Cas no 22149-28-6 (16-Hydroxytabersonine)
16-Hydroxytabersonine Chemical and Physical Properties
Names and Identifiers
-
- Aspidospermidine-3-carboxylicacid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5a,12R,19a)-
- 11-Hydroxytabersonine
- Methyl (5α,12β,19α)-16-hydroxy-2,3,6,7-tetradehydroaspidospermidi ne-3-carboxylate
- 11-hydroxyoleic acid
- 9-Octadecenoic acid, 11-hydroxy-
- 9-Octadecenoic acid, 11-hydroxy-, (Z)-
- AGN-PC-0CPW4C
- CTK3F8137
- [ "" ]
- 16-Hydroxytabersonine
- W1101
- C11643
- Q20179989
- HY-N1021
- methyl (1R,12R,19S)-12-ethyl-5-hydroxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate
- CS-0016257
- methyl (1R, 12R, 19S)-12-ethyl-5-hydroxy-8, 16-diazapentacyclo[10.6.1.01, 9.02, 7.016, 19]nonadeca-2(7), 3, 5, 9, 13-pentaene-10-carboxylate
- DTXSID601032123
- AKOS032962286
- UNII-GV2G76UPD2
- 1H-Indolizino(8,1-cd)carbazole, aspidospermidine-3-carboxylic acid deriv.
- ASPIDOSPERMIDINE-3-CARBOXYLIC ACID, 2,3,6,7-TETRADEHYDRO-16-HYDROXY-, METHYL ESTER, (5.ALPHA.,12R,19.ALPHA.)-
- methyl 16-hydroxy-2,3,6,7-tetradehydro-5alpha,12beta,19alpha-aspidospermidine-3-carboxylate
- CHEMBL2011510
- CHEBI:17699
- 22149-28-6
- GV2G76UPD2
- Tabersonine, 11-hydroxy-
- NSC-815331
- SCHEMBL4131340
- Aspidospermidine-3-carboxylic acid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5alpha,12R,19alpha)-
- FS-9603
- NSC815331
- NS00094508
- Methyl 12-ethyl-5-hydroxy-8,16-diazapentacyclo(10.6.1.0,.0,.0,)nonadeca-2(7),3,5,9,13-pentaene-10-carboxylic acid
- methyl (1R,12R,19S)-12-ethyl-5-hydroxy-8,16-diazapentacyclo(10.6.1.01,9.02,7.016,19)nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate
- Methyl 12-ethyl-5-hydroxy-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylic acid
- DA-69443
-
- Inchi: 1S/C21H24N2O3/c1-3-20-7-4-9-23-10-8-21(19(20)23)15-6-5-13(24)11-16(15)22-17(21)14(12-20)18(25)26-2/h4-7,11,19,22,24H,3,8-10,12H2,1-2H3/t19-,20-,21-/m0/s1
- InChI Key: FXUFRJQCBVSCRZ-ACRUOGEOSA-N
- SMILES: O(C)C(C1C[C@@]2(C=CCN3CC[C@@]4(C5C=CC(=CC=5NC4=1)O)[C@@H]32)CC)=O
Computed Properties
- Exact Mass: 352.17869263g/mol
- Monoisotopic Mass: 352.17869263g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 5
- Heavy Atom Count: 26
- Rotatable Bond Count: 3
- Complexity: 701
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 3
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- XLogP3: 3
- Topological Polar Surface Area: 61.8
Experimental Properties
- Color/Form: Powder
16-Hydroxytabersonine Security Information
- Storage Condition:Store at room temperature, 2-8 ℃ is better
16-Hydroxytabersonine Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd. | H62470-5 mg |
Aspidospermidine-3-carboxylicacid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5a,12R,19a)- |
22149-28-6 | 5mg |
¥5600.0 | 2021-09-09 | ||
| SHANG HAI TAO SHU Biotechnology Co., Ltd. | TN2587-1 mg |
11-Hydroxytabersonine |
22149-28-6 | 1mg |
¥2835.00 | 2022-03-01 | ||
| TargetMol Chemicals | TN2587-5 mg |
11-Hydroxytabersonine |
22149-28-6 | 98% | 5mg |
¥ 3,940 | 2023-07-11 | |
| TargetMol Chemicals | TN2587-1 mL * 10 mM (in DMSO) |
11-Hydroxytabersonine |
22149-28-6 | 98% | 1 mL * 10 mM (in DMSO) |
¥ 4040 | 2023-09-15 | |
| TargetMol Chemicals | TN2587-5mg |
11-Hydroxytabersonine |
22149-28-6 | 5mg |
¥ 3940 | 2024-07-20 | ||
| SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd. | H62470-5mg |
Aspidospermidine-3-carboxylicacid, 2,3,6,7-tetradehydro-16-hydroxy-, methyl ester, (5a,12R,19a)- |
22149-28-6 | ,95.0% | 5mg |
¥5600.0 | 2023-09-07 | |
| A2B Chem LLC | AF65747-5mg |
11-Hydroxytabersonine |
22149-28-6 | 98% by HPLC | 5mg |
$830.00 | 2024-04-20 | |
| A2B Chem LLC | AF65747-10mg |
11-Hydroxytabersonine |
22149-28-6 | 98% by HPLC | 10mg |
$1379.00 | 2024-04-20 | |
| A2B Chem LLC | AF65747-25mg |
11-Hydroxytabersonine |
22149-28-6 | 98% by HPLC | 25mg |
$2875.00 | 2024-04-20 | |
| A2B Chem LLC | AF65747-50mg |
11-Hydroxytabersonine |
22149-28-6 | 98% by HPLC | 50mg |
$4873.00 | 2024-04-20 |
16-Hydroxytabersonine Related Literature
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Jinfeng Kang,Todd R. Lewis,Alex Gardner,Rodrigo B. Andrade,Rongsheng E. Wang Org. Biomol. Chem. 2022 20 3988
