Compounds > 3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propylnaphthalene-1-carboxylic acid
Page last updated: 2024-11-12

3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propylnaphthalene-1-carboxylic acid

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Description

3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propylnaphthalene-1-carboxylic acid: inhibits lactate dehydrogenase A [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10498042
CHEMBL ID126519
SCHEMBL ID233361
MeSH IDM0544051

Synonyms (18)

Synonym
7-benzyl-2,3-dihydroxy-6-methyl-4-propyl-naphthalene-1-carboxylic acid
CHEMBL126519 ,
3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propylnaphthalene-1-carboxylic acid
bdbm50066974
ldha inhibitor, 3
NCGC00249596-01
SCHEMBL233361
fx 11
fx11
2,3-dihydroxy-6-methyl-7-(phenylmethyl)-4-propyl-1-naphthalenecarboxylic acid
213971-34-7
fx-11
HY-16214
CS-0006190
ldha inhibitor fx11
7-benzyl-2,3-dihydroxy-6-methyl-4-propylnaphthalene-1-carboxylic acid
MS-25412
AKOS040741776
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
L-lactate dehydrogenase A chainHomo sapiens (human)Ki4.08750.05003.76508.5000AID1267459; AID1276043; AID586286; AID99234
L-lactate dehydrogenase B chainHomo sapiens (human)Ki0.68330.05000.77001.4000AID1276044; AID99238; AID99239
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
lactate metabolic processL-lactate dehydrogenase A chainHomo sapiens (human)
pyruvate metabolic processL-lactate dehydrogenase A chainHomo sapiens (human)
glycolytic processL-lactate dehydrogenase A chainHomo sapiens (human)
lactate metabolic processL-lactate dehydrogenase B chainHomo sapiens (human)
pyruvate metabolic processL-lactate dehydrogenase B chainHomo sapiens (human)
NAD metabolic processL-lactate dehydrogenase B chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
L-lactate dehydrogenase activityL-lactate dehydrogenase A chainHomo sapiens (human)
protein bindingL-lactate dehydrogenase A chainHomo sapiens (human)
identical protein bindingL-lactate dehydrogenase A chainHomo sapiens (human)
cadherin bindingL-lactate dehydrogenase A chainHomo sapiens (human)
L-lactate dehydrogenase activityL-lactate dehydrogenase B chainHomo sapiens (human)
protein bindingL-lactate dehydrogenase B chainHomo sapiens (human)
kinase bindingL-lactate dehydrogenase B chainHomo sapiens (human)
identical protein bindingL-lactate dehydrogenase B chainHomo sapiens (human)
NAD bindingL-lactate dehydrogenase B chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
nucleusL-lactate dehydrogenase A chainHomo sapiens (human)
cytosolL-lactate dehydrogenase A chainHomo sapiens (human)
membraneL-lactate dehydrogenase A chainHomo sapiens (human)
extracellular exosomeL-lactate dehydrogenase A chainHomo sapiens (human)
oxidoreductase complexL-lactate dehydrogenase A chainHomo sapiens (human)
mitochondrionL-lactate dehydrogenase A chainHomo sapiens (human)
cytoplasmL-lactate dehydrogenase B chainHomo sapiens (human)
mitochondrial inner membraneL-lactate dehydrogenase B chainHomo sapiens (human)
cytosolL-lactate dehydrogenase B chainHomo sapiens (human)
membraneL-lactate dehydrogenase B chainHomo sapiens (human)
membrane raftL-lactate dehydrogenase B chainHomo sapiens (human)
extracellular exosomeL-lactate dehydrogenase B chainHomo sapiens (human)
oxidoreductase complexL-lactate dehydrogenase B chainHomo sapiens (human)
mitochondrionL-lactate dehydrogenase B chainHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID671898Inhibition of full length human recombinant LDHA expressed in Escherichia coli BL21 (DE3) cells after 10 mins by spectrophotometric analysis2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Design and synthesis of novel lactate dehydrogenase A inhibitors by fragment-based lead generation.
AID724991Inhibition of LDH-A (unknown origin) in presence of 0.1% Triton2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Fragment growing and linking lead to novel nanomolar lactate dehydrogenase inhibitors.
AID626398Inhibition of human LDH52011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
N-Hydroxyindole-based inhibitors of lactate dehydrogenase against cancer cell proliferation.
AID724990Inhibition of LDH-A (unknown origin) in absence of 0.1% Triton2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Fragment growing and linking lead to novel nanomolar lactate dehydrogenase inhibitors.
AID671899Inhibition of human recombinant LDHB (2 to 334 amino acid residue) expressed in Escherichia coli BL21 (DE3) cells after 10 mins by spectrophotometric analysis2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Design and synthesis of novel lactate dehydrogenase A inhibitors by fragment-based lead generation.
AID99234inhibitory activity against Plasmodium falciparum LDH (pLDH)1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
Selective inhibitors of human lactate dehydrogenases and lactate dehydrogenase from the malarial parasite Plasmodium falciparum.
AID626399Selectivity for human LDH5 over human LDH12011European journal of medicinal chemistry, Nov, Volume: 46, Issue:11
N-Hydroxyindole-based inhibitors of lactate dehydrogenase against cancer cell proliferation.
AID1276043Competitive inhibition of human LDH5 in presence of NADH2016Journal of medicinal chemistry, Jan-28, Volume: 59, Issue:2
Recent Update on Human Lactate Dehydrogenase Enzyme 5 (hLDH5) Inhibitors: A Promising Approach for Cancer Chemotherapy.
AID1267459Inhibition of human LDHA using pyruvate as substrate assessed as disappearance of NADH2016Bioorganic & medicinal chemistry letters, Jan-01, Volume: 26, Issue:1
Identification of a potent inhibitor targeting human lactate dehydrogenase A and its metabolic modulation for cancer cell line.
AID99238inhibitory activity against Human Lactate Dehydrogenase (LDH-H)1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
Selective inhibitors of human lactate dehydrogenases and lactate dehydrogenase from the malarial parasite Plasmodium falciparum.
AID99239inhibitory activity against Human Lactate Dehydrogenase (LDH-M)1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
Selective inhibitors of human lactate dehydrogenases and lactate dehydrogenase from the malarial parasite Plasmodium falciparum.
AID1276044Competitive inhibition of human LDH1 in presence of NADH2016Journal of medicinal chemistry, Jan-28, Volume: 59, Issue:2
Recent Update on Human Lactate Dehydrogenase Enzyme 5 (hLDH5) Inhibitors: A Promising Approach for Cancer Chemotherapy.
AID586286Inhibition of human LDH-A using pyruvate as substrate and NADH as cofactor at 125 uM after 5 mins by calorimetric assay relative to control2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells.
AID632023Inhibition of human Lactate dehydrogenase isoform 52011Bioorganic & medicinal chemistry letters, Dec-15, Volume: 21, Issue:24
Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5.
AID1799697Enzyme Assay from Article 10.1021/jm201734r: \\Design and synthesis of novel lactate dehydrogenase a inhibitors by fragment-based lead generation.\\2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Design and synthesis of novel lactate dehydrogenase A inhibitors by fragment-based lead generation.
[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's1 (5.88)18.2507
2000's0 (0.00)29.6817
2010's15 (88.24)24.3611
2020's1 (5.88)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.27

