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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:36:41 UTC

Update Date

2022-03-07 02:54:34 UTC

HMDB ID

HMDB0035602

Secondary Accession Numbers

HMDB35602

Metabolite Identification

Common Name

Kahweol

Description

Kahweol, also known as ccris 1521, 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. Kahweol 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 kahweol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Kahweol.

Structure

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

HMDB0035602
     RDKit          3D
Kahweol
 49 53  0  0  0  0  0  0  0  0999 V2000
    1.6339    1.6562    2.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.7757    0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    1.7346   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600    1.6190   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489    0.5417   -1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656    0.2499   -2.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -0.8150   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208   -1.2533   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -0.3669   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830   -0.3530    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.7381    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3354   -1.9643    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -0.7947    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9506   -1.2174    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -0.1303    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.2411    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.2917    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    0.2577    1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718   -0.4209   -1.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -1.7896   -1.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457    0.4172   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5142    0.3152   -2.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.2773   -1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209    1.6594    2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    1.2604    3.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    2.6895    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    2.5419   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215    2.3542   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386   -1.3254   -2.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4286   -2.1124   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.2334    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -1.9354    2.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -2.4528    0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175   -2.1858   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -2.8359    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -2.1844    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9257   -1.1446    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825   -0.3345    0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    1.8295   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    1.7645    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5029    1.2279    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    2.2886    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682   -0.3147    2.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -1.8969   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.4558   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    0.0174   -3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    1.0431   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    0.7630   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -0.9179   -1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END

  Mrv0541 05061308352D          

 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  2  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>
HMDB0035602

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/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/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3

> <INCHI_KEY>
JEKMKNDURXDJAD-UHFFFAOYSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.4186

> <EXACT_MASS>
314.188194698

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.08044022665105

> <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),6,10-trien-17-ol

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
2.5537135876666657

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.309317857918415

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.685413916695513

> <JCHEM_PKA_STRONGEST_BASIC>
-2.530063437585873

> <JCHEM_POLAR_SURFACE_AREA>
53.6

> <JCHEM_REFRACTIVITY>
89.51269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035602
     RDKit          3D
Kahweol
 49 53  0  0  0  0  0  0  0  0999 V2000
    1.6339    1.6562    2.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.7757    0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    1.7346   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600    1.6190   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489    0.5417   -1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656    0.2499   -2.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -0.8150   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208   -1.2533   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -0.3669   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830   -0.3530    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.7381    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3354   -1.9643    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -0.7947    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9506   -1.2174    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -0.1303    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.2411    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.2917    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    0.2577    1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718   -0.4209   -1.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -1.7896   -1.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457    0.4172   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5142    0.3152   -2.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.2773   -1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209    1.6594    2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    1.2604    3.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    2.6895    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    2.5419   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215    2.3542   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386   -1.3254   -2.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4286   -2.1124   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.2334    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -1.9354    2.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -2.4528    0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175   -2.1858   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -2.8359    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -2.1844    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9257   -1.1446    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825   -0.3345    0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    1.8295   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    1.7645    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5029    1.2279    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    2.2886    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682   -0.3147    2.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -1.8969   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.4558   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    0.0174   -3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    1.0431   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    0.7630   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -0.9179   -1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  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    HMDB0035602
HETATM    1  C1  UNL     1       1.634   1.656   2.114  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.253   0.776   0.872  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.233   1.735  -0.226  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.060   1.619  -1.230  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.049   0.542  -1.335  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.966   0.250  -2.242  1.00  0.00           O  
HETATM    7  C6  UNL     1       4.627  -0.815  -1.909  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.121  -1.253  -0.715  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.101  -0.367  -0.356  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.183  -0.353   0.821  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.599  -1.738   0.978  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.335  -1.964   0.223  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.615  -0.795   0.292  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.951  -1.217   0.940  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.836  -0.130   0.299  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.359   1.241   0.651  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.136   1.292   1.512  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.116   0.258   1.241  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.472  -0.421  -1.140  1.00  0.00           C  
HETATM   20  O2  UNL     1      -2.741  -1.790  -1.346  1.00  0.00           O  
HETATM   21  C19 UNL     1      -3.146   0.417  -2.156  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.514   0.315  -2.180  1.00  0.00           O  
HETATM   23  C20 UNL     1      -0.981  -0.277  -1.077  1.00  0.00           C  
HETATM   24  H1  UNL     1       2.721   1.659   2.243  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.167   1.260   3.020  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.270   2.689   1.970  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.516   2.542  -0.186  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.022   2.354  -2.034  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.439  -1.325  -2.420  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.429  -2.112  -0.138  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.914  -0.233   1.693  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.470  -1.935   2.056  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.360  -2.453   0.616  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.517  -2.186  -0.842  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.195  -2.836   0.643  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.212  -2.184   0.519  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.926  -1.145   2.021  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.883  -0.335   0.532  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.147   1.829  -0.263  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.206   1.764   1.157  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.503   1.228   2.577  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.654   2.289   1.450  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.068  -0.315   2.205  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.722  -1.897  -1.230  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.760   1.456  -2.152  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.802   0.017  -3.159  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.909   1.043  -1.609  1.00  0.00           H  
HETATM   48  H25 UNL     1      -0.738   0.763  -1.269  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.530  -0.918  -1.872  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   10   18
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6    9    9
CONECT    6    7
CONECT    7    8    8   29
CONECT    8    9   30
CONECT    9   10
CONECT   10   11   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   18   23
CONECT   14   15   36   37
CONECT   15   16   19   38
CONECT   16   17   39   40
CONECT   17   18   41   42
CONECT   18   43
CONECT   19   20   21   23
CONECT   20   44
CONECT   21   22   45   46
CONECT   22   47
CONECT   23   48   49
END

