Showing Compound 4-Oxo-9-cis-retinoyl-beta-glucuronide (FDB034575)

Record Information

Version

1.0

Creation date

2019-08-07 19:37:30 UTC

Update date

2020-04-06 23:39:25 UTC

Primary ID

FDB034575

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Oxo-9-cis-retinoyl-beta-glucuronide

Description

4-Oxo-9-cis-retinoyl-beta-glucuronide belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 4-Oxo-9-cis-retinoyl-beta-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.78 m³·mol⁻¹	ChemAxon
Polarizability	51.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C26H34O9

IUPAC name

(2R,3S,4R,5R,6S)-6-{[(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

InChI Identifier

InChI=1S/C26H34O9/c1-14(9-11-17-16(3)10-12-18(27)26(17,4)5)7-6-8-15(2)13-19(28)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h6-9,11,13,20-23,25,29-31H,10,12H2,1-5H3,(H,32,33)/b8-6+,11-9+,14-7-,15-13+/t20-,21+,22-,23-,25-/m1/s1

InChI Key

XEIKLAKHCVSUMR-CAHRZYSUSA-N

Isomeric SMILES

C\C(\C=C\C1=C(C)CCC(=O)C1(C)C)=C\C=C\C(\C)=C\C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O

Average Molecular Weight

490.5428

Monoisotopic Molecular Weight

490.220282686

Classification

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Retinoid ester
Diterpenoid
Retinoid skeleton
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Beta-hydroxy acid
Fatty acid ester
Cyclohexenone
Fatty acyl
Dicarboxylic acid or derivatives
Pyran
Oxane
Hydroxy acid
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Ketone
Polyol
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Organ and components:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

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	Not Available
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	4-Oxo-9-cis-retinoyl-beta-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adi-9231400000-f062086043505a587de1	Spectrum
Predicted GC-MS	4-Oxo-9-cis-retinoyl-beta-glucuronide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-7492038000-50aa6f79fbde093a1d92	Spectrum
Predicted GC-MS	4-Oxo-9-cis-retinoyl-beta-glucuronide, non-derivatized, 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	splash10-00r2-0694500000-91987c2043e2552a452e	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0891000000-6a3ed9a7d797b6072d2f	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gvk-2930000000-9791536a6efa84f501af	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0193400000-d1ffe770458ed14d70b9	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fs-4955200000-e103a6edf04db4033d48	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dm-9553000000-817f5bc84a337bc13856	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0351900000-03ecdbb80192ae1778aa	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0290100000-251862ceb1f90d6faa16	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00p0-1910000000-7cfc19f92754fc0c94fd	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000900000-d680a79baa48678abf41	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0171-1291300000-b72c0e54a1bfedc47fd6	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bta-4941000000-1513d9b76716e2f19275	2021-10-12	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

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

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

Show entries

Search:

Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB