ChemFOnt: Showing chemical card for 6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000163611)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:54:35 UTC

Chemfont ID

CFc000163611

Molecule Identification

Common Name

Definition

6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone. Based on a literature review very few articles have been published on 6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₈H₆₀O₂₀

Average Molecular Weight

836.878

Monoisotopic Molecular Weight

836.367794332

IUPAC Name

6-{[(1E,5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])CCC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C=C)=C(\C)CC(OC1OC(C(O)C(O)C1O)C(O)=O)C([H])=C(C)C(O)=O

InChI Identifier

InChI=1S/C38H60O20/c1-6-38(5,58-37-32(27(45)24(42)22(16-40)55-37)57-36-29(47)25(43)23(41)21(15-39)54-36)12-8-11-17(2)9-7-10-18(3)13-20(14-19(4)33(49)50)53-35-30(48)26(44)28(46)31(56-35)34(51)52/h6,10-11,14,20-32,35-37,39-48H,1,7-9,12-13,15-16H2,2-5H3,(H,49,50)(H,51,52)/b17-11+,18-10+,19-14+

InChI Key

NZIQSBNAYUSQML-DFTZOVBQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Sophorolipids

Alternative Parents

Substituents

Sophorolipid
Diterpene glycoside
Diterpenoid
Terpene glycoside
Long-chain fatty acid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Methyl-branched fatty acid
Beta-hydroxy acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Pyran
Hydroxy acid
Oxane
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxide
Organic oxygen compound
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	0.48 g/L	ALOGPS
logP	-0.15	ALOGPS
logP	-1.1	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	332.28 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	198.15 m³·mol⁻¹	ChemAxon
Polarizability	85.03 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

HMDB0183220

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-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000163611)

MOL for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000163611 (6-{[(5E,9E)-1-carboxy-13-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-1,5,9,13-tetramethylpentadeca-1,5,9,14-tetraen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)