HMDB0035602
     RDKit          3D
Kahweol
 49 53  0  0  0  0  0  0  0  0999 V2000
    1.6339    1.6562    2.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.7757    0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330    1.7346   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0600    1.6190   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489    0.5417   -1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656    0.2499   -2.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6269   -0.8150   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208   -1.2533   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -0.3669   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1830   -0.3530    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.7381    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3354   -1.9643    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -0.7947    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9506   -1.2174    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -0.1303    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.2411    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.2917    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1163    0.2577    1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718   -0.4209   -1.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -1.7896   -1.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457    0.4172   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5142    0.3152   -2.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.2773   -1.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209    1.6594    2.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671    1.2604    3.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696    2.6895    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    2.5419   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215    2.3542   -2.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4386   -1.3254   -2.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4286   -2.1124   -0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142   -0.2334    1.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -1.9354    2.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602   -2.4528    0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175   -2.1858   -0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945   -2.8359    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -2.1844    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9257   -1.1446    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8825   -0.3345    0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1467    1.8295   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    1.7645    1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5029    1.2279    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    2.2886    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682   -0.3147    2.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -1.8969   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.4558   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    0.0174   -3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    1.0431   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    0.7630   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -0.9179   -1.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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
  4 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CCRIS 1521	HMDB
CCRIS-1521	HMDB

Chemical Formula

C₂₀H₂₆O₃

Average Molecular Weight

314.4186

Monoisotopic Molecular Weight

314.188194698

IUPAC Name

17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-ol

Traditional Name

17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-ol

CAS Registry Number

6894-43-5

SMILES

CC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3

InChI Identifier

InChI=1S/C20H26O3/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/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3

InChI Key

JEKMKNDURXDJAD-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
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: HMDB0035602)

Source

Endogenous

Endogenous (HMDB: HMDB0035602)

Plant

Coffea (HMDB: HMDB0035602)

Exogenous

Food

Food (HMDB: HMDB0035602)

Coffee and coffee product

Coffee

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0035602)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035602)

Role

Biological role

Energy source (HMDB: HMDB0035602)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035602)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 143.5 °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	0.02 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.55	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-2.5	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	89.51 m³·mol⁻¹	ChemAxon
Polarizability	35.08 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]+	171.574	31661259
DarkChem	[M-H]-	168.82	31661259
DeepCCS	[M-2H]-	203.057	30932474
DeepCCS	[M+Na]+	178.284	30932474
AllCCS	[M+H]+	177.8	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	184.0	32859911
AllCCS	[M+Na-2H]-	183.8	32859911
AllCCS	[M+HCOO]-	183.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kahweol	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3	3476.2	Standard polar	33892256
Kahweol	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3	2630.8	Standard non polar	33892256
Kahweol	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC21)C(O)(CO)C3	2733.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kahweol,1TMS,isomer #1	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C)C3	2838.6	Semi standard non polar	33892256
Kahweol,1TMS,isomer #2	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C)C3	2822.6	Semi standard non polar	33892256
Kahweol,2TMS,isomer #1	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C3	2824.4	Semi standard non polar	33892256
Kahweol,1TBDMS,isomer #1	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO)(O[Si](C)(C)C(C)(C)C)C3	3111.8	Semi standard non polar	33892256
Kahweol,1TBDMS,isomer #2	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(O)(CO[Si](C)(C)C(C)(C)C)C3	3102.3	Semi standard non polar	33892256
Kahweol,2TBDMS,isomer #1	CC12C=CC3=C(C=CO3)C1CCC13CC(CCC12)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C3	3339.7	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 - Kahweol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000m-0590000000-cbf3c432ffc87aed9e80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kahweol GC-MS (2 TMS) - 70eV, Positive	splash10-002f-9534800000-58b55eccff30839320c3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kahweol 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 - Kahweol 10V, Positive-QTOF	splash10-014i-0149000000-db23928410381e9a18f3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 20V, Positive-QTOF	splash10-00kb-0392000000-f4b88a6891473473ddf0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 40V, Positive-QTOF	splash10-0frw-5970000000-c8c248c27bb4efc9fdc0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 10V, Negative-QTOF	splash10-03di-0039000000-61fb732de24a5e6c886a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 20V, Negative-QTOF	splash10-03e9-0094000000-1c828fa69ffecae29c5b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 40V, Negative-QTOF	splash10-0uxr-1090000000-4bc978ebbf2a0ccf815c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 10V, Negative-QTOF	splash10-03di-0009000000-d8638daf32922c227464	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 20V, Negative-QTOF	splash10-03di-0019000000-f86639b6d0fdd901510d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 40V, Negative-QTOF	splash10-02t9-0093000000-15f5c908f4472d8d4215	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 10V, Positive-QTOF	splash10-014i-0009000000-88e0e67fa31725f576fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 20V, Positive-QTOF	splash10-014l-3194000000-bb658b1aa87085b0e9e7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kahweol 40V, Positive-QTOF	splash10-001r-2930000000-0ebed8f5e58f9f6f24a4	2021-09-23	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

FDB014295

KNApSAcK ID

C00053387

Chemspider ID

102755

KEGG Compound ID

Not Available

BioCyc ID

CPD-16468

BiGG ID

Not Available

Wikipedia Link

Kahweol

METLIN ID

Not Available

PubChem Compound

114778

PDB ID

Not Available

ChEBI ID

138308

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1039871

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Oh JH, Lee JT, Yang ES, Chang JS, Lee DS, Kim SH, Choi YH, Park JW, Kwon TK: The coffee diterpene kahweol induces apoptosis in human leukemia U937 cells through down-regulation of Akt phosphorylation and activation of JNK. Apoptosis. 2009 Nov;14(11):1378-86. doi: 10.1007/s10495-009-0407-x. [PubMed:19768546 ]
Kim HG, Kim JY, Hwang YP, Lee KJ, Lee KY, Kim DH, Kim DH, Jeong HG: The coffee diterpene kahweol inhibits tumor necrosis factor-alpha-induced expression of cell adhesion molecules in human endothelial cells. Toxicol Appl Pharmacol. 2006 Dec 15;217(3):332-41. Epub 2006 Oct 4. [PubMed:17097123 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Kahweol (HMDB0035602)

MOL for HMDB0035602 (Kahweol)

3D MOL for HMDB0035602 (Kahweol)

3D SDF for HMDB0035602 (Kahweol)

3D-SDF for HMDB0035602 (Kahweol)

PDB for HMDB0035602 (Kahweol)

3D PDB for HMDB0035602 (Kahweol)

SMILES for HMDB0035602 (Kahweol)

INCHI for HMDB0035602 (Kahweol)

Structure for HMDB0035602 (Kahweol)

3D Structure for HMDB0035602 (Kahweol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra