Compounds > Retrofractamide C
Page last updated: 2024-11-13

Retrofractamide C

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

Cross-References

ID SourceID
PubMed CID25255091
CHEMBL ID271630
CHEBI ID174438
SCHEMBL ID22397851

Synonyms (9)

Synonym
retrofractamide c
(2e,8e)-9-(1,3-benzodioxol-5-yl)-n-(2-methylpropyl)nona-2,8-dienamide
CHEBI:174438
CHEMBL271630
96386-33-3
SCHEMBL22397851
(2e,8e)-9-(2h-1,3-benzodioxol-5-yl)-n-(2-methylpropyl)nona-2,8-dienamide
bdbm50479143
DTXSID101316344
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzodioxoles
[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]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1165212Antiproliferative activity against human MDA-MB-231 cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID404406Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 30 uM2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID1165211Antiproliferative activity against human SK-BR-3 cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID404403Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 1 uM2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID316621Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 30 uM after 20 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID453015Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 100 uM after 44 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID362089Cytotoxicity against human THP1 cells assessed as cell viability at 3.13 to 25.00 ug/mL by MTT assay2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID316620Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 10 uM after 20 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID316619Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 3 uM after 20 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID453013Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 10 uM after 44 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID362090Antiinflammatory activity in mouse2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID453014Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 30 uM after 44 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1165213Antiproliferative activity against human DU145 cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362087Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 6.25 ug/mL after 1 hr by ELISA2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165208Antiproliferative activity against human A549 cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID404404Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 3 uM2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID404405Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 10 uM2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID453018Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 3 uM after 20 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID453012Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine-induced cytotoxicity at 3 uM after 44 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID453017Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 1 uM after 20 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID316618Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 1 uM after 20 hrs by MTT assay2008Bioorganic & medicinal chemistry letters, Mar-15, Volume: 18, Issue:6
Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes.
AID453019Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 10 uM after 20 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
AID1165209Antiproliferative activity against human MCF7 cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362086Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 12.50 ug/mL after 1 hr by ELISA2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165214Antiproliferative activity against human KB cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362084Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion after 1 hr by ELISA2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID362088Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 3.13 ug/mL after 1 hr by ELISA2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165215Antiproliferative activity against human KBVIN cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362085Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 25 ug/mL after 1 hr by ELISA2008Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165210Antiproliferative activity against human ZR-75-1 cells after 3 days by SRB assay2014Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20
Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID453020Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity at 30 uM after 20 hrs by MTT assay relative to untreated control2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Hepatoprotective amide constituents from the fruit of Piper chaba: Structural requirements, mode of action, and new amides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (80.00)29.6817
2010's1 (20.00)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: 12.50

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.50 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.50)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
troglitazone
Troglitazone: A chroman and thiazolidinedione derivative that acts as a PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS (PPAR) agonist. It was formerly used in the treatment of TYPE 2 DIABETES MELLITUS, but has been withdrawn due to hepatotoxicity.		2.0410chromanes;
thiazolidinone		anticoagulant;
anticonvulsant;
antineoplastic agent;
antioxidant;
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor;
ferroptosis inhibitor;
hypoglycemic agent;
platelet aggregation inhibitor;
vasodilator agent
piperonal
piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.		2.4520arenecarbaldehyde;
benzodioxoles		fragrance;
insect repellent;
plant metabolite
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).		2.110taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
lovastatin
Lovastatin: A fungal metabolite isolated from cultures of Aspergillus terreus. The compound is a potent anticholesteremic agent. It inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase (HYDROXYMETHYLGLUTARYL COA REDUCTASES), which is the rate-limiting enzyme in cholesterol biosynthesis. It also stimulates the production of low-density lipoprotein receptors in the liver.. lovastatin : A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom).		2.0410delta-lactone;
fatty acid ester;
hexahydronaphthalenes;
polyketide;
statin (naturally occurring)		anticholesteremic drug;
antineoplastic agent;
Aspergillus metabolite;
prodrug
piperine
piperine : A N-acylpiperidine that is piperidine substituted by a (1E,3E)-1-(1,3-benzodioxol-5-yl)-5-oxopenta-1,3-dien-5-yl group at the nitrogen atom. It is an alkaloid isolated from the plant Piper nigrum.		2.7330benzodioxoles;
N-acylpiperidine;
piperidine alkaloid;
tertiary carboxamide		food component;
human blood serum metabolite;
NF-kappaB inhibitor;
plant metabolite
silybin
[no description available]		2.0510
feruloyltyramine
feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer		2.110tyraminesmetabolite
caffeic acid phenethyl ester
phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.		2.0510alkyl caffeate esteranti-inflammatory agent;
antibacterial agent;
antineoplastic agent;
antioxidant;
antiviral agent;
immunomodulator;
metabolite;
neuroprotective agent
pellitorine
pellitorine: consists of piper sylvaticum Roxb.; structure		2.9640fatty amidemetabolite
Piperanine
[no description available]		2.7330benzodioxoles
piperlonguminine
piperlonguminine: from Piper longum; structure in first source		2.7330benzodioxoles
pipercallosidine
pipercallosidine : An enamide that is (2E)-N-isobutylhept-2-enamide which is substituted at position 7 by a 3,4-methylenedioxyphenyl group. A natural product found in Piper sarmentosum.		2.110alkaloid;
benzodioxoles;
enamide;
secondary carboxamide		apoptosis inducer;
metabolite;
plant metabolite
Pipercide
[no description available]		2.9740benzodioxoles
dehydropipernonaline
dehydropipernonaline: coronary vasodilator from Piper longum L; structure given in first source		2.7330benzodioxoles
guineensine
guineensine: an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum; structure in first sourc		2.9640benzodioxoles
(2E,4E)-N-isobutyl-2,4-dodecadienamide
[no description available]		2.7330fatty amidemetabolite
pipernonaline
pipernonaline: derived from long pepper, Piper longum; structure in first source		2.9640benzodioxoles
retrofractamide a
retrofractamide A: structure in first source		2.7330benzodioxoles
4,5-dihydropiperlonguminine
4,5-dihydropiperlonguminine: in insecticide isolated from Piper tuberculatum; structure in first source		2.4520benzodioxoles
N-trans-sinapoyltyramine
[no description available]		2.110hydroxycinnamic acidmetabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Liver Dysfunction
[description not available]		02.0410
Liver Diseases
Pathological processes of the LIVER.		02.0410