ContaminantDB: Madecassoside

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 04:08:52 UTC

Update Date

2016-11-09 01:20:55 UTC

Accession Number

CHEM033415

Identification

Common Name

Madecassoside

Class

Small Molecule

Description

Madecassoside is found in green vegetables. Madecassoside is isolated from whole plants of Centella asiatica (Ji Xue Cao).

Contaminant Sources

FooDB Chemicals

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

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

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	0	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	View
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-1000000009-1514f9a005de8d37fa38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0710090000-36ac87f2d49ea70dec9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0fa9-0221911012-383879a6d8fe31462b2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0112020009-c8aae0b49ab9bbda40b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01b9-0201910000-46ab97f6d3e1dd039b1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0100710009-319fcd649102fc946bff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0gb9-0422950000-16ca9209482d4e7d10d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-00xr-0000830009-ec55540eb2fe1b2df257	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0fa9-0221911012-a543e04e1df1b2c664b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0fk9-0000070009-e58f572a5ea9becc52ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0704960003-b58f6f62803f694bfe51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-2811090000-1c2b7491c32c741a5c13	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0000000009-057565a69873a88304c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0200090010-60198b412c614e6bc10b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0001920047-98e1b7e96c967e98973b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-07br-0201923071-d7048d8205ba3ebae8cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvr-2616940062-ba4c29fe57c5a95aac9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-1111731039-bec186e7638d7fb24b44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4725940168-b7b3b2d773136d069553	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-7951280110-81a0114e6e022e676aa2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000210019-a59e55bbfb3c04b68fe9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05bg-2200100209-2e30dd401fe5791905f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-2100900110-4ee1d65bdbc977fe24e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0500300029-aab3659ddb8d6c15997d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fs-1601211093-304aa039d20b7fb2ff06	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum