Page last updated: 2024-12-04

perillic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

perillic acid: d-limonene metabolite; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1256
CHEMBL ID1373981
CHEBI ID36999
SCHEMBL ID465998
MeSH IDM0210866

Synonyms (60)

Synonym
NCI60_013759
LOPAC0_001001
nsc-641067
nsc641067
CHEBI:36999 ,
4-(1-methylethenyl)-1-cyclohexene-1-carboxylic acid
4-isopropenylcyclohex-1-enecarboxylic acid
EU-0101001
4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
1-cyclohexene-1-carboxylic acid, 4-(1-methylethenyl)-
4-isopropenylcyclohex-1-ene carboxylic acid
4-(2-propenyl)-1-cyclohexane-1-carboxylic acid
einecs 231-709-5
perillic acid
7694-45-3
NCGC00094295-03
NCGC00094295-02
NCGC00094295-04
(-)-perillic acid
NCGC00094295-01
LMPR0102090041
NCGC00015832-02
P 7083
4-isopropenyl-1-cyclohexene-1-carboxylic acid
1A4758DA-6365-4FD5-BAEA-16032D3488FF
NCGC00015832-06
FT-0693829
4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
HMS3263I03
AKOS006230667
CCG-205081
pks69du4zq ,
unii-pks69du4zq
1-cyclohexene-1-carboxylicacid, 4-(1-methylethenyl)-
NCGC00015832-04
NCGC00015832-03
NCGC00015832-05
LP01001
CDSMSBUVCWHORP-UHFFFAOYSA-N
tox21_501001
NCGC00261686-01
SCHEMBL465998
CHEMBL1373981
mfcd00062539
SR-01000076076-1
SR-01000076076-5
sr-01000076076
SR-01000076076-6
perillic acid [inci]
DTXSID60864105
perillicacid
FT-0771613
Q27104388
SDCCGSBI-0050974.P002
NCGC00015832-07
5-amino-1h-pyrazole-1,3-dicarboxylicacidethylmethylester
CS-0062325
HY-113471
(s)-4-(1-propen-2-yl)cyclohex-1-enecarboxylic acid
SY316382

Research Excerpts

Overview

Perillic acid is a terpenoid plant extract that has antiinfective and anticancer properties. It is extensively used in eastern medicine.

ExcerptReferenceRelevance
"Perillic acid is a terpenoid plant extract that has antiinfective and anticancer properties, and is extensively used in eastern medicine."( Interaction of salicylate and a terpenoid plant extract with model membranes: reconciling experiments and simulations.
Khandelia, H; Mouritsen, OG; Witzke, S, 2010
)
1.08

Treatment

In perillic acid treated animals, bone marrow cellularity was increased to 14.8 ± 1.8 × 106 cells/femur and α-esterase positive cells were 941 ± 56.5 /4000 cells. Levels of phosphorylated but not total MAPK were also decreased in a dose-dependent manner.

ExcerptReferenceRelevance
"In perillic acid treated animals, bone marrow cellularity was increased to 14.8 ± 1.8 × 106 cells/femur and α-esterase positive cells were 941 ± 56.5 /4000 cells, similar to normal level (935 ± 51.4/4000 cells)."( Protective role of perillic acid against radiation-induced oxidative stress, cytokine profile, DNA damage, and intestinal toxicity in mice.
Kuttan, G; Pratheeshkumar, P; Raphael, TJ, 2010
)
1.2
"In perillic acid-treated cells, the levels of phosphorylated but not total MAPK were also decreased in a dose-dependent manner."( Perillic acid inhibits Ras/MAP kinase-driven IL-2 production in human T lymphocytes.
Ansorge, S; Höllt, V; Reinhold, D; Schmidt, H; Schulz, S, 1997
)
2.25

Pharmacokinetics

ExcerptReferenceRelevance
" Day 15 DHPA Cmax values ranged from a mean +/- SD of 22."( Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies.
Adams, A; Gallo, JM; Halberr, T; Hudes, GR; Langer, CJ; Litwin, S; McCauley, RA; Qian, M; Ranganathan, S; Szarka, CE; Weiner, LM; Yeslow, G, 2000
)
0.31

Dosage Studied

ExcerptRelevanceReference
" three times daily is well tolerated on a 14-day on/14-day off dosing schedule."( Phase I pharmacokinetic trial of perillyl alcohol (NSC 641066) in patients with refractory solid malignancies.
Adams, A; Gallo, JM; Halberr, T; Hudes, GR; Langer, CJ; Litwin, S; McCauley, RA; Qian, M; Ranganathan, S; Szarka, CE; Weiner, LM; Yeslow, G, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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 (2)

ClassDescription
cyclohexenecarboxylic acid
alpha,beta-unsaturated monocarboxylic acidA monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond.
[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]

Pathways (1)

PathwayProteinsCompounds
Limonene and Pinene Degradation210

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency1.33710.100020.879379.4328AID588453
USP1 protein, partialHomo sapiens (human)Potency44.66840.031637.5844354.8130AID504865
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency25.11890.28189.721235.4813AID2326
arylsulfatase AHomo sapiens (human)Potency37.93301.069113.955137.9330AID720538
lamin isoform A-delta10Homo sapiens (human)Potency0.00450.891312.067628.1838AID1487
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings 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.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
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.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (55)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (16.36)18.2507
2000's15 (27.27)29.6817
2010's20 (36.36)24.3611
2020's11 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.99

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 Index28.99 (24.57)
Research Supply Index4.08 (2.92)
Research Growth Index4.72 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (3.57%)5.53%
Reviews2 (3.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other52 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]