NP-MRD: Showing NP-Card for Undecanoyl-CoA (NP0339187)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 20:16:25 UTC

Updated at

2024-09-11 20:16:26 UTC

NP-MRD ID

NP0339187

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Undecanoyl-CoA

Description

Undecanoyl-CoA belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain. Undecanoyl-CoA is a strong basic compound (based on its pKa). Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303262014182D          

 60 62  0  0  1  0            999 V2000
    1.3869  -15.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074  -15.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923  -16.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128  -16.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9978  -16.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8182  -16.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3032  -17.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237  -17.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086  -17.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4291  -17.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9140  -18.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7345  -18.3877    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5784  -19.2276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0032  -17.2206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1747  -18.0276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5552  -16.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1427  -15.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9284  -18.3631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8422  -19.1836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.3358  -16.0646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2495  -16.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6227  -18.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0352  -19.3552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5552  -15.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3802  -16.6075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4553  -19.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3802  -15.1785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6996  -20.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7927  -15.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8791  -20.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6429  -17.9506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1427  -14.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2837  -20.5426    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.4768  -20.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0907  -20.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1122  -21.3497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5436  -20.9487    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.2080  -21.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2972  -21.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7899  -20.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3875  -21.7887    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.5670  -21.8749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4738  -22.6092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3013  -20.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2195  -19.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0399  -18.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5248  -19.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3454  -19.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8303  -20.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6508  -20.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1357  -20.7988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9562  -20.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4411  -21.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2616  -21.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0821  -21.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1753  -20.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3479  -22.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1056  -22.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2917  -19.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6809  -18.7964    0.0000 O   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  1  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  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 15 14  1  1  0  0  0
 16 14  1  0  0  0  0
 21 14  1  0  0  0  0
 18 15  1  0  0  0  0
 22 15  1  0  0  0  0
 17 16  2  0  0  0  0
 25 16  1  0  0  0  0
 24 17  1  0  0  0  0
 20 17  1  0  0  0  0
 19 18  1  0  0  0  0
 18 31  1  6  0  0  0
 19 26  1  6  0  0  0
 23 19  1  0  0  0  0
 21 20  2  0  0  0  0
 23 22  1  0  0  0  0
 23 28  1  1  0  0  0
 32 24  1  0  0  0  0
 27 24  2  0  0  0  0
 29 25  2  0  0  0  0
 33 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 37 30  1  0  0  0  0
 34 33  1  0  0  0  0
 35 33  2  0  0  0  0
 36 33  1  0  0  0  0
 38 37  1  0  0  0  0
 39 37  2  0  0  0  0
 40 37  1  0  0  0  0
 41 38  1  0  0  0  0
 42 41  1  0  0  0  0
 43 41  2  0  0  0  0
 44 41  1  0  0  0  0
 55 42  1  0  0  0  0
 46 45  1  0  0  0  0
 12 45  1  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 60 48  2  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
 59 52  2  0  0  0  0
 54 53  1  0  0  0  0
 58 53  1  0  0  0  0
 55 54  1  0  0  0  0
 56 54  1  0  0  0  0
 57 54  1  0  0  0  0
M  END


  Mrv1652303262014182D          

 60 62  0  0  1  0            999 V2000
    1.3869  -15.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074  -15.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923  -16.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128  -16.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9978  -16.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8182  -16.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3032  -17.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237  -17.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086  -17.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4291  -17.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9140  -18.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7345  -18.3877    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5784  -19.2276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0032  -17.2206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1747  -18.0276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5552  -16.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1427  -15.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9284  -18.3631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8422  -19.1836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.3358  -16.0646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2495  -16.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6227  -18.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0352  -19.3552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5552  -15.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3802  -16.6075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4553  -19.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3802  -15.1785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6996  -20.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7927  -15.8930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8791  -20.1951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6429  -17.9506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1427  -14.4640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2837  -20.5426    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.4768  -20.3711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0907  -20.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1122  -21.3497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5436  -20.9487    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.2080  -21.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2972  -21.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7899  -20.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3875  -21.7887    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.5670  -21.8749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4738  -22.6092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3013  -20.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2195  -19.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0399  -18.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5248  -19.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3454  -19.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8303  -20.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6508  -20.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1357  -20.7988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9562  -20.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4411  -21.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2616  -21.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0821  -21.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1753  -20.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3479  -22.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1056  -22.1336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2917  -19.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6809  -18.7964    0.0000 O   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  1  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  1  0  0  0  0
 12 11  1  0  0  0  0
 13 11  2  0  0  0  0
 15 14  1  1  0  0  0
 16 14  1  0  0  0  0
 21 14  1  0  0  0  0
 18 15  1  0  0  0  0
 22 15  1  0  0  0  0
 17 16  2  0  0  0  0
 25 16  1  0  0  0  0
 24 17  1  0  0  0  0
 20 17  1  0  0  0  0
 19 18  1  0  0  0  0
 18 31  1  6  0  0  0
 19 26  1  6  0  0  0
 23 19  1  0  0  0  0
 21 20  2  0  0  0  0
 23 22  1  0  0  0  0
 23 28  1  1  0  0  0
 32 24  1  0  0  0  0
 27 24  2  0  0  0  0
 29 25  2  0  0  0  0
 33 26  1  0  0  0  0
 29 27  1  0  0  0  0
 30 28  1  0  0  0  0
 37 30  1  0  0  0  0
 34 33  1  0  0  0  0
 35 33  2  0  0  0  0
 36 33  1  0  0  0  0
 38 37  1  0  0  0  0
 39 37  2  0  0  0  0
 40 37  1  0  0  0  0
 41 38  1  0  0  0  0
 42 41  1  0  0  0  0
 43 41  2  0  0  0  0
 44 41  1  0  0  0  0
 55 42  1  0  0  0  0
 46 45  1  0  0  0  0
 12 45  1  0  0  0  0
 47 46  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 60 48  2  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
 59 52  2  0  0  0  0
 54 53  1  0  0  0  0
 58 53  1  0  0  0  0
 55 54  1  0  0  0  0
 56 54  1  0  0  0  0
 57 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339187

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C32H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-23(41)60-16-15-34-22(40)13-14-35-30(44)27(43)32(2,3)18-53-59(50,51)56-58(48,49)52-17-21-26(55-57(45,46)47)25(42)31(54-21)39-20-38-24-28(33)36-19-37-29(24)39/h19-21,25-27,31,42-43H,4-18H2,1-3H3,(H,34,40)(H,35,44)(H,48,49)(H,50,51)(H2,33,36,37)(H2,45,46,47)/t21-,25-,26-,27?,31-/m1/s1

> <INCHI_KEY>
IZWCGXGZGYKDHR-WMMBNDHFSA-N

> <FORMULA>
C32H56N7O17P3S

> <MOLECULAR_WEIGHT>
935.81

> <EXACT_MASS>
935.266623627

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
89.34766260809188

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
-1.6245339461479598

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761846

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398228

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.62999999999994

> <JCHEM_REFRACTIVITY>
213.64290000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0       2.589 -29.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.120 -28.899   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.026 -30.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.557 -29.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.463 -31.230   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.994 -31.069   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.899 -32.315   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.431 -32.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.336 -33.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.868 -33.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.773 -34.485   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      16.304 -34.324   0.000  0.00  0.00           S+0
HETATM   13  O   UNK     0      14.146 -35.892   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      37.339 -32.145   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      37.659 -33.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.370 -31.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.600 -29.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.066 -34.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.905 -35.809   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      36.093 -29.987   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      35.932 -31.519   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      36.629 -34.796   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      37.399 -36.130   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.370 -28.333   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      39.910 -31.001   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      40.050 -36.840   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      39.910 -28.333   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      36.773 -37.536   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.680 -29.667   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      35.241 -37.698   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      40.400 -33.508   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0      37.600 -26.999   0.000  0.00  0.00           N+0
HETATM   33  P   UNK     0      39.730 -38.346   0.000  0.00  0.00           P+0
HETATM   34  O   UNK     0      38.223 -38.026   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      41.236 -38.666   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      39.409 -39.853   0.000  0.00  0.00           O+0
HETATM   37  P   UNK     0      34.615 -39.104   0.000  0.00  0.00           P+0
HETATM   38  O   UNK     0      33.988 -40.511   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      36.021 -39.731   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      33.208 -38.478   0.000  0.00  0.00           O+0
HETATM   41  P   UNK     0      32.457 -40.672   0.000  0.00  0.00           P+0
HETATM   42  O   UNK     0      30.925 -40.833   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      32.618 -42.204   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      32.296 -39.141   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      17.210 -35.570   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      18.741 -35.408   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0      19.646 -36.654   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0      21.178 -36.494   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      22.083 -37.739   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      23.615 -37.578   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0      24.520 -38.824   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0      26.052 -38.663   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      26.957 -39.909   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      28.488 -39.748   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      30.020 -39.587   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      28.327 -38.217   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      28.649 -41.280   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      26.330 -41.316   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      26.678 -37.256   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      21.804 -35.087   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   45                                                       
CONECT   13   11                                                            
CONECT   14   15   16   21                                                  
CONECT   15   14   18   22                                                  
CONECT   16   14   17   25                                                  
CONECT   17   16   24   20                                                  
CONECT   18   15   19   31                                                  
CONECT   19   18   26   23                                                  
CONECT   20   17   21                                                       
CONECT   21   14   20                                                       
CONECT   22   15   23                                                       
CONECT   23   19   22   28                                                  
CONECT   24   17   32   27                                                  
CONECT   25   16   29                                                       
CONECT   26   19   33                                                       
CONECT   27   24   29                                                       
CONECT   28   23   30                                                       
CONECT   29   25   27                                                       
CONECT   30   28   37                                                       
CONECT   31   18                                                            
CONECT   32   24                                                            
CONECT   33   26   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   30   38   39   40                                             
CONECT   38   37   41                                                       
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   38   42   43   44                                             
CONECT   42   41   55                                                       
CONECT   43   41                                                            
CONECT   44   41                                                            
CONECT   45   46   12                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   60                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   59                                                  
CONECT   53   52   54   58                                                  
CONECT   54   53   55   56   57                                             
CONECT   55   42   54                                                       
CONECT   56   54                                                            
CONECT   57   54                                                            
CONECT   58   53                                                            
CONECT   59   52                                                            
CONECT   60   48                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

View in JSmol

Synonyms

Value	Source
2-Methyloctanoyl CoA, 21	HMDB
2-Methyloctanoyl coenzyme A, 21	HMDB
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(undecanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate	Generator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(undecanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate	Generator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(undecanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid	Generator

Chemical Formula

C₃₂H₅₆N₇O₁₇P₃S

Average Mass

935.8100 Da

Monoisotopic Mass

935.26662 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C32H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-23(41)60-16-15-34-22(40)13-14-35-30(44)27(43)32(2,3)18-53-59(50,51)56-58(48,49)52-17-21-26(55-57(45,46)47)25(42)31(54-21)39-20-38-24-28(33)36-19-37-29(24)39/h19-21,25-27,31,42-43H,4-18H2,1-3H3,(H,34,40)(H,35,44)(H,48,49)(H,50,51)(H2,33,36,37)(H2,45,46,47)/t21-,25-,26-,27?,31-/m1/s1

InChI Key

IZWCGXGZGYKDHR-WMMBNDHFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2,3,4-saturated fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.12	ALOGPS
logP	-1.6	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	213.64 m³·mol⁻¹	ChemAxon
Polarizability	89.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0013114

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029290

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

53481608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Undecanoyl-CoA (NP0339187)

MOL for NP0339187 (Undecanoyl-CoA)

3D MOL for NP0339187 (Undecanoyl-CoA)

3D SDF for NP0339187 (Undecanoyl-CoA)

3D-SDF for NP0339187 (Undecanoyl-CoA)

PDB for NP0339187 (Undecanoyl-CoA)

3D PDB for NP0339187 (Undecanoyl-CoA)

SMILES for NP0339187 (Undecanoyl-CoA)

INCHI for NP0339187 (Undecanoyl-CoA)

Structure for NP0339187 (Undecanoyl-CoA)

3D Structure for NP0339187 (Undecanoyl-CoA)