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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid (NP0245599)

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Record Information

Version

2.0

Created at

2022-09-07 06:44:33 UTC

Updated at

2022-09-07 06:44:33 UTC

NP-MRD ID

NP0245599

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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid

Description

Butyryl-CoA, also known as 4:0-CoA or butanoyl-CoA, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, butyryl-CoA is considered to be a fatty ester lipid molecule. A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of butyric acid. Butyryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Butyryl-CoA may be a unique E. Coli metabolite. In humans, butyryl-CoA is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. Outside of the human body, Butyryl-CoA has been detected, but not quantified in, several different foods, such as ucuhuba, lemon verbena, lettuces, alfalfa, and canola. (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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid is found in Streptomyces cinnamonensis. (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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid was first documented in 1976 (PMID: 1269146). This could make butyryl-CoA a potential biomarker for the consumption of these foods (PMID: 10517585) (PMID: 14570270) (PMID: 15222752) (PMID: 3117785).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308111919232D          

 53 55  0  0  1  0            999 V2000
   25.1304   -3.1759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4630   -2.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8755   -3.9605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7955   -3.1759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.0505   -3.9605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3603   -4.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3847   -7.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1275   -7.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6702   -7.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9558   -7.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2413   -7.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6986   -5.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9558   -6.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6986   -5.1544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   23.0109   -2.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.2506   -2.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2426   -3.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5282   -4.2980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0711   -2.2535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9570   -3.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.6715   -3.0604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8420   -7.2169    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5565   -8.4544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5565   -7.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.9853   -7.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6999   -7.2169    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
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
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 31 28  2  0  0  0  0
 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
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
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 43 40  2  0  0  0  0
 44 41  1  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
 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
M  END

     RDKit          3D

 95 97  0  0  0  0  0  0  0  0999 V2000
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    3.8976    0.8101   -0.6065 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5655    0.4789   -0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196   -0.4293    0.6429 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5940    1.8863    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310    2.9310    0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424    0.9108    1.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15 17  1  0
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 17 19  1  0
 19 20  1  0
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 22 23  1  0
 24 23  1  1
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 28 30  1  0
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 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 46  1  0
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 46 48  1  0
 48 49  1  0
 49 50  1  0
 50 52  1  0
 50 53  1  0
 50 51  2  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 45  2  0
 45 44  1  0
 44 43  2  0
 43 42  1  0
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 40 41  1  0
 48 33  1  0
 45 36  1  0
 40 39  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  2 57  1  0
  2 58  1  0
  3 59  1  0
  3 60  1  0
  7 61  1  0
  7 62  1  0
  8 63  1  0
  8 64  1  0
  9 65  1  0
 12 66  1  0
 12 67  1  0
 13 68  1  0
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 14 70  1  0
 17 71  1  6
 18 72  1  0
 20 73  1  0
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 20 75  1  0
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 22 79  1  0
 22 80  1  0
 26 81  1  0
 30 82  1  0
 32 83  1  0
 32 84  1  0
 33 85  1  1
 35 86  1  1
 46 91  1  6
 47 92  1  0
 48 93  1  6
 52 94  1  0
 53 95  1  0
 37 87  1  0
 43 90  1  0
 41 88  1  0
 41 89  1  0
M  END


  Mrv1652308111919232D          

 53 55  0  0  1  0            999 V2000
   25.1304   -3.1759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4630   -2.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8755   -3.9605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7955   -3.1759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.0505   -3.9605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3603   -4.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3847   -7.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1275   -7.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6702   -7.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9558   -7.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2413   -7.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6986   -5.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9558   -6.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6986   -5.1544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2697   -5.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9841   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4130   -3.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2861   -2.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6986   -3.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1111   -2.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9841   -3.9168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2696   -3.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1275   -3.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7775   -3.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4275   -3.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9525   -2.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9525   -4.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6025   -2.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6025   -4.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9525   -3.5043    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.6025   -3.5043    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.0109   -2.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5655   -4.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7405   -5.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3905   -5.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5655   -5.4530    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.5655   -6.2779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9150   -2.9210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5282   -3.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2506   -2.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2426   -3.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5282   -4.2980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0711   -2.2535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9570   -3.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2427   -4.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9570   -4.2978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6715   -3.0604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8420   -7.2169    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5565   -8.4544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5565   -7.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2710   -7.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9853   -7.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6999   -7.2169    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
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 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
 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
M  END
> <DATABASE_ID>
NP0245599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=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/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
CRFNGMNYKDXRTN-CITAKDKDSA-N

> <FORMULA>
C25H42N7O17P3S

> <MOLECULAR_WEIGHT>
837.624

> <EXACT_MASS>
837.157073179

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
75.14239332882603

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-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)-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid

