pederin profile

pederin: isolated from beetles, Paederus fuscipes; minor descriptor (75-84); on-line & Index Medicus search PYRANS (75-84); RN given refers to (2S-(2alpha(R*(R*(2S*,5S*,6S*))),4beta,6beta(R*)))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

pederin : A polyketide and carboxamide produced by a (Pseudomonas) bacterial endosymbiont of certain rove beetles (genus Paederus). Pederin is the agent responsible for the vesicant effects (linear or Paederus dermatitis) when the beetle is crushed against the skin. It is a powerful inhibitor of protein biosynthesis and mitosis and a potent antitumour agent. [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]

Cross-References

ID Source	ID
PubMed CID	5381287
CHEBI ID	78591
SCHEMBL ID	452974
MeSH ID	M0262743

Synonyms (24)

Synonym
2h-pyran-2-acetamide, n-(6-(2,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5-dimethyl-2h-pyran-2-yl)tetrahydro-alpha-hydroxy-2-methoxy-5,6-dimethyl-4-methylene-, (2s-(2alpha(r(r (2s,5s,6s))),4beta,6beta(r)))-
2h-pyran-2-glycolamide, n-((6-(2,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5-dimethyl-2h-pyran-2-yl)methoxymethyl)tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-
d-manno-nonitol, 2,6-anhydro-3,5,7-trideoxy-1-c-(((2s)-hydroxy((2r,5r,6r)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2h-pyran-2-yl)acetyl)amino)-5,5-dimethyl-1,8,9-tri-o-methyl-, (1s)-
nsc 114781
2h-puran-2-acetamide,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5- dimethyl-2h-pyran-2-yl]tetrahydro-.alpha.-hydroxy-2- methoxy-5,6-dimethyl-4-methylene-, [2s-[2.alpha.[r[r (2s,5s,6s)]],4.beta.,6.beta.(r)]]-
nsc-114781
pederine
2h-pyran-2-glycolamide,3-dimethoxypropyl0tetrahydro-3-hydroxy-5,5- dimethyl-2h-pyran-2-yl]methoxymethyl]tetrahydro-2-methoxy- 5,6-dimethyl-4-methylene-
27973-72-4
pederin
(2s)-n-[(s)-[(2s,4r,6r)-6-[(2s)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyloxan-2-yl]-methoxymethyl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
b8f7j348gj ,
unii-b8f7j348gj
SCHEMBL452974
pederin, (+)-
(+)-pederin
pederin [mi]
d-manno-nonitol, 2,6-anhydro-3,5,7-trideoxy-1-c-(((2s)-2-hydroxy-2-((2r,5r,6r)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2h-pyran-2-yl)acetyl)amino)-5,5-dimethyl-1,8,9-tri-o-methyl-, (1s)-
(+)-pederine
paederine
CHEBI:78591
(2s)-n-[(s)-{(2s,4r,6r)-6-[(2s)-2,3-dimethoxypropyl]-4-hydroxy-5,5-dimethyltetrahydro-2h-pyran-2-yl}(methoxy)methyl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2h-pyran-2-yl]acetamide
DTXSID90182248
Q8214251

Role	Description
bacterial metabolite	Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
vesicant	Any compound that causes severe skin, eye and mucosal pain and irritation.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
antimitotic	Any compound that inhibits cell division (mitosis).
[role 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]

