ChemFOnt: Showing chemical card for Ponasteroside A (CFc000015170)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:13 UTC

Chemfont ID

CFc000015170

Molecule Identification

Common Name

Ponasteroside A

Definition

Ponasteroside A, also known as warabisterone, is a member of the class of compounds known as steroidal glycosides. Steroidal glycosides are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Ponasteroside A is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ponasteroside A is found in green vegetables. Ponasteroside A has been isolated from Pteridium aquilinum (bracken fern).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Methylcyclobutanol	HMDB
Warabisterone	HMDB

Chemical Formula

C₃₃H₅₄O₁₁

Average Molecular Weight

626.7753

Monoisotopic Molecular Weight

626.36661257

IUPAC Name

14-(2,3-dihydroxy-6-methylheptan-2-yl)-4,11-dihydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

14-(2,3-dihydroxy-6-methylheptan-2-yl)-4,11-dihydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

20117-33-3

SMILES

CC(C)CCC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(OC5OC(CO)C(O)C(O)C5O)C(O)CC4(C)C3CCC12C

InChI Identifier

InChI=1S/C33H54O11/c1-16(2)6-7-25(37)32(5,41)24-9-11-33(42)18-12-20(35)19-13-22(43-29-28(40)27(39)26(38)23(15-34)44-29)21(36)14-30(19,3)17(18)8-10-31(24,33)4/h12,16-17,19,21-29,34,36-42H,6-11,13-15H2,1-5H3

InChI Key

CNAKQRUFJWYXIC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Cholesterol
Steroidal glycoside
Tetrahydroxy bile acid, alcohol, or derivatives
Cholestane-skeleton
Ecdysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Bile acid, alcohol, or derivatives
20-hydroxysteroid
Diterpenoid
Oxosteroid
Hydroxysteroid
2-hydroxysteroid
14-hydroxysteroid
6-oxosteroid
Delta-7-steroid
Terpene glycoside
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034091)

Source

Exogenous

Exogenous (HMDB: HMDB0034091)

Food

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Endogenous (HMDB: HMDB0034091)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.93 g/L	ALOGPS
logP	0.33	ALOGPS
logP	0.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	159.45 m³·mol⁻¹	ChemAxon
Polarizability	68.33 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012352

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

631338

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Ponasteroside A (CFc000015170)

MOL for CFc000015170 (Ponasteroside A)

3D MOL for CFc000015170 (Ponasteroside A)

3D SDF for CFc000015170 (Ponasteroside A)

3D-SDF for CFc000015170 (Ponasteroside A)

PDB for CFc000015170 (Ponasteroside A)

3D PDB for CFc000015170 (Ponasteroside A)

SMILES for CFc000015170 (Ponasteroside A)

INCHI for CFc000015170 (Ponasteroside A)

Structure for CFc000015170 (Ponasteroside A)

3D Structure for CFc000015170 (Ponasteroside A)