MiMeDB: Showing metabocard for gamma-Butyrobetainyl-CoA (MMDBc0030190)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:57:43 UTC

Update Date

2022-08-31 17:40:33 UTC

Metabolite ID

MMDBc0030190

Metabolite Identification

Common Name

gamma-Butyrobetainyl-CoA

Description

Gamma-butyrobetainyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine. When gamma-butyrobetainyl-CoA was used as a cosubstrate (CoA donor), the first reaction is the CoA transfer. (PMID 11551212 ) E. coli protein CaiB, which is a member of the recently identified type-III coenzyme A (CoA) transferase family and catalyzes the transfer of the CoA moiety between gamma-butyrobetaine-CoA and carnitine forming carnityl-CoA and gamma-butyrobetaine. (PMID 15518548 )

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241207312D          

 57 59  0  0  0  0            999 V2000
   26.5489   -0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3739    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5298    0.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8318   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6568    0.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6732    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3877   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3890    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1035   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2456   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9588   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5311    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9627   -0.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6758   -0.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9366    1.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2158   -0.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6771   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6745   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1022    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1090    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5703    0.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7634    0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2469    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7765    0.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3554    0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5324   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9828    0.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9614   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5301    0.4696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9601    0.2639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8180    0.2639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6902    1.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2691    1.4763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0228   -0.5003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8033    0.0427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2443    0.2639    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   22.6745   -0.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1022    1.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9059    1.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2469    1.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5324   -0.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1288    1.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5148    2.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4933    2.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9462   -1.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1212    0.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6923   -1.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5173    0.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2482   -0.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3903   -0.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4308   -0.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1503    1.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8192   -0.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3218    2.0309    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.5337   -0.5611    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1048   -0.5611    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.8167   -0.1486    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 28  1  0  0  0  0
  3 36  1  0  0  0  0
  4 36  1  0  0  0  0
  5 36  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8 18  1  0  0  0  0
 31  9  1  4  0  0  0
 10 12  1  0  0  0  0
 30 10  1  4  0  0  0
 11 36  1  0  0  0  0
 12 57  1  0  0  0  0
 13 17  1  0  0  0  0
 13 49  1  0  0  0  0
 14 28  1  0  0  0  0
 14 50  1  0  0  0  0
 15 32  2  0  0  0  0
 15 33  1  0  0  0  0
 16 34  2  0  0  0  0
 16 35  1  0  0  0  0
 17 22  1  0  0  0  0
 17 51  1  0  0  0  0
 18 30  2  0  0  0  0
 18 37  1  0  0  0  0
 19 38  2  0  0  0  0
 19 57  1  0  0  0  0
 20 24  2  0  0  0  0
 20 25  1  0  0  0  0
 20 34  1  0  0  0  0
 21 22  1  0  0  0  0
 21 27  1  0  0  0  0
 21 39  1  0  0  0  0
 22 52  1  0  0  0  0
 23 26  1  0  0  0  0
 23 28  1  0  0  0  0
 23 40  1  0  0  0  0
 24 29  1  0  0  0  0
 24 32  1  0  0  0  0
 25 33  2  0  0  0  0
 25 35  1  0  0  0  0
 26 31  2  0  0  0  0
 26 41  1  0  0  0  0
 27 35  1  0  0  0  0
 27 51  1  0  0  0  0
 42 54  2  0  0  0  0
 43 54  1  0  0  0  0
 44 54  1  0  0  0  0
 45 55  1  0  0  0  0
 46 55  2  0  0  0  0
 47 56  2  0  0  0  0
 48 56  1  0  0  0  0
 49 55  1  0  0  0  0
 50 56  1  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
M  CHG  1  36   1
M  END

