Terrein

Names
IUPAC name

(4S,5R)-4,5-Dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one

Identifiers

CAS Number

* 582-46-7

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL506722

ChemSpider |

* 4941440

PubChem CID

* 6436830

UNII |

* 3I47HPE16N

InChI

* InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1

Key: MHOOPNKRBMHHEC-HZIBQTDNSA-N

SMILES

* C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O

Properties

Chemical formula

| C8H10O3
Molar mass | 154.165 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Terrein is a fungal metabolite of Aspergillus species.[1] Terrein forms pale yellow crystal needles.[1][2] Terrein has a strong cytotoxic activity against cells with colorectal carcinoma.[1] The strain S020 from the fungus Aspergillus terreus has the highest rate in producing terrein.[1]

## References

1. ↑ 1.0 1.1 1.2 1.3 Asfour, Hani Z.; Awan, Zuhier A.; Bagalagel, Alaa A.; Elfaky, Mahmoud A.; Abdelhameed, Reda F. A.; Elhady, Sameh S. (12 September 2019). "Large-Scale Production of Bioactive Terrein by Aspergillus terreus Strain S020 Isolated from the Saudi Coast of the Red Sea". Biomolecules 9 (9): 480. doi:10.3390/biom9090480. ISSN 2218-273X. PMID 31547354.
2. ↑ "Terrein" (in de). Biomol GMBH - Life Science Shop. https://www.biomol.com/de/produkte/chemikalien/biochemikalien/terrein-cay23496-1.

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*[CID]: Compound ID