Class	Description
polyketide	Natural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides.
cyclic ketal	A ketal in the molecule of which the ketal carbon and one or both oxygen atoms thereon are members of a ring.
diol	A compound that contains two hydroxy groups, generally assumed to be, but not necessarily, alcoholic. Aliphatic diols are also called glycols.
oxanes	Any organic heteromonocyclic compoundthat is oxane or its substituted derivatives.
secondary alcohol	A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
secondary carboxamide	A carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.00)	18.7374
1990's	8 (16.00)	18.2507
2000's	18 (36.00)	29.6817
2010's	19 (38.00)	24.3611
2020's	4 (8.00)	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	7 (13.46%)	6.00%
Case Studies	7 (13.46%)	4.05%
Observational	0 (0.00%)	0.25%
Other	38 (73.08%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	2.01	1	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fluocinolone acetonide Fluocinolone Acetonide: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). fluocinolone acetonide : A fluorinated steroid that is flunisolide in which the hydrogen at position 9 is replaced by fluorine. A corticosteroid with glucocorticoid activity, it is used (both as the anhydrous form and as the dihydrate) in creams, gels and ointments for the treatment of various skin disorders.	2.06	1	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; cyclic ketal; fluorinated steroid; glucocorticoid; organic heteropentacyclic compound; primary alpha-hydroxy ketone	anti-inflammatory drug; antipruritic drug
fluocinonide Fluocinonide: A topical glucocorticoid used in the treatment of ECZEMA.	2.11	1	organic molecular entity
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.06	1	zinc molecular entity
tellurous acid tellurous acid: tellurite anion inhibits oxidation of NAD-linked substrates in kidney & liver mitochondria; RN given refers to parent cpd	2.02	1	tellurium oxoacid
fluocinolone [no description available]	2.06	1	fluorinated steroid
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.5	2	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
potassium permanganate Potassium Permanganate: Permanganic acid (HMnO4), potassium salt. A highly oxidative, water-soluble compound with purple crystals, and a sweet taste. (From McGraw-Hill Dictionary of Scientific and Technical Information, 4th ed)	2.06	1
malonyl coenzyme a Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.	2.07	1	malonyl-CoAs	EC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor; Escherichia coli metabolite; metabolite; mouse metabolite
tellurium Tellurium: An element that is a member of the chalcogen family. It has the atomic symbol Te, atomic number 52, and atomic weight 127.60. It has been used as a coloring agent and in the manufacture of electrical equipment. Exposure may cause nausea, vomiting, and CNS depression.	2.02	1	chalcogen; metalloid atom
beta-escin [no description available]	2.01	1
onnamide onnamide: structure given in first source; isolated from marine sponges	2.02	1
psymberin psymberin: from the Indo-Pacific marine sponge Ircinia ramosa; structure in first source	5.04	7	hydroxybenzoic acid
calamine (pharmaceutical preparation) [no description available]	2.06	1
bacillaene bacillaene: an inhibitor of procaryotic protein synthesis; produced by the PksX megacomplex; isolated from Bacillus subtilis; a hexaene with molecular formula C35-H48-O7. bacillaene : A polyene antibiotic obtained from Bacillus subtilis 168 that is active against a broad spectrum of bacteria. It is notoriously unstable.	2.07	1	enamine; monocarboxylic acid amide; polyene antibiotic; polyketide; secondary alcohol	antibacterial agent; antimicrobial agent; bacterial metabolite
mycalamide a mycalamide A: structure given in first source; RN given refers to (2R-(2alpha,2(S(S)),5beta,6beta))-isomer; isolated from marine sponges	4.58	4	disaccharide
mycalamide b mycalamide B: structure given in first source; isolated from marine sponges; ChemLine lists mycalamide B incorrectly under RN 122752-21-0	3.55	2	organic heterobicyclic compound; oxacycle
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	5.04	7	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Allergic Contact Dermatitis [description not available]	2.25	1
Travel Sickness [description not available]	2.25	1
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.25	1
Contact Dermatitis [description not available]	4.47	8
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	4.47	8
Dermatitis, Irritant A non-allergic contact dermatitis caused by prolonged exposure to irritants and not explained by delayed hypersensitivity mechanisms.	4.33	7
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	3.35	2
Bleb [description not available]	2.71	3
Diseases, Occupational [description not available]	2.05	1
Acute Disease Disease having a short and relatively severe course.	2.05	1
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	3.38	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.06	1
Insect Bites [description not available]	2.43	2
Insect Bites and Stings Bites and stings inflicted by insects.	2.43	2
Dermatitis Any inflammation of the skin.	3.09	5
Benign Neoplasms [description not available]	2.99	1
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.	2.99	1
Allodynia [description not available]	2.01	1
Innate Inflammatory Response [description not available]	2.01	1
Ache [description not available]	2.01	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.01	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.01	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.03	1
Facial Dermatoses Skin diseases involving the FACE.	1.98	1
Pink Eye [description not available]	3.3	2
Conjunctivitis INFLAMMATION of the CONJUNCTIVA.	3.3	2

pederin

Description

Cross-References

Synonyms (24)

Roles (4)

Drug Classes (6)

Research

Studies (50)

Market Indicators

Research Demand Index: 44.38

Study Types

pederin

Description

Cross-References

Synonyms (24)

Roles (4)

Drug Classes (6)

Research

Studies (50)

Market Indicators

Research Demand Index: 44.38

Study Types

Related Drugs (18)

Related Conditions (26)