retrofractamide a

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

Description

retrofractamide A: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	11012859
CHEMBL ID	255152
CHEBI ID	168909
SCHEMBL ID	14025730
MeSH ID	M0423850

Synonyms (18)

Synonym
retrofractamide a
(2e,4e,8e)-9-(1,3-benzodioxol-5-yl)-n-(2-methylpropyl)nona-2,4,8-trienamide
CHEBI:168909
CHEMBL255152
retrofractamide-a
BPSWISYORIWKCT-FCGWLDPVSA-N
SCHEMBL14025730
94079-67-1
(2e,4e,8e)-9-(2h-1,3-benzodioxol-5-yl)-n-(2-methylpropyl)nona-2,4,8-trienamide
retrofractamid-a
DTXSID901316243
HY-N12120
CS-0891876
2,4,8-nonatrienamide, 9-(1,3-benzodioxol-5-yl)-n-(2-methylpropyl)-, (2e,4e,8e)-
piperlongumine a
2,4,8-nonatrienamide, 9-(1,3-benzodioxol-5-yl)-n-(2-methylpropyl)-, (e,e,e)-
VVK45GJ3K5
(2e,4e,8e)-9-(1,3-benzodioxol-5-yl)-n-(2-methylpropyl)-2,4,8-nonatrienamide

[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 (42)

Assay ID	Title	Year	Journal	Article
AID404411	Increase in adiponectin mRNA expression in mouse 3T3L1 cells at 10 uM after 4 days by RT-PCR	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
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.
AID765257	Cytotoxicity against mouse 3T3L1 cells assessed as cell viability at 3 uM by CCK8 assay relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
AID404414	Increase in IRS1 mRNA expression in mouse 3T3L1 cells at 30 uM after 4 days by RT-PCR	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID765263	Adipogenetic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 0.3 uM relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
AID453024	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 10 uM after 20 hrs by Griess method 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.
AID453021	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-galactosamine/TNFalpha-induced cytotoxicity 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.
AID404413	Increase in PPARgamma2 mRNA expression in mouse 3T3L1 cells after 4 days by RT-PCR	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID609511	Inhibition of human recombinant HDAC6 expressed in baculovirus infected insect High5 cells using Boc-Lys(epsilon-acetyl)-AMC as substrate at 20 ug/ml by fluorescence assay	2011	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16	Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
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.
AID453025	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 30 uM after 20 hrs by Griess method 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.
AID1233715	Larvicidal activity against Aedes aegypti	2015	European journal of medicinal chemistry, Jul-15, Volume: 100	Thiosemicarbazones as Aedes aegypti larvicidal.
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.
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.
AID453026	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 100 uM after 20 hrs by Griess method 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.
AID404409	Increase in 2-deoxyglucose uptake in mouse 3T3L1 cells at 3 uM by liquid scintillation counter	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID765262	Adipogenetic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 3 uM relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
AID453023	Hepatoprotective activity in ddY mouse peritoneal macrophages assessed as inhibition of LPS-induced nitric oxide production at 3 uM after 20 hrs by Griess method 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.
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.
AID765264	Adipogenetic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 1 uM relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
AID765261	Adipogenetic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 10 uM relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
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.
AID609509	Inhibition of human recombinant HDAC1 expressed in baculovirus infected insect High5 cells using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC as substrate at 20 ug/ml by fluorescence assay	2011	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16	Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
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.
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.
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.
AID404412	Increase in GLUT4 mRNA expression in mouse 3T3L1 cells after 4 days by RT-PCR	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
AID765259	Cytotoxicity against mouse 3T3L1 cells assessed as cell viability at 0.3 uM by CCK8 assay relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
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.
AID404408	Increase in 2-deoxyglucose uptake in mouse 3T3L1 cells by liquid scintillation counter	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
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.
AID609510	Inhibition of human recombinant HDAC3 expressed in baculovirus infected insect High5 cells using Ac-Lys-Tyr-Lys(epsilon-acetyl)-AMC as substrate at 20 ug/ml by fluorescence assay	2011	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16	Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
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.
AID765255	Cytotoxicity against mouse 3T3L1 cells assessed as cell viability at 30 uM by CCK8 assay relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
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.
AID609508	Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay	2011	Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16	Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
AID765258	Cytotoxicity against mouse 3T3L1 cells assessed as cell viability at 1 uM by CCK8 assay relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
AID765260	Adipogenetic activity in mouse 3T3L1 cells assessed as increase in triglyceride level at 30 uM relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
AID765256	Cytotoxicity against mouse 3T3L1 cells assessed as cell viability at 10 uM by CCK8 assay relative to control	2013	Bioorganic & medicinal chemistry letters, Sep-01, Volume: 23, Issue:17	Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells.
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.
AID404410	Induction of adiponectin release to medium in mouse 3T3L1 cells at 10 uM by ELISA	2008	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11	Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	5 (41.67)	29.6817
2010's	7 (58.33)	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: 11.94

