NP-MRD: Showing NP-Card for alcar (NP0154077)

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Record Information

Version

2.0

Created at

2022-09-02 10:50:28 UTC

Updated at

2022-09-02 10:50:28 UTC

NP-MRD ID

NP0154077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alcar

Description

DL-Acetylcarnitine 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. Thus, DL-acetylcarnitine is considered to be a fatty ester lipid molecule. alcar is found in Pseudo-nitzschia multistriata and Trypanosoma brucei. DL-Acetylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310061800322D          

 14 13  0  0  0  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  0  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
  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
 14  8  1  0  0  0  0
M  CHG  2  10   1  13  -1
M  END
> <DATABASE_ID>
NP0154077

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
RDHQFKQIGNGIED-UHFFFAOYSA-N

> <FORMULA>
C9H17NO4

> <MOLECULAR_WEIGHT>
203.2356

> <EXACT_MASS>
203.115758037

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
20.882992325723116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
alcar

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-OCT-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-18         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
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                                                  
CONECT    9    5   12   13                                                  
CONECT   10    2    3    4    6                                             
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
3-(Acetyloxy)-4-(trimethylammonio)butanoate	ChEBI
Acetyl-DL-carnitine	ChEBI
Acetylcarnitine	ChEBI
DL-O-Acetylcarnitine	ChEBI
3-(Acetyloxy)-4-(trimethylammonio)butanoic acid	Generator
(+-)-Acetylcarnitine	HMDB
(-)-Acetylcarnitine	HMDB
(R)-Acetylcarnitine	HMDB
Acetyl-carnitine	HMDB
Acetyl-L-(-)-carnitine	HMDB
Acetyl-L-carnitine	HMDB, MeSH
ALCAR	HMDB, MeSH
L-Carnitine acetyl ester	HMDB
L-O-Acetylcarnitine	HMDB
Levocarnitine acetyl	HMDB, MeSH
Nicetile	HMDB
O-Acetyl-L-carnitine	HMDB
O-Acetylcarnitine	HMDB
Acetylcarnitine, (R)-isomer	MeSH
Carnitine, acetyl	MeSH
Acetyl L carnitine	MeSH
Medosan	MeSH
Sigma-tau brand OF acetyl L-carnitine	MeSH
Acetyl carnitine	MeSH
Branigen	MeSH
glaxo Brand OF acetyl L-carnitine	MeSH
Sigma tau brand OF acetyl L carnitine	MeSH
glaxo Brand OF acetyl L carnitine	MeSH

Chemical Formula

C₉H₁₇NO₄

Average Mass

203.2356 Da

Monoisotopic Mass

203.11576 Da

IUPAC Name

3-(acetyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

alcar

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

RDHQFKQIGNGIED-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudo-nitzschia multistriata	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

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
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 Framework

Aliphatic acyclic compounds

External Descriptors

O-acylcarnitine (CHEBI:73024 )
an <i>O</i>-acyl-L-carnitine (O-ACETYLCARNITINE )

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	-2.4	ALOGPS
logP	-4.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-7	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	6	ChemAxon
Refractivity	72.64 m³·mol⁻¹	ChemAxon
Polarizability	20.88 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021904

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

PDB ID

Not Available

ChEBI ID

73024

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for alcar (NP0154077)

MOL for NP0154077 (alcar)

3D MOL for NP0154077 (alcar)

3D SDF for NP0154077 (alcar)

3D-SDF for NP0154077 (alcar)

PDB for NP0154077 (alcar)

3D PDB for NP0154077 (alcar)

SMILES for NP0154077 (alcar)

INCHI for NP0154077 (alcar)

Structure for NP0154077 (alcar)

3D Structure for NP0154077 (alcar)