ChemFOnt: Showing chemical card for Saponins (CFc000281732)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:25 UTC

Chemfont ID

CFc000281732

Molecule Identification

Common Name

Saponins

Definition

Saponins, also known as aescin or opino, is a member of the class of compounds known as triterpene saponins. Triterpene saponins 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. Saponins is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Saponins can be found in a number of food items such as dandelion, soy bean, fenugreek, and carob, which makes saponins a potential biomarker for the consumption of these food products. Saponins are a class of chemical compounds found in particular abundance in various plant species. More specifically, they are amphipathic glycosides grouped phenomenologically by the soap-like foaming they produce when shaken in aqueous solutions, and structurally by having one or more hydrophilic glycoside moieties combined with a lipophilic triterpene derivative .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S,4S,5R,6R)-6-{[(3S,4S,6ar,6BS,8R,8ar,9R,10R,14BR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxane-2-carboxylate	Generator
Aescin	MeSH
Feparil	MeSH
Flebostasin	MeSH
Escin	MeSH
Opino	MeSH
beta Escin	MeSH
Escina	MeSH
sankyo Brand OF escin	MeSH
opino Biomo	MeSH
beta Aescin	MeSH
beta-Escin	MeSH
Reparil	MeSH
beta-Aescin	MeSH
biomo Brand OF escin	MeSH
Opinobiomo	MeSH
Aescusan	MeSH
Eskuzan	MeSH
Fepalitan	MeSH
opino-Biomo	MeSH
Madaus brand OF escin	MeSH

Chemical Formula

C₅₅H₈₆O₂₄

Average Molecular Weight

1131.269

Monoisotopic Molecular Weight

1130.550903649

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(3S,4S,6aR,6bS,8R,8aR,9R,10R,14bR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(3S,4S,6aR,6bS,8R,8aR,9R,10R,14bR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxane-2-carboxylic acid

CAS Registry Number

8047-15-2

SMILES

[H]\C(C)=C(/C)C(=O)O[C@@]1([H])[C@]([H])(OC(C)=O)[C@]2(CO)[C@]([H])(O)C[C@]3(C)C(=CCC4([H])[C@@]5(C)CC[C@]([H])(O[C@]6([H])O[C@]([H])(C(O)=O)[C@@]([H])(O[C@]7([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]7([H])O)[C@]([H])(O)[C@@]6([H])O[C@]6([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]6([H])O)[C@](C)(CO)C5([H])CC[C@@]34C)C2([H])CC1(C)C

InChI Identifier

InChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26?,27-,28-,29?,30?,31-,32+,33-,34-,35+,36+,37-,38-,39+,40+,41-,42+,43+,44+,47+,48+,49-,51+,52-,53-,54-,55+/m1/s1

InChI Key

AXNVHPCVMSNXNP-ZELRDNAQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Polyol
Carboxylic acid derivative
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302216)

Lentils (FooDB: FOOD00098)

Pea

Chickpea (FooDB: FOOD00047)

Soy

Soy bean (FooDB: FOOD00085)

Vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)
Taro (FooDB: FOOD00488)

Leaf vegetable

Spinach (FooDB: FOOD00178)
Jute (FooDB: FOOD00389)

Onion-family vegetable

Wild leek (FooDB: FOOD00396)
Garden onion (FooDB: FOOD00006)

Other vegetable

Carob (FooDB: FOOD00321)

Herb and spice

Herb

Oilseed crop

Sesame (FooDB: FOOD00170)
Borage (FooDB: FOOD00026)

Spice

Capers (FooDB: FOOD00039)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Fruit

Tropical fruit

Sapodilla (FooDB: FOOD00458)

Gourd

Calabash (FooDB: FOOD00318)

Not Available

Immunomodulator (HMDB: HMDB0302216)

Anti hepatomic (HMDB: HMDB0302216)
Anti mutagenic (HMDB: HMDB0302216)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0302216)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.77 g/L	ALOGPS
logP	1.17	ALOGPS
logP	-0.88	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.35	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	388.04 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	269.78 m³·mol⁻¹	ChemAxon
Polarizability	118.36 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

External Links

HMDB ID

HMDB0302216

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003695

KNApSAcK ID

Not Available

Chemspider ID

78433297

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6540709

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Saponins (CFc000281732)

MOL for CFc000281732 (Saponins)

3D MOL for CFc000281732 (Saponins)

3D SDF for CFc000281732 (Saponins)

3D-SDF for CFc000281732 (Saponins)

PDB for CFc000281732 (Saponins)

3D PDB for CFc000281732 (Saponins)

SMILES for CFc000281732 (Saponins)

INCHI for CFc000281732 (Saponins)

Structure for CFc000281732 (Saponins)

3D Structure for CFc000281732 (Saponins)