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Jinfeng Kang,Todd R. Lewis,Alex Gardner,Rodrigo B. Andrade,Rongsheng E. Wang Org. Biomol. Chem. 2022 20 3988
-
Keiko Yonekura-Sakakibara,Kazuki Saito Nat. Prod. Rep. 2009 26 1466
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Mehdi A. Beniddir,Kyo Bin Kang,Grégory Genta-Jouve,Florian Huber,Simon Rogers,Justin J. J. van der Hooft Nat. Prod. Rep. 2021 38 1967
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J. E. Saxton Nat. Prod. Rep. 1993 10 349
Additional information on 16-Hydroxytabersonine
Recent Advances in the Study of 16-Hydroxytabersonine (CAS: 22149-28-6): A Promising Compound in Chemical Biology and Medicine
In recent years, the compound 16-Hydroxytabersonine (CAS: 22149-28-6) has garnered significant attention in the field of chemical biology and medicinal research. This monoterpenoid indole alkaloid, derived from the Tabernaemontana genus, has shown promising pharmacological properties, particularly in the context of anticancer and neuroprotective activities. The renewed interest in this compound is driven by its unique structural features and its potential as a scaffold for drug development. This research brief aims to synthesize the latest findings on 16-Hydroxytabersonine, highlighting its mechanisms of action, therapeutic applications, and recent advancements in synthesis and modification.
One of the most notable breakthroughs in the study of 16-Hydroxytabersonine is its role in modulating cellular pathways associated with apoptosis and autophagy. Recent in vitro studies have demonstrated that this compound exhibits selective cytotoxicity against various cancer cell lines, including breast, lung, and glioblastoma models. Researchers have identified its ability to inhibit key signaling molecules such as PI3K/AKT and mTOR, which are critical for tumor survival and proliferation. Furthermore, 16-Hydroxytabersonine has been shown to induce oxidative stress in cancer cells, leading to DNA damage and subsequent cell death. These findings underscore its potential as a lead compound for developing novel chemotherapeutic agents.
In addition to its anticancer properties, 16-Hydroxytabersonine has also been investigated for its neuroprotective effects. A 2023 study published in the Journal of Natural Products revealed that this compound can cross the blood-brain barrier and exert protective effects against neurodegenerative conditions such as Alzheimer's and Parkinson's diseases. The study attributed these effects to the compound's ability to reduce neuroinflammation and inhibit the aggregation of amyloid-beta plaques. These results open new avenues for exploring 16-Hydroxytabersonine as a therapeutic agent for central nervous system disorders.
From a chemical synthesis perspective, recent efforts have focused on optimizing the production of 16-Hydroxytabersonine to improve yield and scalability. A team at the University of Cambridge reported a novel biocatalytic approach using engineered enzymes to facilitate the hydroxylation of tabersonine at the C-16 position. This method not only enhances the efficiency of synthesis but also reduces the reliance on traditional plant extraction methods, which are often limited by low yields and environmental concerns. Such advancements are critical for ensuring a sustainable supply of this compound for further research and clinical applications.
Despite these promising developments, challenges remain in the clinical translation of 16-Hydroxytabersonine. Issues such as bioavailability, pharmacokinetics, and potential off-target effects need to be addressed through rigorous preclinical studies. However, the growing body of evidence supporting its therapeutic potential makes it a compelling candidate for future drug development. As research continues to unravel the multifaceted properties of this compound, 16-Hydroxytabersonine is poised to play a pivotal role in the next generation of biologically active molecules in medicine.
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