Showing Compound 3-Demethylsimmondsin 2'-(Z)-ferulate (FDB013327)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:39 UTC

Update date

2019-11-26 03:08:18 UTC

Primary ID

FDB013327

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Demethylsimmondsin 2'-(Z)-ferulate

Description

3-Demethylsimmondsin 2'-(Z)-ferulate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 3-Demethylsimmondsin 2'-(Z)-ferulate has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, fats and oils, nuts, and robusta coffees (Coffea canephora). This could make 3-demethylsimmondsin 2'-(Z)-ferulate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Demethylsimmondsin 2'-(Z)-ferulate.

CAS Number

162290-39-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
2-{[(2E)-2-(cyanomethylidene)-3,4-dihydroxy-5-methoxycyclohexyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator
3-Demethylsimmondsin 2'-(4-hydroxy-3-methoxy-Z-cinnamate)	manual
3-Demethylsimmondsin 2'-(Z)-ferulate	manual
3-Demethylsimmondsin 2'-(Z)-ferulic acid	Generator
3-O-Demethylsimmondsin 2'-(4-hydroxy-3-methoxy-Z-cinnamate)	manual

Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.98	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	208.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.11 m³·mol⁻¹	ChemAxon
Polarizability	51.22 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

C25H31NO12

IUPAC name

2-{[(2E)-2-(cyanomethylidene)-3,4-dihydroxy-5-methoxycyclohexyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C25H31NO12/c1-34-16-9-12(3-5-14(16)28)4-6-19(29)38-24-23(33)22(32)18(11-27)37-25(24)36-15-10-17(35-2)21(31)20(30)13(15)7-8-26/h3-7,9,15,17-18,20-25,27-28,30-33H,10-11H2,1-2H3/b6-4-,13-7-

InChI Key

RSANRMXIULPPSK-LNPZZTDESA-N

Isomeric SMILES

COC1CC(OC2OC(CO)C(O)C(O)C2OC(=O)\C=C/C2=CC(OC)=C(O)C=C2)\C(=C\C#N)C(O)C1O

Average Molecular Weight

537.5131

Monoisotopic Molecular Weight

537.184625461

Classification

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Hexose monosaccharide
Coumaric acid or derivatives
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Phenol ether
Styrene
Phenoxy compound
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Fatty acid ester
Benzenoid
Cyclitol or derivatives
Oxane
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Coffea

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

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	C 55.86%; H 5.81%; N 2.61%; O 35.72%	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	3-Demethylsimmondsin 2'-(Z)-ferulate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-9402140000-005b92c69c13e11346d8	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0gdj-2910124000-18602e4c1be8d4c8f888	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Demethylsimmondsin 2'-(Z)-ferulate, TMS_3_3, 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	splash10-0ff9-0933040000-0051ddaf65a9214b1123	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0931000000-014f838b202dcb4d711a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9841000000-13d3a6356177fa87b5bd	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000g-0913040000-e27c123eff39eef0bd4e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0037-0901010000-a1ef49cf32c30cbb8523	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004m-1900000000-df88e214a1f7fcec52d1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0400190000-4a08bad431c6a6378206	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0910220000-29598717280bb7602fd5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-4911100000-03a8520904397eac5bef	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0201090000-2d34e1166c1ff73591e5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052s-1606960000-f643236692075e29541d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0541-2902100000-e620614ba2281024214b	2021-09-24	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

HMDB34774

CRC / DFC (Dictionary of Food Compounds) ID

CHN95-J:HSV27-G

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

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 3-Demethylsimmondsin 2'-(Z)-ferulate (FDB013327)

Structure for FDB013327 (3-Demethylsimmondsin 2'-(Z)-ferulate)