DIMETHYLAMINOPARTHENOLIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H27NO3
Molecular Weight	293.4012
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC(C)=CCC[C@@]3(C)O[C@@H]3[C@@]1([H])OC(=O)[C@@H]2CN(C)C

InChI

InChIKey=UJNSFDHVIBGEJZ-CMRIBGNTSA-N

InChI=1S/C17H27NO3/c1-11-6-5-9-17(2)15(21-17)14-12(8-7-11)13(10-18(3)4)16(19)20-14/h6,12-15H,5,7-10H2,1-4H3/b11-6-/t12-,13+,14-,15+,17+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H27NO3
Molecular Weight	293.4012
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:32:25 UTC 2023` Edited by `admin` on `Sat Dec 16 11:32:25 UTC 2023`
Record UNII	U41S5CG0SG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMETHYLAMINOPARTHENOLIDE

Common Name

English

(1AR,4E,7AS,8S,10AS,10BR)-8-((DIMETHYLAMINO)METHYL)-2,3,6,7,7A,8,10A,10B-OCTAHYDRO-1A,5-DIMETHYLOXIRENO(9,10)CYCLODECA(1,2-B)FURAN-9(1AH)-ONE

Systematic Name

English

DMAPT

Common Name

English

NSC-734325

Code

English

OXIRENO(9,10)CYCLODECA(1,2-B)FURAN-9(1AH)-ONE, 8-((DIMETHYLAMINO)METHYL)-2,3,6,7,7A,8,10A,10B-OCTAHYDRO-1A,5-DIMETHYL-, (1AR,4E,7AS,8S,10AS,10BR)-

Systematic Name

English

LC-1

Code

English

Code System Code Type Description

FDA UNII

U41S5CG0SG

Created by admin on Sat Dec 16 11:32:25 UTC 2023 , Edited by admin on Sat Dec 16 11:32:25 UTC 2023

PRIMARY

NSC

734325

Created by admin on Sat Dec 16 11:32:25 UTC 2023 , Edited by admin on Sat Dec 16 11:32:25 UTC 2023

PRIMARY

CAS

870677-05-7

Created by admin on Sat Dec 16 11:32:25 UTC 2023 , Edited by admin on Sat Dec 16 11:32:25 UTC 2023

PRIMARY

PUBCHEM

129395999

Created by admin on Sat Dec 16 11:32:25 UTC 2023 , Edited by admin on Sat Dec 16 11:32:25 UTC 2023

PRIMARY

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DIMETHYLAMINOPARTHENOLIDE

ACTIVE MOIETY

Comments:

Class: Antineoplastic, Sesquiterpene, Small molecule; Mechanism of Action: Apoptosis stimulant, NF-kappa B inhibitor; Highest Development Phase: Suspended for Acute myeloid leukaemia; Most Recent Events: 31 Dec 2009 Suspended - Phase-I for Acute myeloid leukaemia in United Kingdom (PO), 28 Jan 2009 Phase I clinical trials in Acute myeloid leukaemia in United Kingdom (PO)


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DIMETHYLAMINOPARTHENOLIDE

ACTIVE MOIETY

Comments:

RESULTS: The 32-week trial showed that 40 mg/kg DMAPT alone significantly decreased the size of gross pancreatic cancers relative to placebo. No significant difference in gross tumor number was observed between the treatment groups and placebo with the exception of 50 mg/kg celecoxib with a higher tumor incidence this group also exhibited lower lymphotactin levels suggestive of decreased immune surveillance. Tumor invasion into adjacent organs and metastasis were not observed in the DMAPT/celecoxib treatment groups. Drug targets including prostaglandin E2, prostaglandin E2 metabolite and activated nuclear factor kappaB were significantly decreased.


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DIMETHYLAMINOPARTHENOLIDE

ACTIVE MOIETY

Comments:

Abstract #1718: Dimethylaminoparthenolide targets apoptotic machinery in glioblastoma through ROS generation and NF\#954-B inhibition