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Showing metabocard for (S)-3-Hydroxyisobutyryl-CoA (HMDB0001052)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:37:14 UTC
HMDB IDHMDB0001052
Secondary Accession Numbers
  • HMDB01052
Metabolite Identification
Common Name(S)-3-Hydroxyisobutyryl-CoA
Description(S)-3-Hydroxyisobutyryl-CoA is s metabolite of 3-hydroxyisobutyryl-CoA hydrolase (EC 3.1.2.4 ) during beta-alanine metabolism (KEGG 00410), propanoate metabolism (KEGG 00640), and valine, leucine and isoleucine degradation (KEGG 00280). Deficiencies of this enzyme in valine degradation can result in hypotonia, poor feeding, motor delay, and subsequent neurological regression in infancy, episodes of ketoacidosis and Leigh-like changes in the basal ganglia on a magnetic resonance imaging scan (PMID 17160907 ).
Structure
Data?1582752173
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)


  Mrv1652309042000172D          

 54 56  0  0  0  0            999 V2000
   26.0583  -17.7878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7810  -17.4565    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3554  -18.4792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.7767  -18.3324    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2642  -19.9350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2279  -18.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1704  -19.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6870  -18.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3341  -16.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1688  -16.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0237  -17.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5299  -18.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3932  -18.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8391  -19.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7892  -19.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8716  -17.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1136  -17.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4399  -19.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2878  -17.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1307  -17.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8962  -18.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9011  -17.4939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -20.9728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -22.3006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -20.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -22.0492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -23.2867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1258  -18.7123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9686  -18.4184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4814  -18.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9954  -19.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2656  -19.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4791  -20.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9340  -18.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7044  -21.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -22.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9512  -18.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7044  -18.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1982  -18.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -22.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2882  -17.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6144  -19.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3727  -18.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7941  -18.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5472  -18.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2155  -18.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6368  -17.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3900  -18.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4797  -17.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8114  -18.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2328  -17.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3949  -16.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 50  1  0  0  0  0
  1 52  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 34  1  0  0  0  0
 12 40  1  0  0  0  0
 15 39  1  0  0  0  0
 19 45  2  0  0  0  0
 20 48  2  0  0  0  0
 21 52  2  0  0  0  0
 22 53  1  0  0  0  0
 23 33  1  0  0  0  0
 23 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 36  2  0  0  0  0
 24 37  1  0  0  0  0
 25 35  2  0  0  0  0
 25 44  1  0  0  0  0
 26 41  1  0  0  0  0
 26 44  2  0  0  0  0
 27 41  1  0  0  0  0
 28 45  1  0  0  0  0
 28 46  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 35 37  1  0  0  0  0
 37 41  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
 38 43  1  0  0  0  0
 39 45  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 49 50  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 51 54  1  0  0  0  0
M  END
Download

3D MOL for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

Download
3D SDF for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

  Mrv1652309042000172D          

 54 56  0  0  0  0            999 V2000
   26.0583  -17.7878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7810  -17.4565    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3554  -18.4792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.7767  -18.3324    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2642  -19.9350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2279  -18.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1704  -19.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6870  -18.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3341  -16.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1688  -16.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0237  -17.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5299  -18.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3932  -18.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8391  -19.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7892  -19.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8716  -17.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1136  -17.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4399  -19.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2878  -17.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1307  -17.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8962  -18.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9011  -17.4939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -20.9728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -22.3006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -20.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -22.0492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -23.2867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1258  -18.7123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9686  -18.4184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4814  -18.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9954  -19.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2656  -19.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4791  -20.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9340  -18.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7044  -21.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -22.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9512  -18.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7044  -18.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1982  -18.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -22.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2882  -17.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6144  -19.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3727  -18.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7941  -18.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5472  -18.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2155  -18.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6368  -17.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3900  -18.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4797  -17.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8114  -18.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2328  -17.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3949  -16.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 50  1  0  0  0  0
  1 52  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 34  1  0  0  0  0
 12 40  1  0  0  0  0
 15 39  1  0  0  0  0
 19 45  2  0  0  0  0
 20 48  2  0  0  0  0
 21 52  2  0  0  0  0
 22 53  1  0  0  0  0
 23 33  1  0  0  0  0
 23 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 36  2  0  0  0  0
 24 37  1  0  0  0  0
 25 35  2  0  0  0  0
 25 44  1  0  0  0  0
 26 41  1  0  0  0  0
 26 44  2  0  0  0  0
 27 41  1  0  0  0  0
 28 45  1  0  0  0  0
 28 46  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 35 37  1  0  0  0  0
 37 41  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
 38 43  1  0  0  0  0
 39 45  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 49 50  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 51 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001052

