NP-MRD: Showing NP-Card for Geranylgeranylcysteine (NP0091550)

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Record Information

Version

2.0

Created at

2022-05-11 18:41:06 UTC

Updated at

2022-05-11 18:41:06 UTC

NP-MRD ID

NP0091550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geranylgeranylcysteine

Description

Geranylgeranylcysteine belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Geranylgeranylcysteine is a moderately basic compound (based on its pKa). Prenylcysteine lyase deficiency leads to the accumulation of farnesylcysteine and geranylgeranylcysteine in brain and liver. Geranylgeranylcysteine is typically formed through posttranslational (prenylation) protein modification whereupon degradation of the parent protein leaves the modified (prenylated) amino acid. Geranylgeranylcysteine is a modified thioether amino acid in which an isoprenyl group (geranylgeranyl) has been attached to the sulfhydryl group of cysteine through a thioether bond. Geranylgeranylcysteine was first documented in 1997 (PMID: 9287348). Prenylation is a relatively recently discovered post-translational modification of proteins that directs cytosollic proteins to membranes while at the same time activating them functionally.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201502D          

 28 27  0  0  1  0            999 V2000
    3.1152  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4021  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5455  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2599  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9744  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -13.6428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.0553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2613  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9757  -14.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1152  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -12.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -15.2928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  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  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 21  1  1  0  0  0  0
 22 18  2  0  0  0  0
 17 23  1  6  0  0  0
 24 23  1  0  0  0  0
 25 15  2  0  0  0  0
 26 13  1  0  0  0  0
 27  9  1  0  0  0  0
 28  5  1  0  0  0  0
M  END

     RDKit          3D

 65 64  0  0  0  0  0  0  0  0999 V2000
    5.6064   -0.5143    2.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0264   -1.0291    1.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6759   -2.4140    0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7017   -0.2475    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1540   -0.6655   -0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6011    0.2215   -2.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139    0.2155   -2.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256   -1.0158   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4494    1.3455   -1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623    1.4020   -1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605    1.9146   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804    1.9590   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    2.8034   -1.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    1.2563    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2225    1.3321    0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8615   -0.0114   -0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3455    0.2273   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145    1.1466   -1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1103   -0.4162    0.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5569   -0.2450    0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1368    0.5158   -0.1470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3522   -0.9436    1.5929 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7887   -0.8160    1.6558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3535   -2.2169    1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1489   -2.1628    1.4462 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2529   -0.4414    3.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4878   -0.2591    3.9918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6104   -0.2829    3.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947   -0.3466    2.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652   -1.2523    3.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0435    0.4735    2.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7868   -2.3892    0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3719   -2.9647    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5229   -2.9446    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9367    0.7567    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8709   -1.7017   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -0.6092   -0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9479   -0.0985   -2.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067    1.2357   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0497   -1.8610   -2.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091   -0.9354   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6004   -1.1871   -1.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979    2.2500   -1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072    2.0894   -2.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003    0.4180   -2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948    2.9200   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7902    1.2166    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3212    3.5935   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    3.3357   -2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    2.1394   -2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111    0.6320    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512    2.0726   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    1.6891    1.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341   -0.4645   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136   -0.7139    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    0.6267   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833    1.5399   -1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507    2.0187   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360   -1.0818    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8952   -1.5849    2.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1519   -0.1104    0.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9679   -2.5954    0.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9808   -2.8565    2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7322   -3.0815    0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1664   -0.8860    3.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
 23 26  1  0
 26 28  1  0
 26 27  2  0
 25 64  1  0
 24 62  1  0
 24 63  1  0
 23 61  1  6
 22 60  1  0
 19 59  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 16 54  1  0
 16 55  1  0
 15 52  1  0
 15 53  1  0
 14 51  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 11 46  1  0
 11 47  1  0
 10 44  1  0
 10 45  1  0
  9 43  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
  6 38  1  0
  6 39  1  0
  5 36  1  0
  5 37  1  0
  4 35  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
 28 65  1  0
M  END


  Mrv0541 02241201502D          

 28 27  0  0  1  0            999 V2000
    3.1152  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6876  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4021  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5455  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2599  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9744  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4034  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -13.6428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.0553    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2613  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9757  -14.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1152  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -12.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5468  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2613  -15.2928    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179  -14.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6889  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8310  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9731  -14.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  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  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 21  1  1  0  0  0  0
 22 18  2  0  0  0  0
 17 23  1  6  0  0  0
 24 23  1  0  0  0  0
 25 15  2  0  0  0  0
 26 13  1  0  0  0  0
 27  9  1  0  0  0  0
 28  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091550

> <DATABASE_NAME>
NP-MRD

> <SMILES>
SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1

> <INCHI_KEY>
UBCKUGRWFMEXIF-WONWMLGISA-N

> <FORMULA>
C23H37NO3S

> <MOLECULAR_WEIGHT>
407.61

> <EXACT_MASS>
407.249414745

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
48.78785754192435

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

> <ALOGPS_LOGP>
5.58

> <JCHEM_LOGP>
5.654119356

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.049435375930052

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.041595471416822

> <JCHEM_PKA_STRONGEST_BASIC>
1.452563358758466

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
123.67839999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.815 -26.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.149 -25.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.482 -26.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.816 -25.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.150 -26.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.484 -25.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.817 -26.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.151 -25.467   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.485 -26.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.818 -25.467   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.152 -26.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.486 -25.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.819 -26.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.153 -25.467   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.487 -26.237   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      25.820 -25.467   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      27.154 -26.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.488 -25.467   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      29.821 -26.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.481 -25.467   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.815 -27.777   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      28.488 -23.927   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      27.154 -27.777   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0      28.488 -28.547   0.000  0.00  0.00           S+0
HETATM   25  O   UNK     0      24.487 -27.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.819 -27.777   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.485 -27.777   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.150 -27.777   0.000  0.00  0.00           C+0
CONECT    1    2   20   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22   18                                                            
CONECT   23   17   24                                                       
CONECT   24   23                                                            
CONECT   25   15                                                            
CONECT   26   13                                                            
CONECT   27    9                                                            
CONECT   28    5                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
S-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl)-(e,e,e)-L-cysteine	HMDB
S-[(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl]- (9ci)-L-cysteine	HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulfanylpropanoate	HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulphanylpropanoate	HMDB
(2R)-2-{[(2E,6E,10E)-1-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ylidene]amino}-3-sulphanylpropanoic acid	HMDB

Chemical Formula

C₂₃H₃₇NO₃S

Average Mass

407.6100 Da

Monoisotopic Mass

407.24941 Da

IUPAC Name

(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

Traditional Name

(2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid

CAS Registry Number

Not Available

SMILES

SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O

InChI Identifier

InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1

InChI Key

UBCKUGRWFMEXIF-WONWMLGISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid or derivatives
N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Alkylthiol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.58	ALOGPS
logP	5.65	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	1.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	123.68 m³·mol⁻¹	ChemAxon
Polarizability	48.79 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0011678

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028366

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481025

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang L, Tschantz WR, Casey PJ: Isolation and characterization of a prenylcysteine lyase from bovine brain. J Biol Chem. 1997 Sep 12;272(37):23354-9. doi: 10.1074/jbc.272.37.23354. [PubMed:9287348 ]

Showing NP-Card for Geranylgeranylcysteine (NP0091550)

MOL for NP0091550 (Geranylgeranylcysteine)

3D MOL for NP0091550 (Geranylgeranylcysteine)

3D SDF for NP0091550 (Geranylgeranylcysteine)

3D-SDF for NP0091550 (Geranylgeranylcysteine)

PDB for NP0091550 (Geranylgeranylcysteine)

3D PDB for NP0091550 (Geranylgeranylcysteine)

SMILES for NP0091550 (Geranylgeranylcysteine)

INCHI for NP0091550 (Geranylgeranylcysteine)

Structure for NP0091550 (Geranylgeranylcysteine)

3D Structure for NP0091550 (Geranylgeranylcysteine)