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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-03-31 19:28:37 UTC

Update Date

2022-10-24 19:45:17 UTC

HMDB ID

HMDB0241661

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine

Description

(2E)-4-hydroxy-3-methylpent-2-enedioylcarnitine is an acylcarnitine. More specifically, it is an (2E)-4-hydroxy-3-methylpent-2-enedioic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. (2E)-4-hydroxy-3-methylpent-2-enedioylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine (2E)-4-hydroxy-3-methylpent-2-enedioylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. In particular (2E)-4-hydroxy-3-methylpent-2-enedioylcarnitine is elevated in the blood or plasma of individuals with 3-hydroxy-3-ethylglutarylCoA lyase deficiency (PMID: 32685354 ). Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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

HMDB0241661
     RDKit          3D
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine
 42 41  0  0  0  0  0  0  0  0999 V2000
    3.0253   -1.9451    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -0.7221    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061   -0.9141   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442    0.0827   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0538   -0.2390   -2.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    1.4440   -1.5559 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352    0.5699    0.9073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937    0.5512    2.2263 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    0.6971    1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650    0.7602    2.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    0.7500    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7940    0.8739    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    2.2182   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    2.8401   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3113    2.5081    0.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    4.0089   -0.9349 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3876   -0.2825   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -0.6523   -0.2978 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6440   -0.0713   -1.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338   -0.6641    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -2.1238   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -2.3417    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -2.7315    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -1.7166    1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -1.9636   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    2.0818   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4759    1.4633    0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052   -0.1052    2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    0.9251    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014    2.9524    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838    2.1737   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -0.1748   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7288   -1.1868   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    0.3963   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854    0.7171   -1.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0511   -0.8185   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495   -1.6795    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915    0.1304    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283   -0.5259    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2668   -2.7142    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -2.3470   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -2.2248   -1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
M  CHG  2  16  -1  18   1
M  END

  Mrv1652303312121282D          

 21 20  0  0  0  0            999 V2000
    5.1118   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
M  CHG  2  16  -1  18   1
M  END
> <DATABASE_ID>
HMDB0241661

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=CC(O)=O)C(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO7/c1-8(5-10(15)16)12(19)13(20)21-9(6-11(17)18)7-14(2,3)4/h5,9,12,19H,6-7H2,1-4H3,(H-,15,16,17,18)

> <INCHI_KEY>
JBMXEKVFHRDFCQ-UHFFFAOYSA-N

> <FORMULA>
C13H21NO7

> <MOLECULAR_WEIGHT>
303.311

> <EXACT_MASS>
303.13180202

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.021438194400435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-carboxy-2-hydroxy-3-methylbut-3-enoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <JCHEM_LOGP>
-4.650922925138413

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.188018662158861

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3982148245344104

> <JCHEM_PKA_STRONGEST_BASIC>
-4.078951278703262

> <JCHEM_POLAR_SURFACE_AREA>
123.96000000000001

> <JCHEM_REFRACTIVITY>
94.84459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4-carboxy-2-hydroxy-3-methylbut-3-enoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241661
     RDKit          3D
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine
 42 41  0  0  0  0  0  0  0  0999 V2000
    3.0253   -1.9451    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -0.7221    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061   -0.9141   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442    0.0827   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0538   -0.2390   -2.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    1.4440   -1.5559 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352    0.5699    0.9073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937    0.5512    2.2263 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    0.6971    1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650    0.7602    2.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    0.7500    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7940    0.8739    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    2.2182   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    2.8401   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3113    2.5081    0.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    4.0089   -0.9349 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3876   -0.2825   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -0.6523   -0.2978 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6440   -0.0713   -1.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338   -0.6641    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -2.1238   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -2.3417    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -2.7315    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -1.7166    1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -1.9636   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    2.0818   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4759    1.4633    0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052   -0.1052    2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    0.9251    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014    2.9524    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838    2.1737   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -0.1748   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7288   -1.1868   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    0.3963   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854    0.7171   -1.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0511   -0.8185   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495   -1.6795    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915    0.1304    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283   -0.5259    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2668   -2.7142    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -2.3470   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -2.2248   -1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
M  CHG  2  16  -1  18   1
M  END

