MiMeDB: Showing metabocard for Farnesylcysteine (MMDBc0049458)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:34:12 UTC

Update Date

2024-04-30 20:38:11 UTC

Metabolite ID

MMDBc0049458

Metabolite Identification

Common Name

Farnesylcysteine

Description

In patients with chronic fatigue syndrome (CFS) we found increased IgM levels to S-farnesyl-L-cysteine. S-farnesyl-L-cysteine plays a key role in regulating cell growth, differentiation and apoptosis through RAS protein activity. The latter depends on their anchorage to the inner surface of the plasma membrane, which is promoted by their common carboxy-terminal S-farnesyl-cysteine. The presence of antibodies to S-farnesyl-L-cysteine suggest that RAS functions may have undergone damage by oxidative/nitrosative stress, causing disturbed functional activity in the regulation of cell growth. (PMID 17159817 ).

Structure

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

HMDB0011627
     RDKit          3D
Farnesylcysteine
 53 52  0  0  0  0  0  0  0  0999 V2000
    5.7516    1.1382   -1.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0454   -0.1140   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826   -1.2688   -2.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597   -0.2109   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    0.9494    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    1.3820    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019    0.2868    1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -0.2926    3.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208   -0.1704    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -1.2688    1.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.7421    1.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -0.3021    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -1.2522   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    0.9601    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    1.5441   -0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1012    2.2051   -0.3932 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2363    0.8521    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4996   -0.0170   -1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0869    0.8555   -2.2117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4532   -1.0918   -0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5791   -1.1249   -1.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0530   -2.0163    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0601    1.9888   -1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5727    1.3828   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2187    1.0647   -2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385   -1.9321   -1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070   -1.8208   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229   -0.8610   -3.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.1295    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521    0.6242    1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0621    1.7879    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.6923    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    2.2240    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768   -0.3458    3.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1532   -1.3001    2.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.4188    3.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.2975    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8018   -1.6610    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4200   -2.1013    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    0.1070    2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -1.5138    2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -2.1767   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4164   -0.8414   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -1.6304   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919    1.6262    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    2.3846   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    0.8610   -1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2018    1.3124    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708    0.2596    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -0.4719   -1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6655    1.8124   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0339    0.4702   -3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6434   -2.8299    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  6
 19 51  1  0
 19 52  1  0
 22 53  1  0
M  END


  Mrv1652309042000342D          

 22 21  0  0  1  0            999 V2000
    4.2682  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827  -11.5167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6972  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4117  -11.5167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1261  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8406  -11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5551  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2696  -11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9841  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6985  -11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4130  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1275  -11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8420  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5565  -11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2710  -11.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9854  -11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2710  -12.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537  -11.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682  -12.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9827  -10.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5551  -12.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4130  -12.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 15  1  0  0  0  0
 18  1  1  0  0  0  0
 19  1  2  0  0  0  0
  2 20  1  1  0  0  0
 21  7  1  0  0  0  0
 22 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049458

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CSC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H31NO2S/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-22-13-17(19)18(20)21/h7,9,11,17H,5-6,8,10,12-13,19H2,1-4H3,(H,20,21)/b15-9+,16-11+/t17-/m0/s1

> <INCHI_KEY>
SYSLNQMKLROGCL-BCYUYYMPSA-N

> <FORMULA>
C18H31NO2S

> <MOLECULAR_WEIGHT>
325.509

> <EXACT_MASS>
325.207549931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.42506667991615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
2.1725843935013525

