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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-02-18 09:46:10 UTC

Update Date

2022-10-24 19:44:12 UTC

HMDB ID

HMDB0013325

Secondary Accession Numbers

HMDB13325

Metabolite Identification

Common Name

2-trans,4-cis-Decadienoylcarnitine

Description

2-trans,4-cis-Decadienoylcarnitine is an acylcarnitine. More specifically, it is an (2E,4Z)-deca-2,4-dienoic 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. 2-trans,4-cis-Decadienoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine 2-trans,4-cis-decadienoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. In particular 2-trans,4-cis-decadienoylcarnitine is elevated in the blood or plasma of individuals with 2,4-dienoyl-coenzyme a reductase deficiency (PMID: 2332510 , PMID: 15344554 , PMID: 19578400 ). It is also decreased in the blood or plasma of individuals with familial mediterranean fever (PMID: 29900937 ) and schizophrenia (PMID: 31161852 ). Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). 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

HMDB0013325
     RDKit          3D
2-trans,4-cis-Decadienoylcarnitine
 51 50  0  0  0  0  0  0  0  0999 V2000
    7.1278    2.2412    1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5563    1.3016    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8581    0.1334    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173   -0.7625   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139   -0.0933   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899   -1.1127   -1.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554   -1.4990   -2.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -0.9353   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.3586   -1.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -0.7655   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    0.1150    0.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0236   -1.1483   -0.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939   -0.5444    0.2346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7260   -1.6433    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -2.4870    1.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945   -2.2847    1.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -3.5616    2.5002 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9585    0.2000   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332    0.8653   -0.0402 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8922    1.2447    1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345    2.0864   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2099   -0.0116   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4151    2.4417    2.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3218    3.2101    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    1.8098    1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4201    0.9215   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8327    1.8787   -0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0207    0.4318    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5540   -0.4778    1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931   -1.6507    0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665   -1.1459   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381    0.3565   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957    0.7459   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6672   -1.5570   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -2.2763   -2.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -0.1856   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.1081   -2.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4671    0.1444    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531   -2.3246    0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200   -1.2495    1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3486   -0.5011   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.9588   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161    1.0665    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0484    2.3640    1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7240    0.7939    1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180    1.7902   -1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488    2.8246   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3316    2.4721   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9834   -0.9476   -0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0077    0.5285   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5839   -0.2944    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
M  CHG  2  17  -1  19   1
M  END

      
  Mrv1652301312018072D          

 22 21  0  0  0  0            999 V2000
10005.359310008.3657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10006.073710007.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.788110008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.502410007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.216710008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.931810007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.755010007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.468910008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.184810007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.900810008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.614810007.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.328710008.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.788110009.1905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.359310009.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.645010009.6011    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10003.926610009.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.645010010.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.791510010.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.653310007.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.653310007.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.367410006.7038    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10003.939010006.7038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  6  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
M  CHG  2  15   1  21  -1
M  END
> <DATABASE_ID>
HMDB0013325

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC\C=C/C=C/C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C17H29NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h9-12,15H,5-8,13-14H2,1-4H3/b10-9-,12-11+/t15-/m1/s1

> <INCHI_KEY>
URTBCBICNCMCPB-CWUOWYQYSA-N

> <FORMULA>
C17H29NO4

> <MOLECULAR_WEIGHT>
311.422

> <EXACT_MASS>
311.209658418

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.44748060172833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(2E,4Z)-deca-2,4-dienoyloxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-0.7646289694717456

> <ALOGPS_LOGS>
-6.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.126861144182948

