Showing Compound Cafestol (FDB014432)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:16 UTC

Update date

2019-11-26 03:10:02 UTC

Primary ID

FDB014432

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cafestol

Description

Cafestol, also known as coffeol, belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Cafestol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cafestol has been detected, but not quantified in, a few different foods, such as arabica coffee, coffee, and coffee and coffee products. This could make cafestol a potential biomarker for the consumption of these foods.

CAS Number

469-83-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Cafesterol	HMDB
Coffeol	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.04	ALOGPS
logP	2.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.55 m³·mol⁻¹	ChemAxon
Polarizability	36.17 Å³	ChemAxon
Number of Rings	5	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

C20H28O3

IUPAC name

17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-ol

InChI Identifier

InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3

InChI Key

DNJVYWXIDISQRD-UHFFFAOYSA-N

Isomeric SMILES

CC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

Classification

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Benzofuran
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
1,2-diol
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 75.91%; H 8.92%; O 15.17%	DFC
Melting Point	Mp 160-162° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -101 (CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cafestol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-0491000000-8b320a709d91d7ff1ffe	Spectrum
Predicted GC-MS	Cafestol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0092-9434700000-2e50a5d7a6928201b152	Spectrum
Predicted GC-MS	Cafestol, 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, Negative	splash10-014i-0039000000-e55c424af8a4bb5abfe5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0094000000-f399341e0f5dd8ad74b9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pvr-0090000000-f793b7dac060dcfa0106	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-d337ec43015bf5d00be6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0019000000-9e44ccfae91118d36eab	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-0093000000-f1f44de6b38a9b8fea79	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0149000000-3a6b96b7f47db8b6922b	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00l2-0293000000-513aa1e79d3e41b9441a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ffx-7960000000-dd534580ddb824a054ba	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-7a45cf767c0416b1cc05	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ke-0093000000-4524e55457ed7eb79471	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rj-3951000000-2c42c767d2b59afdb32e	2021-09-24	View Spectrum