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5632352114487555

> <JCHEM_PKA_STRONGEST_BASIC>
9.137260247302265

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
99.64719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-farnesylcysteine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011627
     RDKit          3D
Farnesylcysteine
 53 52  0  0  0  0  0  0  0  0999 V2000
    5.7516    1.1382   -1.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0454   -0.1140   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826   -1.2688   -2.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597   -0.2109   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    0.9494    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    1.3820    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019    0.2868    1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -0.2926    3.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208   -0.1704    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -1.2688    1.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.7421    1.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -0.3021    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -1.2522   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    0.9601    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    1.5441   -0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1012    2.2051   -0.3932 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2363    0.8521    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4996   -0.0170   -1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0869    0.8555   -2.2117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4532   -1.0918   -0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5791   -1.1249   -1.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0530   -2.0163    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0601    1.9888   -1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5727    1.3828   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2187    1.0647   -2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385   -1.9321   -1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070   -1.8208   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229   -0.8610   -3.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.1295    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521    0.6242    1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0621    1.7879    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.6923    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    2.2240    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768   -0.3458    3.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1532   -1.3001    2.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.4188    3.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.2975    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8018   -1.6610    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4200   -2.1013    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    0.1070    2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -1.5138    2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -2.1767   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4164   -0.8414   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -1.6304   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919    1.6262    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    2.3846   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    0.8610   -1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2018    1.3124    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708    0.2596    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -0.4719   -1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6655    1.8124   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0339    0.4702   -3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6434   -2.8299    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  6
 19 51  1  0
 19 52  1  0
 22 53  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       7.967 -22.268   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.301 -21.498   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.635 -22.268   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      11.969 -21.498   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      13.302 -22.268   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.636 -21.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.970 -22.268   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.303 -21.498   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.637 -22.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.971 -21.498   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.304 -22.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.638 -21.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.972 -22.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.305 -21.498   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.639 -22.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.973 -21.498   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.639 -23.808   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.634 -21.498   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.967 -23.808   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       9.301 -19.958   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      15.970 -23.808   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.304 -23.808   0.000  0.00  0.00           C+0
CONECT    1    2   18   19                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    7                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0011627
HETATM    1  C1  UNL     1       5.752   1.138  -1.630  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.045  -0.114  -1.265  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.983  -1.269  -2.202  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.460  -0.211  -0.090  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.524   0.949   0.846  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.101   1.382   1.120  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.302   0.287   1.735  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.723  -0.293   3.052  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.221  -0.170   1.118  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.382  -1.269   1.691  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.031  -0.742   1.911  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.557  -0.302   0.604  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.689  -1.252  -0.505  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.904   0.960   0.461  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.444   1.544  -0.786  1.00  0.00           C  
HETATM   16  S1  UNL     1      -4.101   2.205  -0.393  1.00  0.00           S  
HETATM   17  C16 UNL     1      -5.236   0.852   0.006  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.500  -0.017  -1.209  1.00  0.00           C  
HETATM   19  N1  UNL     1      -6.087   0.855  -2.212  1.00  0.00           N  
HETATM   20  C18 UNL     1      -6.453  -1.092  -0.835  1.00  0.00           C  
HETATM   21  O1  UNL     1      -7.579  -1.125  -1.389  1.00  0.00           O  
HETATM   22  O2  UNL     1      -6.053  -2.016   0.115  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.060   1.989  -1.633  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.573   1.383  -0.902  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.219   1.065  -2.636  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.839  -1.932  -2.000  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.007  -1.821  -2.095  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.023  -0.861  -3.227  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.936  -1.130   0.192  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.052   0.624   1.741  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.062   1.788   0.391  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.608   1.692   0.194  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.083   2.224   1.852  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.877  -0.346   3.735  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.153  -1.300   2.939  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.449   0.419   3.522  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.970   0.297   0.164  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.802  -1.661   2.627  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.420  -2.101   0.967  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.968   0.107   2.641  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.694  -1.514   2.323  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.078  -2.177  -0.396  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.416  -0.841  -1.499  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.750  -1.630  -0.502  1.00  0.00           H  
HETATM   45  H23 UNL     1      -1.792   1.626   1.302  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.785   2.385  -1.076  1.00  0.00           H  
HETATM   47  H25 UNL     1      -2.526   0.861  -1.624  1.00  0.00           H  
HETATM   48  H26 UNL     1      -6.202   1.312   0.299  1.00  0.00           H  
HETATM   49  H27 UNL     1      -4.871   0.260   0.870  1.00  0.00           H  
HETATM   50  H28 UNL     1      -4.565  -0.472  -1.548  1.00  0.00           H  
HETATM   51  H29 UNL     1      -5.665   1.812  -2.169  1.00  0.00           H  
HETATM   52  H30 UNL     1      -6.034   0.470  -3.172  1.00  0.00           H  
HETATM   53  H31 UNL     1      -6.643  -2.830   0.263  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    4
CONECT    3   26   27   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8    9    9
CONECT    8   34   35   36
CONECT    9   10   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   14   14
CONECT   13   42   43   44
CONECT   14   15   45
CONECT   15   16   46   47
CONECT   16   17
CONECT   17   18   48   49
CONECT   18   19   20   50
CONECT   19   51   52
CONECT   20   21   21   22
CONECT   22   53
END