Structure #1
  Mrv0541 02241207312D          

 57 59  0  0  0  0            999 V2000
   26.5489   -0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3739    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5298    0.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8318   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6568    0.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6732    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3877   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3890    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1035   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2456   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9588   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5311    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9627   -0.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6758   -0.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9366    1.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2158   -0.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6771   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6745   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1022    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1090    0.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5703    0.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7634    0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2469    0.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7765    0.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3554    0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5324   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9828    0.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9614   -0.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5301    0.4696    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9601    0.2639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8180    0.2639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6902    1.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2691    1.4763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0228   -0.5003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8033    0.0427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2443    0.2639    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   22.6745   -0.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1022    1.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9059    1.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2469    1.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5324   -0.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1288    1.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5148    2.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4933    2.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9462   -1.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1212    0.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6923   -1.2756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5173    0.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2482   -0.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3903   -0.1486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4308   -0.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1503    1.2239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8192   -0.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3218    2.0309    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.5337   -0.5611    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1048   -0.5611    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.8167   -0.1486    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 28  1  0  0  0  0
  3 36  1  0  0  0  0
  4 36  1  0  0  0  0
  5 36  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8 18  1  0  0  0  0
 31  9  1  4  0  0  0
 10 12  1  0  0  0  0
 30 10  1  4  0  0  0
 11 36  1  0  0  0  0
 12 57  1  0  0  0  0
 13 17  1  0  0  0  0
 13 49  1  0  0  0  0
 14 28  1  0  0  0  0
 14 50  1  0  0  0  0
 15 32  2  0  0  0  0
 15 33  1  0  0  0  0
 16 34  2  0  0  0  0
 16 35  1  0  0  0  0
 17 22  1  0  0  0  0
 17 51  1  0  0  0  0
 18 30  2  0  0  0  0
 18 37  1  0  0  0  0
 19 38  2  0  0  0  0
 19 57  1  0  0  0  0
 20 24  2  0  0  0  0
 20 25  1  0  0  0  0
 20 34  1  0  0  0  0
 21 22  1  0  0  0  0
 21 27  1  0  0  0  0
 21 39  1  0  0  0  0
 22 52  1  0  0  0  0
 23 26  1  0  0  0  0
 23 28  1  0  0  0  0
 23 40  1  0  0  0  0
 24 29  1  0  0  0  0
 24 32  1  0  0  0  0
 25 33  2  0  0  0  0
 25 35  1  0  0  0  0
 26 31  2  0  0  0  0
 26 41  1  0  0  0  0
 27 35  1  0  0  0  0
 27 51  1  0  0  0  0
 42 54  2  0  0  0  0
 43 54  1  0  0  0  0
 44 54  1  0  0  0  0
 45 55  1  0  0  0  0
 46 55  2  0  0  0  0
 47 56  2  0  0  0  0
 48 56  1  0  0  0  0
 49 55  1  0  0  0  0
 50 56  1  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
M  CHG  1  36   1
M  END
> <DATABASE_ID>
MMDBc0030190

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H49N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,39-40H,6-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1