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 Index18.27 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.97 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.27)

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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
lactic acid
Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.		2.59202-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
malonic acid
malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.		2.0710alpha,omega-dicarboxylic acidhuman metabolite
oxamic acid
Oxamic Acid: Amino-substituted glyoxylic acid derivative.. oxamic acid : A dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia.		4.1140dicarboxylic acid monoamideEscherichia coli metabolite
pyruvic acid
Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.		2.11102-oxo monocarboxylic acidcofactor;
fundamental metabolite
gossypol
Gossypol: A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.		3.2310
adenosine monophosphate
Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.		2.0710adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
1-hydroxy-2-naphthoic acid
1-hydroxy-2-naphthoic acid: RN given refers to parent cpd. 1-hydroxy-2-naphthoic acid : A naphthoic acid with the carboxy group at position 2 and carrying a hydroxy substituent at the 1-position. It is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.		2.0710hydroxy monocarboxylic acid;
naphthoic acid;
naphthols		bacterial xenobiotic metabolite;
fungal xenobiotic metabolite
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0510acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
fluorodeoxyglucose f18
Fluorodeoxyglucose F18: The compound is given by intravenous injection to do POSITRON-EMISSION TOMOGRAPHY for the assessment of cerebral and myocardial glucose metabolism in various physiological or pathological states including stroke and myocardial ischemia. It is also employed for the detection of malignant tumors including those of the brain, liver, and thyroid gland. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1162)		2.11102-deoxy-2-((18)F)fluoro-D-glucose;
2-deoxy-2-fluoro-aldehydo-D-glucose
gossylic nitrile-1,1'-diacetate
gossylic nitrile-1,1'-diacetate: inhibits human immunodeficiency virus Type I replication; structure given in first source		3.2310
casein kinase ii
Casein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.		2.1710
fk 866
N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide: inhibits nicotinamide phosphoribosyltransferase; structure in first source		2.3110benzamides;
N-acylpiperidine
adenosine monophosphate
adenosine 5'-monophosphate(2-) : A nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of adenosine 5'-monophosphate (AMP).		2.0710nucleoside 5'-monophosphate(2-)cofactor;
fundamental metabolite;
human metabolite
piperidines
Piperidines: A family of hexahydropyridines.		2.3110
gossylic iminolactone
gossylic iminolactone: inhibits human immunodeficiency virus type I replication; structure given in first source		3.2310
gossylic lactone
gossylic lactone: inhibits human immunodeficiency virus type I replication; structure given in first source		3.2310
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		03.0410
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.0410
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		02.3110
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		02.3110
Cancer of Colon
[description not available]		02.1710
Colonic Neoplasms
Tumors or cancer of the COLON.		02.1710
Disease Exacerbation
[description not available]		02.8530
Androgen-Independent Prostatic Cancer
[description not available]		02.2110
Prostatic Neoplasms, Castration-Resistant
Tumors or cancer of the PROSTATE which can grow in the presence of low or residual amount of androgen hormones such as TESTOSTERONE.		02.2110
Innate Inflammatory Response
[description not available]		02.2110
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.2110
Cancer of Pancreas
[description not available]		02.1110
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.1110
Osteogenic Sarcoma
[description not available]		02.1310
Invasiveness, Neoplasm
[description not available]		02.1310
Osteosarcoma
A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)		02.1310
Cell Transformation, Neoplastic
Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.		02.1510
Hepatocellular Carcinoma
[description not available]		02.1510
Cancer of Liver
[description not available]		02.1510
Metastase
[description not available]		02.1510
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.1510
Liver Neoplasms
Tumors or cancer of the LIVER.		02.1510
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.1510
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.1510
Experimental Neoplasms
[description not available]		02.0510