HMDB0011627
     RDKit          3D
Farnesylcysteine
 53 52  0  0  0  0  0  0  0  0999 V2000
    5.7516    1.1382   -1.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0454   -0.1140   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826   -1.2688   -2.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597   -0.2109   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    0.9494    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    1.3820    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019    0.2868    1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -0.2926    3.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2208   -0.1704    1.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -1.2688    1.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -0.7421    1.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -0.3021    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -1.2522   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9036    0.9601    0.4611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    1.5441   -0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1012    2.2051   -0.3932 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2363    0.8521    0.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4996   -0.0170   -1.2095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0869    0.8555   -2.2117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4532   -1.0918   -0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5791   -1.1249   -1.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0530   -2.0163    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0601    1.9888   -1.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5727    1.3828   -0.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2187    1.0647   -2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385   -1.9321   -1.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070   -1.8208   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0229   -0.8610   -3.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.1295    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0521    0.6242    1.7413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0621    1.7879    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.6923    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    2.2240    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768   -0.3458    3.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1532   -1.3001    2.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4490    0.4188    3.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.2975    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8018   -1.6610    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4200   -2.1013    0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    0.1070    2.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944   -1.5138    2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0781   -2.1767   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4164   -0.8414   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497   -1.6304   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919    1.6262    1.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    2.3846   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262    0.8610   -1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2018    1.3124    0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8708    0.2596    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5649   -0.4719   -1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6655    1.8124   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0339    0.4702   -3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6434   -2.8299    0.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  6
 19 51  1  0
 19 52  1  0
 22 53  1  0
M  END

Synonyms

Value	Source
S-(2E,6E)-Farnesyl-L-cysteine	ChEBI
S-trans-trans-Farnesylcysteine	Kegg
(e,e)-L-S-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-cysteine	HMDB
S-all-trans-Farnesyl-L-cysteine	HMDB
S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl]-L-cysteine	HMDB
S-[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienyl]-L-cysteine,(9ci)	HMDB
S-Farnesyl cysteine	MeSH, HMDB
S-Farnesylcysteine	MeSH, HMDB

Molecular Formula

C₁₈H₃₁NO₂S

Average Mass

325.509

Monoisotopic Mass

325.207549931

IUPAC Name

(2R)-2-amino-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid

Traditional Name

S-farnesylcysteine

CAS Registry Number

68000-92-0

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CSC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C18H31NO2S/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-22-13-17(19)18(20)21/h7,9,11,17H,5-6,8,10,12-13,19H2,1-4H3,(H,20,21)/b15-9+,16-11+/t17-/m0/s1

