ChemFOnt: Showing chemical card for Asperulosidic acid (CFc000228203)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:53:54 UTC

Chemfont ID

CFc000228203

Molecule Identification

Common Name

Asperulosidic acid

Definition

7-[(acetyloxy)methyl]-5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid 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. 7-[(acetyloxy)methyl]-5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-[(Acetyloxy)methyl]-5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator

Chemical Formula

C₁₈H₂₄O₁₂

Average Molecular Weight

432.378

Monoisotopic Molecular Weight

432.126776213

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=CC(O)C2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O

InChI Identifier

InChI=1S/C18H24O12/c1-6(20)27-4-7-2-9(21)12-8(16(25)26)5-28-17(11(7)12)30-18-15(24)14(23)13(22)10(3-19)29-18/h2,5,9-15,17-19,21-24H,3-4H2,1H3,(H,25,26)

InChI Key

DGDWCRWJRNMRKX-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
Vinylogous ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	19.6 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3.3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	94.33 m³·mol⁻¹	ChemAxon
Polarizability	40.85 Å³	ChemAxon
Number of Rings	3	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

Not Available

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

13935238

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Asperulosidic acid (CFc000228203)

MOL for CFc000228203 (Asperulosidic acid)

3D MOL for CFc000228203 (Asperulosidic acid)

3D SDF for CFc000228203 (Asperulosidic acid)

3D-SDF for CFc000228203 (Asperulosidic acid)

PDB for CFc000228203 (Asperulosidic acid)

3D PDB for CFc000228203 (Asperulosidic acid)

SMILES for CFc000228203 (Asperulosidic acid)

INCHI for CFc000228203 (Asperulosidic acid)

Structure for CFc000228203 (Asperulosidic acid)

3D Structure for CFc000228203 (Asperulosidic acid)