NP-MRD: Showing NP-Card for Cafestol (NP0048297)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:13 UTC

Updated at

2022-03-17 20:54:13 UTC

NP-MRD ID

NP0048297

Secondary Accession Numbers

None

Natural Product Identification

Common 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). Outside of the human body, 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. Cafestol is a diterpenoid molecule present in coffee beans. A typical bean of Coffea arabica contains about 0.4-0.7% Cafestol by weight. Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee or Turkish coffee/Greek coffee. Cafestol has also shown anticarcinogenic properties in rats. Coffee consumption has been associated with a number of effects on health and cafestol has been proposed to produce these through a number of biological actions. Studies have shown that regular consumption of boiled coffee increases serum cholesterol whereas filtered coffee does not. Thus cafestol can increase cholesterol synthesis. It is one of the compounds that may be responsible for proposed biological and pharmacological effects of coffee. Cafestol is found in Coffea arabica, Coffea congensis, Coffea spp. and Diplospora dubia. Cafestol was first documented in 2011 (PMID: 21334318). Cafestol may act as an agonist ligand for the nuclear receptor farnesoid X receptor and pregnane X receptor, blocking cholesterol homeostasis.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308402D          

 23 27  0  0  0  0            999 V2000
    2.4990    0.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8699   -0.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    2.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483    0.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7330    2.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234    0.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1166    2.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4812    1.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0447    1.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760    2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    2.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4107    0.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1712    1.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463    1.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722    0.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869    0.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6205    1.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588    1.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0645    2.2766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6012    1.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3818    0.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  2  0  0  0  0
 13  2  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 15  4  1  0  0  0  0
 15 14  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  3  1  0  0  0  0
 18  1  1  0  0  0  0
 18  7  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 19 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 12  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3

> <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

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.17017648206851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.6770277843333323

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.309321353899517

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.685426593369503

> <JCHEM_PKA_STRONGEST_BASIC>
-2.205382524896674

> <JCHEM_POLAR_SURFACE_AREA>
53.6

> <JCHEM_REFRACTIVITY>
88.55009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.665   0.120   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.624  -0.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.220  -0.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.508   4.124   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.743   0.071   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.835   3.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.204   0.096   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.951   4.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.232   3.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.950   2.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.635   3.803   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.447   4.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.767   1.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.786   2.739   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.246   2.763   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.535   1.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.896   1.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.455   1.442   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.025   2.862   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.296   2.871   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.987   4.250   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.122   2.272   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.046   1.689   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3   13                                                       
CONECT    3    2   17                                                       
CONECT    4    8   15                                                       
CONECT    5    7   16                                                       
CONECT    6    9   14                                                       
CONECT    7    5   18                                                       
CONECT    8    4   19                                                       
CONECT    9    6   23                                                       
CONECT   10   13   19                                                       
CONECT   11   19   20                                                       
CONECT   12   20   21                                                       
CONECT   13    2   10   20                                                  
CONECT   14    6   15   16                                                  
CONECT   15    4   14   18                                                  
CONECT   16    5   14   23                                                  
CONECT   17    3   18   19                                                  
CONECT   18    1    7   15   17                                             
CONECT   19    8   10   11   17                                             
CONECT   20   11   12   13   22                                             
CONECT   21   12                                                            
CONECT   22   20                                                            
CONECT   23    9   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
Cafesterol	HMDB
Coffeol	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4345 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

469-83-0

SMILES

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

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea congensis	LOTUS Database	35616633
Coffea spp.	Plant	KNApSAcK
Diplospora dubia	LOTUS Database	35616633

Chemical Taxonomy

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0035710

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cafestol

METLIN ID

Not Available

PubChem Compound

2516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Choi MJ, Park EJ, Oh JH, Min KJ, Yang ES, Kim YH, Lee TJ, Kim SH, Choi YH, Park JW, Kwon TK: Cafestol, a coffee-specific diterpene, induces apoptosis in renal carcinoma Caki cells through down-regulation of anti-apoptotic proteins and Akt phosphorylation. Chem Biol Interact. 2011 Apr 25;190(2-3):102-8. doi: 10.1016/j.cbi.2011.02.013. Epub 2011 Feb 18. [PubMed:21334318 ]

Showing NP-Card for Cafestol (NP0048297)

MOL for NP0048297 (Cafestol)

3D MOL for NP0048297 (Cafestol)

3D SDF for NP0048297 (Cafestol)

3D-SDF for NP0048297 (Cafestol)

PDB for NP0048297 (Cafestol)

3D PDB for NP0048297 (Cafestol)

SMILES for NP0048297 (Cafestol)

INCHI for NP0048297 (Cafestol)

Structure for NP0048297 (Cafestol)

3D Structure for NP0048297 (Cafestol)