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)

> <INCHI_KEY>
WWEOGFZEFHPUAM-UHFFFAOYSA-N

> <FORMULA>
C25H42N7O18P3S

> <MOLECULAR_WEIGHT>
853.623

> <EXACT_MASS>
853.151987801

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
75.70314825666493

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-5.918868144481294

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776185

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398193

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.8599999999999

> <JCHEM_REFRACTIVITY>
183.18410000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)
https://cactus.nci.nih.gov/chemical/structure/CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:95})
 96 98  0  0  0  0  0  0  0  0999 V2000
   14.7913    4.1323    1.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0842    2.6638    1.6122 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6886    2.5523    3.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9597    3.2047    3.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8032    1.8723    1.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4119    1.2773    2.5356 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8999    1.8126    0.1002 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5274    0.7565    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5608    0.5563   -0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4499   -0.2985   -0.1167 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0299    3.1175   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4736    4.2408   -0.9528 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4157    5.0721   -1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4049    6.3764   -1.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6805    6.2174   -2.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7383    4.9936   -1.8530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6411    4.3858   -1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3607    4.2118    0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0866    4.5266    2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7179    4.7048    1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7890    2.2695    0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0232    3.0264    3.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8150    1.5009    3.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4019    3.1734    3.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9152   -0.2104    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0018    1.2301    1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1730    1.5233   -0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0864    0.0828   -1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4198   -0.6382    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2192   -2.8869   -0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -4.6233   -2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859   -3.7500    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7542   -1.2192   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4530   -3.4372   -3.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -2.1765   -3.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1453   -1.8381   -3.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782   -4.8956   -1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689   -4.3938   -0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259   -4.9145   -2.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6514   -3.6032   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9656   -1.4900    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9691   -1.1173    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4489    1.1348    1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0917    2.0764   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6281    3.2074    1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7352    3.0819    0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3330    1.3255    2.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5089    2.2766   -0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
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 52 96  1  0  0  0  0
 53 54  2  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)
HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  S   UNK     0      48.642 -33.204   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      23.858 -32.585   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      28.663 -34.495   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      31.317 -34.220   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      24.760 -37.212   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      22.825 -33.728   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      20.851 -36.435   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      27.416 -35.398   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.890 -31.443   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.715 -31.553   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      29.911 -33.592   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      32.722 -34.849   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      25.001 -33.618   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      29.566 -35.742   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      36.940 -36.736   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      27.760 -33.247   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      31.945 -32.815   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      30.688 -35.626   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      37.871 -32.769   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      43.177 -32.220   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      50.206 -35.365   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      53.949 -32.655   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      22.816 -39.149   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      22.816 -41.628   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      20.025 -38.848   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      18.691 -41.159   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      20.025 -43.469   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      39.435 -34.930   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      44.741 -34.381   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      23.299 -35.193   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.391 -36.438   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.762 -35.672   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.294 -37.685   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.010 -34.769   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.359 -39.619   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.715 -40.389   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.359 -41.159   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      35.376 -34.575   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      36.782 -35.204   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      33.970 -33.946   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.025 -41.929   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      36.005 -33.169   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      34.747 -35.981   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.691 -39.619   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      38.029 -34.301   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      40.682 -34.027   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      42.088 -34.655   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      43.336 -33.752   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      45.989 -33.478   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      47.395 -34.107   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      51.295 -32.930   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      50.048 -33.833   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      52.701 -33.558   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      51.137 -31.398   0.000  0.00  0.00           C+0
CONECT    1   50   52                                                       
CONECT    2    6    9   10   13                                             
CONECT    3    8   11   14   16                                             
CONECT    4   11   12   17   18                                             
CONECT    5   32   33                                                       
CONECT    6    2   30                                                       
CONECT    7   31                                                            
CONECT    8    3   34                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3    4                                                       
CONECT   12    4   40                                                       
CONECT   13    2                                                            
CONECT   14    3                                                            
CONECT   15   39                                                            
CONECT   16    3                                                            
CONECT   17    4                                                            
CONECT   18    4                                                            
CONECT   19   45                                                            
CONECT   20   48                                                            
CONECT   21   52                                                            
CONECT   22   53                                                            
CONECT   23   33   35   36                                                  
CONECT   24   36   37                                                       
CONECT   25   35   44                                                       
CONECT   26   41   44                                                       
CONECT   27   41                                                            
CONECT   28   45   46                                                       
CONECT   29   48   49                                                       
CONECT   30    6   31   32                                                  
CONECT   31    7   30   33                                                  
CONECT   32    5   30   34                                                  
CONECT   33    5   23   31                                                  
CONECT   34    8   32                                                       
CONECT   35   23   25   37                                                  
CONECT   36   23   24                                                       
CONECT   37   24   35   41                                                  
CONECT   38   39   40   42   43                                             
CONECT   39   15   38   45                                                  
CONECT   40   12   38                                                       
CONECT   41   26   27   37                                                  
CONECT   42   38                                                            
CONECT   43   38                                                            
CONECT   44   25   26                                                       
CONECT   45   19   28   39                                                  
CONECT   46   28   47                                                       
CONECT   47   46   48                                                       
CONECT   48   20   29   47                                                  
CONECT   49   29   50                                                       
CONECT   50    1   49                                                       
CONECT   51   52   53   54                                                  
CONECT   52    1   21   51                                                  
CONECT   53   22   51                                                       
CONECT   54   51                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

