piperolactam a profile

piperolactam A: isolated from Houttynia cordata; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	3081016
CHEMBL ID	387864
CHEBI ID	174488
MeSH ID	M0427917

Synonym
aristolactam f1
dibenz(cd,f)indol-4(5h)-one, 1-hydroxy-2-methoxy-
1-hydroxy-2-methoxydibenz(cd,f)indol-4(5h)-one
112501-42-5
15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,4,6,8,12,14-heptaen-11-one
CHEBI:174488
dibenz[cd,f]indol-4(5h)-one, 1-hydroxy-2-methoxy-
piperolactam a
CHEMBL387864
aristolactam fi
1-hydroxy-2-methoxydibenz[cd,f]indol-4(5h)-one; aristololactam fi
DTXSID90150083
AKOS028108734
15-hydroxy-14-methoxy-10-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one
1-hydroxy-2-methoxy-dibenz[cd,f]indol-4(5h)-one
1-hydroxy-2-methoxy-dibenz(cd,f)indol-4(5h)-one
1-hydroxy-2-methoxydibenz[cd,f]indol-4(5h)-one, 9ci
ncgc00385457-01_c16h11no3_1-hydroxy-2-methoxydibenzo[cd,f]indol-4(5h)-one
NCGC00385457-01
F92851
B0005-189391
HY-N2894
CS-0023479
FS-10150
1-hydroxy-2-methoxydibenzo[cd,f]indol-4(5h)-one
1-hydroxy-2-methoxydibenz[cd,f]indol-4(5h)-one
CXQ3T84KLC
14-methoxy-15-oxidanyl-10-azatetracyclo(7.6.1.02,7.012,16)hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

Excerpt	Reference	Relevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

Class	Description
alkaloid	Any of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
[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 (26)

