Showing Compound (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) (FDB018545)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:47 UTC

Update date

2019-11-26 03:16:18 UTC

Primary ID

FDB018545

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate)

Description

(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, green vegetables, herbs and spices, and robusta coffees (Coffea canephora). This could make (5a,6a,8a,11a)-8-hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate).

CAS Number

374536-44-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate)	manual
(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetic acid)	Generator
9-Formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetic acid	HMDB

Showing 1 to 3 of 3 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.93 m³·mol⁻¹	ChemAxon
Polarizability	41.31 Å³	ChemAxon
Number of Rings	4	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

C23H22O7

IUPAC name

9-formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

InChI Identifier

InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9-10,12,17,20-22,25H,7-8H2,1-2H3

InChI Key

CICWEHOIACOOIN-UHFFFAOYSA-N

Isomeric SMILES

CC1C2C(OC1=O)C1C(C=O)=CC(=O)C1=C(C)CC2OC(=O)CC1=CC=C(O)C=C1

Average Molecular Weight

410.4166

Monoisotopic Molecular Weight

410.136553058

Classification

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Coffea

Biological location:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

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 67.31%; H 5.40%; O 27.29%	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	(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-1911000000-f44713eeb340bbd449d2	Spectrum
Predicted GC-MS	(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-2910100000-5a6df1bda200920832a2	Spectrum
Predicted GC-MS	(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate), 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	splash10-03du-0769800000-adb07d2b251d93067dff	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0952000000-c1720c337cef5b9db29f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-2920000000-d9d262fbf09b9c54febb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0354900000-a455a0055ad1cf86e657	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a7i-0594200000-0db247652e733d312270	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-1970000000-263b0d2f35564dffd2a1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a59-0090000000-8567295fc2dea93cc2a9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0591000000-0eabccb0bde6621a8eee	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2920000000-3ecfa0ab6fa60240b16e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004j-0090000000-85c4287ade83b8719d09	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-1890000000-9a605821e8f0df920c65	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f75-4594000000-1696603b047087f3e175	2021-09-23	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

HMDB39048

CRC / DFC (Dictionary of Food Compounds) ID

JFR52-Z:LLO03-I

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 (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) (FDB018545)

Structure for FDB018545 ((5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate))