ChemFOnt: Showing chemical card for 3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol (CFc000336910)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:20 UTC

Chemfont ID

CFc000336910

Molecule Identification

Common Name

3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol

Definition

Cucurbitachrome 1 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. Cucurbitachrome 1 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitachrome 1 can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and red bell pepper, which makes cucurbitachrome 1 a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S,3's,5R,5'r,6R,8'r)-3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-3',5-dihydroxy-beta,beta-carotene	HMDB
Curcurbitachrome 1	HMDB

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-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]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

CAS Registry Number

126-29-4

SMILES

C\C(\C=C\C=C(/C)\C=C\C12OC(CC1(C)C)CC2(C)O)=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)26-33(43-40)27-39(40,10)42)15-11-12-16-29(2)19-14-20-31(4)34-23-35-36(5,6)24-32(41)25-38(35,9)44-34/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

YMNKXGQZDVGTFM-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
Monosaccharide
Cyclic alcohol
Dihydrofuran
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0003101)

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00054 g/L	ALOGPS
logP	8.15	ALOGPS
logP	6.99	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	192.2 m³·mol⁻¹	ChemAxon
Polarizability	73.85 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

HMDB0041581

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021572

KNApSAcK ID

C00022956

Chemspider ID

35015205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753168

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol (CFc000336910)

MOL for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

3D MOL for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

3D SDF for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

3D-SDF for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

PDB for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

3D PDB for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

SMILES for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

INCHI for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

Structure for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)

3D Structure for CFc000336910 (3,6:5',8'-Diepoxy-5,5',6,8'-tetrahydro-b,b-carotene-3',5-diol)