GIRINIMBINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H17NO
Molecular Weight	263.3337
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C2OC(C)(C)C=CC2=C3NC4=C(C=CC=C4)C3=C1

InChI

InChIKey=GAEQWKVGMHUUKO-UHFFFAOYSA-N

InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C18H17NO
Molecular Weight	263.3337
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase (cyclooxygenase) 4 Target ID: CHEMBL2111358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8053931	Inhibitor 8297
angiogenesis 17 Target ID: GO:0001525 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25767375	Inhibitor 8297
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22522395	Inhibitor 8297
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21862957 \| https://www.ncbi.nlm.nih.gov/pubmed/30084434 \| https://www.ncbi.nlm.nih.gov/pubmed/12450250 \| https://www.ncbi.nlm.nih.gov/pubmed/23573145	Activator 1430

PubMed

Title	Date	PubMed
Synthesis of girinimbine and (plus or minus) mahanimbine.	1970 Apr	5430996
On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine.	1970 Mar	5419188
Antimicrobial activity of carbazole derivatives.	1982 May 15	7047201
Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia.	1994 Jul 19	8053931
Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena dunniana Levl.	2002 Dec	12450250
Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids--first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine.	2011 Apr 7	21279228
The growth suppressing effects of girinimbine on HepG2 involve induction of apoptosis and cell cycle arrest.	2011 Aug 23	21862957
A new carbazole alkaloid from the leaves of Malayan Murraya koenigii.	2011 Oct	21972815
Anti-tumour promoting activity and antioxidant properties of girinimbine isolated from the stem bark of Murraya koenigii S.	2012 Apr 20	22522395
In vitro and in vivo anti-angiogenic activity of girinimbine isolated from Murraya koenigii.	2015	25767375
Four new carbazole alkaloids from Murraya koenigii that display anti-inflammatory and anti-microbial activities.	2016 Mar 28	26947457
Anticancer and anti-inflammatory activities of girinimbine isolated from Murraya koenigii.	2017	28096658
Pleiotropic Effect of Mahanine and Girinimbine Analogs: Anticancer Mechanism and its Therapeutic Versatility.	2018	30173653
Girinimbine Inhibits the Proliferation of Human Ovarian Cancer Cells In Vitro via the Phosphatidylinositol-3-Kinase (PI3K)/Akt and the Mammalian Target of Rapamycin (mTOR) and Wnt/β-Catenin Signaling Pathways.	2018 Aug 7	30084434
[Chemical constituents from stems and leaves of Clausena emarginata].	2019 May	31355567

Substance Class	Chemical Created by `admin` on `Sat Dec 16 12:55:29 GMT 2023` Edited by `admin` on `Sat Dec 16 12:55:29 GMT 2023`
Record UNII	WH639V7QSF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GIRINIMBINE

Common Name

English

Pyrano[3,2-a]carbazole, 3,11-dihydro-3,3,5-trimethyl-

Systematic Name

English

NSC-94932

Code

English

3,3,5-Trimethyl-11H-pyrano[3,2-a]carbazole

Systematic Name

English

Girinimbin

Common Name

English

3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Girinimbine