> <ALOGPS_LOGP>
-0.22

> <JCHEM_LOGP>
-4.4739573918092725

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8867291245447841

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8191835608277751

> <JCHEM_PKA_STRONGEST_BASIC>
6.456347200670775

> <JCHEM_POLAR_SURFACE_AREA>
370.61000000000007

> <JCHEM_REFRACTIVITY>
182.47930000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(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-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-AUG-19         0                                  
HETATM    1  C   UNK     0      46.910  -5.928   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      45.664  -5.023   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      46.434  -7.393   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      44.418  -5.928   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.894  -7.393   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      47.339  -8.639   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      34.318 -13.472   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.705 -14.242   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      32.984 -14.242   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      31.651 -13.472   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      30.317 -14.242   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      33.037 -11.162   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.651 -11.932   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      33.037  -9.622   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      30.370  -9.622   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      31.704  -8.851   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.371  -7.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.267  -5.208   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.037  -6.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.807  -5.208   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.704  -7.311   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      30.370  -6.541   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      35.705  -6.541   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      38.785  -6.541   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      41.865  -6.541   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      37.245  -5.001   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      37.245  -8.081   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      40.325  -5.001   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      40.325  -8.081   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      37.245  -6.541   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      40.325  -6.541   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      42.954  -5.453   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      43.989  -8.639   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      42.449 -10.179   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      45.529 -10.179   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      43.989 -10.179   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      43.989 -11.719   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      48.375  -5.453   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      49.519  -6.483   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      49.001  -4.046   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      50.853  -5.713   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      49.519  -8.023   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      50.533  -4.207   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      52.186  -6.483   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      50.853  -8.793   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      52.186  -8.023   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      53.520  -5.713   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      37.038 -13.472   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      38.372 -15.782   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      38.372 -14.242   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      39.706 -13.472   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      41.039 -14.242   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      42.373 -13.472   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                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

View in JSmol

Synonyms

Value	Source
4:0-CoA	ChEBI
Butanoyl-CoA	ChEBI
Butanoyl-coenzyme A	ChEBI
Butyryl-coenzyme A	ChEBI
C4:0-CoA	ChEBI
coenzyme A, S-Butanoate	ChEBI
S-Butanoyl-CoA	ChEBI
S-Butanoyl-coenzyme A	ChEBI
S-Butyryl-CoA	ChEBI
S-Butyryl-coenzym-a	ChEBI
S-Butyryl-coenzyme A	ChEBI
coenzyme A, S-Butanoic acid	Generator
Butyryl-CoA	MeSH, KEGG

Chemical Formula

C₂₅H₄₂N₇O₁₇P₃S

Average Mass

837.6240 Da

Monoisotopic Mass

837.15707 Da

IUPAC Name

(2R)-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)-N-(2-{[2-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid

Traditional 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-(butanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid

CAS Registry Number

Not Available

SMILES

CCCC(=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/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,18-,19-,20+,24-/m1/s1

InChI Key

CRFNGMNYKDXRTN-CITAKDKDSA-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
Streptomyces cinnamonensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

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
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Imidolactam
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Thiocarboxylic acid ester
Secondary alcohol
Amino acid or derivatives
Carbothioic s-ester
Thiocarboxylic acid or derivatives
Sulfenyl compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic oxide
Amine
Hydrocarbon derivative
Primary amine
Carbonyl group
Alcohol
Organosulfur compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

butanoyl-CoAs (CHEBI:15517 )

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	-0.22	ALOGPS
logP	-4.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.46	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	182.48 m³·mol⁻¹	ChemAxon
Polarizability	75.14 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

FDB030704

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00136

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butyryl-CoA

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15517

Good Scents ID

Not Available

References

General References

Tanaka K, Ramsdell HS, Baretz BH, Keefe MB, Kean EA, Johnson B: Identification of ethylmalonic acid in urine of two patients with the vomitting sickness of Jamaica. Clin Chim Acta. 1976 May 17;69(1):105-12. [PubMed:1269146 ]
Zhang YX, Denoya CD, Skinner DD, Fedechko RW, McArthur HAI, Morgenstern MR, Davies RA, Lobo S, Reynolds KA, Hutchinson CR: Genes encoding acyl-CoA dehydrogenase (AcdH) homologues from Streptomyces coelicolor and Streptomyces avermitilis provide insights into the metabolism of small branched-chain fatty acids and macrolide antibiotic production. Microbiology (Reading). 1999 Sep;145 ( Pt 9):2323-2334. doi: 10.1099/00221287-145-9-2323. [PubMed:10517585 ]
Asanuma N, Kawato M, Ohkawara S, Hino T: Characterization and transcription of the genes encoding enzymes involved in butyrate production in Butyrivibrio fibrisolvens. Curr Microbiol. 2003 Sep;47(3):203-7. doi: 10.1007/s00284-002-3976-2. [PubMed:14570270 ]
Vlasie MD, Banerjee R: When a spectator turns killer: suicidal electron transfer from cobalamin in methylmalonyl-CoA mutase. Biochemistry. 2004 Jul 6;43(26):8410-7. doi: 10.1021/bi036299q. [PubMed:15222752 ]
Mukherjee JJ, Dekker EE: Purification, properties, and N-terminal amino acid sequence of homogeneous Escherichia coli 2-amino-3-ketobutyrate CoA ligase, a pyridoxal phosphate-dependent enzyme. J Biol Chem. 1987 Oct 25;262(30):14441-7. [PubMed:3117785 ]
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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid (NP0245599)

MOL for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D MOL for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D SDF for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D-SDF for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

PDB for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D PDB for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

SMILES for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

INCHI for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

Structure for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)

3D Structure for NP0245599 ((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-(butanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid)