ChemFOnt: Showing chemical card for Luteoxanthin (CFc000282580)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:04 UTC

Chemfont ID

CFc000282580

Molecule Identification

Common Name

Luteoxanthin

Definition

Luteoxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Luteoxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Luteoxanthin can be found in a number of food items such as yellow bell pepper, pepper (c. annuum), green bell pepper, and apple, which makes luteoxanthin a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-beta,beta-carotene-3,3'-diol	ChEBI
5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-b,b-carotene-3,3'-diol	Generator
5,6:5',8'-Diepoxy-5,6,5',8'-tetrahydro-β,β-carotene-3,3'-diol	Generator

Chemical Formula

C₄₀H₅₆O₄

Average Molecular Weight

600.8702

Monoisotopic Molecular Weight

600.41786028

IUPAC Name

2-[(2E,4E,6E,8E,10E,12E,14E,16E)-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-6-ol

Traditional Name

luteoxanthin

CAS Registry Number

None

SMILES

C\C(\C=C\C=C(/C)\C=C\C12OC1(C)CC(O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C1

InChI Identifier

InChI=1S/C40H56O4/c1-28(17-13-18-30(3)21-22-40-37(7,8)25-33(42)27-39(40,10)44-40)15-11-12-16-29(2)19-14-20-31(4)34-23-35-36(5,6)24-32(41)26-38(35,9)43-34/h11-23,32-34,41-42H,24-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21+,28-15+,29-16+,30-18+,31-20+

InChI Key

YNNRPBRNWWIQPQ-OMSIYMKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Benzofuran
Oxepane
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxycarotenol (CHEBI:35334 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303064)

Food

Fruit

Pome

Apple (FooDB: FOOD00105)

Berry

Common grape (FooDB: FOOD00204)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00063 g/L	ALOGPS
logP	8.21	ALOGPS
logP	6.99	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.22 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	192.2 m³·mol⁻¹	ChemAxon
Polarizability	74.79 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

HMDB0303064

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007578

KNApSAcK ID

Not Available

Chemspider ID

16736329

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14251665

PDB ID

Not Available

ChEBI ID

35334

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Luteoxanthin (CFc000282580)

MOL for CFc000282580 (Luteoxanthin)

3D MOL for CFc000282580 (Luteoxanthin)

3D SDF for CFc000282580 (Luteoxanthin)

3D-SDF for CFc000282580 (Luteoxanthin)

PDB for CFc000282580 (Luteoxanthin)

3D PDB for CFc000282580 (Luteoxanthin)

SMILES for CFc000282580 (Luteoxanthin)

INCHI for CFc000282580 (Luteoxanthin)

Structure for CFc000282580 (Luteoxanthin)

3D Structure for CFc000282580 (Luteoxanthin)