Download
3D PDB for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      14.791   4.132   1.299  1.00  0.00           C  
HETATM    2  C   UNL     1      15.084   2.664   1.612  1.00  0.00           C  
HETATM    3  C   UNL     1      15.689   2.552   3.013  1.00  0.00           C  
HETATM    4  O   UNL     1      16.960   3.205   3.037  1.00  0.00           O  
HETATM    5  C   UNL     1      13.803   1.872   1.553  1.00  0.00           C  
HETATM    6  O   UNL     1      13.412   1.277   2.536  1.00  0.00           O  
HETATM    7  S   UNL     1      12.900   1.813   0.100  1.00  0.00           S  
HETATM    8  C   UNL     1      11.527   0.756   0.626  1.00  0.00           C  
HETATM    9  C   UNL     1      10.561   0.556  -0.543  1.00  0.00           C  
HETATM   10  N   UNL     1       9.450  -0.298  -0.117  1.00  0.00           N  
HETATM   11  C   UNL     1       8.470  -0.613  -0.987  1.00  0.00           C  
HETATM   12  O   UNL     1       8.507  -0.188  -2.122  1.00  0.00           O  
HETATM   13  C   UNL     1       7.327  -1.492  -0.548  1.00  0.00           C  
HETATM   14  C   UNL     1       6.360  -1.692  -1.718  1.00  0.00           C  
HETATM   15  N   UNL     1       5.249  -2.547  -1.292  1.00  0.00           N  
HETATM   16  C   UNL     1       4.269  -2.862  -2.162  1.00  0.00           C  
HETATM   17  O   UNL     1       4.258  -2.365  -3.268  1.00  0.00           O  
HETATM   18  C   UNL     1       3.187  -3.831  -1.760  1.00  0.00           C  
HETATM   19  O   UNL     1       3.505  -4.399  -0.488  1.00  0.00           O  
HETATM   20  C   UNL     1       1.850  -3.093  -1.668  1.00  0.00           C  
HETATM   21  C   UNL     1       1.991  -1.896  -0.725  1.00  0.00           C  
HETATM   22  C   UNL     1       1.443  -2.601  -3.058  1.00  0.00           C  
HETATM   23  C   UNL     1       0.779  -4.043  -1.129  1.00  0.00           C  
HETATM   24  O   UNL     1      -0.470  -3.354  -1.044  1.00  0.00           O  
HETATM   25  P   UNL     1      -1.822  -4.051  -0.516  1.00  0.00           P  
HETATM   26  O   UNL     1      -2.256  -5.221  -1.534  1.00  0.00           O  
HETATM   27  O   UNL     1      -1.588  -4.628   0.827  1.00  0.00           O  
HETATM   28  O   UNL     1      -2.995  -2.952  -0.430  1.00  0.00           O  
HETATM   29  P   UNL     1      -4.395  -2.869   0.360  1.00  0.00           P  
HETATM   30  O   UNL     1      -5.472  -3.830  -0.352  1.00  0.00           O  
HETATM   31  O   UNL     1      -4.196  -3.303   1.761  1.00  0.00           O  
HETATM   32  O   UNL     1      -4.933  -1.352   0.341  1.00  0.00           O  
HETATM   33  C   UNL     1      -6.102  -0.931   1.047  1.00  0.00           C  
HETATM   34  C   UNL     1      -6.329   0.564   0.815  1.00  0.00           C  
HETATM   35  O   UNL     1      -6.657   0.820  -0.568  1.00  0.00           O  
HETATM   36  C   UNL     1      -7.333   2.087  -0.611  1.00  0.00           C  
HETATM   37  C   UNL     1      -8.001   2.297   0.762  1.00  0.00           C  
HETATM   38  O   UNL     1      -9.422   2.353   0.624  1.00  0.00           O  
HETATM   39  C   UNL     1      -7.585   1.051   1.581  1.00  0.00           C  
HETATM   40  O   UNL     1      -8.613   0.059   1.558  1.00  0.00           O  
HETATM   41  P   UNL     1      -9.316  -0.506   2.892  1.00  0.00           P  
HETATM   42  O   UNL     1     -10.134   0.680   3.611  1.00  0.00           O  
HETATM   43  O   UNL     1     -10.327  -1.696   2.502  1.00  0.00           O  
HETATM   44  O   UNL     1      -8.280  -1.020   3.815  1.00  0.00           O  
HETATM   45  N   UNL     1      -6.367   3.159  -0.865  1.00  0.00           N  
HETATM   46  C   UNL     1      -5.030   3.118  -0.603  1.00  0.00           C  
HETATM   47  N   UNL     1      -4.474   4.241  -0.953  1.00  0.00           N  
HETATM   48  C   UNL     1      -5.416   5.072  -1.459  1.00  0.00           C  
HETATM   49  C   UNL     1      -5.405   6.376  -1.982  1.00  0.00           C  
HETATM   50  N   UNL     1      -4.227   7.099  -2.057  1.00  0.00           N  
HETATM   51  N   UNL     1      -6.552   6.900  -2.402  1.00  0.00           N  
HETATM   52  C   UNL     1      -7.681   6.217  -2.334  1.00  0.00           C  
HETATM   53  N   UNL     1      -7.738   4.994  -1.853  1.00  0.00           N  
HETATM   54  C   UNL     1      -6.641   4.386  -1.414  1.00  0.00           C  
HETATM   55  H   UNL     1      14.361   4.212   0.300  1.00  0.00           H  
HETATM   56  H   UNL     1      14.087   4.527   2.031  1.00  0.00           H  
HETATM   57  H   UNL     1      15.718   4.705   1.341  1.00  0.00           H  
HETATM   58  H   UNL     1      15.789   2.269   0.880  1.00  0.00           H  
HETATM   59  H   UNL     1      15.023   3.026   3.735  1.00  0.00           H  
HETATM   60  H   UNL     1      15.815   1.501   3.272  1.00  0.00           H  
HETATM   61  H   UNL     1      17.402   3.173   3.897  1.00  0.00           H  
