MiMeDB: Showing metabocard for Malonyl-CoA (MMDBc0029578)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:33:01 UTC

Update Date

2024-04-30 19:38:18 UTC

Metabolite ID

MMDBc0029578

Metabolite Identification

Common Name

Malonyl-CoA

Description

Malonyl-CoA is a coenzyme A derivative which plays a key role in fatty acid synthesis in E. coli Fatty acids must be activated with CoA before any chemical modification can be applied. Also fatty acid metabolic intermediates will also exists as CoA derivatives until the CoA is enzymatically cleaved. The fatty acid group is linked to the terminal thiol moiety of CoA

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023492D          

 59 61  0  0  1  0            999 V2000
   -1.7347   14.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   15.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4948   13.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8542   12.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0379   15.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1599   12.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3436   14.9402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7916   15.5532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6077   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9136   12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0737   13.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   14.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9998   11.3240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791   14.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   14.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5810   12.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7411   13.7854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4062   12.1444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2667   13.4720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1641   15.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7980   16.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9021   17.5253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7369   17.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1242   14.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9631   16.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500   16.9123    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   15.2177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0811   16.0416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6393   15.7104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6201   14.7463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   15.6302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7550   14.1825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 12  8  1  1  0  0  0
 13  3  1  0  0  0  0
 14  7  1  0  0  0  0
 15  7  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 24  1  1  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26  5  1  4  0  0  0
 26 13  2  0  0  0  0
 27  4  1  4  0  0  0
 27 22  2  0  0  0  0
 28 10  2  0  0  0  0
 28 20  1  0  0  0  0
 29 10  1  0  0  0  0
 29 21  2  0  0  0  0
 30 11  2  0  0  0  0
 30 16  1  0  0  0  0
 31 11  1  0  0  0  0
 31 21  1  0  0  0  0
 23 31  1  1  0  0  0
 32 13  1  0  0  0  0
 33 14  2  0  0  0  0
 34 14  1  0  0  0  0
 35 15  2  0  0  0  0
 17 36  1  6  0  0  0
 37 19  1  0  0  0  0
 38 22  1  0  0  0  0
 46  8  1  0  0  0  0
 47  9  1  0  0  0  0
 48 12  1  0  0  0  0
 48 23  1  0  0  0  0
 18 49  1  1  0  0  0
 51 39  1  0  0  0  0
 51 40  1  0  0  0  0
 51 41  2  0  0  0  0
 51 49  1  0  0  0  0
 52 42  1  0  0  0  0
 52 43  2  0  0  0  0
 52 46  1  0  0  0  0
 52 50  1  0  0  0  0
 53 44  1  0  0  0  0
 53 45  2  0  0  0  0
 53 47  1  0  0  0  0
 53 50  1  0  0  0  0
 54  6  1  0  0  0  0
 54 15  1  0  0  0  0
 12 55  1  6  0  0  0
 17 56  1  1  0  0  0
 18 57  1  1  0  0  0
 58 19  1  0  0  0  0
 23 59  1  6  0  0  0
M  END


  Mrv1652306222023492D          

 59 61  0  0  1  0            999 V2000
   -1.7347   14.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   15.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4948   13.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8542   12.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0379   15.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1599   12.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3436   14.9402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7916   15.5532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6077   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9136   12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0737   13.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   14.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9998   11.3240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791   14.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   14.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5810   12.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7411   13.7854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4062   12.1444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2667   13.4720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1641   15.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7980   16.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9021   17.5253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7369   17.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1242   14.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9631   16.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500   16.9123    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   15.2177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0811   16.0416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6393   15.7104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6201   14.7463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   15.6302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7550   14.1825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 12  8  1  1  0  0  0
 13  3  1  0  0  0  0
 14  7  1  0  0  0  0
 15  7  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 24  1  1  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26  5  1  4  0  0  0
 26 13  2  0  0  0  0
 27  4  1  4  0  0  0
 27 22  2  0  0  0  0
 28 10  2  0  0  0  0
 28 20  1  0  0  0  0
 29 10  1  0  0  0  0
 29 21  2  0  0  0  0
 30 11  2  0  0  0  0
 30 16  1  0  0  0  0
 31 11  1  0  0  0  0
 31 21  1  0  0  0  0
 23 31  1  1  0  0  0
 32 13  1  0  0  0  0
 33 14  2  0  0  0  0
 34 14  1  0  0  0  0
 35 15  2  0  0  0  0
 17 36  1  6  0  0  0
 37 19  1  0  0  0  0
 38 22  1  0  0  0  0
 46  8  1  0  0  0  0
 47  9  1  0  0  0  0
 48 12  1  0  0  0  0
 48 23  1  0  0  0  0
 18 49  1  1  0  0  0
 51 39  1  0  0  0  0
 51 40  1  0  0  0  0
 51 41  2  0  0  0  0
 51 49  1  0  0  0  0
 52 42  1  0  0  0  0
 52 43  2  0  0  0  0
 52 46  1  0  0  0  0
 52 50  1  0  0  0  0
 53 44  1  0  0  0  0
 53 45  2  0  0  0  0
 53 47  1  0  0  0  0
 53 50  1  0  0  0  0
 54  6  1  0  0  0  0
 54 15  1  0  0  0  0
 12 55  1  6  0  0  0
 17 56  1  1  0  0  0
 18 57  1  1  0  0  0
 58 19  1  0  0  0  0
 23 59  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029578