HEADER    PROTEIN                                 31-MAR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-21         0                                  
HETATM    1  O   UNK     0       9.542  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.208  -3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.208  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.875  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.541  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.541  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.207  -6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.540  -4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.461  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.127  -0.000   0.000  0.00  0.00           O-1
HETATM   17  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.874   0.770   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0241661
HETATM    1  C1  UNL     1       3.025  -1.945   1.149  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.404  -0.722   0.325  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.006  -0.914  -0.787  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.444   0.083  -1.703  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.054  -0.239  -2.801  1.00  0.00           O  
HETATM    6  O2  UNL     1       4.287   1.444  -1.556  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.035   0.570   0.907  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.594   0.551   2.226  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.555   0.697   1.087  1.00  0.00           C  
HETATM   10  O4  UNL     1       1.065   0.760   2.241  1.00  0.00           O  
HETATM   11  O5  UNL     1       0.678   0.750   0.022  1.00  0.00           O  
HETATM   12  C7  UNL     1      -0.794   0.874   0.343  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.053   2.218  -0.261  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.339   2.840  -0.153  1.00  0.00           C  
HETATM   15  O6  UNL     1      -3.311   2.508   0.540  1.00  0.00           O  
HETATM   16  O7  UNL     1      -2.577   4.009  -0.935  1.00  0.00           O1-
HETATM   17  C10 UNL     1      -1.388  -0.282  -0.363  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.727  -0.652  -0.298  1.00  0.00           N1+
HETATM   19  C11 UNL     1      -3.644  -0.071  -1.246  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.334  -0.664   1.012  1.00  0.00           C  
HETATM   21  C13 UNL     1      -2.793  -2.124  -0.676  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.903  -2.342   1.699  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.616  -2.731   0.474  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.244  -1.717   1.879  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.219  -1.964  -1.088  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.027   2.082  -1.249  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.476   1.463   0.460  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.105  -0.105   2.761  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.893   0.925   1.418  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.301   2.952   0.203  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.784   2.174  -1.364  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.126  -0.175  -1.473  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.729  -1.187  -0.095  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.472   0.396  -0.683  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.185   0.717  -1.874  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.051  -0.819  -1.975  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.250  -1.679   1.511  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.992   0.130   1.691  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.428  -0.526   0.871  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.267  -2.714   0.068  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.874  -2.347  -0.606  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.427  -2.225  -1.703  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    7
CONECT    3    4   25
CONECT    4    5    5    6
CONECT    6   26
CONECT    7    8    9   27
CONECT    8   28
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   17   29
CONECT   13   14   30   31
CONECT   14   15   15   16
CONECT   17   18   32   33
CONECT   18   19   20   21
CONECT   19   34   35   36
CONECT   20   37   38   39
CONECT   21   40   41   42
END

HMDB0241661
     RDKit          3D
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine
 42 41  0  0  0  0  0  0  0  0999 V2000
    3.0253   -1.9451    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -0.7221    0.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061   -0.9141   -0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4442    0.0827   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0538   -0.2390   -2.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2872    1.4440   -1.5559 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352    0.5699    0.9073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937    0.5512    2.2263 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    0.6971    1.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650    0.7602    2.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6779    0.7500    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7940    0.8739    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    2.2182   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    2.8401   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3113    2.5081    0.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5772    4.0089   -0.9349 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3876   -0.2825   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -0.6523   -0.2978 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6440   -0.0713   -1.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338   -0.6641    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -2.1238   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -2.3417    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -2.7315    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2439   -1.7166    1.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2195   -1.9636   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    2.0818   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4759    1.4633    0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052   -0.1052    2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    0.9251    1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014    2.9524    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7838    2.1737   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -0.1748   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7288   -1.1868   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    0.3963   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1854    0.7171   -1.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0511   -0.8185   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495   -1.6795    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9915    0.1304    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4283   -0.5259    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2668   -2.7142    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -2.3470   -0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266   -2.2248   -1.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
M  CHG  2  16  -1  18   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₁NO₇

