ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid (CFc000149430)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:31:14 UTC

Chemfont ID

CFc000149430

Molecule Identification

Common Name

3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid

Definition

3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-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 3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylate	Generator

Chemical Formula

C₄₁H₇₄O₁₃

Average Molecular Weight

775.03

Monoisotopic Molecular Weight

774.512942443

IUPAC Name

3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC(OC1OC(C(O)C(O)C1O)C(O)=O)C1CCC(O1)C(O)CCCC(O)CCCCCCC(O)CC1CC(C)OC1=O

InChI Identifier

InChI=1S/C41H74O13/c1-3-4-5-6-7-8-9-10-11-16-22-33(53-41-37(47)35(45)36(46)38(54-41)39(48)49)34-24-23-32(52-34)31(44)21-17-20-29(42)18-14-12-13-15-19-30(43)26-28-25-27(2)51-40(28)50/h27-38,41-47H,3-26H2,1-2H3,(H,48,49)

InChI Key

VNRORCLNXJOWOZ-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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Long chain fatty alcohol
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Pyran
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Gamma butyrolactone
Hydroxy acid
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Dialkyl ether
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
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	0.014 g/L	ALOGPS
logP	4.29	ALOGPS
logP	6.02	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	200.9 m³·mol⁻¹	ChemAxon
Polarizability	91.01 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

HMDB0169022

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 3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid (CFc000149430)

MOL for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

3D MOL for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

3D SDF for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

3D-SDF for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

PDB for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

3D PDB for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

SMILES for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

INCHI for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

Structure for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)

3D Structure for CFc000149430 (3,4,5-trihydroxy-6-[(1-{5-[1,5,12-trihydroxy-13-(5-methyl-2-oxooxolan-3-yl)tridecyl]oxolan-2-yl}tridecyl)oxy]oxane-2-carboxylic acid)