Madecassoside

Identification

Generic Name

Madecassoside

DrugBank Accession Number

DB15532

Background

Not Available

Type

Small Molecule

Groups

Experimental

Structure

Download

MOLSDFPDBSMILESInChI

Similar Structures

Structure for Madecassoside (DB15532)

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Weight

Average: 975.132
Monoisotopic: 974.508644912

Chemical Formula

C₄₈H₇₈O₂₀

Synonyms

• Asiaticoside A
• Redermic

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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

Not Available

Products

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
CareMe Madecassoside Cica Derma Repair Control Treatment	Cream	0.1 g/100mL	Topical	MIRINAGLOBAL	2020-03-21	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dr.Different CICA Metal	Madecassoside (0.26 g/100g) + Asiaticoside (0.012 g/100g)	Cream	Topical	Dareun Cosmetics Co., Ltd.	2021-05-01	Not applicable
Dr.Different CICA Metal Calming Pad	Madecassoside (0.009 g/90mL) + Centella asiatica (0.045 g/90mL)	Liquid	Topical	Dareun Cosmetics Co., Ltd.	2021-09-01	Not applicable
Karatica Im Cica Essence Pack	Madecassoside (0.01 g/100mL) + Asiatic acid (0.01 g/100mL) + Asiaticoside (0.01 g/100mL) + Madecassic acid (0.01 g/100mL)	Liquid	Topical	Karatica Co., Ltd	2019-08-17	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
CareMe Madecassoside Cica Derma Repair Control Treatment	Madecassoside (0.1 g/100mL)	Cream	Topical	MIRINAGLOBAL	2020-03-21	Not applicable
Dr.Different CICA Metal	Madecassoside (0.26 g/100g) + Asiaticoside (0.012 g/100g)	Cream	Topical	Dareun Cosmetics Co., Ltd.	2021-05-01	Not applicable
Dr.Different CICA Metal Calming Pad	Madecassoside (0.009 g/90mL) + Centella asiatica (0.045 g/90mL)	Liquid	Topical	Dareun Cosmetics Co., Ltd.	2021-09-01	Not applicable
Karatica Im Cica Essence Pack	Madecassoside (0.01 g/100mL) + Asiatic acid (0.01 g/100mL) + Asiaticoside (0.01 g/100mL) + Madecassic acid (0.01 g/100mL)	Liquid	Topical	Karatica Co., Ltd	2019-08-17	Not applicable

Categories

Drug Categories

• Terpenes

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Triterpenoids / Oligosaccharides / 12-beta-hydroxysteroids / 7-alpha-hydroxysteroids / O-glycosyl compounds / Oxanes / Secondary alcohols / Cyclic alcohols and derivatives / Carboxylic acid esters / Polyols / Monocarboxylic acids and derivatives / Acetals / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Primary alcohols

show 7 more

Substituents

12-beta-hydroxysteroid / 12-hydroxysteroid / 7-alpha-hydroxysteroid / 7-hydroxysteroid / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Glycosyl compound / Hydrocarbon derivative / Hydroxysteroid / Monocarboxylic acid or derivatives / O-glycosyl compound / Oligosaccharide / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound / Oxacycle / Oxane / Polyol / Primary alcohol / Secondary alcohol / Steroid / Triterpene saponin / Triterpenoid

show 19 more

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

carboxylic ester, trisaccharide derivative, triterpenoid saponin, pentacyclic triterpenoid (CHEBI:66651)

Affected organisms

Not Available

Chemical Identifiers

UNII

CQ2F5O6YIY

CAS number

34540-22-2

InChI Key

BNMGUJRJUUDLHW-HCZMHFOYSA-N

InChI

InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46-,47-,48+/m1/s1

IUPAC Name

(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (1S,2R,4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

SMILES

[H][C@@]1(O[C@@H]2[C@@H](CO)O[C@@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CC[C@@H](C)[C@H](C)[C@@]4([H])C4=CC[C@]6([H])[C@@]7(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@]7([H])[C@H](O)C[C@@]6(C)[C@]4(C)CC5)[C@H](O)[C@@H](O)[C@@H]3O)[C@H](O)[C@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

References

General References

Not Available

External Links

ChemSpider

28639016

BindingDB

23212

RxNav

87855

ChEBI

66651

ZINC

ZINC000253529433

Wikipedia

Centella_asiatica

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Cream	Topical	0.1 g/100mL
Cream	Topical
Liquid	Topical

Prices

Not Available

Patents

Not Available

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.71 mg/mL	ALOGPS
logP	-0.03	ALOGPS
logP	-1.8	Chemaxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.75	Chemaxon
pKa (Strongest Basic)	-3.6	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	19	Chemaxon
Hydrogen Donor Count	13	Chemaxon
Polar Surface Area	335.44 Å2	Chemaxon
Rotatable Bond Count	10	Chemaxon
Refractivity	234.14 m3·mol-1	Chemaxon
Polarizability	103.17 Å3	Chemaxon
Number of Rings	8	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0570-0200510039-2d8c7e1430c1937c3a69
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0000210029-f434d0164dd2e6531045
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01t9-0500210093-4996a23d43f72864a410
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0300110119-00b6196da79957522215
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a6r-2542093324-21b0d329ca5610d4ed8e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00g0-0230911341-39af8b75ee6a24fc8952

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	308.5596663	predicted	DarkChem Lite v0.1.0

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Drug created at October 09, 2019 21:52 / Updated at June 12, 2020 16:53