Assay ID	Title	Year	Journal	Article
AID377205	Inhibition of arachidonic acid-induced rabbit platelet aggregation at 20 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID284363	Inhibition of LPS-induced BALB/c mouse B cell proliferation	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID1776041	Antineuroinflammatory activity against mouse BV2 cells assessed as inhibition of LPS-induced NO production incubated for 20 hrs by Griess assay
AID284365	Selectivity index, ratio of CC50 for BALB/c mouse T cells to IC50 for BALB/c mouse B cells	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID377200	Inhibition of thrombin-induced rabbit platelet aggregation at 100 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID377201	Inhibition of arachidonic acid-induced rabbit platelet aggregation at 100 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID284362	Inhibition of ConA-induced BALB/c mouse T cell proliferation	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID377203	Inhibition of platelet-activating factor-induced rabbit platelet aggregation at 100 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID284364	Selectivity index, ratio of CC50 for BALB/c mouse spleen cells to IC50 for BALB/c mouse T cells	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID338068	Cytotoxicity against mouse P388 cells
AID377207	Inhibition of collagen-induced rabbit platelet aggregation at 20 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID351330	Antiproliferative activity against human HCT15 cells by SRB assay	2009	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11	Synthesis of aristolactam analogues and evaluation of their antitumor activity.
AID351329	Antiproliferative activity against multidrug resistant human MES-SA/Dx5 cells by SRB assay	2009	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11	Synthesis of aristolactam analogues and evaluation of their antitumor activity.
AID351328	Antiproliferative activity against human MESSA cells by SRB assay	2009	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11	Synthesis of aristolactam analogues and evaluation of their antitumor activity.
AID377206	Inhibition of collagen-induced rabbit platelet aggregation at 50 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID377204	Inhibition of arachidonic acid-induced rabbit platelet aggregation at 50 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID377202	Inhibition of collagen-induced rabbit platelet aggregation at 100 ug/ml	2000	Journal of natural products, Aug, Volume: 63, Issue:8	Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii.
AID1293873	Inhibition of HDAC in mouse C127-LT cells assessed as activation of EGFP expression at 10 uM after 24 hrs by fluorescence microscopy	2016	Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9	Identification of new quinic acid derivatives as histone deacetylase inhibitors by fluorescence-based cellular assay.
AID338069	Cytotoxicity against human KB cells
AID284361	Cytotoxicity against BALB/c mouse spleen cells	2007	Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2	Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID351331	Antiproliferative activity against multidrug resistant human HCT15/CLO2 cells by SRB assay	2009	Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11	Synthesis of aristolactam analogues and evaluation of their antitumor activity.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings 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.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	5 (38.46)	29.6817
2010's	5 (38.46)	24.3611
2020's	3 (23.08)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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	14 (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
aspirin Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.	2	1	benzoic acids; phenyl acetates; salicylates	anticoagulant; antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; EC 1.1.1.188 (prostaglandin-F synthase) inhibitor; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; plant activator; platelet aggregation inhibitor; prostaglandin antagonist; teratogenic agent
berberine [no description available]	2.13	1	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
entinostat [no description available]	2.13	1	benzamides; carbamate ester; primary amino compound; pyridines; substituted aniline	antineoplastic agent; apoptosis inducer; EC 3.5.1.98 (histone deacetylase) inhibitor
3-hydroxybutanal [no description available]	2.04	1
glaucine glaucine: RN given refers to (+-)-isomer	2.03	1	aporphine alkaloid; organic heterotetracyclic compound; polyether; tertiary amino compound	antibacterial agent; antineoplastic agent; antitussive; muscle relaxant; NF-kappaB inhibitor; plant metabolite; platelet aggregation inhibitor; rat 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).	2.05	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.05	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
cynaropicrin cynaropicrin: structure given in first source; RN given for ((3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta)))-isomer	2.13	1	sesquiterpene lactone
sauristolactam sauristolactam: lactam of 10-aminomethyl-3-hydroxy-4-methoxyphenanthrene-1-carboxylic acid isolated from Saururus cernuus; structure given in first source	2.45	2
isoteolin isoteolin: mixture of isomers isoboldine (RN 3019-51-0) & bracteoline (RN 25651-04-1)	2.03	1	aporphine alkaloid
liridine liridine: Antibacterial from Artabotrys crassifolius; structure in first source	2.03	1
aristololactam a ii aristololactam A II: from the stems of Uvaria kweichowensis; structure in first source	2.42	2
corytuberine corytuberine: structure. (S)-corytuberine : An aporphine alkaloid that is aporphine which is substituted by hydroxy groups at positions 1 and 11, and by methoxy groups at positions 2 and 10 (the S enantiomer).	2.03	1	aporphine alkaloid; aromatic ether; organic heterotetracyclic compound; polyphenol; tertiary amino compound	plant metabolite
aristololactam bii aristololactam BII: isolated from Saururus cernuus; structure given in first source	2.94	4
norcepharadione b norcepharadione B: isolated from Houttynia cordata; structure in first source	2.42	2
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.13	1	cyclodextrin
trichostatin a trichostatin A: chelates zinc ion in the active site of histone deacetylases, resulting in preventing histone unpacking so DNA is less available for transcription; do not confuse with TRICHOSANTHIN which is a protein; found in STREPTOMYCES	2.13	1	antibiotic antifungal agent; hydroxamic acid; trichostatin	bacterial metabolite; EC 3.5.1.98 (histone deacetylase) inhibitor; geroprotector
gamma-sitosterol clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.	2.1	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; phytosterols	marine metabolite; plant metabolite
piplartine piplartine: Antineoplastic Agent, Phytogenic; alkaloid from Piper; structure in first source	2.1	1	cinnamamides; dicarboximide
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.13	1	cinnamate ester; tannin	food component; plant metabolite
cytellin cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982	2.1	1
5'-o-caffeoylquinic acid trans-5-O-caffeoyl-D-quinic acid : A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.	2.13	1	cinnamate ester; cyclitol carboxylic acid	plant metabolite
cyclosporine ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF	2.03	1	homodetic cyclic peptide	anti-asthmatic drug; anticoronaviral agent; antifungal agent; antirheumatic drug; carcinogenic agent; dermatologic drug; EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor; geroprotector; immunosuppressive agent; metabolite
narcissin flavonol narcissin flavonol: flavanol glycoside from Strumpfia maritima; do not confuse with other narcissin in Chemline, an alkaloid (lycorine (NM))	2.13	1	disaccharide derivative; glycosyloxyflavone; monomethoxyflavone; trihydroxyflavone
indigo carmine 3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.	2.13	1
methyl 3,5-di-o-caffeoyl quinate 3,5-dicaffeoylquinic acid methyl ester: results suggest that the effect of 3,5-dicaffeoylquinic esters on CHS is associated with a decrease in the production of interleukins, but not with the inhibition of iNOS expression. Moreover, esterification of the carboxyl group at C-1 enhanced protection against tyrosine nitration in the skin. methyl 3,5-di-O-caffeoyl quinate : A methyl ester resulting from the formal condensation of the carboxy group of 3,5-di-O-caffeoyl quinic acid with methanol. Isolated from Suaeda glauca and Dichrocephala bicolor, it exhibits hepatoprotective activity.	2.13	1
aristolactam aiiia Aristolactam AIIIa: polo-like kinase 1 (Plk1) inhibitor; structure in first source	2.42	2
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.04	1

Condition	Relationship Strength	Studies
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.25	1
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Leishmania Infection [description not available]	2.13	1
Leishmaniasis A disease caused by any of a number of species of protozoa in the genus LEISHMANIA. There are four major clinical types of this infection: cutaneous (Old and New World) (LEISHMANIASIS, CUTANEOUS), diffuse cutaneous (LEISHMANIASIS, DIFFUSE CUTANEOUS), mucocutaneous (LEISHMANIASIS, MUCOCUTANEOUS), and visceral (LEISHMANIASIS, VISCERAL).	2.13	1

piperolactam a

Description

Cross-References

Synonyms (28)

Research Excerpts

Bioavailability

Drug Classes (1)

Bioassays (26)

Research

Studies (13)

Market Indicators

Research Demand Index: 12.33

Study Types

piperolactam a

Description

Cross-References

Synonyms (28)

Research Excerpts

Bioavailability

Drug Classes (1)

Bioassays (26)

Research

Studies (13)

Market Indicators

Research Demand Index: 12.33

Study Types

Related Drugs (28)

Related Conditions (5)