Madecassoside (CED0008472)

Record Information

Version

1.0

Creation Date

2016-05-26 04:08:52 UTC

Update Date

2026-05-14 19:51:42 UTC

SynCED ID

CED0008472

Secondary Accession Numbers

CHEM033415

Identification

Common Name

Madecassoside

Class

Small Molecule

Description

Madecassoside is an organic compound with the chemical formula C48H78O20. Madecassoside belongs to the terpene glycosides, a subclass of prenol lipids within the organic compounds. With an average molecular weight of 975.12 g/mol, Madecassoside is a heavy molecule. In industrial applications, this substance is utilized as an antioxidant, as well as a softener and conditioner.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Asiaticoside a	HMDB, MeSH
6-({[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 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-carboxylic acid	Generator
Madecassoside	MeSH

Chemical Formula

C₄₈H₇₈O₂₀

Average Molecular Mass

975.121 g/mol

Monoisotopic Mass

974.509 g/mol

CAS Registry Number

34540-22-2

IUPAC Name

6-({[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 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

Traditional Name

6-({[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl 8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1H-picene-4a-carboxylate

SMILES

CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(CO)C5C(O)CC34C)C2C1C)C(=O)OC1OC(COC2OC(CO)C(OC3OC(C)C(O)C(O)C3O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

