MW 456.7 Da. Triterpenoid with various biological activities. Apoptosis inducer, with anticancer properties. Also shows anti-HIV, antimalarial and anti-inflammatory activity. TGR5 agonist (EC50 = 1.04 μM).
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- Immunity 50:1172-1187.e72019T-bet Transcription Factor Promotes Antibody-Secreting Cell Differentiation by Limiting the Inflammatory Effects of IFN-γ on B Cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesSara L Stone et. al.PubMed 31076359
Key facts
- CAS number
- 472-15-1
- Form
- Solid
- Molecular weight
- 456.7 Da
- Molecular formula
- C30H48O3
- PubChem identifier
- 64971
- Nature
- Synthetic
Target data
Alternative names
ADR, AI838772, AKR1B 1, ALDR_HUMAN, ALR2, AOS1, AR, AW493413, Activator of SUMO1, Aldehyde reductase, Aldehyde reductase 1, Aldo-keto reductase family 1 member B1, Aldose reductase, Anthracycline-associated resistance ARX, BG 37, C358B7.1, DNA directed DNA polymerase beta, DNA pol beta, DNA polymerase beta, DNA polymerase beta subunit, DPOLB_HUMAN, FLJ11090, FLJ13058, G protein coupled bile acid receptor BG 37, G-protein coupled bile acid receptor 1, G-protein coupled receptor GPCR19, GPBAR 1, GPBAR_HUMAN, GPCR, GPCR 19, GPR 131, HRIHFB2115, HSPC140, IF 1, IFG, IFI, IFN immune, IFN-gamma, IFNG_HUMAN, Immune interferon, Interferon gamma, LXR a, Lii5 2 CTCL tumor antigen, Liver X receptor alpha, Low Km aldose reductase, M-BAR, MGC104252, MGC112732, MGC125976, MGC1804, MGC40597, Membrane bile acid receptor, Membrane-type receptor for bile acids, NR1H3_HUMAN, Nuclear receptor subfamily 1 group H member 3, Oxysterols receptor LXR-alpha, Pol B, Pol beta, Polymerase (DNA directed) beta, RLD 1, RP24-311F12.2, SAE1_HUMAN, SAE2_HUMAN, SCAN1, SUA1, SUMO 1 activating enzyme E1 N subunit, SUMO 1 activating enzyme subunit 1, SUMO 1 activating enzyme subunit 2, SUMO 1 protein ligase, SUMO-activating enzyme subunit 1, SUMO-activating enzyme subunit 2, SUMO-conjugating enzyme UBC9, SUMO-protein ligase, Sentrin/SUMO activating protein AOS1, TGR 5, TYDP, TYDP1_HUMAN, Type II Interferon, Tyr-DNA phosphodiesterase 1, Tyrosyl-DNA phosphodiesterase 1, UBA2, UBA2 ubiquitin activating enzyme E1 homolog, UBC9_HUMAN, UBCE9, UBL E1A, UBLE1B, Ube2i, Ubiquitin carrier protein, Ubiquitin carrier protein 9, Ubiquitin carrier protein I, Ubiquitin conjugating enzyme 9, Ubiquitin conjugating enzyme E2I (UBC9 homolog, yeast), Ubiquitin conjugating enzyme E2I (homologous to yeast UBC9), Ubiquitin conjugating enzyme UbcE2A, Ubiquitin like modifier activating enzyme 2, Ubiquitin like protein SUMO 1 conjugating enzyme, Ubiquitin like protein SUMO1 activating enzyme, Ubiquitin protein ligase E2I, Ubiquitin-conjugating enzyme E2 I, Ubiquitin-like 1-activating enzyme E1A, Ubiquitin-like 1-activating enzyme E1B, Ubiquitin-protein ligase I, aldo-keto reductase family 1, member B1 (aldose reductase), aldr 1, hBG 37, hGPCR 19, p18
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MW 456.7 Da. Triterpenoid with various biological activities. Apoptosis inducer, with anticancer properties. Also shows anti-HIV, antimalarial and anti-inflammatory activity. TGR5 agonist (EC50 = 1.04 μM).
