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 8297		10.0 µM [IC50]
sPLA2 1 Target ID: sPLA2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833149	Inhibitor 8297		1.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psoriasis 84 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20833149	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 substrate 1737	substrate 1037 inhibitor 1767	inhibitor 1852 substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Renal Organic Cation Transporter 1 CYP2C19 1478 CYP1A2 1524 P-gp 1461	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2C19 1553	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2C9 1819	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2D6 1891	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP3A4 1925	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
P-gp 1650	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
Renal Organic Cation Transporter 1	inhibitor 3277 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no

Drug as victim

Target	Modality	Activity
CYP2C9 1037	substrate 3367 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP2D6 1217	substrate 3367 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	no
CYP3A4 1737	substrate 3367 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	yes
P-gp 1537	substrate 3367 Sources: https://innovareacademics.in/journals/index.php/ijpps/article/view/25309	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
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
eMolecules	48601007	https://orderbb.emolecules.com/search/#?query=48601007

PubMed

Title	Date	PubMed
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 Sep 28	7575673
Simultaneous inhibition of renal phospholipase A(2) and glutathione synthesis by manoalide and DL-buthionine sulfoximine induces acute tubular dysfunction in rats.	2000 Mar-Apr	10729747

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 `Fri Dec 15 15:28:50 UTC 2023` Edited by `admin` on `Fri Dec 15 15:28:50 UTC 2023`
Record UNII	E1DK0157K9
Record Status	`Validated (UNII)`
Record Version

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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

Systematic Name

English

Code System Code Type Description

CAS

75088-80-1