> <JCHEM_PKA_STRONGEST_BASIC>
-6.827438151598193

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
111.68059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(2E,4Z)-deca-2,4-dienoyloxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013325
     RDKit          3D
2-trans,4-cis-Decadienoylcarnitine
 51 50  0  0  0  0  0  0  0  0999 V2000
    7.1278    2.2412    1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5563    1.3016    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8581    0.1334    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173   -0.7625   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139   -0.0933   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899   -1.1127   -1.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554   -1.4990   -2.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -0.9353   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.3586   -1.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -0.7655   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    0.1150    0.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0236   -1.1483   -0.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939   -0.5444    0.2346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7260   -1.6433    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -2.4870    1.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945   -2.2847    1.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -3.5616    2.5002 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9585    0.2000   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332    0.8653   -0.0402 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8922    1.2447    1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345    2.0864   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2099   -0.0116   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4151    2.4417    2.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3218    3.2101    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    1.8098    1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4201    0.9215   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8327    1.8787   -0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0207    0.4318    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5540   -0.4778    1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931   -1.6507    0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665   -1.1459   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381    0.3565   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957    0.7459   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6672   -1.5570   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -2.2763   -2.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -0.1856   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.1081   -2.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4671    0.1444    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531   -2.3246    0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200   -1.2495    1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3486   -0.5011   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.9588   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161    1.0665    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0484    2.3640    1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7240    0.7939    1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180    1.7902   -1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488    2.8246   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3316    2.4721   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9834   -0.9476   -0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0077    0.5285   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5839   -0.2944    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
M  CHG  2  17  -1  19   1
M  END

HEADER    PROTEIN                                 31-JAN-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JAN-20         0                                  
HETATM    1  C   UNK     0    8676.6718682.283   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8678.0048681.511   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8679.3388682.283   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8680.6718681.511   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8682.0058682.283   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8683.3398681.511   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8684.8768681.511   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8686.2098682.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8687.5458681.511   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8688.8818682.283   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8690.2148681.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8691.5478682.283   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8679.3388683.822   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8676.6718683.822   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    8675.3378684.589   0.000  0.00  0.00           N+1
HETATM   16  C   UNK     0    8673.9968683.818   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8675.3378686.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8673.7448685.509   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8675.3538681.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.3538679.952   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8676.6868679.180   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0    8674.0198679.180   0.000  0.00  0.00           O+0
CONECT    1    2   14   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    3                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19    1   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0013325
HETATM    1  C1  UNL     1       7.128   2.241   1.505  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.556   1.302   0.448  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.858   0.133   1.055  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.317  -0.763  -0.005  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.314  -0.093  -0.927  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.890  -1.113  -1.894  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.655  -1.499  -2.022  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.596  -0.935  -1.199  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.328  -1.359  -1.358  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.695  -0.765  -0.512  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.414   0.115   0.342  1.00  0.00           O  
HETATM   12  O2  UNL     1      -2.024  -1.148  -0.616  1.00  0.00           O  
HETATM   13  C11 UNL     1      -2.994  -0.544   0.235  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.726  -1.643   0.945  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.830  -2.487   1.767  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.595  -2.285   1.843  1.00  0.00           O  
HETATM   17  O4  UNL     1      -3.355  -3.562   2.500  1.00  0.00           O1-
HETATM   18  C14 UNL     1      -3.959   0.200  -0.675  1.00  0.00           C  
HETATM   19  N1  UNL     1      -5.033   0.865  -0.040  1.00  0.00           N1+
HETATM   20  C15 UNL     1      -4.892   1.245   1.321  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.335   2.086  -0.813  1.00  0.00           C  
HETATM   22  C17 UNL     1      -6.210  -0.012  -0.132  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.415   2.442   2.317  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.322   3.210   0.984  1.00  0.00           H  
HETATM   25  H3  UNL     1       8.080   1.810   1.847  1.00  0.00           H  
HETATM   26  H4  UNL     1       7.420   0.921  -0.135  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.833   1.879  -0.169  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.021   0.432   1.729  1.00  0.00           H  
HETATM   29  H7  UNL     1       6.554  -0.478   1.673  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.793  -1.651   0.423  1.00  0.00           H  
HETATM   31  H9  UNL     1       6.166  -1.146  -0.610  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.538   0.356  -0.325  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.796   0.746  -1.490  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.667  -1.557  -2.530  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.390  -2.276  -2.772  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.726  -0.186  -0.446  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.118  -2.108  -2.092  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.467   0.144   0.887  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.253  -2.325   0.248  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.520  -1.250   1.629  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.349  -0.501  -1.472  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.370   0.959  -1.268  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.916   1.066   1.794  1.00  0.00           H  
HETATM   44  H22 UNL     1      -5.048   2.364   1.444  1.00  0.00           H  
HETATM   45  H23 UNL     1      -5.724   0.794   1.947  1.00  0.00           H  
HETATM   46  H24 UNL     1      -5.318   1.790  -1.876  1.00  0.00           H  
HETATM   47  H25 UNL     1      -4.549   2.825  -0.602  1.00  0.00           H  
HETATM   48  H26 UNL     1      -6.332   2.472  -0.565  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.983  -0.948  -0.678  1.00  0.00           H  
HETATM   50  H28 UNL     1      -7.008   0.528  -0.662  1.00  0.00           H  
HETATM   51  H29 UNL     1      -6.584  -0.294   0.878  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9    9   36
CONECT    9   10   37
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   18   38
CONECT   14   15   39   40
CONECT   15   16   16   17
CONECT   18   19   41   42
CONECT   19   20   21   22
CONECT   20   43   44   45
CONECT   21   46   47   48
CONECT   22   49   50   51
END

