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Showing metabocard for Acetyl-D-carnitine (HMDB0240771)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-02-24 01:46:50 UTC
Update Date2022-10-24 19:44:17 UTC
HMDB IDHMDB0240771
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetyl-D-carnitine
DescriptionAcetyl-D-carnitine is an acylcarnitine. More specifically, it is an acetic 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. Acetyl-D-carnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine Acetyl-D-carnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular Acetyl-D-carnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211 ), colorectal cancer (PMID: 25105552 ), short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (PMID: 11489939 ), paclitaxel induced neuropathy (PMID: 29946863 ), type 2 diabetes Mellitus (PMID: 28726959 ; PMID: 25964024 , PMID: 28726959 , PMID: 19369366 , PMID: 24358186 ), chronic heart failure (PMID: 22622056 ), ornithine transcarbamylase (PMID: 3346778 ), pre-diabetes (PMID: 23010998 , PMID: 24358186 ), type 1 diabetes mellitus (PMID: 16789638 ), methylmalonic acidemia (PMID: 8214594 ), myeloma (PMID: 30096165 ), and diastolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with 3-methyl-crotonyl-glycinuria (PMID: 25732994 ), antiviral drug induced neuropathy (PMID: 9030365 , PMID: 11364244 ), Alzheimer Disease (PMID: 27196316 ), major depressive disorder (PMID: 30061399 ), carnitine palmitoyltransferase 2 deficiency (PMID: 20543534 ), Familial Mediterranean Fever (PMID: 29900937 ), chronic fatigue syndrome (PMID: 9854142 ), methylmalonic acidemia (PMID: 15164354 ), hepatocellular carcinoma (PMID: 26976432 , PMID: 31662827 ), and coronary artery disease (PMID: 20173117 ). Acetyl-D-carnitine is elevated in the urine of individuals with colorectal cancer (25105552 ), uterine fibroids (32590215), heart failure (8070147), diabetes mellitus (10221661), and hepatocellular carcinoma (24923488). It is also decreased in the urine of individuals with carnitine palmitoyltransferase 2 deficiency (20543534 ). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0240771 (Acetyl-D-carnitine)


  Mrv1652304032017282D          

 15 14  0  0  1  0            999 V2000
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  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
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 N   0  3  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
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
  8 14  1  6  0  0  0
  8 15  1  6  0  0  0
M  CHG  2  10   1  13  -1
M  END
Download

3D MOL for HMDB0240771 (Acetyl-D-carnitine)

HMDB0240771
     RDKit          3D
Acetyl-D-carnitine
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.0448   -1.8159    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -0.7735    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535   -0.5436    1.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    0.0023   -0.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591    0.9715    0.1209 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8401    2.3989   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448    2.8424    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005    3.0203   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0715    3.0706    1.9040 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.8226    0.7079   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308   -0.4781   -0.3234 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9668   -0.6382    1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -1.7149   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721   -0.3907   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002   -1.9870    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651   -1.4592   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -2.7589    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    0.9724    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    2.5856   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0014    3.0242    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455    0.6677   -1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5157    1.6014   -0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    0.3301    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689   -1.1224    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296   -1.3444    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -1.5220   -1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -2.4118   -1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883   -2.1945    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137   -0.5303   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1002    0.6485   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -1.1584   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
 10 21  1  0
 10 22  1  0
 12 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  CHG  2   9  -1  11   1
M  END
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3D SDF for HMDB0240771 (Acetyl-D-carnitine)


  Mrv1652304032017282D          

 15 14  0  0  1  0            999 V2000
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  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
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 N   0  3  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
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
  8 14  1  6  0  0  0
  8 15  1  6  0  0  0
M  CHG  2  10   1  13  -1
M  END
> <DATABASE_ID>
HMDB0240771

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m0/s1

> <INCHI_KEY>
RDHQFKQIGNGIED-QMMMGPOBSA-N

> <FORMULA>
C9H17NO4

> <MOLECULAR_WEIGHT>
203.238

> <EXACT_MASS>
203.115758031

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
20.87852887081889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-4.4463806378050785

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.089406374301865

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0182421930796055

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
72.63680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0240771 (Acetyl-D-carnitine)

HMDB0240771
     RDKit          3D
Acetyl-D-carnitine
 31 30  0  0  0  0  0  0  0  0999 V2000
    3.0448   -1.8159    0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512   -0.7735    0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535   -0.5436    1.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    0.0023   -0.1658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591    0.9715    0.1209 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8401    2.3989   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448    2.8424    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005    3.0203   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0715    3.0706    1.9040 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.8226    0.7079   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308   -0.4781   -0.3234 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9668   -0.6382    1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -1.7149   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721   -0.3907   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7002   -1.9870    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651   -1.4592   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5245   -2.7589    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    0.9724    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    2.5856   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0014    3.0242    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455    0.6677   -1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5157    1.6014   -0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    0.3301    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689   -1.1224    1.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296   -1.3444    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380   -1.5220   -1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -2.4118   -1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883   -2.1945    0.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137   -0.5303   -2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1002    0.6485   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -1.1584   -0.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
 10 21  1  0
 10 22  1  0
 12 23  1  0
 12 24  1  0
 12 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
M  CHG  2   9  -1  11   1
M  END
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PDB for HMDB0240771 (Acetyl-D-carnitine)

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.127  -1.540   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.207   0.000   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       0.206  -0.770   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    8    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1   11   14                                                  
CONECT    8    5    6   14   15                                             
CONECT    9    5   12   13                                                  
CONECT   10    2    3    4    6                                             
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    7    8                                                       
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END
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3D PDB for HMDB0240771 (Acetyl-D-carnitine)

COMPND    HMDB0240771
HETATM    1  C1  UNL     1       3.045  -1.816   0.455  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.051  -0.774   0.760  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.753  -0.544   1.959  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.389   0.002  -0.166  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.459   0.972   0.121  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.840   2.399  -0.191  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.045   2.842   0.535  1.00  0.00           C  
HETATM    8  O3  UNL     1       3.100   3.020  -0.117  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.072   3.071   1.904  1.00  0.00           O1-
HETATM   10  C6  UNL     1      -0.823   0.708  -0.595  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.531  -0.478  -0.323  1.00  0.00           N1+
HETATM   12  C7  UNL     1      -1.967  -0.638   1.045  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.905  -1.715  -0.723  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.772  -0.391  -1.125  1.00  0.00           C  
HETATM   15  H1  UNL     1       3.700  -1.987   1.327  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.665  -1.459  -0.402  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.524  -2.759   0.122  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.335   0.972   1.245  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.890   2.586  -1.276  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.001   3.024   0.190  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.545   0.668  -1.695  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.516   1.601  -0.569  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.139   0.330   1.575  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.969  -1.122   1.026  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.330  -1.344   1.629  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.338  -1.522  -1.682  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.745  -2.412  -1.042  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.288  -2.194   0.057  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.414  -0.530  -2.188  1.00  0.00           H  
HETATM   30  H16 UNL     1      -3.100   0.648  -1.039  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.490  -1.158  -0.819  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   10   18
CONECT    6    7   19   20
CONECT    7    8    8    9
CONECT   10   11   21   22
CONECT   11   12   13   14
CONECT   12   23   24   25
CONECT   13   26   27   28
CONECT   14   29   30   31
END
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SMILES for HMDB0240771 (Acetyl-D-carnitine)

[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O
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INCHI for HMDB0240771 (Acetyl-D-carnitine)

InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
SynonymsNot Available
Chemical FormulaC9H17NO4
Average Molecular Weight203.238
Monoisotopic Molecular Weight203.115758031
IUPAC Name(3S)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Nameacetylcarnitine
CAS Registry NumberNot Available
SMILES
[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O
InChI Identifier
InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m0/s1
InChI KeyRDHQFKQIGNGIED-QMMMGPOBSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-2.4ALOGPS
logP-4.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.64 m³·mol⁻¹ChemAxon
Polarizability20.88 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+124.80130932474
DeepCCS[M-H]-122.42130932474
DeepCCS[M-2H]-155.63130932474
DeepCCS[M+Na]+130.53330932474
AllCCS[M+H]+145.232859911
AllCCS[M+H-H2O]+141.732859911
AllCCS[M+NH4]+148.432859911
AllCCS[M+Na]+149.332859911
AllCCS[M-H]-152.232859911
AllCCS[M+Na-2H]-153.532859911
AllCCS[M+HCOO]-154.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetyl-D-carnitine[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O1839.0Standard polar33892256
Acetyl-D-carnitine[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O1117.2Standard non polar33892256
Acetyl-D-carnitine[H][C@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O1355.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl-D-carnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetyl-D-carnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl-D-carnitine 40V, Positive-QTOFsplash10-000i-9000000000-3c13460eec4ce2002d262021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl-D-carnitine 10V, Positive-QTOFsplash10-0udi-1090000000-2b69a1e2543749d994702021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetyl-D-carnitine 20V, Positive-QTOFsplash10-000i-9000000000-9d43a27ce302cf2b1aeb2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-D-carnitine 10V, Positive-QTOFsplash10-0udi-0090000000-71230651236adb31fa6f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-D-carnitine 20V, Positive-QTOFsplash10-0f79-9050000000-2a63f200e23202870ebe2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetyl-D-carnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB098089
KNApSAcK IDNot Available
Chemspider ID17219
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18230
PDB IDNot Available
ChEBI ID86045
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. [PubMed:11489939 ]
  2. Minkler PE, Hoppel CL: Quantification of free carnitine, individual short- and medium-chain acylcarnitines, and total carnitine in plasma by high-performance liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):510-8. [PubMed:8214594 ]
  3. Vernez L, Wenk M, Krahenbuhl S: Determination of carnitine and acylcarnitines in plasma by high-performance liquid chromatography/electrospray ionization ion trap tandem mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(11):1233-8. [PubMed:15164354 ]
  4. Kuratsune H, Yamaguti K, Lindh G, Evengard B, Takahashi M, Machii T, Matsumura K, Takaishi J, Kawata S, Langstrom B, Kanakura Y, Kitani T, Watanabe Y: Low levels of serum acylcarnitine in chronic fatigue syndrome and chronic hepatitis type C, but not seen in other diseases. Int J Mol Med. 1998 Jul;2(1):51-6. [PubMed:9854142 ]
  5. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
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  7. Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
  8. Thomsen JA, Lund AM, Olesen JH, Mohr M, Rasmussen J: Is L-Carnitine Supplementation Beneficial in 3-Methylcrotonyl-CoA Carboxylase Deficiency? JIMD Rep. 2015;21:79-88. doi: 10.1007/8904_2014_393. Epub 2015 Mar 3. [PubMed:25732994 ]
  9. Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
  10. 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 ]
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  12. Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
  13. Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
  14. Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
  15. 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 ]
  16. Abu Bakar MH, Sarmidi MR: Association of cultured myotubes and fasting plasma metabolite profiles with mitochondrial dysfunction in type 2 diabetes subjects. Mol Biosyst. 2017 Aug 22;13(9):1838-1853. doi: 10.1039/c7mb00333a. [PubMed:28726959 ]
  17. Mai M, Tonjes A, Kovacs P, Stumvoll M, Fiedler GM, Leichtle AB: Serum levels of acylcarnitines are altered in prediabetic conditions. PLoS One. 2013 Dec 16;8(12):e82459. doi: 10.1371/journal.pone.0082459. eCollection 2013. [PubMed:24358186 ]
  18. Shah SH, Bain JR, Muehlbauer MJ, Stevens RD, Crosslin DR, Haynes C, Dungan J, Newby LK, Hauser ER, Ginsburg GS, Newgard CB, Kraus WE: Association of a peripheral blood metabolic profile with coronary artery disease and risk of subsequent cardiovascular events. Circ Cardiovasc Genet. 2010 Apr;3(2):207-14. doi: 10.1161/CIRCGENETICS.109.852814. Epub 2010 Feb 19. [PubMed:20173117 ]
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  20. Sun Y, Kim JH, Vangipuram K, Hayes DF, Smith EML, Yeomans L, Henry NL, Stringer KA, Hertz DL: Pharmacometabolomics reveals a role for histidine, phenylalanine, and threonine in the development of paclitaxel-induced peripheral neuropathy. Breast Cancer Res Treat. 2018 Oct;171(3):657-666. doi: 10.1007/s10549-018-4862-3. Epub 2018 Jun 26. [PubMed:29946863 ]
  21. Ciborowski M, Adamska E, Rusak M, Godzien J, Wilk J, Citko A, Bauer W, Gorska M, Kretowski A: CE-MS-based serum fingerprinting to track evolution of type 2 diabetes mellitus. Electrophoresis. 2015 Sep;36(18):2286-2293. doi: 10.1002/elps.201500021. Epub 2015 Jun 26. [PubMed:25964024 ]
  22. Ueland T, Svardal A, Oie E, Askevold ET, Nymoen SH, Bjorndal B, Dahl CP, Gullestad L, Berge RK, Aukrust P: Disturbed carnitine regulation in chronic heart failure--increased plasma levels of palmitoyl-carnitine are associated with poor prognosis. Int J Cardiol. 2013 Sep 1;167(5):1892-9. doi: 10.1016/j.ijcard.2012.04.150. Epub 2012 May 22. [PubMed:22622056 ]
  23. Ohtani Y, Ohyanagi K, Yamamoto S, Matsuda I: Secondary carnitine deficiency in hyperammonemic attacks of ornithine transcarbamylase deficiency. J Pediatr. 1988 Mar;112(3):409-14. doi: 10.1016/s0022-3476(88)80321-4. [PubMed:3346778 ]
  24. Wang-Sattler R, Yu Z, Herder C, Messias AC, Floegel A, He Y, Heim K, Campillos M, Holzapfel C, Thorand B, Grallert H, Xu T, Bader E, Huth C, Mittelstrass K, Doring A, Meisinger C, Gieger C, Prehn C, Roemisch-Margl W, Carstensen M, Xie L, Yamanaka-Okumura H, Xing G, Ceglarek U, Thiery J, Giani G, Lickert H, Lin X, Li Y, Boeing H, Joost HG, de Angelis MH, Rathmann W, Suhre K, Prokisch H, Peters A, Meitinger T, Roden M, Wichmann HE, Pischon T, Adamski J, Illig T: Novel biomarkers for pre-diabetes identified by metabolomics. Mol Syst Biol. 2012;8:615. doi: 10.1038/msb.2012.43. [PubMed:23010998 ]
  25. Adal E, Koyuncu G, Aydin A, Celebi A, Kavunoglu G, Cam H: Asymptomatic cardiomyopathy in children and adolescents with type 1 diabetes mellitus: association of echocardiographic indicators with duration of diabetes mellitus and metabolic parameters. J Pediatr Endocrinol Metab. 2006 May;19(5):713-26. doi: 10.1515/jpem.2006.19.5.713. [PubMed:16789638 ]
  26. Steiner N, Muller U, Hajek R, Sevcikova S, Borjan B, Johrer K, Gobel G, Pircher A, Gunsilius E: The metabolomic plasma profile of myeloma patients is considerably different from healthy subjects and reveals potential new therapeutic targets. PLoS One. 2018 Aug 10;13(8):e0202045. doi: 10.1371/journal.pone.0202045. eCollection 2018. [PubMed:30096165 ]
  27. Famularo G, Moretti S, Marcellini S, Trinchieri V, Tzantzoglou S, Santini G, Longo A, De Simone C: Acetyl-carnitine deficiency in AIDS patients with neurotoxicity on treatment with antiretroviral nucleoside analogues. AIDS. 1997 Feb;11(2):185-90. doi: 10.1097/00002030-199702000-00008. [PubMed:9030365 ]
  28. James JS: Drug-related neuropathy: low acetylcarnitine levels found. AIDS Treat News. 1997 Feb 21;(No 265):6-7. [PubMed:11364244 ]
  29. Cristofano A, Sapere N, La Marca G, Angiolillo A, Vitale M, Corbi G, Scapagnini G, Intrieri M, Russo C, Corso G, Di Costanzo A: Serum Levels of Acyl-Carnitines along the Continuum from Normal to Alzheimer's Dementia. PLoS One. 2016 May 19;11(5):e0155694. doi: 10.1371/journal.pone.0155694. eCollection 2016. [PubMed:27196316 ]
  30. Nasca C, Bigio B, Lee FS, Young SP, Kautz MM, Albright A, Beasley J, Millington DS, Mathe AA, Kocsis JH, Murrough JW, McEwen BS, Rasgon N: Acetyl-l-carnitine deficiency in patients with major depressive disorder. Proc Natl Acad Sci U S A. 2018 Aug 21;115(34):8627-8632. doi: 10.1073/pnas.1801609115. Epub 2018 Jul 30. [PubMed:30061399 ]
  31. Hori T, Fukao T, Kobayashi H, Teramoto T, Takayanagi M, Hasegawa Y, Yasuno T, Yamaguchi S, Kondo N: Carnitine palmitoyltransferase 2 deficiency: the time-course of blood and urinary acylcarnitine levels during initial L-carnitine supplementation. Tohoku J Exp Med. 2010 Jul;221(3):191-5. doi: 10.1620/tjem.221.191. [PubMed:20543534 ]
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