Showing Compound (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid (FDB018417)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:42 UTC

Update date

2019-11-26 03:16:08 UTC

Primary ID

FDB018417

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid

Description

(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, also known as 2-(2,3,5-trihydroxy-3H-indol-3-yl)acetate, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make (R)-2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	18.1 g/L	ALOGPS
logP	0.11	ALOGPS
logP	-0.16	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.65 m³·mol⁻¹	ChemAxon
Polarizability	20.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H9NO5

IUPAC name

2-(3,5-dihydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid

InChI Identifier

InChI=1S/C10H9NO5/c12-5-1-2-7-6(3-5)10(16,4-8(13)14)9(15)11-7/h1-3,12,16H,4H2,(H,11,15)(H,13,14)

InChI Key

BSACCBRVBZORKX-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2

Average Molecular Weight

223.1822

Monoisotopic Molecular Weight

223.048072403

Classification

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary alcohol
Cyclic carboximidic acid
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Alcohol
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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 53.82%; H 4.06%; N 6.28%; O 35.84%	DFC
Melting Point	Not Available
Optical Rotation	[a]21D +6 (c, 1 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06ri-0900000000-802ca84f9c8917632e18	Spectrum
Predicted GC-MS	(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-5009100000-24092c763183b6874a67	Spectrum
Predicted GC-MS	(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, 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	splash10-05fr-0390000000-9ae1653b7127d67352b2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0910000000-ae29c18428ce13334c64	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08i9-3900000000-c1c3bfaab6cfef0a8fe0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0950000000-3ea8f4c2c4bc8389a3dd	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-2920000000-9e215db23f2c2fed6153	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-5900000000-1a48e3d8d2c3e2bb48aa	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0h9r-0980000000-b38377def1d725ed8f4c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-e0d9c04380c1ee4ba994	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-47513399be5dc2a706d3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0090000000-665cd6e298eb489bf3f9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0790000000-50fe9d15d3f70d6316b5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9500000000-591ae4cc04c8edc4ddee	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

32681552

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

85880351

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38941

CRC / DFC (Dictionary of Food Compounds) ID

LKN07-A:LKN08-B

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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Food	Content Range	Average	Reference

Processing...

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 (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid (FDB018417)

Structure for FDB018417 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)