ChemFOnt: Showing chemical card for (13Z)-Violaxanthin (CFc000283300)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:26 UTC

Chemfont ID

CFc000283300

Molecule Identification

Common Name

(13Z)-Violaxanthin

Definition

(all-e)-violaxanthin 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 (all-e)-violaxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (all-e)-violaxanthin can be found in a number of food items such as pepper (c. annuum), mango, yellow bell pepper, and red bell pepper, which makes (all-e)-violaxanthin a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₀H₅₆O₄

Average Molecular Weight

600.8702

Monoisotopic Molecular Weight

600.41786028

IUPAC Name

6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Traditional Name

violaxanthin

CAS Registry Number

75715-58-1

SMILES

[H]/C(=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])C12OC1(C)CC(O)CC2(C)C)/C(/[H])=C(\C)/C(/[H])=C(\[H])/C(/[H])=C(\C)/C(/[H])=C(\[H])C12OC1(C)CC(O)CC2(C)C

InChI Identifier

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

InChI Key

SZCBXWMUOPQSOX-DKLMTRRASA-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
Oxepane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303784)

Food

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00057 g/L	ALOGPS
logP	8.33	ALOGPS
logP	7.26	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14.84	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.52 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	192.33 m³·mol⁻¹	ChemAxon
Polarizability	74.98 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

HMDB0303784

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021675

KNApSAcK ID

Not Available

Chemspider ID

22252489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6384269

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (13Z)-Violaxanthin (CFc000283300)

MOL for CFc000283300 ((13Z)-Violaxanthin)

3D MOL for CFc000283300 ((13Z)-Violaxanthin)

3D SDF for CFc000283300 ((13Z)-Violaxanthin)

3D-SDF for CFc000283300 ((13Z)-Violaxanthin)

PDB for CFc000283300 ((13Z)-Violaxanthin)

3D PDB for CFc000283300 ((13Z)-Violaxanthin)

SMILES for CFc000283300 ((13Z)-Violaxanthin)

INCHI for CFc000283300 ((13Z)-Violaxanthin)

Structure for CFc000283300 ((13Z)-Violaxanthin)

3D Structure for CFc000283300 ((13Z)-Violaxanthin)