MiMeDB: Showing metabocard for Acetyl adenylate (MMDBc0047799)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:43:16 UTC

Update Date

2024-04-30 20:30:29 UTC

Metabolite ID

MMDBc0047799

Metabolite Identification

Common Name

Acetyl adenylate

Description

Acetyl adenylate is an intermediate in acetyl-CoA synthesis. It is converted from acetate via the enzyme acetyl-CoA synthetase. It is involved in the non-enzymatic acetylation of histones in chromatin (PMID:8619849 ). In microbes acetyl adenylate also plays a role in the direction of flagellar rotation (PMID:2901103 ).

Structure

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

 
  Mrv0541 02231220542D          
 
 26 28  0  0  1  0            999 V2000
   18.1583  -11.6207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7941  -12.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3981  -11.8694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4451  -10.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5265  -11.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8735  -12.9025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7209  -11.3615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1424  -12.6123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.3054  -10.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2730  -11.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6614  -13.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0644  -11.8349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3200  -12.6123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5329  -13.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3697  -12.7333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9294  -11.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2800  -11.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0125  -13.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6650  -12.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8357  -12.1285    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0099  -12.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -12.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -11.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5953  -11.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7694  -11.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0099  -10.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
M  END

HMDB0006880
     RDKit          3D
Acetyl adenylate
 42 44  0  0  0  0  0  0  0  0999 V2000
    5.6690    2.6749    1.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638    1.5145    0.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    1.4576   -0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230    0.3964    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1656   -0.9235    0.3944 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9463   -2.1445    0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.6593   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -1.2428    0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9916   -1.5475   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238   -1.8185   -0.6312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783   -0.6790   -0.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -0.8526   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2169    0.3175   -0.2360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1881    1.4852   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152    2.3369   -0.3387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7392    1.6747    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7529    2.0816    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3293    3.3777    1.4291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1737    1.1733    2.3991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6215   -0.0678    2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341   -0.4473    1.6303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1738    0.4123    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182   -1.1562   -1.9360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4683   -1.7369   -2.4452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -2.1180   -1.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6584   -3.4113   -1.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702    2.6756    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7698    2.5894    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5004    3.5877    1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6717   -1.4916   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -2.4518   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.6583   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604   -2.6283    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -1.7516    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.7247   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6298    3.7657    0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4717    3.9768    2.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -0.8074    3.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -0.2620   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -2.4540   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251   -1.9538   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -3.9585   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 10  1  0
 22 13  1  0
 22 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  1
 12 34  1  1
 14 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 23 39  1  6
 24 40  1  0
 25 41  1  6
 26 42  1  0
M  END

 
  Mrv0541 02231220542D          
 
 26 28  0  0  1  0            999 V2000
   18.1583  -11.6207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7941  -12.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3981  -11.8694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4451  -10.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5265  -11.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8735  -12.9025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7209  -11.3615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1424  -12.6123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.3054  -10.7948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2730  -11.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6614  -13.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0644  -11.8349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3200  -12.6123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5329  -13.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3697  -12.7333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9294  -11.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2800  -11.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0125  -13.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6650  -12.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8357  -12.1285    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0099  -12.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -12.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8323  -11.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5953  -11.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7694  -11.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0099  -10.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047799

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N5O8P/c1-5(18)25-26(21,22)23-2-6-8(19)9(20)12(24-6)17-4-16-7-10(13)14-3-15-11(7)17/h3-4,6,8-9,12,19-20H,2H2,1H3,(H,21,22)(H2,13,14,15)/t6-,8-,9-,12-/m1/s1

> <INCHI_KEY>
UBPVOHPZRZIJHM-WOUKDFQISA-N

> <FORMULA>
C12H16N5O8P

> <MOLECULAR_WEIGHT>
389.2579

> <EXACT_MASS>
389.073649025

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
33.78506478674841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.44

