NP-MRD: Showing NP-Card for Methylmalonylcarnitine (NP0136840)

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Record Information

Version

2.0

Created at

2022-05-12 15:25:00 UTC

Updated at

2022-05-12 15:25:00 UTC

NP-MRD ID

NP0136840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methylmalonylcarnitine

Description

(2R)-3-{[(2R)-1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoate 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 (2R)-3-{[(2R)-1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    2.5889   -1.1405   -1.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7960    0.0732   -0.8079 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7354   -0.1837    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8028    0.4524    0.4510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466   -1.1720    1.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667    0.6691   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2497    1.8719   -0.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -0.0170    0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5034    0.5427    1.0429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4907    0.6444    2.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6231    1.4798    3.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7572    0.9553    3.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945    2.7858    3.4116 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7747   -0.1222    0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0633   -0.1762   -0.7438 N   0  0  2  0  0  4  0  0  0  0  0  0
   -1.2970   -1.2181   -1.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104    1.0682   -1.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4784   -0.5726   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6029   -1.3905   -2.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085   -0.8874   -2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728   -2.0305   -1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2905    0.8374   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -1.6747    1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5527    1.6027    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -0.3985    2.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.9386    2.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818   -1.1520    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6045    0.4628    1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -1.9058   -0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424   -1.7724   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4183   -0.7676   -1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7165    1.1565   -2.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588    1.1465   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592    1.9138   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6366   -1.5722   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0934    0.1415   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8093   -0.5888   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  9 14  1  0
 15 14  1  1
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  5 23  1  0
  9 24  1  6
 10 25  1  0
 10 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2  13  -1  15   1
M  END


  Mrv1652304202021252D          

 18 17  0  0  0  0            999 V2000
 2493.9443 2499.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2494.6583 2499.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0863 2499.3872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2496.8003 2499.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5143 2499.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2495.3723 2500.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9443 2500.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.0360    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2492.5122 2500.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2303 2501.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2492.3773 2501.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2499.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.2365 2498.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2493.9526 2498.1392    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2492.5246 2498.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.8003 2500.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0863 2498.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  6  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  5 17  2  0  0  0  0
  4 18  1  1  0  0  0
  5  6  1  0  0  0  0
M  CHG  2   9   1  15  -1
M  END
> <DATABASE_ID>
NP0136840

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO6/c1-7(10(15)16)11(17)18-8(5-9(13)14)6-12(2,3)4/h7-8H,5-6H2,1-4H3,(H-,13,14,15,16)/t7-,8-/m1/s1

> <INCHI_KEY>
XROYFEWIXXCPAW-HTQZYQBOSA-N

> <FORMULA>
C11H19NO6

> <MOLECULAR_WEIGHT>
261.274

> <EXACT_MASS>
261.121237336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.619008029173237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-{[(2R)-2-carboxy-2-methylacetyl]oxy}-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.62

> <JCHEM_LOGP>
-4.0111659134717454

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.23841297010917

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.534250036378786

> <JCHEM_PKA_STRONGEST_BASIC>
-7.208415042403216

> <JCHEM_POLAR_SURFACE_AREA>
103.72999999999999

> <JCHEM_REFRACTIVITY>
83.55539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-{[(2R)-2-carboxy-2-methylacetyl]oxy}-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    4655.3634666.294   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4656.6954665.523   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4658.0284666.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4659.3614665.523   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4660.6944666.294   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4662.0274665.523   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4658.0284667.833   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    4655.3634667.833   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    4654.0304668.601   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0    4652.6894667.830   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4654.0304670.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4652.4384669.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4654.0414665.504   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4654.0414663.965   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    4655.3784663.193   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0    4652.7134663.193   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4660.6944667.834   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    4659.3614663.983   0.000  0.00  0.00           C+0
CONECT    1    2    8   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4   17    6                                                  
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5                                                            
CONECT   18    4                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(2R)-3-{[(2R)-1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoic acid	Generator
Methylmalonyl-L-carnitine	HMDB
Methylmalonylcarnitine	HMDB

Chemical Formula

C₁₁H₁₉NO₆

Average Mass

261.2740 Da

Monoisotopic Mass

261.12124 Da

IUPAC Name

(3R)-3-{[(2R)-2-carboxy-2-methylacetyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-{[(2R)-2-carboxy-2-methylacetyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H19NO6/c1-7(10(15)16)11(17)18-8(5-9(13)14)6-12(2,3)4/h7-8H,5-6H2,1-4H3,(H-,13,14,15,16)/t7-,8-/m1/s1

InChI Key

XROYFEWIXXCPAW-HTQZYQBOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
1,3-dicarbonyl compound
Tetraalkylammonium salt
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

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.6	ALOGPS
logP	-4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.56 m³·mol⁻¹	ChemAxon
Polarizability	25.62 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

External Links

HMDB ID

HMDB0013133

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029306

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

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methylmalonylcarnitine (NP0136840)

MOL for NP0136840 (Methylmalonylcarnitine)

3D MOL for NP0136840 (Methylmalonylcarnitine)

3D SDF for NP0136840 (Methylmalonylcarnitine)

3D-SDF for NP0136840 (Methylmalonylcarnitine)

PDB for NP0136840 (Methylmalonylcarnitine)

3D PDB for NP0136840 (Methylmalonylcarnitine)

SMILES for NP0136840 (Methylmalonylcarnitine)

INCHI for NP0136840 (Methylmalonylcarnitine)

Structure for NP0136840 (Methylmalonylcarnitine)

3D Structure for NP0136840 (Methylmalonylcarnitine)