Stachybotrin B
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| Category | Bioactive by-products |
| Catalog number | BBF-02954 |
| CAS | 144385-02-4 |
| Molecular Weight | 385.50 |
| Molecular Formula | C23H31NO4 |
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Description
It is produced by the strain of Stachyborrys sp. It has antimicrobial and antifungal activity.
Specification
| Synonyms | (+)-Stachybotrin B |
| IUPAC Name | (2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3,5-dihydroxy-2-methyl-3,4,8,9-tetrahydropyrano[2,3-e]isoindol-7-one |
| Canonical SMILES | CC(=CCCC(=CCCC1(C(CC2=C(C=C3C(=C2O1)CNC3=O)O)O)C)C)C |
| InChI | InChI=1S/C23H31NO4/c1-14(2)7-5-8-15(3)9-6-10-23(4)20(26)12-17-19(25)11-16-18(21(17)28-23)13-24-22(16)27/h7,9,11,20,25-26H,5-6,8,10,12-13H2,1-4H3,(H,24,27)/b15-9+/t20-,23-/m0/s1 |
| InChI Key | XGUHYRYUXUVLOK-BHNVPJQESA-N |
Properties
| Antibiotic Activity Spectrum | Fungi |
| Melting Point | 178-180°C |
| Solubility | Soluble in Methanol, Chloroform, Ethyl Acetate |
Reference Reading
1. Synthesis of tricyclic pyrano[2,3-e]isoindolin-3-ones as the core structure of stachybotrin A, B, and C
Seiichi Inoue, Riyoung Kim, Yujiro Hoshino, Kiyoshi Honda Chem Commun (Camb). 2006 May 14;(18):1974-6. doi: 10.1039/b601433j. Epub 2006 Apr 3.
The substituted tricyclic pyrano[2,3-e]isoindolin-3-ones and , as the core structure of stachybotrin A, B, and C (), have been regioselectively synthesized for the first time by a short route which involved Mannich reaction and Claisen rearrangement.
2. Isolation and absolute configuration of SMTP-0, a simplest congener of the SMTP family nonlysine-analog plasminogen modulators
Keiji Hasumi, Keiko Hasegawa, Yoshikazu Kitano J Antibiot (Tokyo). 2007 Jul;60(7):463-8. doi: 10.1038/ja.2007.60.
SMTP-0, a new simple congener of the SMTP nonlysine-analog plasminogen modulators, was isolated from a culture of Stachybotrys microspora. Based on the physico-chemical data, SMTP-0 was shown to be an enantiomer of the antimicrobial compound stachybotrin B. The absolute configuration of SMTP-0 was determined by the modified Mosher method. The stereochemistry was further confirmed using an epimer of SMTP-0. Unlike most SMTPs with an amino acid side chain linked to the nitrogen atom of the lactam moiety, SMTP-0, which lacks the N-linked side chain, showed no plasminogen modulator activity.
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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 ╳