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)CC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1

> <INCHI_KEY>
LTYOQGRJFJAKNA-VFLPNFFSSA-N

> <FORMULA>
C24H38N7O19P3S

> <MOLECULAR_WEIGHT>
853.58

> <EXACT_MASS>
853.115602295

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
74.33796477662072

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-oxopropanoic acid

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-5.989775961268886

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.894671247515889

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.820480609980446

> <JCHEM_PKA_STRONGEST_BASIC>
4.198301701266371

> <JCHEM_POLAR_SURFACE_AREA>
400.9299999999999

> <JCHEM_REFRACTIVITY>
178.55210000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      -3.238  27.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.698  29.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.200  27.636   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.867  28.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.201  28.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.535  27.636   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.536  28.406   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.804  29.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.802  29.176   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -19.590  25.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.661  23.814   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.137  28.406   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.534  28.406   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.870  27.636   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.202  27.636   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -17.098  23.296   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -15.575  27.888   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -14.544  29.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.134  27.636   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -18.505  22.670   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -16.938  24.828   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.199  28.406   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -14.805  26.555   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.468  28.406   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0     -18.666  21.138   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       6.868  27.636   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       1.533  27.636   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0     -19.751  23.575   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0     -18.183  25.733   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0     -15.692  22.670   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -15.431  25.148   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0       5.534  29.946   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      16.203  28.406   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.870  26.096   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      12.202  26.096   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -17.106  28.049   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.134  26.096   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.199  29.946   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -12.690  30.425   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -14.751  32.714   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -12.576  32.600   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -8.366  27.843   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -9.906  30.510   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -7.239  27.843   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -5.699  30.510   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -10.470  28.406   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -5.135  28.406   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -13.299  26.875   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -14.864  30.539   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -7.803  29.946   0.000  0.00  0.00           O+0
HETATM   51  P   UNK     0     -13.720  31.570   0.000  0.00  0.00           P+0
HETATM   52  P   UNK     0      -9.136  29.176   0.000  0.00  0.00           P+0
HETATM   53  P   UNK     0      -6.469  29.176   0.000  0.00  0.00           P+0
HETATM   54  S   UNK     0      10.869  28.406   0.000  0.00  0.00           S+0
HETATM   55  H   UNK     0     -13.218  29.944   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0     -16.127  29.326   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -14.224  27.526   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.134  29.176   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0     -16.343  26.474   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2   24                                                            
CONECT    3    4   13                                                       
CONECT    4    3   27                                                       
CONECT    5    6   26                                                       
CONECT    6    5   54                                                       
CONECT    7   14   15                                                       
CONECT    8   12   46                                                       
CONECT    9   24   47                                                       
CONECT   10   28   29                                                       
CONECT   11   30   31                                                       
CONECT   12    8   18   48   55                                             
CONECT   13    3   26   32                                                  
CONECT   14    7   33   34                                                  
CONECT   15    7   35   54                                                  
CONECT   16   20   21   30                                                  
CONECT   17   18   23   36   56                                             
CONECT   18   12   17   49   57                                             
CONECT   19   22   24   37   58                                             
CONECT   20   16   25   28                                                  
CONECT   21   16   29   31                                                  
CONECT   22   19   27   38                                                  
CONECT   23   17   31   48   59                                             
CONECT   24    1    2    9   19                                             
CONECT   25   20                                                            
CONECT   26    5   13                                                       
CONECT   27    4   22                                                       
CONECT   28   10   20                                                       
CONECT   29   10   21                                                       
CONECT   30   11   16                                                       
CONECT   31   11   21   23                                                  
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   19                                                            
CONECT   38   22                                                            
CONECT   39   51                                                            
CONECT   40   51                                                            
CONECT   41   51                                                            
CONECT   42   52                                                            
CONECT   43   52                                                            
CONECT   44   53                                                            
CONECT   45   53                                                            
CONECT   46    8   52                                                       
CONECT   47    9   53                                                       
CONECT   48   12   23                                                       
CONECT   49   18   51                                                       
CONECT   50   52   53                                                       
CONECT   51   39   40   41   49                                             
CONECT   52   42   43   46   50                                             
CONECT   53   44   45   47   50                                             
CONECT   54    6   15                                                       
CONECT   55   12                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   23                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