HMDB0013325
     RDKit          3D
2-trans,4-cis-Decadienoylcarnitine
 51 50  0  0  0  0  0  0  0  0999 V2000
    7.1278    2.2412    1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5563    1.3016    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8581    0.1334    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3173   -0.7625   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139   -0.0933   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899   -1.1127   -1.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554   -1.4990   -2.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -0.9353   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -1.3586   -1.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -0.7655   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    0.1150    0.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0236   -1.1483   -0.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9939   -0.5444    0.2346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7260   -1.6433    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -2.4870    1.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5945   -2.2847    1.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555   -3.5616    2.5002 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.9585    0.2000   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332    0.8653   -0.0402 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8922    1.2447    1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345    2.0864   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2099   -0.0116   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4151    2.4417    2.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3218    3.2101    0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803    1.8098    1.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4201    0.9215   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8327    1.8787   -0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0207    0.4318    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5540   -0.4778    1.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931   -1.6507    0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665   -1.1459   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381    0.3565   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957    0.7459   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6672   -1.5570   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3898   -2.2763   -2.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -0.1856   -0.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.1081   -2.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4671    0.1444    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2531   -2.3246    0.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5200   -1.2495    1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3486   -0.5011   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3704    0.9588   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161    1.0665    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0484    2.3640    1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7240    0.7939    1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180    1.7902   -1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488    2.8246   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3316    2.4721   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9834   -0.9476   -0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0077    0.5285   -0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5839   -0.2944    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 13 38  1  1
 14 39  1  0
 14 40  1  0
 18 41  1  0
 18 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
M  CHG  2  17  -1  19   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R)-3-[(2E,4Z)-Deca-2,4-dienoyloxy]-4-(trimethylazaniumyl)butanoic acid	HMDB

Chemical Formula

C₁₇H₂₉NO₄

Average Molecular Weight

311.422

Monoisotopic Molecular Weight

311.209658418

IUPAC Name

(3R)-3-[(2E,4Z)-deca-2,4-dienoyloxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-[(2E,4Z)-deca-2,4-dienoyloxy]-4-(trimethylammonio)butanoate

CAS Registry Number

128305-29-3

SMILES

CCCCC\C=C/C=C/C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C17H29NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h9-12,15H,5-8,13-14H2,1-4H3/b10-9-,12-11+/t15-/m1/s1

InChI Key

URTBCBICNCMCPB-CWUOWYQYSA-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
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Quaternary ammonium salt
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
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

Diabetes mellitus type 2 (PMID: 35710135)
Celiac disease (PMID: 35710135)
Inflammatory bowel disease (PMID: 35710135)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 35710135)
Heart failure (PMID: 35710135)

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24847004)

Excreta

Biofluid or Excreta

Urine (PMID: 32340350)

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

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
Water Solubility	0.00021 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.76	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	111.68 m³·mol⁻¹	ChemAxon
Polarizability	35.45 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]+	192.661	30932474
DeepCCS	[M-H]-	188.641	30932474
DeepCCS	[M-2H]-	225.185	30932474
DeepCCS	[M+Na]+	201.476	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-trans,4-cis-Decadienoylcarnitine	CCCCC\C=C/C=C/C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2840.6	Standard polar	33892256
2-trans,4-cis-Decadienoylcarnitine	CCCCC\C=C/C=C/C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2037.5	Standard non polar	33892256
2-trans,4-cis-Decadienoylcarnitine	CCCCC\C=C/C=C/C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2175.8	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 - 2-trans,4-cis-Decadienoylcarnitine 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 - 2-trans,4-cis-Decadienoylcarnitine 10V, Positive-QTOF	splash10-03xu-2495000000-8ea8efea088360bb6b6f	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans,4-cis-Decadienoylcarnitine 20V, Positive-QTOF	splash10-0gvo-2900000000-ba83aaee9dfa15af89b6	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans,4-cis-Decadienoylcarnitine 40V, Positive-QTOF	splash10-052f-9400000000-3af3463effa0acceaefa	2018-11-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans,4-cis-Decadienoylcarnitine 10V, Positive-QTOF	splash10-03di-0009000000-eb0b9744056fdaf45158	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans,4-cis-Decadienoylcarnitine 20V, Positive-QTOF	splash10-01p9-9005000000-2813ab724ca28bcf842a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans,4-cis-Decadienoylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	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

