Showing Compound (3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one (FDB016940)

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

FDB016940

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one

Description

(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one.

CAS Number

256505-54-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3S,3's,5R,5'r,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-b,kappa-caroten-6'-one	Generator
(3S,3's,5R,5'r,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-β,kappa-caroten-6'-one	Generator

Showing 1 to 2 of 2 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00096 g/L	ALOGPS
logP	6.9	ALOGPS
logP	6.72	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	8.88	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	197.25 m³·mol⁻¹	ChemAxon
Polarizability	75.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C40H56O5

IUPAC name

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

InChI Key

WFHXPAQOVQBWGU-UVMKZGRBSA-N

Isomeric SMILES

C\C(\C=C\C=C(/C)C=C=C1C(C)(C)CC(O)CC1(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C(/O)=C/C(=O)C1(C)CC(O)CC1(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
Acryloyl-group
Cyclic alcohol
Enone
Tertiary alcohol
Alpha,beta-unsaturated ketone
Vinylogous acid
Ketone
Secondary alcohol
Enol
Organooxygen compound
Carbonyl group
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uka-1000192000-82de77e5e7ba675abe30	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2100029000-b0a4f363d2ea38744de0	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-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)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one, TBDMS_2_6, 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	splash10-000t-0300691000-1ee66e7e05359e4b0763	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0730910000-f146a0193e4bd612f088	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pdi-0934300000-a36befdb6ca40f644faa	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014j-0900467000-bf9d4c98b7c79af80e15	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-0800962000-48b31a75333326633d69	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066s-0800390000-8c59c913d6eb6bfc183f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05u2-0001391000-c04fd18dcf7ca026384e	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g5a-1109850000-c702410d26558b01f71b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0551-1956700000-b8dd0e1879628f95707d	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0600009000-ff63be22385237c07fb7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1515596000-0a75636c5591c775cc7c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053e-0597830000-a4bce77dba79d2857884	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

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ChEMBL ID

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KEGG Compound ID

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Pubchem Compound ID

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Pubchem Substance ID

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ChEBI ID

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Phenol-Explorer ID

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DrugBank ID

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HMDB ID

HMDB37796

CRC / DFC (Dictionary of Food Compounds) ID

KVG17-I:KVL25-I

EAFUS ID

Not Available

Dr. Duke ID

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BIGG ID

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KNApSAcK ID

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HET ID

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Food Biomarker Ontology

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VMH ID

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Flavornet ID

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GoodScent ID

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SuperScent ID

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Wikipedia ID

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Phenol-Explorer Metabolite ID

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Duplicate IDS

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Old DFC IDS

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Biological Effects and Interactions

Health Effects / Bioactivities

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Enzymes

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Pathways

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Metabolism

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References

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General Reference

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Content Reference

Showing Compound (3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one (FDB016940)

Structure for FDB016940 ((3S,3'S,5R,5'R,6R)-6,7-Didehydro-5,6-dihydro-3,3',5,8'-tetrahydroxy-beta,kappa-caroten-6'-one)