HETATM   62  H   UNL     1      11.915  -0.210   0.947  1.00  0.00           H  
HETATM   63  H   UNL     1      11.002   1.230   1.456  1.00  0.00           H  
HETATM   64  H   UNL     1      10.173   1.523  -0.863  1.00  0.00           H  
HETATM   65  H   UNL     1      11.086   0.083  -1.372  1.00  0.00           H  
HETATM   66  H   UNL     1       9.420  -0.638   0.791  1.00  0.00           H  
HETATM   67  H   UNL     1       7.715  -2.459  -0.228  1.00  0.00           H  
HETATM   68  H   UNL     1       6.801  -1.019   0.281  1.00  0.00           H  
HETATM   69  H   UNL     1       5.973  -0.725  -2.038  1.00  0.00           H  
HETATM   70  H   UNL     1       6.886  -2.166  -2.547  1.00  0.00           H  
HETATM   71  H   UNL     1       5.219  -2.887  -0.384  1.00  0.00           H  
HETATM   72  H   UNL     1       3.115  -4.623  -2.504  1.00  0.00           H  
HETATM   73  H   UNL     1       3.586  -3.750   0.224  1.00  0.00           H  
HETATM   74  H   UNL     1       2.754  -1.219  -1.109  1.00  0.00           H  
HETATM   75  H   UNL     1       1.038  -1.371  -0.660  1.00  0.00           H  
HETATM   76  H   UNL     1       2.281  -2.247   0.266  1.00  0.00           H  
HETATM   77  H   UNL     1       1.453  -3.437  -3.757  1.00  0.00           H  
HETATM   78  H   UNL     1       0.440  -2.176  -3.014  1.00  0.00           H  
HETATM   79  H   UNL     1       2.145  -1.838  -3.394  1.00  0.00           H  
HETATM   80  H   UNL     1       0.678  -4.896  -1.801  1.00  0.00           H  
HETATM   81  H   UNL     1       1.069  -4.394  -0.139  1.00  0.00           H  
HETATM   82  H   UNL     1      -2.426  -4.915  -2.435  1.00  0.00           H  
HETATM   83  H   UNL     1      -5.651  -3.603  -1.275  1.00  0.00           H  
HETATM   84  H   UNL     1      -6.966  -1.490   0.686  1.00  0.00           H  
HETATM   85  H   UNL     1      -5.969  -1.117   2.113  1.00  0.00           H  
HETATM   86  H   UNL     1      -5.449   1.135   1.112  1.00  0.00           H  
HETATM   87  H   UNL     1      -8.092   2.076  -1.394  1.00  0.00           H  
HETATM   88  H   UNL     1      -7.628   3.207   1.232  1.00  0.00           H  
HETATM   89  H   UNL     1      -9.735   3.082   0.071  1.00  0.00           H  
HETATM   90  H   UNL     1      -7.333   1.325   2.605  1.00  0.00           H  
HETATM   91  H   UNL     1     -10.831   1.066   3.062  1.00  0.00           H  
HETATM   92  H   UNL     1     -10.787  -2.085   3.259  1.00  0.00           H  
HETATM   93  H   UNL     1      -4.509   2.277  -0.170  1.00  0.00           H  
HETATM   94  H   UNL     1      -3.396   6.706  -1.748  1.00  0.00           H  
HETATM   95  H   UNL     1      -4.233   7.999  -2.420  1.00  0.00           H  
HETATM   96  H   UNL     1      -8.590   6.681  -2.687  1.00  0.00           H  
CONECT    1    2   55   56   57                                       
CONECT    2    1    3    5   58                                       
CONECT    3    2    4   59   60                                       
CONECT    4    3   61                                                 
CONECT    5    2    6    6    7                                       
CONECT    6    5    5                                                 
CONECT    7    5    8                                                 
CONECT    8    7    9   62   63                                       
CONECT    9    8   10   64   65                                       
CONECT   10    9   11   66                                            
CONECT   11   10   12   12   13                                       
CONECT   12   11   11                                                 
CONECT   13   11   14   67   68                                       
CONECT   14   13   15   69   70                                       
CONECT   15   14   16   71                                            
CONECT   16   15   17   17   18                                       
CONECT   17   16   16                                                 
CONECT   18   16   19   20   72                                       
CONECT   19   18   73                                                 
CONECT   20   18   21   22   23                                       
CONECT   21   20   74   75   76                                       
CONECT   22   20   77   78   79                                       
CONECT   23   20   24   80   81                                       
CONECT   24   23   25                                                 
CONECT   25   24   26   27   27                                       
CONECT   25   28                                                      
CONECT   26   25   82                                                 
CONECT   27   25   25                                                 
CONECT   28   25   29                                                 
CONECT   29   28   30   31   31                                       
CONECT   29   32                                                      
CONECT   30   29   83                                                 
CONECT   31   29   29                                                 
CONECT   32   29   33                                                 
CONECT   33   32   34   84   85                                       
CONECT   34   33   35   39   86                                       
CONECT   35   34   36                                                 
CONECT   36   35   37   45   87                                       
CONECT   37   36   38   39   88                                       
CONECT   38   37   89                                                 
CONECT   39   37   34   40   90                                       
CONECT   40   39   41                                                 
CONECT   41   40   42   43   44                                       
CONECT   41   44                                                      
CONECT   42   41   91                                                 
CONECT   43   41   92                                                 
CONECT   44   41   41                                                 
CONECT   45   36   46   54                                            
CONECT   46   45   47   47   93                                       
CONECT   47   46   46   48                                            
CONECT   48   47   49   49   54                                       
CONECT   49   48   48   50   51                                       
CONECT   50   49   94   95                                            
CONECT   51   49   52   52                                            
CONECT   52   51   51   53   96                                       
CONECT   53   52   54   54                                            
CONECT   54   53   53   45   48                                       
CONECT   55    1                                                      
CONECT   56    1                                                      
CONECT   57    1                                                      
CONECT   58    2                                                      
CONECT   59    3                                                      
CONECT   60    3                                                      
CONECT   61    4                                                      
CONECT   62    8                                                      
CONECT   63    8                                                      
CONECT   64    9                                                      
CONECT   65    9                                                      
CONECT   66   10                                                      
CONECT   67   13                                                      
CONECT   68   13                                                      
CONECT   69   14                                                      
CONECT   70   14                                                      
CONECT   71   15                                                      
CONECT   72   18                                                      
CONECT   73   19                                                      
CONECT   74   21                                                      
CONECT   75   21                                                      
CONECT   76   21                                                      
CONECT   77   22                                                      
CONECT   78   22                                                      
CONECT   79   22                                                      
CONECT   80   23                                                      
CONECT   81   23                                                      
CONECT   82   26                                                      
CONECT   83   30                                                      
CONECT   84   33                                                      
CONECT   85   33                                                      
CONECT   86   34                                                      
CONECT   87   36                                                      
CONECT   88   37                                                      
CONECT   89   38                                                      
CONECT   90   39                                                      
CONECT   91   42                                                      
CONECT   92   43                                                      
CONECT   93   46                                                      
CONECT   94   50                                                      
CONECT   95   50                                                      
CONECT   96   52                                                      
MASTER        0    0    0    0    0    0    0    0   96    0   96    0
END

