ChemFOnt: Showing chemical card for (3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal (CFc000281548)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:02 UTC

Chemfont ID

CFc000281548

Molecule Identification

Common Name

(3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal

Definition

(3s,5r,6s)-5,6-epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units (3s,5r,6s)-5,6-epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (3s,5r,6s)-5,6-epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal can be found in sweet orange, which makes (3s,5r,6s)-5,6-epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-b,psi-carotenal	Generator
(3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-β,psi-carotenal	Generator

Chemical Formula

C₃₀H₄₀O₃

Average Molecular Weight

448.6368

Monoisotopic Molecular Weight

448.297745146

IUPAC Name

(2E,4E,6E,8E,10E,12E,14E,16E)-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14,16-octaenal

Traditional Name

(2E,4E,6E,8E,10E,12E,14E,16E)-17-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14,16-octaenal

CAS Registry Number

75715-17-2

SMILES

O=C\C(C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C

InChI Identifier

InChI=1S/C30H40O3/c1-23(12-8-9-13-24(2)15-11-17-26(4)22-31)14-10-16-25(3)18-19-30-28(5,6)20-27(32)21-29(30,7)33-30/h8-19,22,27,32H,20-21H2,1-7H3/b9-8+,14-10+,15-11+,19-18+,23-12+,24-13+,25-16+,26-17+/t27-,29+,30-/m0/s1

InChI Key

TUSQPOXZYYVVMH-WMRQXDNJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxepane
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Enal
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302032)

Food

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	6.86	ALOGPS
logP	5.67	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	147.14 m³·mol⁻¹	ChemAxon
Polarizability	55.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001771

KNApSAcK ID

Not Available

Chemspider ID

59696248

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 (3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal (CFc000281548)

MOL for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

3D MOL for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

3D SDF for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

3D-SDF for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

PDB for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

3D PDB for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

SMILES for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

INCHI for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

Structure for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)

3D Structure for CFc000281548 ((3S,5R,6S)-5,6-Epoxy-5,6-dihydro-3-hydroxy-8'-apo-beta,psi-carotenal)