ChemFOnt: Showing chemical card for 4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid (CFc000237424)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:10:46 UTC

Chemfont ID

CFc000237424

Molecule Identification

Common Name

4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid

Definition

p-Dihydroartemisininoxymethylbenzoic acid belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins. Based on a literature review a significant number of articles have been published on p-Dihydroartemisininoxymethylbenzoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
p-Dihydroartemisininoxymethylbenzoate	Generator
Artelinic acid	Generator
4-[({1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0,.0,]hexadecan-10-yl}oxy)methyl]benzoate	Generator

Chemical Formula

C₂₃H₃₀O₇

Average Molecular Weight

418.486

Monoisotopic Molecular Weight

418.199153306

IUPAC Name

4-[({1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl}oxy)methyl]benzoic acid

Traditional Name

4-[({1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl}oxy)methyl]benzoic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2C(C)C(OCC3=CC=C(C=C3)C(O)=O)OC3OC4(C)CCC1C23OO4

InChI Identifier

InChI=1S/C23H30O7/c1-13-4-9-18-14(2)20(26-12-15-5-7-16(8-6-15)19(24)25)27-21-23(18)17(13)10-11-22(3,28-21)29-30-23/h5-8,13-14,17-18,20-21H,4,9-12H2,1-3H3,(H,24,25)

InChI Key

UVNHKOOJXSALHN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Artemisinins

Alternative Parents

Substituents

Artemisinin skeleton
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Oxepane
Monocyclic benzene moiety
Benzenoid
1,2,4-trioxane
Oxane
Dialkyl peroxide
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.0063 g/L	ALOGPS
logP	3.79	ALOGPS
logP	4.86	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.53 m³·mol⁻¹	ChemAxon
Polarizability	44.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0257900

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

469841

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

539547

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid (CFc000237424)

MOL for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

3D MOL for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

3D SDF for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

3D-SDF for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

PDB for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

3D PDB for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

SMILES for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

INCHI for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

Structure for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)

3D Structure for CFc000237424 (4-[[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxymethyl]benzoic acid)