Showing Compound (3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one (FDB016939)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:44 UTC

Update date

2019-11-26 03:13:59 UTC

Primary ID

FDB016939

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one

Description

(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one 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. Based on a literature review a small amount of articles have been published on (3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one.

CAS Number

256505-53-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Showing 1 to 2 of 2 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00076 g/L	ALOGPS
logP	7.38	ALOGPS
logP	7.44	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	8.88	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	195.39 m³·mol⁻¹	ChemAxon
Polarizability	75.43 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

Chemical Formula

C40H56O5

IUPAC name

(2Z,4E,6E,8E,10E,12E,14E,16E,18E)-3-hydroxy-1-(3-hydroxy-1,2,2-trimethylcyclopentyl)-19-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

InChI Identifier

InChI=1S/C40H56O5/c1-28(17-13-18-30(3)21-24-40-36(5,6)26-32(45-40)27-39(40,10)44)15-11-12-16-29(2)19-14-20-31(4)33(41)25-35(43)38(9)23-22-34(42)37(38,7)8/h11-21,24-25,32,34,41-42,44H,22-23,26-27H2,1-10H3/b12-11+,17-13+,19-14+,24-21+,28-15+,29-16+,30-18+,31-20+,33-25-

InChI Key

JBFAUTAUPAPLMY-UQDXBYLISA-N

Isomeric 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)/C(/O)=C/C(=O)C1(C)CCC(O)C1(C)C

Average Molecular Weight

616.8696

Monoisotopic Molecular Weight

616.412774902

Classification

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
Cyclopentanol
Monosaccharide
Acryloyl-group
Cyclic alcohol
Enone
Vinylogous acid
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Tertiary alcohol
Ketone
Secondary alcohol
Dialkyl ether
Enol
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 77.88%; H 9.15%; O 12.97%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0pb9-7100294000-70b2c68b664763cace64	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-7100049000-2c6595df0e1bea6c74dc	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one, "(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0521942000-06a440d53a07f0e8f10a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-3642930000-1c1db9100109609353de	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-3960100000-cb602f77717137c9f4d8	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0500539000-decbf06136b865825d5c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0800933000-f439dc3a0f87fd1efc0e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-1009-1900240000-02c218983e61abc2d7f1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0710009000-284ccdd7f575875a4713	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0605934000-29bbc3bcd234348c9ca8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6539551000-dded066ce27a07be07ae	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1204097000-3a885104aa0f8a621557	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-3329220000-e25d6418a9339959f363	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00p0-5497300000-430f0c5c73b566084176	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB37795

CRC / DFC (Dictionary of Food Compounds) ID

KVG04-C:KVL24-H

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound (3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one (FDB016939)

Structure for FDB016939 ((3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one)