ChemFOnt: Showing chemical card for 6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000163873)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:55:05 UTC

Chemfont ID

CFc000163873

Molecule Identification

Common Name

Definition

6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-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-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₈H₅₂O₂₀

Average Molecular Weight

828.814

Monoisotopic Molecular Weight

828.305194074

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C38H52O20/c1-17(11-7-13-19(3)34(51)57-36-29(47)25(43)23(41)21(15-39)53-36)9-5-6-10-18(2)12-8-14-20(4)35(52)58-38-32(27(45)24(42)22(16-40)54-38)56-37-30(48)26(44)28(46)31(55-37)33(49)50/h5-14,21-32,36-48H,15-16H2,1-4H3,(H,49,50)/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+

InChI Key

WPSFORSINNWYGT-QHUUTLAPSA-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
Diterpenoid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Pyran
Oxane
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Oxacycle
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Primary alcohol
Hydrocarbon derivative
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	0.28 g/L	ALOGPS
logP	1.15	ALOGPS
logP	-1.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.09	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	329.12 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	200.94 m³·mol⁻¹	ChemAxon
Polarizability	85.99 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

HMDB0183583

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-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000163873)

MOL for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000163873 (6-{[4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-16-oxo-16-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,4,6,8,10,12,14-heptaenoyl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)