MiMeDB: Showing metabocard for (R)-Methylmalonyl-CoA (MMDBc0031721)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:45:46 UTC

Update Date

2022-08-31 18:23:50 UTC

Metabolite ID

MMDBc0031721

Metabolite Identification

Common Name

(R)-Methylmalonyl-CoA

Description

(R)-methylmalonyl-CoA is a member of the chemical class known as Coenzyme A and Derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10241207582D          

 61 63  0  0  0  0            999 V2000
    7.2515   16.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -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
    7.2515   15.2177    0.0000 C   0  0  2  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
   -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  1  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
    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
   -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
   -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
    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
   -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
    7.9660   15.6302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3603   15.9771    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
   -7.3667   16.2604    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
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
 12  1  1  6  0  0  0
 13  8  1  1  0  0  0
 14  4  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 19 15  2  0  0  0  0
 20 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 12  1  0  0  0  0
 24 12  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25  9  1  0  0  0  0
 25 18  1  0  0  0  0
 26 19  1  0  0  0  0
 27  6  1  4  0  0  0
 27 14  2  0  0  0  0
 28  5  1  4  0  0  0
 28 21  2  0  0  0  0
 29 10  2  0  0  0  0
 29 19  1  0  0  0  0
 30 10  1  0  0  0  0
 30 20  2  0  0  0  0
 31 11  2  0  0  0  0
 31 15  1  0  0  0  0
 32 11  1  0  0  0  0
 32 20  1  0  0  0  0
 22 32  1  1  0  0  0
 33 14  1  0  0  0  0
 16 34  1  6  0  0  0
 18 35  1  1  0  0  0
 36 21  1  0  0  0  0
 37 23  2  0  0  0  0
 38 23  1  0  0  0  0
 39 24  2  0  0  0  0
 47  8  1  0  0  0  0
 48  9  1  0  0  0  0
 49 13  1  0  0  0  0
 49 22  1  0  0  0  0
 17 50  1  6  0  0  0
 52 40  1  0  0  0  0
 52 41  1  0  0  0  0
 52 42  2  0  0  0  0
 52 50  1  0  0  0  0
 53 43  1  0  0  0  0
 53 44  2  0  0  0  0
 53 47  1  0  0  0  0
 53 51  1  0  0  0  0
 54 45  1  0  0  0  0
 54 46  2  0  0  0  0
 54 48  1  0  0  0  0
 54 51  1  0  0  0  0
 55  7  1  0  0  0  0
 55 24  1  0  0  0  0
 12 56  1  1  0  0  0
 13 57  1  6  0  0  0
 16 58  1  1  0  0  0
 17 59  1  1  0  0  0
 18 60  1  1  0  0  0
 22 61  1  6  0  0  0
M  END


  Mrv0541 10241207582D          

 61 63  0  0  0  0            999 V2000
    7.2515   16.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -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
    7.2515   15.2177    0.0000 C   0  0  2  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
   -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  1  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
    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
   -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
   -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
    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
   -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
    7.9660   15.6302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3603   15.9771    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
   -7.3667   16.2604    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
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
 12  1  1  6  0  0  0
 13  8  1  1  0  0  0
 14  4  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 19 15  2  0  0  0  0
 20 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 16  1  0  0  0  0
 23 12  1  0  0  0  0
 24 12  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25  9  1  0  0  0  0
 25 18  1  0  0  0  0
 26 19  1  0  0  0  0
 27  6  1  4  0  0  0
 27 14  2  0  0  0  0
 28  5  1  4  0  0  0
 28 21  2  0  0  0  0
 29 10  2  0  0  0  0
 29 19  1  0  0  0  0
 30 10  1  0  0  0  0
 30 20  2  0  0  0  0
 31 11  2  0  0  0  0
 31 15  1  0  0  0  0
 32 11  1  0  0  0  0
 32 20  1  0  0  0  0
 22 32  1  1  0  0  0
 33 14  1  0  0  0  0
 16 34  1  6  0  0  0
 18 35  1  1  0  0  0
 36 21  1  0  0  0  0
 37 23  2  0  0  0  0
 38 23  1  0  0  0  0
 39 24  2  0  0  0  0
 47  8  1  0  0  0  0
 48  9  1  0  0  0  0
 49 13  1  0  0  0  0
 49 22  1  0  0  0  0
 17 50  1  6  0  0  0
 52 40  1  0  0  0  0
 52 41  1  0  0  0  0
 52 42  2  0  0  0  0
 52 50  1  0  0  0  0
 53 43  1  0  0  0  0
 53 44  2  0  0  0  0
 53 47  1  0  0  0  0
 53 51  1  0  0  0  0
 54 45  1  0  0  0  0
 54 46  2  0  0  0  0
 54 48  1  0  0  0  0
 54 51  1  0  0  0  0
 55  7  1  0  0  0  0
 55 24  1  0  0  0  0
 12 56  1  1  0  0  0
 13 57  1  6  0  0  0
 16 58  1  1  0  0  0
 17 59  1  1  0  0  0
 18 60  1  1  0  0  0
 22 61  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031721

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](C)(C(O)=O)C(=O)SCCN=C(O)CCN=C(O)[C@]([H])(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/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13-,16-,17-,18+,22-/m1/s1

> <INCHI_KEY>
MZFOKIKEPGUZEN-AGCMQPJKSA-N

> <FORMULA>
C25H40N7O19P3S

> <MOLECULAR_WEIGHT>
867.607

> <EXACT_MASS>
867.131252359

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
76.00817839872788

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-3.8531381843485266

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8802332363705059

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8202565352422293

> <JCHEM_PKA_STRONGEST_BASIC>
4.822939110849895

> <JCHEM_POLAR_SURFACE_AREA>
407.9100000000001

> <JCHEM_REFRACTIVITY>
184.17000000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.49e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   52  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   53  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   54  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   55  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   56  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4    5   14                                                       
CONECT    5    4   28                                                       
CONECT    6    7   27                                                       
CONECT    7    6   55                                                       
CONECT    8   13   47                                                       
CONECT    9   25   48                                                       
CONECT   10   29   30                                                       
CONECT   11   31   32                                                       
CONECT   12    1   23   24   56                                             
CONECT   13    8   17   49   57                                             
CONECT   14    4   27   33                                                  
CONECT   15   19   20   31                                                  
CONECT   16   17   22   34   58                                             
CONECT   17   13   16   50   59                                             
CONECT   18   21   25   35   60                                             
CONECT   19   15   26   29                                                  
CONECT   20   15   30   32                                                  
CONECT   21   18   28   36                                                  
CONECT   22   16   32   49   61                                             
CONECT   23   12   37   38                                                  
CONECT   24   12   39   55                                                  
CONECT   25    2    3    9   18                                             
CONECT   26   19                                                            
CONECT   27    6   14                                                       
CONECT   28    5   21                                                       
CONECT   29   10   19                                                       
CONECT   30   10   20                                                       
CONECT   31   11   15                                                       
CONECT   32   11   20   22                                                  
CONECT   33   14                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   21                                                            
CONECT   37   23                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   52                                                            
CONECT   41   52                                                            
CONECT   42   52                                                            
CONECT   43   53                                                            
CONECT   44   53                                                            
CONECT   45   54                                                            
CONECT   46   54                                                            
CONECT   47    8   53                                                       
CONECT   48    9   54                                                       
CONECT   49   13   22                                                       
CONECT   50   17   52                                                       
CONECT   51   53   54                                                       
CONECT   52   40   41   42   50                                             
CONECT   53   43   44   47   51                                             
CONECT   54   45   46   48   51                                             
CONECT   55    7   24                                                       
CONECT   56   12                                                            
CONECT   57   13                                                            
CONECT   58   16                                                            
CONECT   59   17                                                            
CONECT   60   18                                                            
CONECT   61   22                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

Synonyms

Value	Source
(R)-2-Methyl-3-oxopropanoyl-CoA	ChEBI
(R)-2-Methyl-3-oxopropionyl-CoA	ChEBI
(R)-3-oxo-2-Methylpropanoyl-CoA	ChEBI
METHYLMALONYL-coenzyme A	ChEBI
L-Methylmalonyl-CoA	Kegg
Methylmalonyl CoA	MeSH

Molecular Formula

C₂₅H₄₀N₇O₁₉P₃S

Average Mass

867.607

Monoisotopic Mass

867.131252359

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(C(O)=O)C(=O)SCCN=C(O)CCN=C(O)[C@]([H])(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/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13-,16-,17-,18+,22-/m1/s1

InChI Key

MZFOKIKEPGUZEN-AGCMQPJKSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
1,3-dicarbonyl compound
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Secondary alcohol
Amino acid
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methylmalonyl-CoA (CHEBI:15465 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.49 g/L	ALOGPS
logP	-0.4	ALOGPS
logP	-3.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.82	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	407.91 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	184.17 m³·mol⁻¹	ChemAxon
Polarizability	76.01 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-3931000120-503dfdefbc3bdbb5e1bc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-1911000000-cd0632f31aad1955e31e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3910000000-6b360fd99bac9c77be27	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00l2-9811041650-6ff1106e71f7373df82d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-4911110010-0041cbe45f5267a47176	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-da5c7610b3b97c5fb82f	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014003	(R)-Methylmalonyl-CoA	(S)-Methylmalonyl-CoA	Ethylmalonyl-CoA/methylmalonyl-CoA epimerase	Epimerization	RHEA	34755880
MMDBr0014004	(S)-Methylmalonyl-CoA	(R)-Methylmalonyl-CoA	Ethylmalonyl-CoA/methylmalonyl-CoA epimerase	Epimerization	RHEA	34755880
MMDBr0014264	(R)-Methylmalonyl-CoA	Succinyl-CoA	Methylmalonyl-CoA mutase	Intramolecular transfer of functional group	RHEA	34755880
MMDBr0014265	(R)-Methylmalonyl-CoA	Succinyl-CoA	Methylmalonyl-CoA mutase	Intramolecular transfer of functional group	RHEA	34755880
MMDBr0014716	(R)-Methylmalonyl-CoA	Carbon dioxide	Methylmalonyl-CoA decarboxylase	Decarboxylation	RHEA	34755880
MMDBr0024354	Hydrogen Ion	Water	Mycocerosic acid synthase	Synthesis	RHEA	34755880
MMDBr0025332	Hydrogen Ion	Water	Mycocerosic acid synthase	Synthesis	RHEA	34755880
MMDBr0038777	(R)-Methylmalonyl-CoA	Methylmalonic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

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	3	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Archaea/Archaea	Euryarchaeota	1
Bacteria	Actinobacteria	5	Cattle ; Human
Bacteria	Bacteroidetes	1	Human ; Human feces

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

External Links

HMDB ID

Not Available

DrugBank ID

DB04045

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01213

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

449534

PDB ID

Not Available

ChEBI ID

15465

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (R)-Methylmalonyl-CoA (MMDBc0031721)

MOL for #<Metabolite:0x00007fe26656e2f8>

3D MOL for #<Metabolite:0x00007fe26656e2f8>

3D SDF for #<Metabolite:0x00007fe26656e2f8>

3D-SDF for #<Metabolite:0x00007fe26656e2f8>

PDB for #<Metabolite:0x00007fe26656e2f8>

3D PDB for #<Metabolite:0x00007fe26656e2f8>

SMILES for #<Metabolite:0x00007fe26656e2f8>

INCHI for #<Metabolite:0x00007fe26656e2f8>

Structure for #<Metabolite:0x00007fe26656e2f8>

3D Structure for #<Metabolite:0x00007fe26656e2f8>