InChI Key

SYSLNQMKLROGCL-BCYUYYMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Farsesane sesquiterpenoid
L-cysteine-s-conjugate
Cysteine or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Amino acid or derivatives
Amino acid
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Organopnictogen compound
Organic oxide
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-farnesyl-L-cysteine (CHEBI:62197 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0051 g/L	ALOGPS
logP	1.48	ALOGPS
logP	2.17	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	99.65 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mx-9751000000-c75df345d8656012bdf0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05aa-8954000000-cb16d7122a6e7b9bef6c	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7i-5396000000-851334288f8263d03d23	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-9860000000-dba878d9fc5362b67195	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adl-9510000000-bd3c119811a4e2799abe	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dr-1659000000-855d9d7f127560943e3d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-4791000000-842def471e9561591a94	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fer-9210000000-618508fb705b5020cbb6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aba-1951000000-c167818276c3885878f5	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-2910000000-002b04adc9b951f37f54	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c29-9410000000-00bddc91238723c07f72	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-1193000000-d24d7910416af3a09863	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-9060000000-023ebf01c668a96e1673	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9110000000-d96ba181641b84daf905	2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0195054	Prenylcysteine oxidase 1	Unknown	Q9UHG3	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010569	Farnesylcysteine	L-Cysteine	prenylcysteine oxidase 1		VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0011627

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028328

KNApSAcK ID

Not Available

Chemspider ID

4942854

KEGG Compound ID

C19691

BioCyc ID

CPD-12581

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438372

PDB ID

Not Available

ChEBI ID

62141

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Havel CM, Fisher P, Watson JA: Isopentenoid synthesis in embryonic Drosophila cells: prenylated protein profile and prenyl group usage. Arch Biochem Biophys. 1992 Jun;295(2):410-20. doi: 10.1016/0003-9861(92)90535-5. [PubMed:1586169 ]
Volker C, Miller RA, McCleary WR, Rao A, Poenie M, Backer JM, Stock JB: Effects of farnesylcysteine analogs on protein carboxyl methylation and signal transduction. J Biol Chem. 1991 Nov 15;266(32):21515-22. [PubMed:1939182 ]
Aharonson Z, Gana-Weisz M, Varsano T, Haklai R, Marciano D, Kloog Y: Stringent structural requirements for anti-Ras activity of S-prenyl analogues. Biochim Biophys Acta. 1998 Feb 27;1406(1):40-50. doi: 10.1016/s0925-4439(97)00077-x. [PubMed:9545527 ]
Elad G, Paz A, Haklai R, Marciano D, Cox A, Kloog Y: Targeting of K-Ras 4B by S-trans,trans-farnesyl thiosalicylic acid. Biochim Biophys Acta. 1999 Dec 9;1452(3):228-42. doi: 10.1016/s0167-4889(99)00144-5. [PubMed:10590312 ]
Lamango NS, Charlton CG: Farnesyl-L-cysteine analogs block SAM-induced Parkinson's disease-like symptoms in rats. Pharmacol Biochem Behav. 2000 Aug;66(4):841-9. doi: 10.1016/s0091-3057(00)00274-4. [PubMed:10973524 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Maes M, Mihaylova I, Leunis JC: Chronic fatigue syndrome is accompanied by an IgM-related immune response directed against neopitopes formed by oxidative or nitrosative damage to lipids and proteins. Neuro Endocrinol Lett. 2006 Oct;27(5):615-21. [PubMed:17159817 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Farnesylcysteine (MMDBc0049458)

MOL for #<Metabolite:0x00007fecb3165ab0>

3D MOL for #<Metabolite:0x00007fecb3165ab0>

3D SDF for #<Metabolite:0x00007fecb3165ab0>

3D-SDF for #<Metabolite:0x00007fecb3165ab0>

PDB for #<Metabolite:0x00007fecb3165ab0>

3D PDB for #<Metabolite:0x00007fecb3165ab0>

SMILES for #<Metabolite:0x00007fecb3165ab0>

INCHI for #<Metabolite:0x00007fecb3165ab0>

Structure for #<Metabolite:0x00007fecb3165ab0>

3D Structure for #<Metabolite:0x00007fecb3165ab0>