MiMeDB: Showing metabocard for Lipoyl-AMP (MMDBc0030077)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:53:02 UTC

Update Date

2022-08-31 17:39:32 UTC

Metabolite ID

MMDBc0030077

Metabolite Identification

Common Name

Lipoyl-AMP

Description

Lipoyl-amp belongs to the class of Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. (inferred from compound structure)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

 
  Mrv0541 02241222112D          
 
 34 37  0  0  1  0            999 V2000
   11.8197  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9932  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7452  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064  -11.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0677  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7702  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5141  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2167  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9193  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -12.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4904  -10.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1103  -10.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7051  -10.7039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7797   -9.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8542  -10.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1929  -11.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0439  -10.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4572  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6062   -9.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5981  -10.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9782  -12.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3827  -10.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6306  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6807  -11.5304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2180  -10.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5974  -10.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9775  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.9518    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -11.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2660  -12.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8165  -12.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 23 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 16 20  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 29 32  1  0  0  0  0
 10 32  1  0  0  0  0
 24 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END

HMDB0059635
     RDKit          3D
Lipoyl-AMP
 60 63  0  0  0  0  0  0  0  0999 V2000
  -10.2338   -0.3316   -0.9209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8289   -0.5342   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3140   -1.3829   -1.9054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9825   -1.5890   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.9440   -1.1709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0949   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9449    0.1166   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1131    1.0009    0.8218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.3247    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.6495    0.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316    0.7401    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7486    0.5831   -0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.4532    0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5940   -0.3249   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.4601   -0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.3135   -1.4221 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1403   -2.7361   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.7036   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903   -1.1954   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.0179   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.0453   -1.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302    0.1490   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.5598   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    1.7221   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    1.3757    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.0224    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -1.0390    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8919   -0.5834   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.3974    1.1630 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2834    0.0224    2.4699 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -0.2221    1.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1259    0.6705    2.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.4201    1.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3907   -0.2851    3.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8815   -1.1232   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741    0.6052   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -2.2941   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    2.0274    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    1.6631    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.4652    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1642   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -1.3461   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -1.4350   -3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -0.2530    0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -0.4314   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0202   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    2.2264   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    2.8519   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672    1.3079   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0857    1.7188    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932    2.0558    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -0.3566    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8944   -1.4506   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -1.9153    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078    0.3944   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2931   -1.4011   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560   -1.1655    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.2567    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.4000    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.0811    3.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  7  2  1  0
 33 11  1  0
 10  6  1  0
 30 26  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  9 38  1  0
 11 39  1  1
 13 40  1  1
 14 41  1  0
 14 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END

 
  Mrv0541 02241222112D          
 
 34 37  0  0  1  0            999 V2000
   11.8197  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9932  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7452  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064  -11.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0677  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7702  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5141  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2167  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9193  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -12.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4904  -10.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1103  -10.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7051  -10.7039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7797   -9.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8542  -10.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1929  -11.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0439  -10.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4572  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6062   -9.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5981  -10.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9782  -12.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3827  -10.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6306  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6807  -11.5304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2180  -10.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5974  -10.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9775  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.9518    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -11.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2660  -12.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8165  -12.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 23 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 16 20  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 29 32  1  0  0  0  0
 10 32  1  0  0  0  0
 24 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030077

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1

> <INCHI_KEY>
QWEGOCJRZOKSOE-NLJBGGCZSA-N

> <FORMULA>
C18H26N5O8PS2

> <MOLECULAR_WEIGHT>
535.532

> <EXACT_MASS>
535.096040725

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
50.70841164834475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
-2.322057993323983

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.457192389903962

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8302712598949102

> <JCHEM_PKA_STRONGEST_BASIC>
4.988470657284801

> <JCHEM_POLAR_SURFACE_AREA>
192.13999999999996

> <JCHEM_REFRACTIVITY>
124.9477

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Lipoyl-AMP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059635
     RDKit          3D
Lipoyl-AMP
 60 63  0  0  0  0  0  0  0  0999 V2000
  -10.2338   -0.3316   -0.9209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8289   -0.5342   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3140   -1.3829   -1.9054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9825   -1.5890   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.9440   -1.1709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0949   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9449    0.1166   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1131    1.0009    0.8218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.3247    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.6495    0.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316    0.7401    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7486    0.5831   -0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.4532    0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5940   -0.3249   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.4601   -0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.3135   -1.4221 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1403   -2.7361   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.7036   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903   -1.1954   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.0179   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.0453   -1.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302    0.1490   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.5598   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    1.7221   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    1.3757    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.0224    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -1.0390    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8919   -0.5834   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.3974    1.1630 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2834    0.0224    2.4699 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -0.2221    1.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1259    0.6705    2.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.4201    1.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3907   -0.2851    3.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8815   -1.1232   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741    0.6052   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -2.2941   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    2.0274    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    1.6631    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.4652    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1642   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -1.3461   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -1.4350   -3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -0.2530    0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -0.4314   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0202   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    2.2264   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    2.8519   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672    1.3079   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0857    1.7188    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932    2.0558    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -0.3566    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8944   -1.4506   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -1.9153    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078    0.3944   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2931   -1.4011   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560   -1.1655    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.2567    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.4000    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.0811    3.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  7  2  1  0
 33 11  1  0
 10  6  1  0
 30 26  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  9 38  1  0
 11 39  1  1
 13 40  1  1
 14 41  1  0
 14 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0      22.063 -18.978   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      20.521 -18.978   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      20.058 -20.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.292 -21.369   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.526 -20.443   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.838 -21.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.226 -20.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.538 -21.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.849 -20.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.238 -21.215   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      29.238 -22.758   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      40.115 -19.518   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      41.273 -20.289   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.650 -19.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.655 -17.975   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.661 -19.286   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      41.427 -21.909   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      37.415 -18.978   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      38.187 -21.369   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      42.198 -17.975   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      44.050 -19.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.893 -22.526   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.181 -19.903   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.644 -21.369   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      44.204 -21.523   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      45.207 -18.978   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      34.715 -19.441   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      33.558 -20.443   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      32.015 -20.443   0.000  0.00  0.00           P+0
HETATM   30  O   UNK     0      32.015 -21.986   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      32.015 -18.901   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      30.472 -20.443   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      35.963 -22.691   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      38.857 -22.698   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10                                                            
CONECT   12   13   14   15                                                  
CONECT   13   12   16   17                                                  
CONECT   14   12   18   19                                                  
CONECT   15   12   20                                                       
CONECT   16   13   21   20                                                  
CONECT   17   13   22                                                       
CONECT   18   14   23                                                       
CONECT   19   14   24   34                                                  
CONECT   20   15   16                                                       
CONECT   21   16   25   26                                                  
CONECT   22   17   25                                                       
CONECT   23   18   27   24                                                  
CONECT   24   19   23   33                                                  
CONECT   25   21   22                                                       
CONECT   26   21                                                            
CONECT   27   23   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   10                                                       
CONECT   33   24                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0059635
HETATM    1  N1  UNL     1     -10.234  -0.332  -0.921  1.00  0.00           N  
HETATM    2  C1  UNL     1      -8.829  -0.534  -0.998  1.00  0.00           C  
HETATM    3  N2  UNL     1      -8.314  -1.383  -1.905  1.00  0.00           N  
HETATM    4  C2  UNL     1      -6.982  -1.589  -1.995  1.00  0.00           C  
HETATM    5  N3  UNL     1      -6.137  -0.944  -1.171  1.00  0.00           N  
HETATM    6  C3  UNL     1      -6.576  -0.095  -0.255  1.00  0.00           C  
HETATM    7  C4  UNL     1      -7.945   0.117  -0.164  1.00  0.00           C  
HETATM    8  N4  UNL     1      -8.113   1.001   0.822  1.00  0.00           N  
HETATM    9  C5  UNL     1      -6.893   1.325   1.322  1.00  0.00           C  
HETATM   10  N5  UNL     1      -5.936   0.649   0.659  1.00  0.00           N  
HETATM   11  C6  UNL     1      -4.532   0.740   0.914  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.749   0.583  -0.230  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.464   0.453   0.231  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.594  -0.325  -0.759  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.303  -0.460  -0.305  1.00  0.00           O  
HETATM   16  P1  UNL     1       0.596  -1.313  -1.422  1.00  0.00           P  
HETATM   17  O3  UNL     1       0.140  -2.736  -1.438  1.00  0.00           O  
HETATM   18  O4  UNL     1       0.367  -0.704  -3.005  1.00  0.00           O  
HETATM   19  O5  UNL     1       2.290  -1.195  -1.116  1.00  0.00           O  
HETATM   20  C9  UNL     1       2.951   0.018  -1.128  1.00  0.00           C  
HETATM   21  O6  UNL     1       2.274   1.045  -1.371  1.00  0.00           O  
HETATM   22  C10 UNL     1       4.430   0.149  -0.864  1.00  0.00           C  
HETATM   23  C11 UNL     1       4.873   1.560  -0.938  1.00  0.00           C  
HETATM   24  C12 UNL     1       6.328   1.722  -0.731  1.00  0.00           C  
HETATM   25  C13 UNL     1       6.988   1.376   0.520  1.00  0.00           C  
HETATM   26  C14 UNL     1       6.999   0.022   1.082  1.00  0.00           C  
HETATM   27  C15 UNL     1       7.591  -1.039   0.216  1.00  0.00           C  
HETATM   28  C16 UNL     1       8.892  -0.583  -0.351  1.00  0.00           C  
HETATM   29  S1  UNL     1       9.928  -0.397   1.163  1.00  0.00           S  
HETATM   30  S2  UNL     1       8.283   0.022   2.470  1.00  0.00           S  
HETATM   31  C17 UNL     1      -2.506  -0.222   1.572  1.00  0.00           C  
HETATM   32  O7  UNL     1      -2.126   0.671   2.601  1.00  0.00           O  
HETATM   33  C18 UNL     1      -4.015  -0.420   1.768  1.00  0.00           C  
HETATM   34  O8  UNL     1      -4.391  -0.285   3.082  1.00  0.00           O  
HETATM   35  H1  UNL     1     -10.881  -1.123  -0.703  1.00  0.00           H  
HETATM   36  H2  UNL     1     -10.674   0.605  -1.077  1.00  0.00           H  
HETATM   37  H3  UNL     1      -6.615  -2.294  -2.755  1.00  0.00           H  
HETATM   38  H4  UNL     1      -6.742   2.027   2.136  1.00  0.00           H  
HETATM   39  H5  UNL     1      -4.215   1.663   1.399  1.00  0.00           H  
HETATM   40  H6  UNL     1      -2.030   1.465   0.350  1.00  0.00           H  
HETATM   41  H7  UNL     1      -1.671   0.164  -1.743  1.00  0.00           H  
HETATM   42  H8  UNL     1      -2.065  -1.346  -0.815  1.00  0.00           H  
HETATM   43  H9  UNL     1       0.523  -1.435  -3.657  1.00  0.00           H  
HETATM   44  H10 UNL     1       4.571  -0.253   0.130  1.00  0.00           H  
HETATM   45  H11 UNL     1       5.007  -0.431  -1.616  1.00  0.00           H  
HETATM   46  H12 UNL     1       4.634   2.020  -1.946  1.00  0.00           H  
HETATM   47  H13 UNL     1       4.285   2.226  -0.229  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.530   2.852  -0.884  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.867   1.308  -1.645  1.00  0.00           H  
HETATM   50  H16 UNL     1       8.086   1.719   0.501  1.00  0.00           H  
HETATM   51  H17 UNL     1       6.593   2.056   1.363  1.00  0.00           H  
HETATM   52  H18 UNL     1       6.134  -0.357   1.608  1.00  0.00           H  
HETATM   53  H19 UNL     1       6.894  -1.451  -0.542  1.00  0.00           H  
HETATM   54  H20 UNL     1       7.821  -1.915   0.892  1.00  0.00           H  
HETATM   55  H21 UNL     1       8.908   0.394  -0.825  1.00  0.00           H  
HETATM   56  H22 UNL     1       9.293  -1.401  -0.966  1.00  0.00           H  
HETATM   57  H23 UNL     1      -1.956  -1.166   1.619  1.00  0.00           H  
HETATM   58  H24 UNL     1      -1.389   0.257   3.091  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.256  -1.400   1.318  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.944  -1.081   3.323  1.00  0.00           H  
CONECT    1    2   35   36
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   37
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   38
CONECT   10   11
CONECT   11   12   33   39
CONECT   12   13
CONECT   13   14   31   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   43
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   44   45
CONECT   23   24   46   47
CONECT   24   25   48   49
CONECT   25   26   50   51
CONECT   26   27   30   52
CONECT   27   28   53   54
CONECT   28   29   55   56
CONECT   29   30
CONECT   31   32   33   57
CONECT   32   58
CONECT   33   34   59
CONECT   34   60
END

HMDB0059635
     RDKit          3D
Lipoyl-AMP
 60 63  0  0  0  0  0  0  0  0999 V2000
  -10.2338   -0.3316   -0.9209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8289   -0.5342   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3140   -1.3829   -1.9054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9825   -1.5890   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.9440   -1.1709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0949   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9449    0.1166   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1131    1.0009    0.8218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.3247    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.6495    0.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316    0.7401    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7486    0.5831   -0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.4532    0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5940   -0.3249   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.4601   -0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.3135   -1.4221 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1403   -2.7361   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.7036   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903   -1.1954   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.0179   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.0453   -1.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302    0.1490   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.5598   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    1.7221   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    1.3757    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.0224    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -1.0390    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8919   -0.5834   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.3974    1.1630 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2834    0.0224    2.4699 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -0.2221    1.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1259    0.6705    2.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.4201    1.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3907   -0.2851    3.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8815   -1.1232   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741    0.6052   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -2.2941   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    2.0274    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    1.6631    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.4652    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1642   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -1.3461   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -1.4350   -3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -0.2530    0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -0.4314   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0202   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    2.2264   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    2.8519   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672    1.3079   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0857    1.7188    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932    2.0558    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -0.3566    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8944   -1.4506   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -1.9153    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078    0.3944   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2931   -1.4011   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560   -1.1655    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.2567    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.4000    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.0811    3.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  7  2  1  0
 33 11  1  0
 10  6  1  0
 30 26  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  9 38  1  0
 11 39  1  1
 13 40  1  1
 14 41  1  0
 14 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END

