NP-MRD: Showing NP-Card for 3-Hydroxybutyrylcarnitine (NP0341791)

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Record Information

Version

2.0

Created at

2024-09-12 10:55:17 UTC

Updated at

2024-09-12 10:55:18 UTC

NP-MRD ID

NP0341791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Hydroxybutyrylcarnitine

Description

(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoate 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 (3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304202022142D          

 17 16  0  0  1  0            999 V2000
   11.8457   -5.2117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5601   -4.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2746   -5.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2746   -6.0367    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.9891   -4.7992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -4.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -3.9742    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.9562   -3.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3062   -3.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1312   -3.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8457   -6.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6968   -6.4485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4113   -6.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -6.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -7.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9824   -6.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6969   -7.2735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  3  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  2  0  0  0  0
 12 16  1  0  0  0  0
 12 17  1  6  0  0  0
  1 11  1  6  0  0  0
M  CHG  2   4  -1   7   1
M  END
> <DATABASE_ID>
NP0341791

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO5/c1-8(13)5-11(16)17-9(6-10(14)15)7-12(2,3)4/h8-9,13H,5-7H2,1-4H3/t8-,9+/m1/s1

> <INCHI_KEY>
UEFRDQSMQXDWTO-BDAKNGLRSA-N

> <FORMULA>
C11H21NO5

> <MOLECULAR_WEIGHT>
247.291

> <EXACT_MASS>
247.14197278

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.514152693911953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.29

> <JCHEM_LOGP>
-4.610040922805079

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.407211276790267

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.137752211470946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.620686071792176

> <JCHEM_POLAR_SURFACE_AREA>
86.66000000000001

> <JCHEM_REFRACTIVITY>
83.45719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-{[(3R)-3-hydroxybutanoyl]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      22.112  -9.729   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.446  -8.959   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.779  -9.729   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      24.779 -11.269   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      26.113  -8.959   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.778  -8.959   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      20.778  -7.419   0.000  0.00  0.00           N+1
HETATM    8  C   UNK     0      22.318  -7.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.238  -7.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.778  -5.879   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.112 -11.269   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.101 -12.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.434 -11.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.768 -12.037   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      20.768 -13.577   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.767 -11.267   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.101 -13.577   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11   14    1                                                       
CONECT   12   13   16   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoic acid	Generator
(3S)-Hydroxybutyrylcarnitine	HMDB
(S)-3-Hydroxybutyrylcarnitine	HMDB
3-Hydroxybutyrylcarnitine	HMDB
Hydroxybutyrylcarnitine	HMDB

Chemical Formula

C₁₁H₂₁NO₅

Average Mass

247.2910 Da

Monoisotopic Mass

247.14197 Da

IUPAC Name

(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-{[(3R)-3-hydroxybutanoyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H21NO5/c1-8(13)5-11(16)17-9(6-10(14)15)7-12(2,3)4/h8-9,13H,5-7H2,1-4H3/t8-,9+/m1/s1

InChI Key

UEFRDQSMQXDWTO-BDAKNGLRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	-2.3	ALOGPS
logP	-4.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.46 m³·mol⁻¹	ChemAxon
Polarizability	25.51 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Hydroxybutyrylcarnitine (NP0341791)

MOL for NP0341791 (3-Hydroxybutyrylcarnitine)

3D MOL for NP0341791 (3-Hydroxybutyrylcarnitine)

3D SDF for NP0341791 (3-Hydroxybutyrylcarnitine)

3D-SDF for NP0341791 (3-Hydroxybutyrylcarnitine)

PDB for NP0341791 (3-Hydroxybutyrylcarnitine)

3D PDB for NP0341791 (3-Hydroxybutyrylcarnitine)

SMILES for NP0341791 (3-Hydroxybutyrylcarnitine)

INCHI for NP0341791 (3-Hydroxybutyrylcarnitine)

Structure for NP0341791 (3-Hydroxybutyrylcarnitine)

3D Structure for NP0341791 (3-Hydroxybutyrylcarnitine)