ChemFOnt: Showing chemical card for 8-O-Acetyl shanzhiside methyl ester (CFc000228409)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:54:16 UTC

Chemfont ID

CFc000228409

Molecule Identification

Common Name

8-O-Acetyl shanzhiside methyl ester

Definition

8-O-Acetyl shanzhiside methyl ester belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Based on a literature review very few articles have been published on 8-O-Acetyl shanzhiside methyl ester.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methyl 7-(acetyloxy)-5-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	HMDB

Chemical Formula

C₁₉H₂₈O₁₂

Average Molecular Weight

448.421

Monoisotopic Molecular Weight

448.158076342

IUPAC Name

methyl 7-(acetyloxy)-5-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl 7-(acetyloxy)-5-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C2C1C(O)CC2(C)OC(C)=O

InChI Identifier

InChI=1S/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3

InChI Key

ARFRZOLTIRQFCI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	21.1 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.6	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.98 m³·mol⁻¹	ChemAxon
Polarizability	43.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0248874

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

11660069

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18759764

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 8-O-Acetyl shanzhiside methyl ester (CFc000228409)

MOL for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

3D MOL for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

3D SDF for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

3D-SDF for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

PDB for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

3D PDB for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

SMILES for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

INCHI for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

Structure for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)

3D Structure for CFc000228409 (8-O-Acetyl shanzhiside methyl ester)