Compounds > ceanothic acid
Page last updated: 2024-11-08

ceanothic acid

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

Description

ceanothic acid: isolated from Ceanothus americanus; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
CeanothusgenusA plant genus of the family RHAMNACEAE. Root nodules host the Frankia (ACTINOMYCETES) nitrogen-fixing bacteria.[MeSH]RhamnaceaeThe buckthorn plant family, of the order Rhamnales, includes some species with edible fruits and some that are medicinal.[MeSH]

Cross-References

ID SourceID
PubMed CID161352
CHEMBL ID491069
SCHEMBL ID965383
MeSH IDM0280693

Synonyms (19)

Synonym
ceanothic acid
CHEMBL491069 ,
21302-79-4
a(1)-norlup-20(29)-en-28-oic acid, 2-carboxy-3-hydroxy-, (2alpha,3beta)-
38p86zu018 ,
unii-38p86zu018
bdbm50377959
2-hydroxy-3,3,5a,5b,12b-pentamethyl-10-(prop-1-en-2-yl)octadecahydrodicyclopenta[a,i]phenanthrene-1,7a(1h)-dicarboxylic acid
ceanothic acid [mi]
3'h-cyclopenta(3,4)-18-norandrost-3-ene-3',13-dicarboxylic acid, tetrahydro-4'-hydroxy-4,5',5',9-tetramethyl-15-(1-methylethenyl)-, (3.beta.,3'.beta.,4.alpha.,4'.alpha.,5.beta.,8.alpha.,9.beta.,10.alpha.,13.alpha.,14.beta.,15.beta.)-
2.alpha.-carboxy-3.beta.-hydroxy-a(1)-norlup-20(29)-en-28-oic acid
SCHEMBL965383
(1r,2r,5s,8r,9r,10r,13r,14r,15r,16s,18r)-16-hydroxy-1,2,14,17,17-pentamethyl-8-prop-1-en-2-ylpentacyclo[11.7.0.02,10.05,9.014,18]icosane-5,15-dicarboxylic acid
DTXSID20943809
CS-0023840
HY-N3558
Q27256803
MS-29047
AKOS040760316
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Zinc finger protein GLI1Homo sapiens (human)IC50 (µMol)200.00000.62002.54507.1000AID389502
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIZinc finger protein GLI1Homo sapiens (human)
osteoblast differentiationZinc finger protein GLI1Homo sapiens (human)
regulation of DNA-templated transcriptionZinc finger protein GLI1Homo sapiens (human)
smoothened signaling pathwayZinc finger protein GLI1Homo sapiens (human)
spermatid developmentZinc finger protein GLI1Homo sapiens (human)
ventral midline developmentZinc finger protein GLI1Homo sapiens (human)
positive regulation of cell population proliferationZinc finger protein GLI1Homo sapiens (human)
regulation of smoothened signaling pathwayZinc finger protein GLI1Homo sapiens (human)
response to woundingZinc finger protein GLI1Homo sapiens (human)
epidermal cell differentiationZinc finger protein GLI1Homo sapiens (human)
dorsal/ventral pattern formationZinc finger protein GLI1Homo sapiens (human)
proximal/distal pattern formationZinc finger protein GLI1Homo sapiens (human)
cerebellar cortex morphogenesisZinc finger protein GLI1Homo sapiens (human)
pituitary gland developmentZinc finger protein GLI1Homo sapiens (human)
lung developmentZinc finger protein GLI1Homo sapiens (human)
prostate gland developmentZinc finger protein GLI1Homo sapiens (human)
regulation of osteoblast differentiationZinc finger protein GLI1Homo sapiens (human)
positive regulation of DNA replicationZinc finger protein GLI1Homo sapiens (human)
positive regulation of smoothened signaling pathwayZinc finger protein GLI1Homo sapiens (human)
positive regulation of DNA-templated transcriptionZinc finger protein GLI1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIZinc finger protein GLI1Homo sapiens (human)
digestive tract morphogenesisZinc finger protein GLI1Homo sapiens (human)
notochord regressionZinc finger protein GLI1Homo sapiens (human)
positive regulation of cardiac muscle cell proliferationZinc finger protein GLI1Homo sapiens (human)
negative regulation of canonical Wnt signaling pathwayZinc finger protein GLI1Homo sapiens (human)
liver regenerationZinc finger protein GLI1Homo sapiens (human)
positive regulation of cell cycle G1/S phase transitionZinc finger protein GLI1Homo sapiens (human)
regulation of hepatocyte proliferationZinc finger protein GLI1Homo sapiens (human)
regulation of transcription by RNA polymerase IIZinc finger protein GLI1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingZinc finger protein GLI1Homo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingZinc finger protein GLI1Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificZinc finger protein GLI1Homo sapiens (human)
DNA bindingZinc finger protein GLI1Homo sapiens (human)
chromatin bindingZinc finger protein GLI1Homo sapiens (human)
protein bindingZinc finger protein GLI1Homo sapiens (human)
microtubule bindingZinc finger protein GLI1Homo sapiens (human)
metal ion bindingZinc finger protein GLI1Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificZinc finger protein GLI1Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingZinc finger protein GLI1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
cytoplasmZinc finger protein GLI1Homo sapiens (human)
nucleusZinc finger protein GLI1Homo sapiens (human)
nucleoplasmZinc finger protein GLI1Homo sapiens (human)
cytoplasmZinc finger protein GLI1Homo sapiens (human)
cytosolZinc finger protein GLI1Homo sapiens (human)
axonemeZinc finger protein GLI1Homo sapiens (human)
ciliary tipZinc finger protein GLI1Homo sapiens (human)
ciliary baseZinc finger protein GLI1Homo sapiens (human)
GLI-SUFU complexZinc finger protein GLI1Homo sapiens (human)
nucleusZinc finger protein GLI1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID691425Antibacterial activity against Staphylococcus aureus2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana.
AID389503Cytotoxicity against human PANC1 after 24 hrs by fluorometric microculture cytotoxicity assay2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.
AID371947Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as EA induction at 10 molar ratio after 48 hrs relative to TPA2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID691424Cytotoxicity against human HeLa cells2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana.
AID371951Cytotoxicity against human Raji cells assessed as cell viability at 100 molar ratio after 48 hrs by trypan blue staining method2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID371950Cytotoxicity against human Raji cells assessed as cell viability at 500 molar ratio after 48 hrs by trypan blue staining method2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID1328431Cytotoxicity against human HepG2 cells assessed as reduction in cell viability measured after 48 hrs by MTT assay2016Journal of natural products, 09-23, Volume: 79, Issue:9
Cytotoxic Ceanothane- and Lupane-Type Triterpenoids from the Roots of Ziziphus jujuba.
AID371948Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as EA induction after 48 hrs relative to TPA2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID389502Inhibition of GLI1-mediated transcriptional activity in human HaCaT cells by luciferase based reporter gene assay2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.
AID371952Cytotoxicity against human Raji cells assessed as cell viability at 10 molar ratio after 48 hrs by trypan blue staining method2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID402784Cytotoxicity against human HeLa cells assessed as cell survival after 48 hrs by MTT assay relative to control1998Journal of natural products, Nov, Volume: 61, Issue:11
Preparation and cytotoxic effect of ceanothic acid derivatives.
AID402785Cytotoxicity against human FS5 cells assessed as cell survival after 48 hrs by MTT assay relative to control1998Journal of natural products, Nov, Volume: 61, Issue:11
Preparation and cytotoxic effect of ceanothic acid derivatives.
AID389505Cytotoxicity against mouse C3H10T1/2 cells after 24 hrs by fluorometric microculture cytotoxicity assay2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.
AID691426Antifungal activity against Candida albicans2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana.
AID371944Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as EA induction at 1000 molar ratio after 48 hrs relative to TPA2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID389512Cytotoxicity against human PANC1 at 100 uM after 24 hrs by fluorometric microculture cytotoxicity assay2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.
AID371945Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as EA induction at 500 molar ratio after 48 hrs relative to TPA2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID389513Cytotoxicity against human DU145 cells at 100 uM after 24 hrs by fluorometric microculture cytotoxicity assay2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.
AID389504Cytotoxicity against human DU145 cells after 24 hrs by fluorometric microculture cytotoxicity assay2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.
AID402783Cytotoxicity against human OVCAR-3 cells assessed as cell survival after 48 hrs by MTT assay relative to control1998Journal of natural products, Nov, Volume: 61, Issue:11
Preparation and cytotoxic effect of ceanothic acid derivatives.
AID691423Cytotoxicity against human BGC823 cells2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana.
AID691422Cytotoxicity against human A549 cells2012Bioorganic & medicinal chemistry letters, Oct-15, Volume: 22, Issue:20
Zizimauritic acids A-C, three novel nortriterpenes from Ziziphus mauritiana.
AID371949Cytotoxicity against human Raji cells assessed as cell viability at 1000 molar ratio after 48 hrs by trypan blue staining method2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
AID371946Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as EA induction at 100 molar ratio after 48 hrs relative to TPA2009Bioorganic & medicinal chemistry letters, Jul-01, Volume: 19, Issue:13
Cancer preventive agents 9. Betulinic acid derivatives as potent cancer chemopreventive agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (28.57)18.2507
2000's2 (28.57)29.6817
2010's3 (42.86)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.18