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

InChI Key

BNMGUJRJUUDLHW-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.71 g/L	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	102.02 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1000000009-1514f9a005de8d37fa38	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0710090000-36ac87f2d49ea70dec9a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fa9-0221911012-383879a6d8fe31462b2e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0112020009-c8aae0b49ab9bbda40b4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-0201910000-46ab97f6d3e1dd039b1f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0100710009-319fcd649102fc946bff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0422950000-16ca9209482d4e7d10d6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xr-0000830009-ec55540eb2fe1b2df257	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fa9-0221911012-a543e04e1df1b2c664b5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fk9-0000070009-e58f572a5ea9becc52ce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0704960003-b58f6f62803f694bfe51	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-2811090000-1c2b7491c32c741a5c13	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0000000009-057565a69873a88304c2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0200090010-60198b412c614e6bc10b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-0001920047-98e1b7e96c967e98973b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-07br-0201923071-d7048d8205ba3ebae8cc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bvr-2616940062-ba4c29fe57c5a95aac9d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4r-1111731039-bec186e7638d7fb24b44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4725940168-b7b3b2d773136d069553	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-7951280110-81a0114e6e022e676aa2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000210019-a59e55bbfb3c04b68fe9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05bg-2200100209-2e30dd401fe5791905f8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dr-2100900110-4ee1d65bdbc977fe24e2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0500300029-aab3659ddb8d6c15997d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fs-1601211093-304aa039d20b7fb2ff06	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-7911140001-6de7e5e6c8ac26633cb8	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000609	Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.	Personal care & cosmetics	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000612	Body Washing Or Cleaning Implements?Body washing or cleaning implements, such as synthetic sponges, loofahs, and washcloths, can be sources of synthetic chemical contamination due to the materials used in their production.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1	P54751	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.466 Applicability Domain 0.466 Statistical Significance 5.00e-05 Supporting Reference Compounds 1 E-value 0.389246
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	Prediction Confidence Score 0.4 Applicability Domain 0.485 Statistical Significance 0.0022 Supporting Reference Compounds 54 E-value 16.8933
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	Prediction Confidence Score 0.373 Applicability Domain 0.414 Statistical Significance 0.0025 Supporting Reference Compounds 197 E-value 19.618
Click to view 3D structure	Hemagglutinin	B4URE7	Influenza A virus	Predicted (SEA)	Prediction Confidence Score 0.352 Applicability Domain 0.488 Statistical Significance 1.50e-04 Supporting Reference Compounds 2 E-value 1.16774
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	Prediction Confidence Score 0.348 Applicability Domain 0.485 Statistical Significance 0.0039 Supporting Reference Compounds 94 E-value 30.7504
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Predicted (SEA)	Prediction Confidence Score 0.338 Applicability Domain 0.485 Statistical Significance 0.0023 Supporting Reference Compounds 49 E-value 17.9832
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 2	P17706	Humans	Predicted (SEA)	Prediction Confidence Score 0.306 Applicability Domain 0.376 Statistical Significance 0.0017 Supporting Reference Compounds 60 E-value 13.3122
Click to view 3D structure	FUN14 domain-containing protein 1	Q8IVP5	Humans	Predicted (SEA)	Prediction Confidence Score 0.305 Applicability Domain 0.305 Statistical Significance 5.50e-04 Supporting Reference Compounds 1 E-value 4.28171
Click to view 3D structure	Endo-beta-N-acetylglucosaminidase	Q9ZB22	Arthrobacter protophormiae	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.294 Low confidence Statistical Significance 1.30e-04 Supporting Reference Compounds 1 E-value 1.01204
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	Prediction Confidence Score 0.291 Applicability Domain 0.414 Statistical Significance 0.029 Supporting Reference Compounds 425 E-value 225.607
Click to view 3D structure	11-beta-hydroxysteroid dehydrogenase 1	P28845	Humans	Predicted (SEA)	Prediction Confidence Score 0.287 Applicability Domain 0.414 Statistical Significance 0.0032 Supporting Reference Compounds 76 E-value 25.0674
Click to view 3D structure	Protease	Q9YQ12	Human immunodeficiency virus 1	Predicted (SEA)	Prediction Confidence Score 0.278 Applicability Domain 0.376 Statistical Significance 0.0064 Supporting Reference Compounds 31 E-value 49.59
Click to view 3D structure	Alpha-amylase	Q7M328	Sus scrofa domesticus	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.266 Low confidence Statistical Significance 1.50e-04 Supporting Reference Compounds 1 E-value 1.16774
Click to view 3D structure	Tissue factor	P13726	Humans	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.343 Statistical Significance 0.0083 Supporting Reference Compounds 29 E-value 64.537
Click to view 3D structure	Solute carrier organic anion transporter family member 1B2	Q9QZX8	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.26 Applicability Domain 0.26 Low confidence Statistical Significance 4.60e-04 Supporting Reference Compounds 1 E-value 3.58106
Click to view 3D structure	Glycogen phosphorylase, muscle form	P00489	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.376 Statistical Significance 5.50e-04 Supporting Reference Compounds 13 E-value 4.28171
Click to view 3D structure	E-selectin	P98105	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.254 Low confidence Statistical Significance 1.70e-04 Supporting Reference Compounds 1 E-value 1.32344
Click to view 3D structure	Chitin synthase 1	P08004	Saccharomyces cerevisiae S288c	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.404 Statistical Significance 1.80e-04 Supporting Reference Compounds 2 E-value 1.40129
Click to view 3D structure	N-acetyllactosaminide alpha-1,3-galactosyltransferase	P50127	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.243 Low confidence Statistical Significance 0.0012 Supporting Reference Compounds 1 E-value 9.73115
Click to view 3D structure	DNA polymerase beta	P06766	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.239 Applicability Domain 0.376 Statistical Significance 6.80e-04 Supporting Reference Compounds 6 E-value 5.29375
Click to view 3D structure	Glycogen [starch] synthase, liver	P54840	Humans	Predicted (SEA)	Prediction Confidence Score 0.235 Applicability Domain 0.235 Low confidence Statistical Significance 0.001 Supporting Reference Compounds 1 E-value 7.86277
Click to view 3D structure	Glucose-6-phosphatase catalytic subunit 1	P43428	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.235 Applicability Domain 0.235 Low confidence Statistical Significance 0.001 Supporting Reference Compounds 1 E-value 7.86277
Click to view 3D structure	Prostaglandin E synthase	O14684	Humans	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.311 Statistical Significance 0.0608 Supporting Reference Compounds 69 E-value 473.012
Click to view 3D structure	Galectin-3	P17931	Humans	Predicted (SEA)	Prediction Confidence Score 0.225 Applicability Domain 0.273 Low confidence Statistical Significance 0.0038 Supporting Reference Compounds 23 E-value 29.6606
Click to view 3D structure	Lysine-specific histone demethylase 1A	O60341	Humans	Predicted (SEA)	Prediction Confidence Score 0.224 Applicability Domain 0.297 Low confidence Statistical Significance 0.1345 Supporting Reference Compounds 85 E-value 1046.99