Average Molecular Weight

303.311

Monoisotopic Molecular Weight

303.13180202

IUPAC Name

3-[(4-carboxy-2-hydroxy-3-methylbut-3-enoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(4-carboxy-2-hydroxy-3-methylbut-3-enoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

CC(=CC(O)=O)C(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C13H21NO7/c1-8(5-10(15)16)12(19)13(20)21-9(6-11(17)18)7-14(2,3)4/h5,9,12,19H,6-7H2,1-4H3,(H-,15,16,17,18)

InChI Key

JBMXEKVFHRDFCQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Tricarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-4.7	ChemAxon
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	123.96 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	94.84 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.194	30932474
DeepCCS	[M-H]-	167.353	30932474
DeepCCS	[M-2H]-	203.889	30932474
DeepCCS	[M+Na]+	179.93	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine	CC(=CC(O)=O)C(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	3579.0	Standard polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine	CC(=CC(O)=O)C(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	1705.8	Standard non polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine	CC(=CC(O)=O)C(O)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	2034.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine,1TMS,isomer #1	CC(=CC(=O)O[Si](C)(C)C)C(O)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2056.0	Semi standard non polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine,1TMS,isomer #2	CC(=CC(=O)O)C(O[Si](C)(C)C)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2108.9	Semi standard non polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine,2TMS,isomer #1	CC(=CC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2090.6	Semi standard non polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine,1TBDMS,isomer #1	CC(=CC(=O)O[Si](C)(C)C(C)(C)C)C(O)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2269.7	Semi standard non polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine,1TBDMS,isomer #2	CC(=CC(=O)O)C(O[Si](C)(C)C(C)(C)C)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2350.4	Semi standard non polar	33892256
(2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine,2TBDMS,isomer #1	CC(=CC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(=O)OC(CC(=O)[O-])C[N+](C)(C)C	2555.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine 10V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine 20V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine 40V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine 10V, Positive-QTOF	splash10-0udi-0009000000-99880ad3b586386c1677	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine 20V, Positive-QTOF	splash10-0f79-9005000000-3d828aa45492e5cea2e0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Acylcarnitine (2E)-4-hydroxy-3-methylpent-2-enedioylcarnitine		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Violante S, Ijlst L, Ruiter J, Koster J, van Lenthe H, Duran M, de Almeida IT, Wanders RJ, Houten SM, Ventura FV: Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism. Biochim Biophys Acta. 2013 Jun;1832(6):773-9. doi: 10.1016/j.bbadis.2013.02.012. Epub 2013 Feb 24. [PubMed:23485643 ]
Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Makarova E, Makrecka-Kuka M, Vilks K, Volska K, Sevostjanovs E, Grinberga S, Zarkova-Malkova O, Dambrova M, Liepinsh E: Decreases in Circulating Concentrations of Long-Chain Acylcarnitines and Free Fatty Acids During the Glucose Tolerance Test Represent Tissue-Specific Insulin Sensitivity. Front Endocrinol (Lausanne). 2019 Dec 17;10:870. doi: 10.3389/fendo.2019.00870. eCollection 2019. [PubMed:31920980 ]
Vaclavik J, Madrova L, Kouril S, de Sousa J, Brumarova R, Janeckova H, Jacova J, Friedecky D, Knapkova M, Kluijtmans LAJ, Grunert SC, Vaz FM, Janzen N, Wanders RJA, Wevers RA, Adam T: A newborn screening approach to diagnose 3-hydroxy-3-methylglutaryl-CoA lyase deficiency. JIMD Rep. 2020 Apr 14;54(1):79-86. doi: 10.1002/jmd2.12118. eCollection 2020 Jul. [PubMed:32685354 ]
Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]

Showing metabocard for (2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine (HMDB0241661)

MOL for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

3D MOL for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

3D SDF for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

3D-SDF for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

PDB for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

3D PDB for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

SMILES for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

INCHI for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

Structure for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

3D Structure for HMDB0241661 ((2E)-4-Hydroxy-3-methylpent-2-enedioylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra