MANOALIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H36O5
Molecular Weight	416.5503
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C\C(CCC1=C(C)CCCC1(C)C)=C/CCC2=CC[C@@H](O[C@H]2O)C3=CC(=O)O[C@H]3O

InChI

InChIKey=FGJIDQWRRLDGDB-CPIXEKRISA-N

InChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C25H36O5
Molecular Weight	416.5503
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3783861 | https://www.ncbi.nlm.nih.gov/pubmed/20833149

Manoalide is a sesquiterpenoid isolated from the Indo-Pacific sponge Luffariella variabilis. It is a potent analgesic and anti-inflammatory agent. Manoalide acts by inhibiting PLA2. At low concentrations, manoalide also inhibited calcium channels with no effect on phosphoinositide metabolism. Manoalide was licensed to Allergan Pharmaceuticals and reached Phase II clinical trials as a topical anti-psoriatic, its development was however, discontinued due to formulation problems.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytosolic phospholipase A2 7 Target ID: P47712 Gene ID: 5321.0 Gene Symbol: PLA2G4A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833149	Inhibitor 8504		10.0 µM [IC50]
sPLA2 1 Target ID: sPLA2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833149	Inhibitor 8504		1.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833149	Primary		Phase II 1147	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946	substrate 1193 inhibitor 2438	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT 1 CYP2C19 2057 CYP1A2 2153 P-gp 1741	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2C19 2141	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2C9 2497	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2D6 2546	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP3A4 2633	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
OCT 1	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
P-gp 1932	inhibitor 4027 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no

Drug as victim

Target	Modality	Activity
CYP2C9 1193	substrate 4014 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2D6 1388	substrate 4014 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP3A4 1946	substrate 4014 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	yes
P-gp 2052	substrate 4014 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309

Sourcing

Vendor/Aggregator	ID	URL
BOC Sciences	75088-80-1	http://www.bocsci.com/description.asp?cas=75088-80-1
Cayman Chemical	14903	http://www.caymanchem.com/app/template/Product.vm/catalog/14903
Compound Cloud	6437368
eMolecules	48601007	https://orderbb.emolecules.com/search/#?query=48601007
MolPort	MolPort-020-000-975	https://www.molport.com/shop/molecule-link/MolPort-020-000-975
MuseChem	R064927	https://www.musechem.com/product/R064927.html
Vesino Industrial Co Ltd	VA11234	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA11234

PubMed

Title	Date	PubMed
Simultaneous inhibition of renal phospholipase A(2) and glutathione synthesis by manoalide and DL-buthionine sulfoximine induces acute tubular dysfunction in rats.	2000-03-24	10729747
Regulation of prostaglandin H synthase 2 expression in human monocytes by the marine natural products manoalide and scalaradial. Novel effects independent of inhibition of lipid mediator production.	1995-09-28	7575673

Sample Use Guides

In Vivo Use Guide

Manoalide was used as a topical formulation.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:31 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:31 GMT 2025`
Record UNII	E1DK0157K9
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MANOALIDE

Common Name

English

(5R)-5-HYDROXY-4-((2R,6R)-6-HYDROXY-5-((E)-4-METHYL-6-(2,6,6-TRIMETHYL-1-CYCLOHEXENYL)HEX-3-ENYL)-3,6-DIHYDRO-2H-PYRAN-2-YL)-5H-FURAN-2-ONE

Preferred Name

English

Code System Code Type Description

CAS

75088-80-1