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.01-0.07 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.03(0.01-0.05) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.03(0.02-0.07) umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.125 uM	Newborn (0-30 days old)	Male	2,4-dienoyl-CoA reductase deficiency	24847004	details
Blood	Detected and Quantified	0.200-1.300 uM	Infant (0-1 year old)	Male	2,4-dienoyl-CoA reductase deficiency	24847004	details

Associated Disorders and Diseases

Disease References

2,4-dienoyl-CoA reductase deficiency
Houten SM, Denis S, Te Brinke H, Jongejan A, van Kampen AH, Bradley EJ, Baas F, Hennekam RC, Millington DS, Young SP, Frazier DM, Gucsavas-Calikoglu M, Wanders RJ: Mitochondrial NADP(H) deficiency due to a mutation in NADK2 causes dienoyl-CoA reductase deficiency with hyperlysinemia. Hum Mol Genet. 2014 Sep 15;23(18):5009-16. doi: 10.1093/hmg/ddu218. Epub 2014 May 8. [PubMed:24847004 ]

Associated OMIM IDs

616034 (2,4-dienoyl-CoA reductase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029385

KNApSAcK ID

Not Available

Chemspider ID

73990428

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155906470

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

DECDICRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. [PubMed:10486279 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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 ]
Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
Cao B, Wang D, Pan Z, McIntyre RS, Brietzke E, Subramanieapillai M, Nozari Y, Wang J: Metabolic profiling for water-soluble metabolites in patients with schizophrenia and healthy controls in a Chinese population: A case-control study. World J Biol Psychiatry. 2020 Jun;21(5):357-367. doi: 10.1080/15622975.2019.1615639. Epub 2019 Jun 4. [PubMed:31161852 ]
Kiykim E, Aktuglu Zeybek AC, Barut K, Zubarioglu T, Cansever MS, Alsancak S, Kasapcopur O: Screening of Free Carnitine and Acylcarnitine Status in Children With Familial Mediterranean Fever. Arch Rheumatol. 2016 Mar 10;31(2):133-138. doi: 10.5606/ArchRheumatol.2016.5696. eCollection 2016 Jun. [PubMed:29900937 ]
Roe CR, Millington DS, Norwood DL, Kodo N, Sprecher H, Mohammed BS, Nada M, Schulz H, McVie R: 2,4-Dienoyl-coenzyme A reductase deficiency: a possible new disorder of fatty acid oxidation. J Clin Invest. 1990 May;85(5):1703-7. doi: 10.1172/JCI114624. [PubMed:2332510 ]
Kimura C, Mizugaki M, Yamanaka H, Fujino M, Morishima T: [2,4-Dienoyl-CoA reductases: from discovery toward pathophysiological significance]. Nihon Rinsho. 2004 Aug;62(8):1577-83. [PubMed:15344554 ]
Miinalainen IJ, Schmitz W, Huotari A, Autio KJ, Soininen R, Ver Loren van Themaat E, Baes M, Herzig KH, Conzelmann E, Hiltunen JK: Mitochondrial 2,4-dienoyl-CoA reductase deficiency in mice results in severe hypoglycemia with stress intolerance and unimpaired ketogenesis. PLoS Genet. 2009 Jul;5(7):e1000543. doi: 10.1371/journal.pgen.1000543. Epub 2009 Jul 3. [PubMed:19578400 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-trans,4-cis-Decadienoylcarnitine (HMDB0013325)

MOL for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

3D MOL for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

3D SDF for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

3D-SDF for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

PDB for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

3D PDB for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

SMILES for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

INCHI for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

Structure for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

3D Structure for HMDB0013325 (2-trans,4-cis-Decadienoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra