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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:43:30 UTC

Update Date

2022-03-07 02:54:36 UTC

HMDB ID

HMDB0035710

Secondary Accession Numbers

HMDB35710

Metabolite Identification

Common Name

Cafestol

Description

Cafestol 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 has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffees (Coffea), coffee and coffee products, and robusta coffees (Coffea canephora). This could make cafestol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cafestol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0035710
     RDKit          3D
Cafestol
 51 55  0  0  0  0  0  0  0  0999 V2000
    1.0251   -0.0124    1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5130    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.8158    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2786    1.6815    1.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102    0.4366    0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.0740    1.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705   -1.0934    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3531   -1.5402   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146   -0.5334    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377   -0.4265   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3296   -1.7404   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -1.6054   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -0.4846   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.0463   -1.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    0.6139   -1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3568    1.7953   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961    1.7560    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.7580   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880   -0.5775   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6994   -1.5858   -0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1677   -0.2431    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3466    0.1824    0.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -0.9016    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -0.1721    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341   -0.9926    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    0.7474    2.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0268    2.2036   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369    2.5187    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291    2.5260    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954    1.7894    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3906   -1.6971    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1934   -2.4692   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444    0.0204   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -2.4126   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893   -2.2603    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -2.5670   -1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -1.5831   -2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.6816   -2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -0.9044   -2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    0.9152   -1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753    1.9987    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    2.6909   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    2.7664    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    1.6029    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    1.2094   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900   -2.1351   -0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.2276    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730    0.4478    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4282   -0.2677   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7025   -1.9745    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -0.2913    1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 19 23  1  0
 10  2  1  0
 18 13  1  0
 18  2  1  0
  9  5  2  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

  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>
HMDB0035710

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0035710
     RDKit          3D
Cafestol
 51 55  0  0  0  0  0  0  0  0999 V2000
    1.0251   -0.0124    1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5130    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.8158    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2786    1.6815    1.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102    0.4366    0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.0740    1.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705   -1.0934    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3531   -1.5402   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146   -0.5334    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377   -0.4265   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3296   -1.7404   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -1.6054   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -0.4846   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.0463   -1.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    0.6139   -1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3568    1.7953   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961    1.7560    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.7580   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880   -0.5775   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6994   -1.5858   -0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1677   -0.2431    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3466    0.1824    0.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -0.9016    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -0.1721    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341   -0.9926    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    0.7474    2.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0268    2.2036   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369    2.5187    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291    2.5260    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954    1.7894    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3906   -1.6971    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1934   -2.4692   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444    0.0204   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -2.4126   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893   -2.2603    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -2.5670   -1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -1.5831   -2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.6816   -2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -0.9044   -2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    0.9152   -1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753    1.9987    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    2.6909   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    2.7664    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    1.6029    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    1.2094   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900   -2.1351   -0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.2276    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730    0.4478    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4282   -0.2677   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7025   -1.9745    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -0.2913    1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 19 23  1  0
 10  2  1  0
 18 13  1  0
 18  2  1  0
  9  5  2  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

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

COMPND    HMDB0035710
HETATM    1  C1  UNL     1       1.025  -0.012   1.758  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.181   0.513   0.382  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.955   1.816   0.453  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.279   1.682   1.111  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.010   0.437   0.755  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.238   0.074   1.050  1.00  0.00           O  
HETATM    7  C6  UNL     1       5.470  -1.093   0.538  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.353  -1.540  -0.132  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.415  -0.533   0.019  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.038  -0.426  -0.468  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.330  -1.740  -0.537  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.003  -1.605  -1.207  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.845  -0.485  -0.713  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.755  -0.046  -1.877  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.853   0.614  -1.028  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.357   1.795  -0.284  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.996   1.756   0.257  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.071   0.758  -0.373  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.188  -0.578  -0.152  1.00  0.00           C  
HETATM   20  O2  UNL     1      -3.699  -1.586  -0.957  1.00  0.00           O  
HETATM   21  C19 UNL     1      -4.168  -0.243   0.934  1.00  0.00           C  
HETATM   22  O3  UNL     1      -5.347   0.182   0.324  1.00  0.00           O  
HETATM   23  C20 UNL     1      -1.806  -0.902   0.382  1.00  0.00           C  
HETATM   24  H1  UNL     1       2.067  -0.172   2.166  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.534  -0.993   1.843  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.577   0.747   2.418  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.027   2.204  -0.588  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.337   2.519   1.053  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.929   2.526   0.754  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.195   1.789   2.198  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.391  -1.697   0.587  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.193  -2.469  -0.675  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.044   0.020  -1.486  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.950  -2.413  -1.200  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.289  -2.260   0.436  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.565  -2.567  -1.026  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.168  -1.583  -2.315  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.257   0.682  -2.517  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.200  -0.904  -2.380  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.703   0.915  -1.661  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.075   1.999   0.554  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.483   2.691  -0.962  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.506   2.766   0.115  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.945   1.603   1.367  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.244   1.209  -1.363  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.390  -2.135  -0.506  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.430  -1.228   1.422  1.00  0.00           H  
HETATM   48  H25 UNL     1      -3.773   0.448   1.677  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.428  -0.268  -0.557  1.00  0.00           H  
HETATM   50  H27 UNL     1      -1.702  -1.975   0.636  1.00  0.00           H  
HETATM   51  H28 UNL     1      -1.694  -0.291   1.304  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   10   18
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    9    9
CONECT    6    7
CONECT    7    8    8   31
CONECT    8    9   32
CONECT    9   10
CONECT   10   11   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   18   23
CONECT   14   15   38   39
CONECT   15   16   19   40
CONECT   16   17   41   42
CONECT   17   18   43   44
CONECT   18   45
CONECT   19   20   21   23
CONECT   20   46
CONECT   21   22   47   48
CONECT   22   49
CONECT   23   50   51
END

