Grundinformationen
- Standard-SMILES
CC1=CC(=O)c2c(O)cccc2C1=O- InChIKey
VCMMXZQDRFWYSE-UHFFFAOYSA-N- Summenformel
- C11H8O3
- Durchschnittliche Molmasse
- 188,18 g/mol
- Monoisotopische Masse
- 188,04734412
Überblick
Plumbagin is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. It has a role as a metabolite, an antineoplastic agent, an anticoagulant and an immunological adjuvant. It is a hydroxy-1,4-naphthoquinone and a member of phenols.
Namen und Bezeichner
- Bevorzugter Name
- Plumbagin
- IUPAC
- 5-hydroxy-2-methylnaphthalene-1,4-dione
- Lokaler Name
- 5-Hydroxy-2-methyl-1,4-naphthochinon
- Englischer Name
- PLUMBAGIN
- Summenformel
- C11H8O3
- Molmasse
- 188.18
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
481-42-5- PubChem CID
- 10205
- DTXSID
DTXSID8075413- ChEMBL
CHEMBL295316- ChEBI
CHEBI:8273- UNII
- YAS4TBQ4OQ
- EC Number
- 207-569-6
- Nikkaji
- J5.778I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,3
- Polarare Oberfläche (TPSA)
- 54,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 316
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
124.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
134.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 76 · 76-78 °C(lit.)
- Siedepunkt
- 283.17 °C · 283.17°C (rough estimate)
- Dichte
- 1.354 · 1.354
- Brechungsindex
- 1.631 · 1.6310 (estimate)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- very faint turbidity in hot Methanol
- pka
- 6.7 · 6.70±0.20(Predicted)
- Aggregatzustand
- Crystals or Crystalline Powder
- Farbe
- Orange
- Biologische Quelle
- Plumbago indica
- Merck
- 7538 · 7538
- Stabilität
- Hygroscopic
- Major Application
- food and beverages
- InChI
- InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
- InChIKey
- VCMMXZQDRFWYSE-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C(O)=CC=C2)C(=O)C=C1C
- LogP
- 2.45 · 2.450 (est)
- EPA chemische Informationen
- 1 · 1,4-Naphthalenedione, 5-hydroxy-2-methyl- (481-42-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P264, P264+P265, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2923 8/PG 2
- hs_code
- 29146990
- RTECS-Nr.
- QL8500000
- risk_code
- 25-34-36/37/38
- Toxizität
- LD50 i.p. in mice: ~0.015 g/kg (Debray)
- hazard_code
- T
- hazard_note
- Toxic
- safety_code
- 22-26-36/37/39-45-37/39-28A
- hazard_class
- 6.1(a)
- packing_group
- II
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.
Agents that prevent BLOOD CLOTTING.
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Chemical substances that prevent or reduce the probability of CONCEPTION.
Anwendungen
BeschreibungPlumbagin is a natural 1,4-naphthoquinone first isolated from plants of the genus Plumbago. It has diverse effects in cells and animals. Plumbagin causes the generation of reactive oxygen species and induces apoptosis in cancer cells. It activates signaling through Nrf2 and the antioxidant response element, inducing the expression of Nrf2 target genes, including NQO1 and heme oxygenase-1 in cultured neuronal cells. Plumbagin also inhibits NADPH oxidase 4 in a time- and dose-dependent manner. It can be protective against peroxide stress or deprivation of glucose or oxygen.
VerwendenPlumbagin from Plumbago indica has been used: as a reactive oxygen species agent (ROS) to induce cytotoxicity in mouse embryonic fibroblastsas an oxidative stress inducer to generate superoxide anion in Saccharomyces cerevisiaeas a reference standard in thin layer chromatography and in spectrophotometric analysis for quantification of plumbagin in Plumbago auriculate samples
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…