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 8504
angiogenesis 17 Target ID: GO:0001525 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25767375	Inhibitor 8504
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22522395	Inhibitor 8504
Apoptosis 156 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 1447

PubMed

Title	Date	PubMed
[Chemical constituents from stems and leaves of Clausena emarginata].	2019-05	31355567
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.	2018-08-07	30084434
Pleiotropic Effect of Mahanine and Girinimbine Analogs: Anticancer Mechanism and its Therapeutic Versatility.	2018	30173653
Anticancer and anti-inflammatory activities of girinimbine isolated from Murraya koenigii.	2017	28096658
Four new carbazole alkaloids from Murraya koenigii that display anti-inflammatory and anti-microbial activities.	2016-03-28	26947457
In vitro and in vivo anti-angiogenic activity of girinimbine isolated from Murraya koenigii.	2015	25767375
Efficient construction of pyrano[3,2-a]carbazoles: application to a biomimetic total synthesis of cyclized monoterpenoid pyrano[3,2-a]carbazole alkaloids.	2013-10-11	24030919
Apoptosis Effect of Girinimbine Isolated from Murraya koenigii on Lung Cancer Cells In Vitro.	2013	23573145
Chemical constituents from stem bark and roots of Clausena anisata.	2012-11-20	23169265
Anti-tumour promoting activity and antioxidant properties of girinimbine isolated from the stem bark of Murraya koenigii S.	2012-04-20	22522395
A new carbazole alkaloid from the leaves of Malayan Murraya koenigii.	2011-10	21972815
The growth suppressing effects of girinimbine on HepG2 involve induction of apoptosis and cell cycle arrest.	2011-08-23	21862957
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.	2011-04-07	21279228
Murrayakoeninol--a new carbazole alkaloid from Murraya koenigii (Linn) Spreng.	2009-03	19413112
Anti-trichomonal, biochemical and toxicological activities of methanolic extract and some carbazole alkaloids isolated from the leaves of Murraya koenigii growing in Nigeria.	2006-03	16492527
Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena dunniana Levl.	2002-12	12450250
[Study on carbazole alkaloids of Murraya microphylla].	1999-09	12571921
Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia.	1994-07-19	8053931
Antimicrobial activity of carbazole derivatives.	1982-05-15	7047201
Synthesis of girinimbine and (plus or minus) mahanimbine.	1970-04	5430996
On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine.	1970-03	5419188

Substance Class	Chemical Created by `admin` on `Tue Apr 01 19:59:04 GMT 2025` Edited by `admin` on `Tue Apr 01 19:59:04 GMT 2025`
Record UNII	WH639V7QSF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-94932

Preferred Name

English

GIRINIMBINE

Common Name

English

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

Systematic Name

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