> <INCHI_KEY>
QAMRRBGWSPTAEJ-UHFFFAOYSA-O

> <FORMULA>
C28H50N8O17P3S

> <MOLECULAR_WEIGHT>
895.726

> <EXACT_MASS>
895.22274744

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
84.92035798417072

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-oxobutyl]trimethylazanium

> <ALOGPS_LOGP>
-1.35

> <JCHEM_LOGP>
-7.924178184454511

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.8332588488333545

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8251640991451614

> <JCHEM_PKA_STRONGEST_BASIC>
4.792449931001448

> <JCHEM_POLAR_SURFACE_AREA>
370.61000000000007

> <JCHEM_REFRACTIVITY>
212.0484000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-[(2-{[3-({4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene}amino)-1-hydroxypropylidene]amino}ethyl)sulfanyl]-4-oxobutyl}trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      49.558  -1.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      51.098   1.056   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.989   1.263   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.553  -0.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.093   1.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.990   0.493   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.324  -0.277   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      43.659   0.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      44.993  -0.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      39.658  -0.277   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.656  -0.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.325   0.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      59.664  -1.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      51.661  -1.047   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      67.082   3.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      65.736  -1.254   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      60.997  -0.277   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.326  -0.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.657   0.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      67.403   0.598   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      62.665   1.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      61.158   1.254   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      48.994   0.493   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      68.649   1.503   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      65.997   1.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      47.660  -0.277   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      63.435   0.241   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      50.328  -0.277   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      70.056   0.877   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      40.992   0.493   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      46.327   0.493   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      68.488   3.034   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      65.836   2.756   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0      67.243  -0.934   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      64.966   0.080   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0      30.323   0.493   0.000  0.00  0.00           N+1
HETATM   37  O   UNK     0      42.326  -1.817   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      35.657   2.033   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      63.291   2.981   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      48.994   2.033   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      47.660  -1.817   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      61.840   3.471   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      58.828   4.111   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      60.654   5.297   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      57.766  -2.381   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      56.226   0.286   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      53.559  -2.381   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      55.099   0.286   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      58.330  -0.277   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      52.995  -0.277   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      62.404  -0.904   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      60.014   2.285   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      55.663  -1.817   0.000  0.00  0.00           O+0
HETATM   54  P   UNK     0      60.334   3.791   0.000  0.00  0.00           P+0
HETATM   55  P   UNK     0      56.996  -1.047   0.000  0.00  0.00           P+0
HETATM   56  P   UNK     0      54.329  -1.047   0.000  0.00  0.00           P+0
HETATM   57  S   UNK     0      36.991  -0.277   0.000  0.00  0.00           S+0
CONECT    1   28                                                            
CONECT    2   28                                                            
CONECT    3   36                                                            
CONECT    4   36                                                            
CONECT    5   36                                                            
CONECT    6    7   11                                                       
CONECT    7    6   19                                                       
CONECT    8    9   18                                                       
CONECT    9    8   31                                                       
CONECT   10   12   30                                                       
CONECT   11    6   36                                                       
CONECT   12   10   57                                                       
CONECT   13   17   49                                                       
CONECT   14   28   50                                                       
CONECT   15   32   33                                                       
CONECT   16   34   35                                                       
CONECT   17   13   22   51                                                  
CONECT   18    8   30   37                                                  
CONECT   19    7   38   57                                                  
CONECT   20   24   25   34                                                  
CONECT   21   22   27   39                                                  
CONECT   22   17   21   52                                                  
CONECT   23   26   28   40                                                  
CONECT   24   20   29   32                                                  
CONECT   25   20   33   35                                                  
CONECT   26   23   31   41                                                  
CONECT   27   21   35   51                                                  
CONECT   28    1    2   14   23                                             
CONECT   29   24                                                            
CONECT   30   10   18                                                       
CONECT   31    9   26                                                       
CONECT   32   15   24                                                       
CONECT   33   15   25                                                       
CONECT   34   16   20                                                       
CONECT   35   16   25   27                                                  
CONECT   36    3    4    5   11                                             
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   21                                                            
CONECT   40   23                                                            
CONECT   41   26                                                            
CONECT   42   54                                                            
CONECT   43   54                                                            
CONECT   44   54                                                            
CONECT   45   55                                                            
CONECT   46   55                                                            
CONECT   47   56                                                            
CONECT   48   56                                                            
CONECT   49   13   55                                                       
CONECT   50   14   56                                                       
CONECT   51   17   27                                                       
CONECT   52   22   54                                                       
CONECT   53   55   56                                                       
CONECT   54   42   43   44   52                                             
CONECT   55   45   46   49   53                                             
CONECT   56   47   48   50   53                                             
CONECT   57   12   19                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

Synonyms

Value	Source
g-Butyrobetainyl-CoA	Generator
Γ-butyrobetainyl-CoA	Generator

Molecular Formula

C₂₈H₅₀N₈O₁₇P₃S

Average Mass

895.726

Monoisotopic Mass

895.22274744

IUPAC Name

[4-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-4-oxobutyl]trimethylazanium

Traditional Name

{4-[(2-{[3-({4-[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-1,2-dihydroxy-3,3-dimethylbutylidene}amino)-1-hydroxypropylidene]amino}ethyl)sulfanyl]-4-oxobutyl}trimethylazanium

CAS Registry Number

Not Available

SMILES

CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(O)=NCCC(O)=NCCSC(=O)CCC[N+](C)(C)C

InChI Identifier

InChI=1S/C28H49N8O17P3S/c1-28(2,23(40)26(41)31-9-8-18(37)30-10-12-57-19(38)7-6-11-36(3,4)5)14-50-56(47,48)53-55(45,46)49-13-17-22(52-54(42,43)44)21(39)27(51-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,39-40H,6-14H2,1-5H3,(H7-,29,30,31,32,33,37,41,42,43,44,45,46,47,48)/p+1

InChI Key

QAMRRBGWSPTAEJ-UHFFFAOYSA-O

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.2 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-7.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	212.05 m³·mol⁻¹	ChemAxon
Polarizability	84.92 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1923030230-d48b9d23973c17c674fa	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0932000000-4f0839c2e3784a9a888a	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1911000000-eb800903e22fa47dc186	2019-02-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010924	gamma-Butyrobetainyl-CoA	Crotonobetainyl-CoA	Not Available		VMH	30371894

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	68	Human feces; Human ; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	4	Human ; Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

726

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for gamma-Butyrobetainyl-CoA (MMDBc0030190)

MOL for #<Metabolite:0x00007fecf48ce1a8>

3D MOL for #<Metabolite:0x00007fecf48ce1a8>

3D SDF for #<Metabolite:0x00007fecf48ce1a8>

3D-SDF for #<Metabolite:0x00007fecf48ce1a8>

PDB for #<Metabolite:0x00007fecf48ce1a8>

3D PDB for #<Metabolite:0x00007fecf48ce1a8>

SMILES for #<Metabolite:0x00007fecf48ce1a8>

INCHI for #<Metabolite:0x00007fecf48ce1a8>

Structure for #<Metabolite:0x00007fecf48ce1a8>

3D Structure for #<Metabolite:0x00007fecf48ce1a8>