Download
SMILES for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)
CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
Download
INCHI for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)
InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
(S)-3-Hydroxyisobutyryl-coenzyme AHMDB
3-Hydroxy-2-methylpropanoyl-CoAHMDB
3-Hydroxy-2-methylpropanoyl-coenzyme AHMDB
3-Hydroxy-2-methylpropionyl-CoAHMDB
3-Hydroxy-2-methylpropionyl-coenzyme AHMDB
3-Hydroxy-isobutyryl-CoAHMDB
3-Hydroxy-isobutyryl-coenzyme AHMDB
3-Hydroxyisobutyryl-CoAHMDB
3-Hydroxyisobutyryl-coenzyme AHMDB
Chemical FormulaC25H42N7O18P3S
Average Molecular Weight853.623
Monoisotopic Molecular Weight853.151987801
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry Number319440-43-2
SMILES
CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)
InChI KeyWWEOGFZEFHPUAM-UHFFFAOYSA-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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acyl thioesters  
Direct ParentAcyl CoAs  
Alternative Parents
Substituents
  • Coenzyme a or derivatives
    • 

  • Purine ribonucleoside diphosphate
    • 

  • Purine ribonucleoside bisphosphate
    • 

  • Purine ribonucleoside 3',5'-bisphosphate
    • 

  • Ribonucleoside 3'-phosphate
    • 

  • Pentose-5-phosphate
    • 

  • Pentose phosphate
    • 

  • Beta amino acid or derivatives
    • 

  • Glycosyl compound
    • 

  • N-glycosyl compound
    • 

  • 6-aminopurine
    • 

  • Monosaccharide phosphate
    • 

  • Organic pyrophosphate
    • 

  • Imidazopyrimidine
    • 

  • Purine
    • 

  • Monoalkyl phosphate
    • 

  • Aminopyrimidine
    • 

  • Fatty amide
    • 

  • Monosaccharide
    • 

  • N-acyl-amine
    • 

  • N-substituted imidazole
    • 

  • Organic phosphoric acid derivative
    • 

  • Imidolactam
    • 

  • Phosphoric acid ester
    • 

  • Alkyl phosphate
    • 

  • Pyrimidine
    • 

  • Tetrahydrofuran
    • 

  • Azole
    • 

  • Heteroaromatic compound
    • 

  • Imidazole
    • 

  • Carbothioic s-ester
    • 

  • Secondary carboxylic acid amide
    • 

  • Secondary alcohol
    • 

  • Thiocarboxylic acid ester
    • 

  • Carboxamide group
    • 

  • Amino acid or derivatives
    • 

  • Thiocarboxylic acid or derivatives
    • 

  • Sulfenyl compound
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Organosulfur compound
    • 

  • Organonitrogen compound
    • 

  • Primary amine
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Amine
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
Role
Biological role:
Industrial application:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.14 g/LALOGPS
logP-0.56ALOGPS
logP-5.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity183.18 m³·mol⁻¹ChemAxon
Polarizability75.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available285.36331661259  
DarkChem[M-H]-PredictedNot Available264.68831661259  
