ChemFOnt: Showing chemical card for 6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000160063)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:48:24 UTC

Chemfont ID

CFc000160063

Molecule Identification

Common Name

6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review very few articles have been published on 6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₄₃H₇₄O₁₄

Average Molecular Weight

815.051

Monoisotopic Molecular Weight

814.507857063

IUPAC Name

6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-5H-furan-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC(O)C1CC(O)C(O1)C1OC(CC1O)C(CCCCCCCCCCCCC1=CC(C)OC1=O)OC1OC(C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C43H74O14/c1-3-4-5-6-7-13-16-19-22-29(44)33-25-30(45)38(54-33)39-31(46)26-34(55-39)32(56-43-37(49)35(47)36(48)40(57-43)41(50)51)23-20-17-14-11-9-8-10-12-15-18-21-28-24-27(2)53-42(28)52/h24,27,29-40,43-49H,3-23,25-26H2,1-2H3,(H,50,51)

InChI Key

UTZFNOULSJPGMS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
C-glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	4.52	ALOGPS
logP	6.32	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	209.64 m³·mol⁻¹	ChemAxon
Polarizability	94.58 Å³	ChemAxon
Number of Rings	4	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

HMDB0179655

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000160063)

MOL for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000160063 (6-({1-[3,3'-dihydroxy-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]-13-(5-methyl-2-oxo-2,5-dihydrofuran-3-yl)tridecyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid)