MiMeDB: Showing metabocard for 4-Phosphopantothenoylcysteine (MMDBc0029561)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:32:21 UTC

Update Date

2024-04-30 19:37:59 UTC

Metabolite ID

MMDBc0029561

Metabolite Identification

Common Name

4-Phosphopantothenoylcysteine

Description

4-Phosphopantothenoylcysteine (PPC) is an intermediate in the biosynthetic machinery (pathway) that converts pantothenate (vitamin B5) into coenzyme A (CoA). The enzyme Phosphopantothenoylcysteine decarboxylase catalyzes the decarboxylation of PPC to 4'-phosphopantetheine. Coenzyme A is the principal acyl carrier and is required for many synthetic and degradative reactions in intermediary metabolism, and is an essential cofactor in all living systems. (PMID: 15450493 , 16371361 , 14501115 )

Structure

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

HMDB0001117
     RDKit          3D
4'-Phosphopantothenoylcysteine
 48 47  0  0  0  0  0  0  0  0999 V2000
    3.0537    0.9765    2.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651    0.5613    1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2043   -0.8231    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.5447    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.5320    0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857    2.5839   -0.6361 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.2789    3.5033    0.1712 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3754    1.7964   -1.7589 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582    3.5883   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    0.5319    1.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6656    1.7892    1.4889 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -0.0140   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328   -1.1544   -0.4597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    0.7405   -0.8756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    0.2789   -2.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094   -0.9908   -2.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -0.7849   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    0.3536   -0.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972   -1.8038   -0.7840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160   -1.6014    0.0802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0278   -1.8931   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3637   -0.8810   -2.0219 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -2.4536    1.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6545   -3.2430    1.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5984   -2.4400    2.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842    2.0848    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    0.5789    3.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    0.6779    2.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -0.9987   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -1.5600    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749   -1.0042    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281    1.3225   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316    2.5753    0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    0.9475   -2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    4.3784   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.1230    2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080    2.4406    0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    1.6904   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    0.1716   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809    1.0499   -2.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994   -1.2284   -3.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8853   -1.8622   -1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -2.7450   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -0.5512    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8232   -1.6478    0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -2.9837   -0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890   -1.6379   -3.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7835   -3.2728    2.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  1
 11 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 19 43  1  0
 20 44  1  1
 21 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
M  END


  Mrv1652305072018462D          

 25 24  0  0  0  0            999 V2000
 9988.8308 9987.7878    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9989.5442 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1133 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.8308 9988.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.2596 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.9565 9986.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.1318 9986.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.3989 9987.7878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.1133 9986.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.9750 9987.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.6843 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6884 9987.7878    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9985.9697 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2760 9988.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4038 9987.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1007 9988.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.2549 9987.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.5403 9987.7878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9985.2549 9986.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.8257 9987.3755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9983.1111 9987.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.8257 9986.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.3963 9987.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.1111 9988.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.1111 9986.1376    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  1  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029561

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/t7-,9-/m0/s1

> <INCHI_KEY>
XQYALQVLCNHCFT-CBAPKCEASA-N

> <FORMULA>
C12H23N2O9PS

> <MOLECULAR_WEIGHT>
402.358

> <EXACT_MASS>
402.086187546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.250626263676736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-1.966908166

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.492691096684799

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7848516255104219

> <JCHEM_PKA_STRONGEST_BASIC>
-3.810580264485595

> <JCHEM_POLAR_SURFACE_AREA>
182.48999999999998

> <JCHEM_REFRACTIVITY>
87.40769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001117
     RDKit          3D
4'-Phosphopantothenoylcysteine
 48 47  0  0  0  0  0  0  0  0999 V2000
    3.0537    0.9765    2.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651    0.5613    1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2043   -0.8231    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.5447    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.5320    0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857    2.5839   -0.6361 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.2789    3.5033    0.1712 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3754    1.7964   -1.7589 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582    3.5883   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    0.5319    1.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6656    1.7892    1.4889 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -0.0140   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328   -1.1544   -0.4597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    0.7405   -0.8756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    0.2789   -2.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094   -0.9908   -2.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -0.7849   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    0.3536   -0.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972   -1.8038   -0.7840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160   -1.6014    0.0802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0278   -1.8931   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3637   -0.8810   -2.0219 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -2.4536    1.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6545   -3.2430    1.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5984   -2.4400    2.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842    2.0848    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    0.5789    3.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    0.6779    2.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -0.9987   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -1.5600    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749   -1.0042    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281    1.3225   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316    2.5753    0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    0.9475   -2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    4.3784   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.1230    2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080    2.4406    0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    1.6904   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    0.1716   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809    1.0499   -2.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994   -1.2284   -3.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8853   -1.8622   -1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -2.7450   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -0.5512    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8232   -1.6478    0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -2.9837   -0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890   -1.6379   -3.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7835   -3.2728    2.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  1
 11 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 19 43  1  0
 20 44  1  1
 21 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
M  END

HEADER    PROTEIN                                 07-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAY-20         0                                  
HETATM    1  C   UNK     0    8645.8178643.871   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8647.1498643.101   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8644.4788643.101   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8645.8178645.410   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8648.4858643.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8647.9198641.769   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8646.3798641.769   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8643.1458643.871   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    8644.4788641.562   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8649.8208643.101   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8641.8118643.101   0.000  0.00  0.00           C+0
HETATM   12  P   UNK     0    8651.1528643.871   0.000  0.00  0.00           P+0
HETATM   13  C   UNK     0    8640.4778643.871   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8650.3828645.210   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8652.4878643.101   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8651.9218645.210   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8639.1438643.101   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8637.8098643.871   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0    8639.1438641.562   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8636.4758643.101   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8635.1418643.871   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8636.4758641.562   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8633.8068643.101   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8635.1418645.410   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0    8635.1418640.790   0.000  0.00  0.00           S+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6    7                                             
CONECT    3    1    8    9                                                  
CONECT    4    1                                                            
CONECT    5    2   10                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    3   11                                                       
CONECT    9    3                                                            
CONECT   10    5   12                                                       
CONECT   11    8   13                                                       
CONECT   12   10   14   15   16                                             
CONECT   13   11   17                                                       
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20   23   24                                                  
CONECT   22   20   25                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0001117
HETATM    1  C1  UNL     1       3.054   0.976   2.693  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.665   0.561   1.304  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.204  -0.823   1.038  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.256   1.545   0.299  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.646   1.532   0.431  1.00  0.00           O  
HETATM    6  P1  UNL     1       5.386   2.584  -0.636  1.00  0.00           P  
HETATM    7  O2  UNL     1       6.279   3.503   0.171  1.00  0.00           O  
HETATM    8  O3  UNL     1       6.375   1.796  -1.759  1.00  0.00           O  
HETATM    9  O4  UNL     1       4.258   3.588  -1.422  1.00  0.00           O  
HETATM   10  C5  UNL     1       1.161   0.532   1.218  1.00  0.00           C  
HETATM   11  O5  UNL     1       0.666   1.789   1.489  1.00  0.00           O  
HETATM   12  C6  UNL     1       0.681  -0.014  -0.067  1.00  0.00           C  
HETATM   13  O6  UNL     1       1.033  -1.154  -0.460  1.00  0.00           O  
HETATM   14  N1  UNL     1      -0.184   0.741  -0.876  1.00  0.00           N  
HETATM   15  C7  UNL     1      -0.700   0.279  -2.146  1.00  0.00           C  
HETATM   16  C8  UNL     1      -1.509  -0.991  -2.000  1.00  0.00           C  
HETATM   17  C9  UNL     1      -2.664  -0.785  -1.108  1.00  0.00           C  
HETATM   18  O7  UNL     1      -2.836   0.354  -0.603  1.00  0.00           O  
HETATM   19  N2  UNL     1      -3.597  -1.804  -0.784  1.00  0.00           N  
HETATM   20  C10 UNL     1      -4.716  -1.601   0.080  1.00  0.00           C  
HETATM   21  C11 UNL     1      -6.028  -1.893  -0.579  1.00  0.00           C  
HETATM   22  S1  UNL     1      -6.364  -0.881  -2.022  1.00  0.00           S  
HETATM   23  C12 UNL     1      -4.645  -2.454   1.307  1.00  0.00           C  
HETATM   24  O8  UNL     1      -3.655  -3.243   1.470  1.00  0.00           O  
HETATM   25  O9  UNL     1      -5.598  -2.440   2.291  1.00  0.00           O  
HETATM   26  H1  UNL     1       2.984   2.085   2.754  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.362   0.579   3.478  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.105   0.678   2.860  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.346  -0.999  -0.057  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.452  -1.560   1.393  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.175  -1.004   1.518  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.928   1.323  -0.728  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.932   2.575   0.545  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.971   0.947  -2.057  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.767   4.378  -1.737  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.819  -0.123   2.065  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.908   2.441   0.763  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.475   1.690  -0.546  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.132   0.172  -2.846  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.381   1.050  -2.548  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.899  -1.228  -3.012  1.00  0.00           H  
HETATM   42  H17 UNL     1      -0.885  -1.862  -1.692  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.442  -2.745  -1.209  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.708  -0.551   0.415  1.00  0.00           H  
HETATM   45  H20 UNL     1      -6.823  -1.648   0.185  1.00  0.00           H  
HETATM   46  H21 UNL     1      -6.163  -2.984  -0.769  1.00  0.00           H  
HETATM   47  H22 UNL     1      -6.489  -1.638  -3.198  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.784  -3.273   2.840  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   10
CONECT    3   29   30   31
CONECT    4    5   32   33
CONECT    5    6
CONECT    6    7    7    8    9
CONECT    8   34
CONECT    9   35
CONECT   10   11   12   36
CONECT   11   37
CONECT   12   13   13   14
CONECT   14   15   38
CONECT   15   16   39   40
CONECT   16   17   41   42
CONECT   17   18   18   19
CONECT   19   20   43
CONECT   20   21   23   44
CONECT   21   22   45   46
CONECT   22   47
CONECT   23   24   24   25
CONECT   25   48
END

HMDB0001117
     RDKit          3D
4'-Phosphopantothenoylcysteine
 48 47  0  0  0  0  0  0  0  0999 V2000
    3.0537    0.9765    2.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651    0.5613    1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2043   -0.8231    1.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2560    1.5447    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6459    1.5320    0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3857    2.5839   -0.6361 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.2789    3.5033    0.1712 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3754    1.7964   -1.7589 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582    3.5883   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    0.5319    1.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6656    1.7892    1.4889 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -0.0140   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0328   -1.1544   -0.4597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    0.7405   -0.8756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    0.2789   -2.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094   -0.9908   -2.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6644   -0.7849   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365    0.3536   -0.6033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5972   -1.8038   -0.7840 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160   -1.6014    0.0802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0278   -1.8931   -0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3637   -0.8810   -2.0219 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -2.4536    1.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6545   -3.2430    1.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5984   -2.4400    2.2908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842    2.0848    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    0.5789    3.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    0.6779    2.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -0.9987   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -1.5600    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1749   -1.0042    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281    1.3225   -0.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316    2.5753    0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    0.9475   -2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7673    4.3784   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.1230    2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080    2.4406    0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    1.6904   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    0.1716   -2.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809    1.0499   -2.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994   -1.2284   -3.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8853   -1.8622   -1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -2.7450   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080   -0.5512    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8232   -1.6478    0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1627   -2.9837   -0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890   -1.6379   -3.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7835   -3.2728    2.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  1
 11 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 19 43  1  0
 20 44  1  1
 21 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
M  END

Synonyms

Value	Source
(R)-4'-Phosphopantothenoyl-L-cysteine	ChEBI
N-((R)-4'-Phosphopantothenoyl)-L-cysteine	ChEBI
N-[(R)-4'-Phosphopantothenoyl]-L-cysteine	ChEBI
(R)-4'-Phospho-N-pantothenoyl-L-cysteine	HMDB
(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-b-alanyl]-L-cysteine	HMDB
(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl]-L-cysteine	HMDB
4'-p-N-Pantothenoylcysteine	HMDB
4'-Phospho-N-pantothenoylcysteine	HMDB
4'-Phosphopantothenoyl-L-cysteine	HMDB
4-p-N-Pantothenoylcysteine	HMDB
N-((R)-4-Phosphopantothenoyl)-L-cysteine	HMDB
Pantothenoylcysteine 4'-phosphate	HMDB
Pantothenylcysteine 4'-phosphate	HMDB
4'-Phosphopantothenoylcysteine	HMDB
4’-Phosphopantothenoyl-L-cysteine	HMDB
4’-Phosphopantothenoylcysteine	HMDB
N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl-L-cysteine	HMDB
N-[(2R)-2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-β-alanyl-L-cysteine	HMDB
Pantothenoylcysteine 4’-phosphate	HMDB

Molecular Formula

C₁₂H₂₃N₂O₉PS

Average Mass

402.358

Monoisotopic Mass

402.086187546

IUPAC Name

(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid

Traditional Name

(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid

CAS Registry Number

7196-09-0

SMILES

CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O

InChI Identifier

InChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/t7-,9-/m0/s1

InChI Key

XQYALQVLCNHCFT-CBAPKCEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Cysteine or derivatives
Beta amino acid or derivatives
Alpha-amino acid or derivatives
Monoalkyl phosphate
Fatty amide
Monosaccharide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic oxide
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-cysteine derivative (CHEBI:15769 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	-0.88	ALOGPS
logP	-2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	182.49 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	87.41 m³·mol⁻¹	ChemAxon
Polarizability	36.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

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
MMDBp0192635	Pantothenate kinase 4	Enzyme	Q9NVE7	Homo sapiens
MMDBp0192636	Pantothenate kinase 2, mitochondrial	Unknown	Q9BZ23	Homo sapiens
MMDBp0192637	Pantothenate kinase 1	Enzyme	Q8TE04	Homo sapiens
MMDBp0192638	Pantothenate kinase 3	Enzyme	Q9H999	Homo sapiens
MMDBp0193763	Phosphopantothenate--cysteine ligase	Enzyme	Q9HAB8	Homo sapiens
MMDBp0193823	Phosphopantothenoylcysteine decarboxylase	Unknown	Q96CD2	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018359	L-Cysteine	Cytidine monophosphate	Coenzyme A biosynthesis bifunctional protein CoaBC	Synthesis	PathBank	31602464
MMDBr0018361	4-Phosphopantothenoylcysteine	4'-phosphopantetheine	Coenzyme A biosynthesis bifunctional protein CoaBC	Synthesis	PathBank	31602464
MMDBr0019432	L-Cysteine	Cytidine monophosphate	Phosphopantothenate--cysteine ligase CAB2	Ligation	PathBank	31602464
MMDBr0019433	4-Phosphopantothenoylcysteine	4'-phosphopantetheine	Phosphopantothenoylcysteine decarboxylase subunit SIS2	Carboxylation	PathBank	31602464
MMDBr0019758	4-Phosphopantothenoylcysteine	4'-phosphopantetheine	Phosphopantothenate--cysteine ligase CAB2	Ligation	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
Bacteria	Proteobacteria	8	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	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	363	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/Eubacteria	Proteobacteria	174	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	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	113	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	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/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	28	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/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
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

HMDB0001117

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

R-4-PHOSPHOPANTOTHENOYL-L-CYSTEINE

BiGG ID

43650

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440304

PDB ID

Not Available

ChEBI ID

15769

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Manoj N, Ealick SE: Unusual space-group pseudosymmetry in crystals of human phosphopantothenoylcysteine decarboxylase. Acta Crystallogr D Biol Crystallogr. 2003 Oct;59(Pt 10):1762-6. doi: 10.1107/s0907444903016214. Epub 2003 Sep 19. [PubMed:14501115 ]
Begley TP, Ealick SE: Enzymatic reactions involving novel mechanisms of carbanion stabilization. Curr Opin Chem Biol. 2004 Oct;8(5):508-15. doi: 10.1016/j.cbpa.2004.08.004. [PubMed:15450493 ]
Kupke T, Schwarz W: 4'-phosphopantetheine biosynthesis in Archaea. J Biol Chem. 2006 Mar 3;281(9):5435-44. doi: 10.1074/jbc.M510056200. Epub 2005 Dec 21. [PubMed:16371361 ]

Showing metabocard for 4-Phosphopantothenoylcysteine (MMDBc0029561)

MOL for #<Metabolite:0x00005645c63fc7c8>

3D MOL for #<Metabolite:0x00005645c63fc7c8>

3D SDF for #<Metabolite:0x00005645c63fc7c8>

3D-SDF for #<Metabolite:0x00005645c63fc7c8>

PDB for #<Metabolite:0x00005645c63fc7c8>

3D PDB for #<Metabolite:0x00005645c63fc7c8>

SMILES for #<Metabolite:0x00005645c63fc7c8>

INCHI for #<Metabolite:0x00005645c63fc7c8>

Structure for #<Metabolite:0x00005645c63fc7c8>

3D Structure for #<Metabolite:0x00005645c63fc7c8>