> <JCHEM_LOGP>
-4.659024191743382

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.457192389904808

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8364534526946747

> <JCHEM_PKA_STRONGEST_BASIC>
4.988471089896406

> <JCHEM_POLAR_SURFACE_AREA>
192.13999999999996

> <JCHEM_REFRACTIVITY>
83.21999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-acetylphosphoadenosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006880
     RDKit          3D
Acetyl adenylate
 42 44  0  0  0  0  0  0  0  0999 V2000
    5.6690    2.6749    1.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638    1.5145    0.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    1.4576   -0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230    0.3964    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1656   -0.9235    0.3944 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9463   -2.1445    0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.6593   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -1.2428    0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9916   -1.5475   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238   -1.8185   -0.6312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783   -0.6790   -0.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -0.8526   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2169    0.3175   -0.2360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1881    1.4852   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152    2.3369   -0.3387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7392    1.6747    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7529    2.0816    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3293    3.3777    1.4291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1737    1.1733    2.3991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6215   -0.0678    2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341   -0.4473    1.6303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1738    0.4123    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182   -1.1562   -1.9360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4683   -1.7369   -2.4452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -2.1180   -1.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6584   -3.4113   -1.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702    2.6756    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7698    2.5894    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5004    3.5877    1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6717   -1.4916   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -2.4518   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.6583   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604   -2.6283    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -1.7516    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.7247   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6298    3.7657    0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4717    3.9768    2.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -0.8074    3.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -0.2620   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -2.4540   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251   -1.9538   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -3.9585   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 10  1  0
 22 13  1  0
 22 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  1
 12 34  1  1
 14 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 23 39  1  6
 24 40  1  0
 25 41  1  6
 26 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      33.895 -21.692   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      35.082 -22.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.476 -22.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.431 -20.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      36.449 -21.505   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      35.231 -24.085   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      31.212 -21.208   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      31.999 -23.543   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      36.037 -20.150   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      37.843 -22.118   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.701 -24.736   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.987 -22.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.464 -23.543   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      32.728 -24.956   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      38.023 -23.769   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      39.068 -21.202   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      28.523 -21.615   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      29.890 -24.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      27.375 -22.640   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      25.827 -22.640   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      24.285 -22.640   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      25.820 -24.188   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      25.820 -21.099   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      23.511 -21.298   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.970 -21.298   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      24.285 -19.963   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4    5                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   15                                                       
CONECT   12    7   17   13                                                  
CONECT   13    8   18   12                                                  
CONECT   14    8                                                            
CONECT   15   10   11                                                       
CONECT   16   10                                                            
CONECT   17   12   19                                                       
CONECT   18   13                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20   24                                                       
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0006880
HETATM    1  C1  UNL     1       5.669   2.675   1.635  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.264   1.515   0.809  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.471   1.458  -0.446  1.00  0.00           O  
HETATM    4  O2  UNL     1       4.623   0.396   1.353  1.00  0.00           O  
HETATM    5  P1  UNL     1       4.166  -0.924   0.394  1.00  0.00           P  
HETATM    6  O3  UNL     1       4.946  -2.144   0.881  1.00  0.00           O  
HETATM    7  O4  UNL     1       4.537  -0.659  -1.234  1.00  0.00           O  
HETATM    8  O5  UNL     1       2.499  -1.243   0.486  1.00  0.00           O  
HETATM    9  C3  UNL     1       1.992  -1.547  -0.776  1.00  0.00           C  
HETATM   10  C4  UNL     1       0.524  -1.818  -0.631  1.00  0.00           C  
HETATM   11  O6  UNL     1      -0.078  -0.679  -0.120  1.00  0.00           O  
HETATM   12  C5  UNL     1      -1.425  -0.853  -0.458  1.00  0.00           C  
HETATM   13  N1  UNL     1      -2.217   0.318  -0.236  1.00  0.00           N  
HETATM   14  C6  UNL     1      -2.188   1.485  -0.865  1.00  0.00           C  
HETATM   15  N2  UNL     1      -3.115   2.337  -0.339  1.00  0.00           N  
HETATM   16  C7  UNL     1      -3.739   1.675   0.650  1.00  0.00           C  
HETATM   17  C8  UNL     1      -4.753   2.082   1.495  1.00  0.00           C  
HETATM   18  N3  UNL     1      -5.329   3.378   1.429  1.00  0.00           N  
HETATM   19  N4  UNL     1      -5.174   1.173   2.399  1.00  0.00           N  
HETATM   20  C9  UNL     1      -4.621  -0.068   2.462  1.00  0.00           C  
HETATM   21  N5  UNL     1      -3.634  -0.447   1.630  1.00  0.00           N  
HETATM   22  C10 UNL     1      -3.174   0.412   0.710  1.00  0.00           C  
HETATM   23  C11 UNL     1      -1.318  -1.156  -1.936  1.00  0.00           C  
HETATM   24  O7  UNL     1      -2.468  -1.737  -2.445  1.00  0.00           O  
HETATM   25  C12 UNL     1      -0.147  -2.118  -1.948  1.00  0.00           C  
HETATM   26  O8  UNL     1      -0.658  -3.411  -1.892  1.00  0.00           O  
HETATM   27  H1  UNL     1       5.070   2.676   2.557  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.770   2.589   1.833  1.00  0.00           H  
HETATM   29  H3  UNL     1       5.500   3.588   1.019  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.672  -1.492  -1.724  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.491  -2.452  -1.155  1.00  0.00           H  
HETATM   32  H6  UNL     1       2.145  -0.658  -1.429  1.00  0.00           H  
HETATM   33  H7  UNL     1       0.360  -2.628   0.111  1.00  0.00           H  
HETATM   34  H8  UNL     1      -1.857  -1.752   0.020  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.521   1.725  -1.682  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.630   3.766   0.512  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.472   3.977   2.269  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.954  -0.807   3.187  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.998  -0.262  -2.520  1.00  0.00           H  
HETATM   40  H14 UNL     1      -2.744  -2.454  -1.846  1.00  0.00           H  
HETATM   41  H15 UNL     1       0.525  -1.954  -2.812  1.00  0.00           H  
HETATM   42  H16 UNL     1      -0.010  -3.959  -1.350  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6    7    8
CONECT    7   30
CONECT    8    9
CONECT    9   10   31   32
CONECT   10   11   25   33
CONECT   11   12
CONECT   12   13   23   34
CONECT   13   14   22
CONECT   14   15   15   35
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   19
CONECT   18   36   37
CONECT   19   20   20
CONECT   20   21   38
CONECT   21   22   22
CONECT   23   24   25   39
CONECT   24   40
CONECT   25   26   41
CONECT   26   42
END

HMDB0006880
     RDKit          3D
Acetyl adenylate
 42 44  0  0  0  0  0  0  0  0999 V2000
    5.6690    2.6749    1.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638    1.5145    0.8094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4710    1.4576   -0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230    0.3964    1.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1656   -0.9235    0.3944 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.9463   -2.1445    0.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -0.6593   -1.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -1.2428    0.4859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9916   -1.5475   -0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238   -1.8185   -0.6312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0783   -0.6790   -0.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -0.8526   -0.4583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2169    0.3175   -0.2360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1881    1.4852   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152    2.3369   -0.3387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7392    1.6747    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7529    2.0816    1.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3293    3.3777    1.4291 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1737    1.1733    2.3991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6215   -0.0678    2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6341   -0.4473    1.6303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1738    0.4123    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182   -1.1562   -1.9360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4683   -1.7369   -2.4452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466   -2.1180   -1.9476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6584   -3.4113   -1.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702    2.6756    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7698    2.5894    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5004    3.5877    1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6717   -1.4916   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -2.4518   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -0.6583   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3604   -2.6283    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -1.7516    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    1.7247   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6298    3.7657    0.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4717    3.9768    2.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539   -0.8074    3.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -0.2620   -2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435   -2.4540   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251   -1.9538   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -3.9585   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 10  1  0
 22 13  1  0
 22 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  1
 12 34  1  1
 14 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 23 39  1  6
 24 40  1  0
 25 41  1  6
 26 42  1  0
M  END

Synonyms

Value	Source
5'-Acetylphosphoadenosine	Kegg
Acetyl adenylic acid	Generator
5'-O-[Acetoxy(hydroxy)phosphoryl]adenosine	HMDB
Acetyl AMP	HMDB
Acetyladenylate	HMDB
[[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] acetate	HMDB

Molecular Formula

C₁₂H₁₆N₅O₈P

Average Mass

389.2579

Monoisotopic Mass

389.073649025

IUPAC Name

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

Traditional Name

5'-acetylphosphoadenosine

CAS Registry Number

Not Available

SMILES

CC(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C12H16N5O8P/c1-5(18)25-26(21,22)23-2-6-8(19)9(20)12(24-6)17-4-16-7-10(13)14-3-15-11(7)17/h3-4,6,8-9,12,19-20H,2H2,1H3,(H,21,22)(H2,13,14,15)/t6-,8-,9-,12-/m1/s1

InChI Key

UBPVOHPZRZIJHM-WOUKDFQISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Alkyl phosphate
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Polyol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-tagatose 6-phosphate (CHEBI:4251 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.02 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-4.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.84	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	6	ChemAxon
Refractivity	83.22 m³·mol⁻¹	ChemAxon
Polarizability	33.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

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
MMDBp0191711	Acetyl-coenzyme A synthetase, cytoplasmic	Enzyme	Q9NR19	Homo sapiens
MMDBp0191716	Acetyl-coenzyme A synthetase 2-like, mitochondrial	Enzyme	Q9NUB1	Homo sapiens
MMDBp0194181	ACSS2 protein	Enzyme	Q96FY7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019667	Adenosine monophosphate	Acetyl adenylate	Acetyl-coenzyme A synthetase 2	Synthesis	PathBank	31602464
MMDBr0019668	Acetyl adenylate	Acetic acid	Acetyl-coenzyme A synthetase 2	Synthesis	PathBank	31602464

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	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

HMDB0006880

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024132

KNApSAcK ID

Not Available

Chemspider ID

389703

KEGG Compound ID

C05993

BioCyc ID

ACETYL_AMP

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440867

PDB ID

Not Available

ChEBI ID

37666

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Camici G, Manao G, Ramponi G: Nonenzymatic reactivation of des-acetyl citrate lyase by acetyl adenylate. First example of enzyme activation by chemotrophic modification. Physiol Chem Phys. 1975;7(5):409-14. [PubMed:698 ]
Ramponi G, Manao G, Camici G: Nonenzymatic acetylation of histones with acetyl phosphate and acetyl adenylate. Biochemistry. 1975 Jun 17;14(12):2681-5. doi: 10.1021/bi00683a018. [PubMed:238571 ]
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Showing metabocard for Acetyl adenylate (MMDBc0047799)

MOL for #<Metabolite:0x00005645c6db54e0>

3D MOL for #<Metabolite:0x00005645c6db54e0>

3D SDF for #<Metabolite:0x00005645c6db54e0>

3D-SDF for #<Metabolite:0x00005645c6db54e0>

PDB for #<Metabolite:0x00005645c6db54e0>

3D PDB for #<Metabolite:0x00005645c6db54e0>

SMILES for #<Metabolite:0x00005645c6db54e0>

INCHI for #<Metabolite:0x00005645c6db54e0>

Structure for #<Metabolite:0x00005645c6db54e0>

3D Structure for #<Metabolite:0x00005645c6db54e0>