peptide.
EC 2.5.1.58 (protein farnesyltransferase) inhibitorAn EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group.
[role 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]

Drug Classes (1)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
[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 (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency4.79570.004023.8416100.0000AID485290
TDP1 proteinHomo sapiens (human)Potency24.81150.000811.382244.6684AID686978
Microtubule-associated protein tauHomo sapiens (human)Potency21.45090.180013.557439.8107AID1460; AID1468
regulator of G-protein signaling 4Homo sapiens (human)Potency0.11920.531815.435837.6858AID504845
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency19.95260.035520.977089.1251AID504332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency22.19690.354828.065989.1251AID504847
[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)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)IC50 (µMol)0.02100.00050.28191.1000AID73110
Squalene synthaseHomo sapiens (human)IC50 (µMol)0.30000.07802.14788.0000AID73579
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)IC50 (µMol)50.00000.00050.471610.0000AID228842
Protein farnesyltransferase subunit betaBos taurus (cattle)IC50 (µMol)0.02100.00050.11831.1000AID73110
Protein farnesyltransferase subunit betaHomo sapiens (human)IC50 (µMol)50.00000.00050.21772.5000AID228842
Squalene synthase Bos taurus (cattle)IC50 (µMol)0.02100.02100.02100.0210AID72966
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
protein farnesylationProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)
protein geranylgeranylationProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)
steroid biosynthetic processSqualene synthaseHomo sapiens (human)
farnesyl diphosphate metabolic processSqualene synthaseHomo sapiens (human)
cholesterol biosynthetic processSqualene synthaseHomo sapiens (human)
transforming growth factor beta receptor signaling pathwayProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein farnesylationProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein geranylgeranylationProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
positive regulation of Rac protein signal transductionProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
skeletal muscle acetylcholine-gated channel clusteringProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
positive regulation of tubulin deacetylationProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
positive regulation of deacetylase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
positive regulation of skeletal muscle acetylcholine-gated channel clusteringProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
lipid metabolic processProtein farnesyltransferase subunit betaBos taurus (cattle)
protein farnesylationProtein farnesyltransferase subunit betaBos taurus (cattle)
lipid metabolic processProtein farnesyltransferase subunit betaHomo sapiens (human)
protein farnesylationProtein farnesyltransferase subunit betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
protein farnesyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)
protein geranylgeranyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)
farnesyltranstransferase activitySqualene synthaseHomo sapiens (human)
protein bindingSqualene synthaseHomo sapiens (human)
metal ion bindingSqualene synthaseHomo sapiens (human)
farnesyl-diphosphate farnesyltransferase activitySqualene synthaseHomo sapiens (human)
squalene synthase activitySqualene synthaseHomo sapiens (human)
protein farnesyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein farnesyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein geranylgeranyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
Rab geranylgeranyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein bindingProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
microtubule bindingProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
receptor tyrosine kinase bindingProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
alpha-tubulin bindingProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
molecular adaptor activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
CAAX-protein geranylgeranyltransferase activityProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein farnesyltransferase activityProtein farnesyltransferase subunit betaBos taurus (cattle)
zinc ion bindingProtein farnesyltransferase subunit betaBos taurus (cattle)
protein farnesyltransferase activityProtein farnesyltransferase subunit betaHomo sapiens (human)
protein farnesyltransferase activityProtein farnesyltransferase subunit betaHomo sapiens (human)
protein bindingProtein farnesyltransferase subunit betaHomo sapiens (human)
zinc ion bindingProtein farnesyltransferase subunit betaHomo sapiens (human)
farnesyltranstransferase activitySqualene synthase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
CAAX-protein geranylgeranyltransferase complexProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)
protein farnesyltransferase complexProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaBos taurus (cattle)
endoplasmic reticulumSqualene synthaseHomo sapiens (human)
endoplasmic reticulum membraneSqualene synthaseHomo sapiens (human)
membraneSqualene synthaseHomo sapiens (human)
endoplasmic reticulum membraneSqualene synthaseHomo sapiens (human)
cytosolProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
plasma membraneProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
CAAX-protein geranylgeranyltransferase complexProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
microtubule associated complexProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein farnesyltransferase complexProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
cytoplasmProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaHomo sapiens (human)
protein farnesyltransferase complexProtein farnesyltransferase subunit betaBos taurus (cattle)
cytosolProtein farnesyltransferase subunit betaHomo sapiens (human)
microtubule associated complexProtein farnesyltransferase subunit betaHomo sapiens (human)
protein farnesyltransferase complexProtein farnesyltransferase subunit betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID72966Compound was evaluated for concentration that caused 50% inhibition of bovine Farnesyltransferase1999Bioorganic & medicinal chemistry letters, Mar-22, Volume: 9, Issue:6
Novel reverse-turn mimics inhibit farnesyl transferase.
AID228842Inhibition of Ras processing in v-Ras-transformed cells1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Ras farnesyltransferase: a new therapeutic target.
AID282452Inhibition of Sprague-Dawley rat brain GGTI by continuous fluorescence assay2004Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27
Potent and selective farnesyl transferase inhibitors.
AID73579Compound was evaluated for concentration that caused 50% inhibition of yeast Farnesyltransferase (expressed as a GST fusion protein in Escherichia coli)1999Bioorganic & medicinal chemistry letters, Mar-22, Volume: 9, Issue:6
Novel reverse-turn mimics inhibit farnesyl transferase.
AID73110Inhibition of bovine Farnesyltransferase1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Ras farnesyltransferase: a new therapeutic target.
AID500998Inhibition of FTase in african green monkey COS7 cells assessed as protein prenylation at 100 uM by Western blot analysis2009Nature chemical biology, Apr, Volume: 5, Issue:4
Analysis of the eukaryotic prenylome by isoprenoid affinity tagging.
AID282451Inhibition of Sprague-Dawley rat brain FTase by continuous fluorescence assay2004Journal of medicinal chemistry, Dec-30, Volume: 47, Issue:27
Potent and selective farnesyl transferase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's8 (47.06)18.2507
2000's5 (29.41)29.6817
2010's2 (11.76)24.3611
2020's2 (11.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.19

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.19 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]