NP-MRD: Showing NP-Card for (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid (NP0251311)

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Record Information

Version

2.0

Created at

2022-09-07 14:28:16 UTC

Updated at

2022-09-07 14:28:16 UTC

NP-MRD ID

NP0251311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid

Description

Docosanoyl-CoA, also known as behenoyl-CoA, belongs to the class of organic compounds known as gangliosides. These are lipid molecules composed of a glycosphingolipid (ceramide and saccharide) with one or more sialic acids linked on the sugar chain. They are usually oligoglycosylceramides derived from lactosylceramide and containing a sialic acid residue such as N-acetylneuraminic acid. Thus, docosanoyl-CoA is considered to be a fatty ester lipid molecule. A very long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of docosanoic (behenic) acid. Docosanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, docosanoyl-CoA participates in a number of enzymatic reactions. In particular, docosanoyl-CoA and glycerol 3-phosphate can be converted into lpa(22:0/0:0) Through its interaction with the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(22:0/0:0) And docosanoyl-CoA can be converted into PA(22:0/22:0); Which is catalyzed by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid is found in Apis cerana. (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid was first documented in 1986 (PMID: 3958710). In humans, docosanoyl-CoA is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway (PMID: 9546340).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303082008092D          

 71 73  0  0  1  0            999 V2000
   12.3686   -2.6360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7012   -2.1511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1137   -3.4206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0337   -2.6360    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2888   -3.4206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5987   -4.0881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6230   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9084   -7.0895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4796   -7.0895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9368   -5.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -5.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2224   -4.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5079   -2.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9098   -2.5205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0801   -6.6770    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6526   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2250   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9394   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.3684   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0829   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7974   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5118   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2262   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9408   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6552   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3697   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0842   -7.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7987   -6.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
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 17 23  1  0  0  0  0
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 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
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 31 25  1  0  0  0  0
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 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
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 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
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 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
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 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
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 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
M  END

     RDKit          3D

149151  0  0  0  0  0  0  0  0999 V2000
   18.0607    3.2047   -2.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6670    2.8481   -1.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8477    1.6353   -1.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5319    1.1282   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9150    2.1508    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6246    1.8910    1.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4136    0.7631    1.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5067   -0.6327    1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5098   -0.8702    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0779   -0.6921    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6340   -1.6272    1.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7426   -3.0578    1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0478   -3.6144    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5927   -3.6197    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0655   -1.6059   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138   -2.2425   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9082   -1.3821   -2.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -0.0480   -2.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328   -0.2646   -2.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3220   -1.3693   -2.7708 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991    0.8417   -1.7575 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0577    2.3362   -1.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7178    2.2068    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594    1.6862    1.3778 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977    0.4066    1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4839   -0.4638    0.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    0.0285    2.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9104   -1.3658    2.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453   -1.4387    1.4237 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2774    0.0350    2.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3933    0.6224   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6454    1.4592   -2.7444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2296   -1.0235   -3.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2044   -0.3573   -1.6636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0798   -0.9534   -0.0809 P   0  0  2  0  0  5  0  0  0  0  0  0
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  -10.5379   -0.8866    0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -18.1807    3.7270    0.5438 N   0  0  0  0  0  0  0  0  0  0  0  0
  -18.2278    2.5838    1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1056    1.8666    1.4213 N   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9506    2.3023    0.8832 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1466   -0.6591    1.0197 C   0  0  2  0  0  0  0  0  0  0  0  0
  -15.1658   -1.7080    1.9398 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1713   -1.0875   -0.0920 C   0  0  2  0  0  0  0  0  0  0  0  0
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  -15.7876   -3.3202   -2.4270 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652303082008092D          

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 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/t32-,36-,37-,38+,42-/m1/s1

> <INCHI_KEY>
NDDZLVOCGALPLR-GNSUAQHMSA-N

> <FORMULA>
C43H78N7O17P3S

> <MOLECULAR_WEIGHT>
1090.11

> <EXACT_MASS>
1089.438776248

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
149

> <JCHEM_AVERAGE_POLARIZABILITY>
115.01139400645468

> <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)-2-({[({[(3R)-3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.2657213688520432