HMDB0035710
     RDKit          3D
Cafestol
 51 55  0  0  0  0  0  0  0  0999 V2000
    1.0251   -0.0124    1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.5130    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.8158    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2786    1.6815    1.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102    0.4366    0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.0740    1.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4705   -1.0934    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3531   -1.5402   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146   -0.5334    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377   -0.4265   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3296   -1.7404   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0035   -1.6054   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454   -0.4846   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.0463   -1.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8534    0.6139   -1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3568    1.7953   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961    1.7560    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.7580   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1880   -0.5775   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6994   -1.5858   -0.9566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1677   -0.2431    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3466    0.1824    0.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -0.9016    0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0673   -0.1721    2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341   -0.9926    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    0.7474    2.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0268    2.2036   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369    2.5187    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291    2.5260    0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954    1.7894    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3906   -1.6971    0.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1934   -2.4692   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444    0.0204   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500   -2.4126   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893   -2.2603    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -2.5670   -1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -1.5831   -2.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.6816   -2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -0.9044   -2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    0.9152   -1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753    1.9987    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826    2.6909   -0.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5055    2.7664    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    1.6029    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    1.2094   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900   -2.1351   -0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.2276    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730    0.4478    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4282   -0.2677   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7025   -1.9745    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -0.2913    1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 19 23  1  0
 10  2  1  0
 18 13  1  0
 18  2  1  0
  9  5  2  0
 23 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  7 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cafesterol	HMDB
Coffeol	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035710)

Source

Endogenous

Endogenous (HMDB: HMDB0035710)

Plant

Coffea (HMDB: HMDB0035710)

Exogenous

Food

Food (HMDB: HMDB0035710)

Coffee and coffee product

Coffee

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0035710)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035710)

Role

Biological role

Energy source (HMDB: HMDB0035710)
Anti-inflammatory (HMDB: HMDB0035710)
Hypercholesterolemic (HMDB: HMDB0035710)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035710)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 162 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.544	31661259
DarkChem	[M-H]-	168.466	31661259
DeepCCS	[M-2H]-	204.081	30932474
DeepCCS	[M+Na]+	179.308	30932474
AllCCS	[M+H]+	179.1	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	181.9	32859911
AllCCS	[M+Na]+	182.7	32859911
AllCCS	[M-H]-	184.7	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	184.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cafestol	CC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3	3142.0	Standard polar	33892256
Cafestol	CC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3	2639.0	Standard non polar	33892256
Cafestol	CC12CCC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3	2756.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cafestol,1TMS,isomer #1	CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C)C3	2850.3	Semi standard non polar	33892256
Cafestol,1TMS,isomer #2	CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C)C3	2828.8	Semi standard non polar	33892256
Cafestol,2TMS,isomer #1	CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C3	2826.4	Semi standard non polar	33892256
Cafestol,1TBDMS,isomer #1	CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C(C)(C)C)C3	3119.3	Semi standard non polar	33892256
Cafestol,1TBDMS,isomer #2	CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C(C)(C)C)C3	3103.2	Semi standard non polar	33892256
Cafestol,2TBDMS,isomer #1	CC12CCC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C3	3353.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cafestol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-0491000000-8b320a709d91d7ff1ffe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cafestol GC-MS (2 TMS) - 70eV, Positive	splash10-0092-9434700000-2e50a5d7a6928201b152	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cafestol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 10V, Negative-QTOF	splash10-014i-0039000000-e55c424af8a4bb5abfe5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 20V, Negative-QTOF	splash10-014i-0094000000-f399341e0f5dd8ad74b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 40V, Negative-QTOF	splash10-0pvr-0090000000-f793b7dac060dcfa0106	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 10V, Negative-QTOF	splash10-014i-0009000000-d337ec43015bf5d00be6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 20V, Negative-QTOF	splash10-014i-0019000000-9e44ccfae91118d36eab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 40V, Negative-QTOF	splash10-014r-0093000000-f1f44de6b38a9b8fea79	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 10V, Positive-QTOF	splash10-014i-0149000000-3a6b96b7f47db8b6922b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 20V, Positive-QTOF	splash10-00l2-0293000000-513aa1e79d3e41b9441a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 40V, Positive-QTOF	splash10-0ffx-7960000000-dd534580ddb824a054ba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 10V, Positive-QTOF	splash10-014i-0009000000-7a45cf767c0416b1cc05	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 20V, Positive-QTOF	splash10-00ke-0093000000-4524e55457ed7eb79471	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cafestol 40V, Positive-QTOF	splash10-06rj-3951000000-2c42c767d2b59afdb32e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1473611

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cafestol (HMDB0035710)

MOL for HMDB0035710 (Cafestol)

3D MOL for HMDB0035710 (Cafestol)

3D SDF for HMDB0035710 (Cafestol)

3D-SDF for HMDB0035710 (Cafestol)

PDB for HMDB0035710 (Cafestol)

3D PDB for HMDB0035710 (Cafestol)

SMILES for HMDB0035710 (Cafestol)

INCHI for HMDB0035710 (Cafestol)

Structure for HMDB0035710 (Cafestol)

3D Structure for HMDB0035710 (Cafestol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra