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Basic Description
| Synonyms | Cuc B | NSC 144154 | SCHEMBL231815 | Cucurbitacin B | AKOS015897085 | Cucurbitacine (B) | CUCURBITACIN R - DATISCA PRINCIPLE B | (R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17- |
|---|---|
| Specifications & Purity | Moligand™, ≥98% |
| Biochemical and Physiological Mechanisms | Cucurbitacin B also exhibits anti-cancer activity by inhibiting telomerase and c-Myc in breast cancer. It also exhibits anti- artherosclerotic activity. Cucurbitacin B also possesses anti-inflammatory and anti-microbial activity. Cucurbitacin B is a trite |
| Storage Temp | Store at 2-8°C |
| Shipped In |
Wet ice This product requires cold chain shipping. Ground and other economy services are not available. |
| Grade | Moligand™ |
| Action Type | AGONIST |
| Mechanism of action | Agonist of TAS2R10 |
| Product Description |
Cucurbitacin B belongs to a class of highly oxidized tetracyclic triterpenoids and is oral active. Cucurbitacin B inhibits tumor cell growth, migration and invasion and cycle arrest, but induces cell apoptosis. Cucurbitacin B has potent anti-inflammatory, antioxidant, antiviral, hypoglycemic, hepatoprotective, neuroprotective activity
Application： Cucurbitacin B hydrate has been used: as a signal transducer and activator of transcription 3 (stat3) inhibitor to determine its effect on the expression of human lysosomal acid lipase (hLAL) in myeloid-derived suppressor cells (MDSCs). as an ecdysone receptor (EcR) antagonist injection to lower the levels of 20-hydoxyecdysone (20E) signaling in butterflies. to determine its effect on the cell viability of pancreatic cancer cell lines. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Lipids and lipid-like molecules
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Class
Steroids and steroid derivatives
- Subclass Cucurbitacins
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Class
Steroids and steroid derivatives
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Superclass
Lipids and lipid-like molecules
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Cucurbitacins |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Cucurbitacins |
| Alternative Parents | Triterpenoids Steroid esters 11-oxosteroids 14-alpha-methylsteroids 16-alpha-hydroxysteroids 3-oxo delta-5-steroids Delta-5-steroids Acyloins Tertiary alcohols Enones Acryloyl compounds Alpha-hydroxy ketones Secondary alcohols Cyclic ketones Cyclic alcohols and derivatives Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Cucurbitacin skeleton - Triterpenoid - 22-oxosteroid - 21-oxosteroid - 20-hydroxysteroid - Steroid ester - 3-oxo-delta-5-steroid - 11-oxosteroid - 16-hydroxysteroid - 16-alpha-hydroxysteroid - Hydroxysteroid - 2-hydroxysteroid - Oxosteroid - 14-alpha-methylsteroid - 3-oxosteroid - Delta-5-steroid - Acyloin - Cyclic alcohol - Alpha-hydroxy ketone - Tertiary alcohol - Alpha,beta-unsaturated ketone - Acryloyl-group - Enone - Cyclic ketone - Secondary alcohol - Carboxylic acid ester - Ketone - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carbonyl group - Organic oxide - Alcohol - Hydrocarbon derivative - Organooxygen compound - Organic oxygen compound - Aliphatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. |
| External Descriptors | Cholesterol and derivatives |
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Associated Targets(Human)
TAS2R10
Tchem
Taste receptor type 2 member 10 (0 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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ACHE
Tclin
Acetylcholinesterase (18204 Activities)
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A498 (42825 Activities)
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ACHN (49357 Activities)
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CAKI-1 (44928 Activities)
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CCRF-CEM (65223 Activities)
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COLO 205 (50209 Activities)
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DU-145 (51482 Activities)
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HL-60 (67320 Activities)
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HT-29 (80576 Activities)
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K562 (73714 Activities)
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KM12 (47707 Activities)
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M14 (47487 Activities)
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MCF7 (126967 Activities)
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MOLT-4 (49676 Activities)
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OVCAR-3 (48710 Activities)
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OVCAR-4 (44535 Activities)
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OVCAR-5 (45555 Activities)
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OVCAR-8 (47708 Activities)
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PC-3 (62116 Activities)
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RPMI-8226 (44974 Activities)
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RXF 393 (41971 Activities)
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SF-295 (48000 Activities)
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SK-MEL-2 (46422 Activities)
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SK-MEL-28 (48833 Activities)
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SK-MEL-5 (47095 Activities)
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SK-OV-3 (52876 Activities)
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SN12C (47755 Activities)
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SNB-19 (46794 Activities)
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TK-10 (45540 Activities)
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U-251 (51189 Activities)
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UACC-257 (46019 Activities)
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UACC-62 (47335 Activities)
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UO-31 (46270 Activities)
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786-0 (47912 Activities)
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A549 (127892 Activities)
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NCI/ADR-RES (33767 Activities)
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T47D (39041 Activities)
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EKVX (44102 Activities)
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NCI-H322M (45589 Activities)
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HCC 2998 (41480 Activities)
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HCT-116 (91556 Activities)
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HOP-92 (41141 Activities)
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Hs-578T (29457 Activities)
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NCI-H460 (60772 Activities)
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SF-268 (49410 Activities)
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IGROV-1 (47897 Activities)
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LNCaP (8286 Activities)
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LOX IMVI (44321 Activities)
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HOP-62 (47048 Activities)
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MDA-MB-435 (38290 Activities)
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Associated Targets(non-human)
Plasmodium falciparum (966862 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CHO (4503 Activities)
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Vero (26788 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| Pubchem Sid | 504763346 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504763346 |
| IUPAC Name | [(E,6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate |
| INCHI | InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1 |
| InChIKey | IXQKXEUSCPEQRD-DKRGWESNSA-N |
| Smiles | CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O)O |
| Isomeric SMILES | CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)C)O)O |
| Alternate CAS | 6199-67-3 |
| NSC Number | 49451 |
| MeSH Entry Terms | cucurbitacin B;cucurbitacin B 2-sulfate |
| Molecular Weight | 558.7 |
| Reaxy-Rn | 2068867 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2068867&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 F2520254 |
Certificate of Analysis | May 29, 2025 | C348066 |
| F2520256 |
Certificate of Analysis | May 29, 2025 | C348066 |
| F2520257 |
Certificate of Analysis | May 29, 2025 | C348066 |
| C2310217 |
Certificate of Analysis | Dec 19, 2022 | C348066 |
| C2310017 |
Certificate of Analysis | Dec 19, 2022 | C348066 |
| C2310218 |
Certificate of Analysis | Dec 19, 2022 | C348066 |
Chemical and Physical Properties
| Sensitivity | Moisture & heat sensitive |
|---|---|
| Molecular Weight | 558.700 g/mol |
| XLogP3 | 2.600 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 6 |
| Exact Mass | 558.319 Da |
| Monoisotopic Mass | 558.319 Da |
| Topological Polar Surface Area | 138.000 Ų |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Complexity | 1210.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 9 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |
Alternative Products
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Cucurbitacin B, Agonist of TAS2R10Starting at $109.90
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