AllCCS[M+H]+PredictedNot Available257.09732859911  
AllCCS[M-H]-PredictedNot Available255.44532859911  
Retention Indices
Underivatized
Not Available
Derivatized
Not Available
Spectra
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-000i-1912000120-c718f8aabcd5b33281932015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-000i-1913000000-86eb8b4e6cdee60b559a2015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-000i-2911000000-2d6f48b3506835c89ffd2015-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-00o9-9730140560-056ac34ed9b661751c572015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-001i-3920110010-37a68eba22e3eecc97572015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-057i-6900100000-e33bac5e5de19c7b719b2015-09-15View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
    • 

  • Membrane
    • 

  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022393  
KNApSAcK IDNot Available
Chemspider ID86  
KEGG Compound IDC06000  
BioCyc IDNot Available
BiGG ID47176  
Wikipedia LinkNot Available
METLIN ID453  
PubChem Compound88  
PDB IDNot Available
ChEBI ID28259  
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceHawes, John W.; Harper, Edwin T.  Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA.    Methods in Enzymology  (2000),  324(Branched-Chain Amino Acids),  73-79.  
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lehnert W, Sass JO: Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I). Med Hypotheses. 2005;65(2):330-3. [PubMed:15922108  ] 
  2. Loupatty FJ, Clayton PT, Ruiter JP, Ofman R, Ijlst L, Brown GK, Thorburn DR, Harris RA, Duran M, Desousa C, Krywawych S, Heales SJ, Wanders RJ: Mutations in the gene encoding 3-hydroxyisobutyryl-CoA hydrolase results in progressive infantile neurodegeneration. Am J Hum Genet. 2007 Jan;80(1):195-9. Epub 2006 Nov 30. [PubMed:17160907  ] 
Enzymes
  Enzyme Details
1. Peroxisomal bifunctional enzyme
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426  
Molecular weight:
69153.26
Reactions
Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoAdetails
  Enzyme Details
2. Enoyl-CoA hydratase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.

Gene Name:
ECHS1
Uniprot ID:
P30084  
Molecular weight:
31387.085
Reactions
Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoAdetails
  Enzyme Details
3. Trifunctional enzyme subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional subunit.

Gene Name:
HADHA
Uniprot ID:
P40939  
Molecular weight:
82998.97
Reactions
Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoAdetails
  Enzyme Details
4. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA.

Gene Name:
HIBCH
Uniprot ID:
Q6NVY1  
Molecular weight:
43481.935
Reactions
(S)-3-Hydroxyisobutyryl-CoA + Water → Coenzyme A + (S)-3-Hydroxyisobutyric aciddetails
(S)-3-Hydroxyisobutyryl-CoA + Water → Coenzyme A + (S)-3-Hydroxyisobutyric aciddetails