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	11.94 (24.57)
Research Supply Index	2.56 (2.92)
Research Growth Index	4.51 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.94)

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	12 (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
vorinostat Vorinostat: A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.. vorinostat : A dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).	2.06	1	dicarboxylic acid diamide; hydroxamic acid	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
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.	2.46	2	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
alkenes [no description available]	2.77	3
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.08	1
piplartine piplartine: Antineoplastic Agent, Phytogenic; alkaloid from Piper; structure in first source	2.04	1	cinnamamides; dicarboximide
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.	2.96	4	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
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
cholesteryl oleate cholesteryl oleate: RN given refers to ((Z)-isomer). cholesteryl oleate : The (Z)-stereoisomer of cholesteryl octadec-9-enoate.	2.03	1	CE(18:1); cholesteryl octadec-9-enoate	mouse metabolite
pellitorine pellitorine: consists of piper sylvaticum Roxb.; structure	3.31	6	fatty amide	metabolite
Piperanine [no description available]	2.73	3	benzodioxoles
piperlonguminine piperlonguminine: from Piper longum; structure in first source	2.96	4	benzodioxoles
piperic acid piperinic acid: from Piper longum; structure in first source. (E,E)-piperic acid : A monocarboxylic acid that is (E)-penta-2,4-dienoic acid substituted by a 1,3-benzodioxol-5-yl group at position 5. It has been isolated from black pepper (Piper nigrum).	2.06	1	alpha,beta-unsaturated monocarboxylic acid; benzodioxoles	plant metabolite
Pipercide [no description available]	2.97	4	benzodioxoles
dehydropipernonaline dehydropipernonaline: coronary vasodilator from Piper longum L; structure given in first source	2.96	4	benzodioxoles
guineensine guineensine: an Acyl-CoA: cholesterol acyltransferase inhibitor, from the fruits of Piper longum; structure in first sourc	3.45	7	benzodioxoles
(2E,4E)-N-isobutyl-2,4-dodecadienamide [no description available]	2.73	3	fatty amide	metabolite
cinnamaldehyde thiosemicarbazone cinnamaldehyde thiosemicarbazone: has antimicrobial activity; structure in first source	2.11	1
pipernonaline pipernonaline: derived from long pepper, Piper longum; 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
Retrofractamide C [no description available]	2.73	3	benzodioxoles
piperidines Piperidines: A family of hexahydropyridines.	2.46	2

Condition	Relationship Strength	Studies
Liver Dysfunction [description not available]	2.04	1
Liver Diseases Pathological processes of the LIVER.	2.04	1
Acute Brain Injuries [description not available]	2.05	1
Brain Injuries Acute and chronic (see also BRAIN INJURIES, CHRONIC) injuries to the brain, including the cerebral hemispheres, CEREBELLUM, and BRAIN STEM. Clinical manifestations depend on the nature of injury. Diffuse trauma to the brain is frequently associated with DIFFUSE AXONAL INJURY or COMA, POST-TRAUMATIC. Localized injuries may be associated with NEUROBEHAVIORAL MANIFESTATIONS; HEMIPARESIS, or other focal neurologic deficits.	2.05	1
Nerve Pain [description not available]	2.08	1
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.08	1

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