Synonyms

Not Available

Molecular Formula

C₁₈H₂₆N₅O₈PS₂

Average Mass

535.532

Monoisotopic Mass

535.096040725

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid

Traditional Name

Lipoyl-AMP

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1

InChI Key

QWEGOCJRZOKSOE-NLJBGGCZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

5'-acylphosphoadenosines

Alternative Parents

Substituents

5'-acylphosphoadenosine
Pentose-5-phosphate
Pentose phosphate
Lipoic_acid_derivative
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Acyl phosphate
Monosaccharide
Imidolactam
N-substituted imidazole
Alkyl phosphate
Organic phosphoric acid derivative
Pyrimidine
Phosphoric acid ester
Azole
Dithiolane
Imidazole
Heteroaromatic compound
1,2-dithiolane
Tetrahydrofuran
Organic disulfide
Secondary alcohol
Amino acid or derivatives
1,2-diol
Carboxylic acid salt
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Primary amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Alcohol
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dithiolanes (CHEBI:55451 )
purine ribonucleoside 5'-monophosphate (CHEBI:55451 )
acyclic mixed acid anhydride (CHEBI:55451 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.12 g/L	ALOGPS
logP	0.25	ALOGPS
logP	-2.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	192.14 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	124.95 m³·mol⁻¹	ChemAxon
Polarizability	50.71 Å³	ChemAxon
Number of Rings	4	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ds-3913010000-e06df70a38935bfec6ca	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03xs-9852448000-ab8656a944a15acff0d2	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_7) - 70eV, Positive	Not Available	2021-10-13	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Lipoyl-AMP,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0911020000-403226dda50e9b19c782	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-09f2e5c022805e4e9fe4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-8cffaab609f0ad97292d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-3779560000-3583b9a6776d5e619ce6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-5911000000-bd5c472188d51d73ad0c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-9500000000-b3956188225c40fb0715	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-97f9a62a74dc17a227c7	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-9100360000-0957a91a14ca65d00ed6	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01u0-9200000000-598cbfd3e15d0060e791	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0101090000-158a5093458bb19523bb	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-55f0391000d477c8c77d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0920000000-c5661a88a8e2cb7260af	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	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
MMDBp0196268	Lipoyltransferase 1, mitochondrial	Enzyme	Q9Y234	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007955	(R)-Lipoic acid	Lipoyl-AMP	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	92	Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human sputum; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	75	Human feces; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria	Firmicutes	215	Human feces; Human ; Human subgingival plaque; Cattle ; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	60	Human feces; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

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

HMDB0059635

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26330628

KEGG Compound ID

C16238

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724672

PDB ID

Not Available

ChEBI ID

55451

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 ]

Showing metabocard for Lipoyl-AMP (MMDBc0030077)

MOL for #<Metabolite:0x00007fecfc82cf08>

3D MOL for #<Metabolite:0x00007fecfc82cf08>

3D SDF for #<Metabolite:0x00007fecfc82cf08>

3D-SDF for #<Metabolite:0x00007fecfc82cf08>

PDB for #<Metabolite:0x00007fecfc82cf08>

3D PDB for #<Metabolite:0x00007fecfc82cf08>

SMILES for #<Metabolite:0x00007fecfc82cf08>

INCHI for #<Metabolite:0x00007fecfc82cf08>

Structure for #<Metabolite:0x00007fecfc82cf08>

3D Structure for #<Metabolite:0x00007fecfc82cf08>