Synonyms

Value	Source
Malonyl CoA	HMDB
Malonyl coenzyme A	HMDB
Malonyl-coenzyme A	HMDB
Omega-carboxyacyl-CoA	HMDB
Omega-carboxyacyl-coenzyme A	HMDB
S-(Hydrogen malonyl)coenzyme A	HMDB
S-(Hydrogen propanedioate	HMDB
S-(Hydrogen propanedioate) CoA	HMDB
S-(Hydrogen propanedioate) coenzyme A	HMDB
S-(Hydrogen propanedioic acid	HMDB
a, Malonyl coenzyme	HMDB
CoA, Malonyl	HMDB
coenzyme A, Malonyl	HMDB

Molecular Formula

C₂₄H₃₈N₇O₁₉P₃S

Average Mass

853.58

Monoisotopic Mass

853.115602295

IUPAC Name

3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-oxopropanoic acid

Traditional Name

3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-3-oxopropanoic acid

CAS Registry Number

524-14-1

SMILES

[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)CC(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1

InChI Key

LTYOQGRJFJAKNA-VFLPNFFSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

1,3-dicarbonyl compounds

Alternative Parents

Substituents

1,3-dicarbonyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-oxo monocarboxylic acid (CHEBI:16256 )
Oxo fatty acids (LMFA01060193 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.66 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	-6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.2	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	400.93 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	178.55 m³·mol⁻¹	ChemAxon
Polarizability	74.34 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-1931000120-97b61b6dd179da9fd5b3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-0911000000-7f4a5a9af638e2913a5d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910000000-3b73db0d454b8cfd10a3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-8930142570-6dff4f741103c444a8bc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4910110000-568b3152fb676f2c38e6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-7900100000-5557b31629ecb124d8ef	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Adipose Tissue
Feces
Fibroblasts
Liver
Pancreas
Skeletal Muscle

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
LPS and Citrate Signaling and Inflammation
Acylcarnitine 3-Hydroxydecanoylcarnitine
Acylcarnitine (7Z,9Z,12Z,15Z,18Z,21Z)-tetracosa-7,9,12,15,18,21-hexaenoylcarnitine
Acylcarnitine Pentacosanoylcarnitine
Acylcarnitine Hexacosanoylcarnitine

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000163	Hydrogen carbonate	Malonyl-CoA	acetyl-CoA carboxylase beta	VMH	10677481
MMDBr0001137	Gamma-linolenoyl-CoA	8Z,11Z,14Z-eicosatrienoyl-CoA	ELOVL fatty acid elongase 2	VMH	11138005 15189125
MMDBr0001138	Malonyl-CoA	Eicosatetranoyl coenzyme A	ELOVL fatty acid elongase 2	VMH	11138005 15189125
MMDBr0001139	Arachidonyl-CoA	Adrenyl coenzyme A	ELOVL fatty acid elongase 2	VMH	11138005 15189125
MMDBr0001140	Malonyl-CoA	Clupanodonyl CoA	ELOVL fatty acid elongase 2	VMH	11138005 15189125
MMDBr0001191	Malonyl-CoA	Decanoyl-CoA (N-C10:0CoA)	ELOVL fatty acid elongase 2	VMH	11756679 15507492 2669958
MMDBr0001192	Decanoyl-CoA (N-C10:0CoA)	Lauroyl-CoA	ELOVL fatty acid elongase 2	VMH	11756679 15507492
MMDBr0001193	Lauroyl-CoA	Tetradecanoyl-CoA	ELOVL fatty acid elongase 2	VMH	11756679 15507492 2669958
MMDBr0001194	Malonyl-CoA	Palmityl-CoA	ELOVL fatty acid elongase 2	VMH	11756679 15507492 2669958
MMDBr0001195	Malonyl-CoA	Stearoyl-CoA	ELOVL fatty acid elongase 2	VMH	11756679 15507492 2669958
MMDBr0001196	Malonyl-CoA	Octanoyl-CoA	fatty acid synthase	VMH	11756679 15507492 2669958
MMDBr0001522	Malonyl-CoA	Palmitic acid	ELOVL fatty acid elongase 2	VMH	11756679 15507492 2669958
MMDBr0002551	L-Carnitine	Malonylcarnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1735445 1988962 2355017 6361812 7892212
MMDBr0002552	L-Carnitine	Malonylcarnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1735445 1988962 2355017 6361812 7892212
MMDBr0002553	L-Carnitine	Malonylcarnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1735445 1988962 2355017 6361812 7892212
MMDBr0002554	Malonylcarnitine	L-Carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1735445 1988962 2355017 6361812 7892212
MMDBr0002972	Gamma-linolenoyl-CoA	8Z,11Z,14Z-eicosatrienoyl-CoA	Not Available	VMH	30371894
MMDBr0003842	Malonyl-CoA	3-oxoicosanoyl-CoA	ELOVL fatty acid elongase 2	VMH	10479480
MMDBr0003846	Eicosanoyl-CoA	3-oxodocosanoyl-CoA	ELOVL fatty acid elongase 2	VMH	10479480
MMDBr0003847	Eicosanoyl-CoA	3-oxodocosanoyl-CoA	lysyl oxidase-like 2	VMH	10479480
MMDBr0003851	Docosanoyl-CoA	3-oxotetracosanoyl-CoA	HIRA interacting protein 3	VMH	10479480
MMDBr0003864	Malonyl-CoA	3-Oxooctadecanoyl-CoA	cathepsin A	VMH	10479480
MMDBr0003865	Malonyl-CoA	3-Oxooctadecanoyl-CoA	ELOVL fatty acid elongase 1	VMH	10479480
MMDBr0004506	Gamma-linolenoyl-CoA	3-Oxo-Dihomo-Gama-Linolenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004507	Gamma-linolenoyl-CoA	3-Oxo-Dihomo-Gama-Linolenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004513	Malonyl-CoA	3-Keto-Eicosa-8,11,14,17-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004514	Malonyl-CoA	3-Keto-Eicosa-8,11,14,17-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004525	Malonyl-CoA	3-Oxo-Docosa-7,10,13,16,19-All-Cis-Pentaenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004526	Malonyl-CoA	3-Oxo-Docosa-7,10,13,16,19-All-Cis-Pentaenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004533	Clupanodonyl CoA	3-Oxo-All-Cis-6,9,12,15,18-Tetracosapentaenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004534	Clupanodonyl CoA	3-Oxo-All-Cis-6,9,12,15,18-Tetracosapentaenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004550	Adrenyl coenzyme A	3-Oxo-All-Cis-6,9,12,15,18-Tetracosapentaenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004551	Adrenyl coenzyme A	3-Oxo-All-Cis-6,9,12,15,18-Tetracosapentaenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004552	Arachidonyl-CoA	3-Oxo-Docosa-7,10,13,16-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004553	Arachidonyl-CoA	3-Oxo-Docosa-7,10,13,16-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004565	Linoleoyl-CoA	3-Oxoeicosa-Cis,Cis-11,14-Dienoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004566	Linoleoyl-CoA	3-Oxoeicosa-Cis,Cis-11,14-Dienoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004573	8Z,11Z,14Z-eicosatrienoyl-CoA	3-Oxo-Docosa-Cis,Cis,Cis-10,13,16-Trienoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004574	8Z,11Z,14Z-eicosatrienoyl-CoA	3-Oxo-Docosa-Cis,Cis,Cis-10,13,16-Trienoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004583	Eicosatetranoyl coenzyme A	3-Oxo-Docosa-10,13,16,19-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004584	Eicosatetranoyl coenzyme A	3-Oxo-Docosa-10,13,16,19-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004591	10Z,13Z,16Z,19Z-Docosatetraenoyl Coenzyme A	3-Oxo-Tetracosa-12,15,18,21-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004592	10Z,13Z,16Z,19Z-Docosatetraenoyl Coenzyme A	3-Oxo-Tetracosa-12,15,18,21-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004618	Malonyl-CoA	3-Oxo-11-Cis-Eicosenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004619	Malonyl-CoA	3-Oxo-11-Cis-Eicosenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004620	11Z-Eicosenoyl Coenzyme A	3-Oxo-13Cis-Docosenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004621	11Z-Eicosenoyl Coenzyme A	3-Oxo-13Cis-Docosenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004622	13Z-docosenoyl-CoA	3-Oxo-Cis-15-Tetracosaenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004623	13Z-docosenoyl-CoA	3-Oxo-Cis-15-Tetracosaenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0004648	Palmitoleyl-CoA	3-Oxo-Cis-9-Octadecenoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004649	Palmitoleyl-CoA	3-Oxo-Cis-9-Octadecenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0005288	L-Carnitine	Malonyl Carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	12651823 18192268
MMDBr0006755	Palmitic acid	Stearic acid	Not Available	VMH	30371894
MMDBr0007614	Hydrogen carbonate	Malonyl-CoA	Not Available	VMH; KEGG	30371894
MMDBr0007664	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available	VMH	30371894
MMDBr0008450	Oleic acid	Malonyl-CoA	Not Available	VMH	30371894
MMDBr0009668	Malonyl-CoA	3-Oxooctadecanoyl-CoA	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009671	Docosanoyl-CoA	3-oxotetracosanoyl-CoA	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009672	Malonyl-CoA	3-oxohexacosanoyl-CoA	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009676	Heptadecanoyl Coenzyme A	3-Oxononadecanoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009680	Nonadecanoyl Coenzyme A	3-Oxoheneicosanoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009684	Heneicosanoyl Coenzyme A	3-Oxotricosanoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009697	Malonyl-CoA	3-oxohexacosanoyl-CoA	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009701	Malonyl-CoA	3-Oxo-13-Cis-Eicosenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009705	7Z-Octadecenoyl Coenzyme A	3-Oxo-9-Cis-Eicosenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009709	9Z-Eicosenoyl Coenzyme A	3-Oxo-11Cis-Docosenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009719	Adrenyl coenzyme A	3-Oxo-Tetracosa-9,12,15,18-All-Cis-Tetraenoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009721	(11Z,14Z)-Icosadienoyl Coenzyme A	(3R)-3-hydroxy-docosanoyl-CoA	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009735	11Z,14Z,17Z-Eicosatrienoyl Coenzyme A	3-Oxo-Docosa-13,16,19-All-Cis-Trienoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0010813	Malonyl-CoA	Malonyl-CoA semialdehyde	Not Available	VMH; KEGG	30371894
MMDBr0010855	Malonyl-CoA	Oxalacetic acid	Not Available	VMH	30371894
MMDBr0010856	Malonic semialdehyde	Malonyl-CoA	Not Available	VMH	30371894
MMDBr0011010	Malonyl-CoA	Stearic acid	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	186	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	379	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	137	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	51	Human feces; Human supragingival plaque; Human saliva	Unknown
Archaea/Archaea	Crenarchaeota	2		Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Adipose tissue	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001175