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 Index20.18 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.18)

All Compounds (24.57)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ampicillin
Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.		2.0710beta-lactam antibiotic;
penicillin allergen;
penicillin		antibacterial drug
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.0710taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		1.9910D-glucopyranoseepitope;
mouse metabolite
betulinic acid
[no description available]		3.1450hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
miconazole nitrate
miconazole nitrate : A racemate composed of equimolar amounts of (R)- and (S)-miconazole nitrate. An antifungal used for the treatment of athlete's foot, jock itch, ringworm and other fungal skin infections. It inhibits the synthesis of ergosterol, a critical component of fungal cell membranes.		2.0710
docetaxel anhydrous
Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.		2.1310secondary alpha-hydroxy ketone;
tetracyclic diterpenoid		antimalarial;
antineoplastic agent;
photosensitizing agent
spinosin
spinosin: isolated from seeds of Ziziph spinosa; structure given in first source. spinosin : A flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5 and 4', a methoxy group at position 7 and a 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 6 via a C-glycosidic linkage.		2.110dihydroxyflavone;
flavone C-glycoside;
monomethoxyflavone		anxiolytic drug;
plant metabolite
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		1.9910
bevirimat
bevirimat: an HIV inhibitor; disrupts late step in processing HIV Major Core Protein p24, preventing the capsid precursor p25 from being converted to mature capsid p24. bevirimat : A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.		2.0510dicarboxylic acid monoester;
monocarboxylic acid;
pentacyclic triterpenoid		HIV-1 maturation inhibitor;
metabolite
2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid
alphitolic acid: from the aerial parts of Gouania longipetala; structure in first source. 2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid : A pentacyclic triterpenoid that is betulinic acid carrying an additional alpha-hydroxy group at position 2. It has been isolated from Breynia fruticosa.		2.4820dihydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Pancreas
[description not available]		02.0410
Cancer of Prostate
[description not available]		02.0410
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).		02.0410
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0410
Benign Neoplasms
[description not available]		02.0710
Infections, Staphylococcal
[description not available]		02.0710
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.		02.0710
Staphylococcal Infections
Infections with bacteria of the genus STAPHYLOCOCCUS.		02.0710