> <ALOGPS_LOGS>
-3.81

> <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>
363.6299999999999

> <JCHEM_REFRACTIVITY>
264.2539

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0      23.088  -4.921   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      21.842  -4.015   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      22.612  -6.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.596  -4.921   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.072  -6.385   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.518  -7.631   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.496 -12.464   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.883 -13.234   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.162 -13.234   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.829 -12.464   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.495 -13.234   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.215 -10.154   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.829 -10.924   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.215  -8.614   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.548  -8.614   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.882  -7.844   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.549  -6.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.445  -4.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.215  -5.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.985  -4.200   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.882  -6.304   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.548  -5.534   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.883  -5.534   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      14.963  -5.534   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      18.043  -5.534   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.423  -3.994   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.423  -7.074   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.503  -3.994   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.503  -7.074   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      13.423  -5.534   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      16.503  -5.534   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      19.132  -4.445   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      20.167  -7.631   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      18.627  -9.171   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      21.707  -9.171   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      20.167  -9.171   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      20.167 -10.711   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      24.553  -4.445   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      25.697  -5.475   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.179  -3.038   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      27.031  -4.705   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      25.697  -7.015   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      26.711  -3.199   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      28.365  -5.475   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.031  -7.785   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      28.365  -7.015   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      29.698  -4.705   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      13.216 -12.464   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      14.550 -14.774   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      14.550 -13.234   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      15.884 -12.464   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      17.217 -13.234   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      18.551 -12.464   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      19.885 -13.234   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      21.219 -12.464   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      22.552 -13.234   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      23.886 -12.464   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      25.220 -13.234   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      26.553 -12.464   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      27.887 -13.234   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      29.220 -12.464   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      30.554 -13.234   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      31.888 -12.464   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      33.222 -13.234   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      34.555 -12.464   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      35.889 -13.234   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      37.223 -12.464   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      38.556 -13.234   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      39.890 -12.464   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      41.224 -13.234   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      42.558 -12.464   0.000  0.00  0.00           C+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  146    0
END

View in JSmol

Synonyms

Value	Source
Behenoyl-CoA	ChEBI
Behenoyl-coenzyme A	ChEBI
Behenyl CoA	ChEBI
Behenyl-coenzyme A	ChEBI
Docosanoyl-coenzyme A	ChEBI
Behenyl-CoA	MeSH
Docosanoyl-CoA	ChEBI

Chemical Formula

C₄₃H₇₈N₇O₁₇P₃S

Average Mass

1090.1100 Da

Monoisotopic Mass

1089.43878 Da

IUPAC Name

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

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/t32-,36-,37-,38+,42-/m1/s1

InChI Key

NDDZLVOCGALPLR-GNSUAQHMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gangliosides. These are lipid molecules composed of a glycosphingolipid (ceramide and saccharide) with one or more sialic acids linked on the sugar chain. They are usually oligoglycosylceramides derived from lactosylceramide and containing a sialic acid residue such as N-acetylneuraminic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Gangliosides

Alternative Parents

Substituents

Neuaca2-3galb1-4glcb-cer_backbone
Glycosyl-n-acylsphingosine
Oligosaccharide
N-acylneuraminic acid
N-acylneuraminic acid or derivatives
Neuraminic acid
Fatty acyl glycoside
C-glucuronide
Alkyl glycoside
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Ketal
Fatty amide
N-acyl-amine
Oxane
Fatty acyl
Pyran
Acetamide
Ketone
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Primary alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.88	ALOGPS
logP	3.27	ChemAxon
logS	-3.8	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	40	ChemAxon
Refractivity	264.25 m³·mol⁻¹	ChemAxon
Polarizability	115.01 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16528

BioCyc ID

CPD-10279

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

168166

PDB ID

Not Available

ChEBI ID

65088

Good Scents ID

Not Available

References

General References

Yoshida S, Takeshita M: Characteristics of synthesis of very-long-chain saturated and tetraenoic fatty acids in swine cerebral microsomes. J Neurochem. 1986 May;46(5):1353-8. doi: 10.1111/j.1471-4159.1986.tb01746.x. [PubMed:3958710 ]
Smelt AH, Poorthuis BJ, Onkenhout W, Scholte HR, Andresen BS, van Duinen SG, Gregersen N, Wintzen AR: Very long chain acyl-coenzyme A dehydrogenase deficiency with adult onset. Ann Neurol. 1998 Apr;43(4):540-4. doi: 10.1002/ana.410430422. [PubMed:9546340 ]
LOTUS database [Link]

Showing NP-Card for (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid (NP0251311)

MOL for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D MOL for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D SDF for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D-SDF for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

PDB for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D PDB for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

SMILES for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

INCHI for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

Structure for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D Structure for NP0251311 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-n-(2-{[2-(docosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)