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 Source	ID
PubMed CID	25255091
CHEMBL ID	271630
CHEBI ID	174438
SCHEMBL ID	22397851

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)

Class	Description
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 ID	Title	Year	Journal	Article
AID1165212	Antiproliferative activity against human MDA-MB-231 cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID404406	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 30 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID1165211	Antiproliferative activity against human SK-BR-3 cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID404403	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 1 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID316621	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 30 uM after 20 hrs by MTT assay	2008	Bioorganic & 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.
AID453015	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID362089	Cytotoxicity against human THP1 cells assessed as cell viability at 3.13 to 25.00 ug/mL by MTT assay	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID316620	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 10 uM after 20 hrs by MTT assay	2008	Bioorganic & 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.
AID316619	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 3 uM after 20 hrs by MTT assay	2008	Bioorganic & 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.
AID453013	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID362090	Antiinflammatory activity in mouse	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID453014	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID1165213	Antiproliferative activity against human DU145 cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362087	Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 6.25 ug/mL after 1 hr by ELISA	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165208	Antiproliferative activity against human A549 cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID404404	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 3 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID404405	Antidiabetic activity in mouse 3T3L1 cells assessed as enhancement of triglyceride accumulation at 10 uM	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID453018	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID453012	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID453017	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID316618	Inhibition of D-galactosamine/TNFalpha-induced cell death in ddY mouse hepatocytes at 1 uM after 20 hrs by MTT assay	2008	Bioorganic & 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.
AID453019	Hepatoprotective 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 control	2009	Bioorganic & 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.
AID1165209	Antiproliferative activity against human MCF7 cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362086	Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 12.50 ug/mL after 1 hr by ELISA	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165214	Antiproliferative activity against human KB cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362084	Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion after 1 hr by ELISA	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID362088	Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 3.13 ug/mL after 1 hr by ELISA	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165215	Antiproliferative activity against human KBVIN cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID362085	Inhibition of sICAM1/LFA1 interaction-mediated human THP1 cell adhesion at 25 ug/mL after 1 hr by ELISA	2008	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 18, Issue:16	Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
AID1165210	Antiproliferative activity against human ZR-75-1 cells after 3 days by SRB assay	2014	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 24, Issue:20	Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.
AID453020	Hepatoprotective 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 control	2009	Bioorganic & 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	4 (80.00)	29.6817
2010's	1 (20.00)	24.3611
2020's	0 (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.

Metric	This Compound (vs All)
Research Demand Index	12.50 (24.57)
Research Supply Index	1.79 (2.92)
Research Growth Index	4.30 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.50)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	5 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.04	1	chromanes; 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.	2.45	2	arenecarbaldehyde; 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).	2.1	1	taxane 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).	2.04	1	delta-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.	2.73	3	benzodioxoles; N-acylpiperidine; piperidine alkaloid; tertiary carboxamide	food component; human blood serum metabolite; NF-kappaB inhibitor; plant metabolite
silybin [no description available]	2.05	1
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	2.1	1	tyramines	metabolite
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.05	1	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
pellitorine pellitorine: consists of piper sylvaticum Roxb.; structure	2.96	4	fatty amide	metabolite
Piperanine [no description available]	2.73	3	benzodioxoles
piperlonguminine piperlonguminine: from Piper longum; structure in first source	2.73	3	benzodioxoles
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.	2.1	1	alkaloid; benzodioxoles; enamide; secondary carboxamide	apoptosis inducer; metabolite; plant metabolite
Pipercide [no description available]	2.97	4	benzodioxoles
dehydropipernonaline dehydropipernonaline: coronary vasodilator from Piper longum L; structure given in first source	2.73	3	benzodioxoles
guineensine guineensine: an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum; structure in first sourc	2.96	4	benzodioxoles
(2E,4E)-N-isobutyl-2,4-dodecadienamide [no description available]	2.73	3	fatty amide	metabolite
pipernonaline pipernonaline: derived from long pepper, Piper longum; structure in first source	2.96	4	benzodioxoles
retrofractamide a retrofractamide A: structure in first source	2.73	3	benzodioxoles
4,5-dihydropiperlonguminine 4,5-dihydropiperlonguminine: in insecticide isolated from Piper tuberculatum; structure in first source	2.45	2	benzodioxoles
N-trans-sinapoyltyramine [no description available]	2.1	1	hydroxycinnamic acid	metabolite

Condition	Indicated	Relationship Strength	Studies	Trials
Liver Dysfunction [description not available]	0	2.04	1	0
Liver Diseases Pathological processes of the LIVER.	0	2.04	1	0

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