TERRETONIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H32O9
Molecular Weight	488.5269
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C(=O)O[C@](C)(C(=O)OC)C(=O)[C@]1(C)C(=C)C[C@@]3(O)[C@]4(C)CCC(=O)C(C)(C)C4=C(O)C(=O)[C@]23C

InChI

InChIKey=CYHGEJACRPDZDP-RSQIKLETSA-N

InChI=1S/C26H32O9/c1-12-11-26(33)22(4)10-9-13(27)21(2,3)15(22)14(28)17(29)24(26,6)16-18(30)35-25(7,20(32)34-8)19(31)23(12,16)5/h16,28,33H,1,9-11H2,2-8H3/t16-,22+,23+,24-,25-,26+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H32O9
Molecular Weight	488.5269
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16124769
Curator's Comment: description was created based on several sources, including http://pubs.acs.org/doi/abs/10.1021/jo00394a023 | https://www.ncbi.nlm.nih.gov/pubmed/25671343

Terretonin is a sesterterpene isolated from Aspergillus terreus. Terretonin possesses a highly oxygenated and unique tetracyclic structure. Terretonin is toxic compound with LD50 on day-old cockerels between 250 and 375 mg/ kg.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Terretonin G, a new sesterterpenoid antibiotic from marine-derived Aspergillus sp. OPMF00272.	2014 Aug	24802208
Uncovering the unusual D-ring construction in terretonin biosynthesis by collaboration of a multifunctional cytochrome P450 and a unique isomerase.	2015 Mar 11	25671343

Patents

Sample Use Guides

In Vivo Use Guide

Terretonin toxicity was evaluated on day-old cockerels. Samples were dissolved in corn oil and administered orally via crop intubation at 1-mL per cockerel. The LD50, of Terretonin was between 250 and 375 mg/ kg.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:25:14 GMT 2023` Edited by `admin` on `Sat Dec 16 10:25:14 GMT 2023`
Record UNII	8795XG0M1T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERRETONIN

Common Name

English

TERRETONIN, (+)-

Common Name

English

2H-PHENANTHRO(1,2-C)PYRAN-2-CARBOXYLIC ACID, 1,4,4A,4B,5,7,8,9,10,10A,10B,11,12,12A-TETRADECAHYDRO-6,10B-DIHYDROXY-2,4B,7,7,10A,12A-HEXAMETHYL-12-METHYLENE-1,4,5,8-TETRAOXO-, METHYL ESTER, (2S,4AS,4BR,10AR,10BR,12AS)-

Systematic Name

English

D-HOMO-16-OXAANDROST-5-ENE-17-CARBOXYLIC ACID, 6,9-DIHYDROXY-4,4,8,17-TETRAMETHYL-12-METHYLENE-3,7,15,17A-TETRAOXO-, METHYL ESTER, (17.ALPHA.)-

Systematic Name

English

Code System Code Type Description

CAS

71911-90-5

Created by admin on Sat Dec 16 10:25:14 GMT 2023 , Edited by admin on Sat Dec 16 10:25:14 GMT 2023

PRIMARY

PUBCHEM

109374149

Created by admin on Sat Dec 16 10:25:14 GMT 2023 , Edited by admin on Sat Dec 16 10:25:14 GMT 2023

PRIMARY

FDA UNII

8795XG0M1T

Created by admin on Sat Dec 16 10:25:14 GMT 2023 , Edited by admin on Sat Dec 16 10:25:14 GMT 2023

PRIMARY

EPA CompTox

DTXSID80992611

Created by admin on Sat Dec 16 10:25:14 GMT 2023 , Edited by admin on Sat Dec 16 10:25:14 GMT 2023

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16124769Curator's Comment: description was created based on several sources, including http://pubs.acs.org/doi/abs/10.1021/jo00394a023 | https://www.ncbi.nlm.nih.gov/pubmed/25671343

Originator

Approval Year

Conditions

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16124769
Curator's Comment: description was created based on several sources, including http://pubs.acs.org/doi/abs/10.1021/jo00394a023 | https://www.ncbi.nlm.nih.gov/pubmed/25671343