Key facts
- CAS number
- 472-15-1
- Form
- Solid
- Molecular weight
- 456.7 Da
- Molecular formula
- C30H48O3
- PubChem identifier
- 64971
- Nature
- Synthetic
- Solubility
Soluble in DMSO to 50 mM (with warming).
- Biochemical name
- Betulinic acid
- Biological description
Triterpenoid with various biological activities. Apoptosis inducer, with anticancer properties. Also shows anti-HIV, antimalarial and anti-inflammatory activity. TGR5 agonist (EC50 = 1.04 μM).
- Canonical SMILES
- CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
- Isomeric SMILES
- CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)O
- InChI
- InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
- InChIKey
- QGJZLNKBHJESQX-FZFNOLFKSA-N
- IUPAC name
- (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
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- +4°C
- Appropriate long-term storage conditions
- +4°C
- Storage information
- The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
DNA polymerase beta often referred to as Pol β plays an essential role in DNA repair specifically base excision repair. It has a molecular mass of approximately 39 kDa and is widely expressed in various tissues. Interferon gamma also known as IFNγ functions in the immune system to activate macrophages and is about 20 kDa in size. Liver X receptor alpha (LXRα) is a nuclear receptor that influences cholesterol homeostasis and is expressed predominantly in liver adipose tissue and macrophages. The protein UBE2I also known as UBC9 functions as an E2 SUMO-conjugating enzyme in the process of sumoylation with a size of about 18 kDa and is found in most cell types.
- Biological function summary
DNA polymerase beta contributes to the maintenance of genome integrity by filling in small gaps left after DNA repair. It works as part of a repair complex ensuring proper function and stability of genetic information. Interferon gamma plays a critical role in immune response regulation and cellular communication. LXRα is involved in lipid metabolism and serves as an important regulator for genes managing cholesterol and fatty acid metabolism. UBE2I/UBC9 is essential for protein post-translational modification influencing protein activity stability and localization.
- Pathways
DNA polymerase beta is significantly integrated within the base excision repair pathway which is important for correcting DNA damage from oxidative stress alongside proteins like AP endonuclease. Interferon gamma is a major participant in the JAK-STAT signaling pathway interacting with proteins such as STAT1 to mediate immune responses. LXRα is part of the lipid metabolism pathway closely related to ATP-binding cassette transporters. UBE2I is implicated in sumoylation pathways affecting pathways for protein degradation and cellular response to stress.
- Associated diseases and disorders
DNA polymerase beta mutations or dysregulation can lead to cancer due to compromised DNA repair mechanisms; it is often studied in relation to BRCA1 protein dysfunction in breast cancer. Interferon gamma is critical in autoimmune and inflammatory diseases such as multiple sclerosis involving abnormal immune responses potentially influenced by GPCR TGR5 interactions. LXRα has been linked to atherosclerosis due to its role in lipid homeostasis interacting with proteins like apolipoprotein E. Aberrant sumoylation via UBE2I can contribute to neurodegenerative disorders with proteins like tau becoming improperly modified.
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2 product images
Chemical Structure - Betulinic acid, TGR5 agonist (ab120654)
2D chemical structure image of ab120654, Betulinic acid, TGR5 agonist
Functional Studies - Betulinic acid, TGR5 agonist (ab120654)
ab32557 staining p38 (phospho T180 + Y182) in MALME-3M cells treated with betulinic acid (ab120654), by ICC/IF. Increase in expression of p38 (phospho T180 + Y182) correlates with increased concentration of betulinic acid, as described in literature.
The cells were incubated at 37°C for 30 minutes in media containing different concentrations of ab120654 (betulinic acid ) in DMSO, fixed with 4% formaldehyde for 10 minutes at room temperature and blocked with PBS containing 10% goat serum, 0.3 M glycine, 1% BSA and 0.1% tween for 2h at room temperature. Staining of the treated cells with ab32557 (1/200 dilution) was performed overnight at 4°C in PBS containing 1% BSA and 0.1% tween. A DyLight 488 goat anti-rabbit polyclonal antibody (Goat Anti-Rabbit IgG H&L (DyLight® 488) preadsorbed ab96899) at 1/250 dilution was used as the secondary antibody. Nuclei were counterstained with DAPI and are shown in blue.
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