Drimentine C
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| Category | Antibiotics |
| Catalog number | BBF-04229 |
| CAS | 204398-92-5 |
| Molecular Weight | 487.68 |
| Molecular Formula | C31H41N3O2 |
| Purity | >98% by HPLC |
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Description
It is produced by the strain of Actinomycete strain MST-8651. It belongs to a novel class of antibiotics, possessing a new terpenylated diketopiperazine structure, with antibacterial, antifungal and anthelmintic activity.
Specification
| Synonyms | [5aS-[5aα,6aβ(1R*,4aR*,8aR*),11aβ,13aα]]-6a-[(Decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl)methyl]-2,3,6,6a,11,11a-hexahydro-1H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH,13aH)-dione; (5aS,6aS,11aS,13aS)-6a-(((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)-1,2,3,6,6a,11,11a,13a-octahydro-13H-pyrrolo[1'',2'':4',5']pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-5,13(5aH)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4S,10S,12S)-12-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-2,8,19-triazapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-13,15,17-triene-3,9-dione |
| Canonical SMILES | CC1(CCCC2(C1CCC(=C)C2CC34CC5C(=O)N6CCCC6C(=O)N5C3NC7=CC=CC=C47)C)C |
| InChI | InChI=1S/C31H41N3O2/c1-19-12-13-25-29(2,3)14-8-15-30(25,4)21(19)17-31-18-24-26(35)33-16-7-11-23(33)27(36)34(24)28(31)32-22-10-6-5-9-20(22)31/h5-6,9-10,21,23-25,28,32H,1,7-8,11-18H2,2-4H3/t21-,23-,24-,25-,28-,30+,31-/m0/s1 |
| InChI Key | FIEHMEZFTNYYIF-RJBXWAARSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Fungi; Parasites; Bacterial |
| Boiling Point | 651.4±55.0°C at 760 mmHg |
| Melting Point | 108-110°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Chloroform |
Reference Reading
1. Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments
Christopher J Douglas, Sarah M Pound, Steven J Underwood European J Org Chem . 2020 May 3;2020(16):2448-2453. doi: 10.1002/ejoc.202000158.
The drimentine family is a class of hybrid isoprenoids derived fromactinomycetebacteria. Members of this family display weak antitumor and antibacterial activity. Herein we report our efforts toward the total synthesis of drimentine C using three distinct approaches incorporating palladium-catalyzed cyanoamidation, reductive cross-coupling, and photoredox-catalyzed α-alkylation of an aldehyde as key steps. Our synthetic efforts use a convergent synthesis to assemble the terpenoid and alkaloid portions of drimentine C from readily available l-tryptophan, l-proline, and (+)-sclareolide.
2. Polycyclic hybrid isoprenoids from a reed rhizosphere soil derived Streptomyces sp. CHQ-64
Tianjiao Zhu, Qianqun Gu, Qian Che, Jing Li, Dehai Li, Robert A Keyzers, Xiaofang Liu J Nat Prod . 2013 Apr 26;76(4):759-63. doi: 10.1021/np3008864.
Two new hybrid isoprenoids, named indotertine B (2) and drimentine H (3), along with the known analogue drimentine C (4), were isolated from the reed rhizosphere soil derived actinomycete Streptomyces sp. CHQ-64. The structures of these compounds, including absolute configurations, were elucidated by extensive NMR, MS, and CD analyses. Indotertine B (2) exists as a pair of rotamers about the N-C(O) bond with a 2:1 ratio and displays activities against HCT-8 and A549 tumor cell lines with IC50 values of 6.96 and 4.88 μM, respectively.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