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15531

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Trevisan CP, Angelini C, Fiorellini LA, Isaya G, Zacchello G: Malonyl-CoA abnormal inhibition of residual enzyme activity in carnitine palmitoyltransferase deficiency. Eur Neurol. 1986;25(4):309-16. doi: 10.1159/000116027. [PubMed:3720808 ]
Prentki M, Corkey BE: Are the beta-cell signaling molecules malonyl-CoA and cystolic long-chain acyl-CoA implicated in multiple tissue defects of obesity and NIDDM? Diabetes. 1996 Mar;45(3):273-83. doi: 10.2337/diab.45.3.273. [PubMed:8593930 ]
Odland LM, Heigenhauser GJ, Lopaschuk GD, Spriet LL: Human skeletal muscle malonyl-CoA at rest and during prolonged submaximal exercise. Am J Physiol. 1996 Mar;270(3 Pt 1):E541-4. doi: 10.1152/ajpendo.1996.270.3.E541. [PubMed:8638703 ]
Odland LM, Howlett RA, Heigenhauser GJ, Hultman E, Spriet LL: Skeletal muscle malonyl-CoA content at the onset of exercise at varying power outputs in humans. Am J Physiol. 1998 Jun;274(6):E1080-5. doi: 10.1152/ajpendo.1998.274.6.E1080. [PubMed:9611159 ]
Ruderman NB, Saha AK, Vavvas D, Witters LA: Malonyl-CoA, fuel sensing, and insulin resistance. Am J Physiol. 1999 Jan;276(1):E1-E18. doi: 10.1152/ajpendo.1999.276.1.E1. [PubMed:9886945 ]
Bavenholm PN, Pigon J, Saha AK, Ruderman NB, Efendic S: Fatty acid oxidation and the regulation of malonyl-CoA in human muscle. Diabetes. 2000 Jul;49(7):1078-83. doi: 10.2337/diabetes.49.7.1078. [PubMed:10909961 ]
Morillas M, Gomez-Puertas P, Bentebibel A, Selles E, Casals N, Valencia A, Hegardt FG, Asins G, Serra D: Identification of conserved amino acid residues in rat liver carnitine palmitoyltransferase I critical for malonyl-CoA inhibition. Mutation of methionine 593 abolishes malonyl-CoA inhibition. J Biol Chem. 2003 Mar 14;278(11):9058-63. doi: 10.1074/jbc.M209999200. Epub 2002 Dec 23. [PubMed:12499375 ]
Napal L, Dai J, Treber M, Haro D, Marrero PF, Woldegiorgis G: A single amino acid change (substitution of the conserved Glu-590 with alanine) in the C-terminal domain of rat liver carnitine palmitoyltransferase I increases its malonyl-CoA sensitivity close to that observed with the muscle isoform of the enzyme. J Biol Chem. 2003 Sep 5;278(36):34084-9. doi: 10.1074/jbc.M305826200. Epub 2003 Jun 25. [PubMed:12826662 ]
Saha AK, Ruderman NB: Malonyl-CoA and AMP-activated protein kinase: an expanding partnership. Mol Cell Biochem. 2003 Nov;253(1-2):65-70. doi: 10.1023/a:1026053302036. [PubMed:14619957 ]
Roepstorff C, Halberg N, Hillig T, Saha AK, Ruderman NB, Wojtaszewski JF, Richter EA, Kiens B: Malonyl-CoA and carnitine in regulation of fat oxidation in human skeletal muscle during exercise. Am J Physiol Endocrinol Metab. 2005 Jan;288(1):E133-42. doi: 10.1152/ajpendo.00379.2004. Epub 2004 Sep 21. [PubMed:15383373 ]
Kuhl JE, Ruderman NB, Musi N, Goodyear LJ, Patti ME, Crunkhorn S, Dronamraju D, Thorell A, Nygren J, Ljungkvist O, Degerblad M, Stahle A, Brismar TB, Andersen KL, Saha AK, Efendic S, Bavenholm PN: Exercise training decreases the concentration of malonyl-CoA and increases the expression and activity of malonyl-CoA decarboxylase in human muscle. Am J Physiol Endocrinol Metab. 2006 Jun;290(6):E1296-303. doi: 10.1152/ajpendo.00341.2005. Epub 2006 Jan 24. [PubMed:16434556 ]
Pender C, Trentadue AR, Pories WJ, Dohm GL, Houmard JA, Youngren JF: Expression of genes regulating malonyl-CoA in human skeletal muscle. J Cell Biochem. 2006 Oct 15;99(3):860-7. doi: 10.1002/jcb.20944. [PubMed:16721829 ]
Bandyopadhyay GK, Yu JG, Ofrecio J, Olefsky JM: Increased malonyl-CoA levels in muscle from obese and type 2 diabetic subjects lead to decreased fatty acid oxidation and increased lipogenesis; thiazolidinedione treatment reverses these defects. Diabetes. 2006 Aug;55(8):2277-85. doi: 10.2337/db06-0062. [PubMed:16873691 ]

Showing metabocard for Malonyl-CoA (MMDBc0029578)

MOL for #<Metabolite:0x00007fecb89fca48>

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Structure for #<Metabolite:0x00007fecb89fca48>

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