Lup-20(29)-en-28-olsure, 3-Hydroxy-, (3β)-
Betulinic Acid
Grundinformationen
- CAS
472-15-1- Standard-SMILES
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12- InChIKey
QGJZLNKBHJESQX-FZFNOLFKSA-N- Summenformel
- C30H48O3
- Durchschnittliche Molmasse
- 456,7 g/mol
- Monoisotopische Masse
- 456,3603454
Überblick
Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an antineoplastic agent, an antimalarial, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane.
Namen und Bezeichner
- Bevorzugter Name
- Betulinic Acid
- IUPAC
- (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
- Lokaler Name
- Lup-20(29)-en-28-olsure, 3-Hydroxy-, (3β)-
- Englischer Name
- Betulinic acid
- Summenformel
- C30H48O3
- Molmasse
- 456.71
Namen und Synonyme
betulinic acid472-15-1MairinBetulic acidLupatic Acidals-3573-Hydroxylup-20(29)-en-28-oic acidbeta-betulinic acidNSC-113090NSC-6775783beta-Hydroxy-lup-20(29)-en-28-oic acid4G6A18707N
Weitere Namen anzeigen
BetulinicBetulinic acid technical grade, 90%(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentaMethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acidPlatanolCcris 6748Nsc 113090Nsc 677578
CHEBI:3087DTXSID80861974(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acidNSC113090(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta(a)chrysene-3a-carboxylic acid3 Epi betulinic AcidRefChem:5606DTXCID301506361
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 8,2
- Polarare Oberfläche (TPSA)
- 57,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 861
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Melting Point316 - 318 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 295 · 295-298 °C (dec.) (lit.)
- Siedepunkt
- 550 · 550.0±33.0 °C(Predicted)
- Dichte
- 1.065 · 1.065±0.06 g/cm3(Predicted)
- Brechungsindex
- 7.8 ° · 7.8 ° (C=0.9, Pyridine)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
- pka
- 4.61 · 4.61±0.70(Predicted)
- Aggregatzustand
- Solid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 96.7% (29 of 30) of all reports.
Not Classified
Aggregated GHS information provided per 30 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesNot Classified
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29181985
- hazard_code
- Xi
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Cellular LocationsExtracellular
Anwendungen
VerwendenBetulinic Acid is a natural pentacyclic triterpenoid. Betulinic Acid displays anti-inflammatory and anti-HIV activity. Betulinic Acid selectively induces apoptosis in tumor cells by directly activati ng the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism. Betulinic Acid also exhibits TGR5 agonist activity
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionChEBI: A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium cla iflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties.
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