NP-MRD: Showing NP-Card for Cerebronic acid (NP0049442)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:12:37 UTC

Updated at

2022-03-17 21:12:37 UTC

NP-MRD ID

NP0049442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cerebronic acid

Description

Cerebronic acid, also known as cerebronsaeure or phrenosic acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. A very long-chain hydroxy fatty acid composed of lignoceric acid having a 2-hydroxy substituent. Cerebronic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Cerebronic acid has been detected, but not quantified in, cereals and cereal products and peanuts. Cerebronic acid is found in Allamanda cathartica, Aplysina archeri, Arabidopsis thaliana, Callyspongia fallax, Cervicornia cuspidifera, Myrmekioderma rea, Smenospongia aurea and Tripneustes ventricosus. Cerebronic acid was first documented in 1975 (PMID: 1150661). This could make cerebronic acid a potential biomarker for the consumption of these foods (PMID: 11104019).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311122D          

 27 26  0  0  0  0            999 V2000
   12.8980    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6125    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3270    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0414    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7559    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4704    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1849    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8993    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6138    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3283    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0427    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7572    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4717    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1862    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9006    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6151    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3296    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0440    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7585    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4730    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1874    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9019    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6164    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3309    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6164    9.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0453    8.2717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3309    7.0342    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
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  2  0  0  0  0
 27 24  1  0  0  0  0
M  END


  Mrv0541 05061311122D          

 27 26  0  0  0  0            999 V2000
   12.8980    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6125    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3270    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0414    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7559    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4704    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1849    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8993    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6138    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3283    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0427    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7572    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4717    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1862    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9006    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6151    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3296    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0440    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7585    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4730    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1874    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9019    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6164    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3309    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6164    9.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0453    8.2717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3309    7.0342    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
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  2  0  0  0  0
 27 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H48O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(25)24(26)27/h23,25H,2-22H2,1H3,(H,26,27)

> <INCHI_KEY>
MSUOLNSQHLHDAS-UHFFFAOYSA-N

> <FORMULA>
C24H48O3

> <MOLECULAR_WEIGHT>
384.6361

> <EXACT_MASS>
384.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.35711469205422

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxytetracosanoic acid

> <ALOGPS_LOGP>
9.03

> <JCHEM_LOGP>
8.942066177000003

> <ALOGPS_LOGS>
-6.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.284148890034412

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.255557640559995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.797528712514443

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
115.38379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.61e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cerebronic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      24.076  15.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.410  14.671   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.744  15.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.077  14.671   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.411  15.441   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.745  14.671   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.078  15.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.412  14.671   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.746  15.441   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.079  14.671   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.413  15.441   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.747  14.671   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.081  15.441   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      41.414  14.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.748  15.441   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      44.082  14.671   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      45.415  15.441   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      46.749  14.671   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      48.083  15.441   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      49.416  14.671   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      50.750  15.441   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      52.084  14.671   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      53.417  15.441   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      54.751  14.671   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      53.417  16.981   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      56.085  15.441   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      54.751  13.131   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
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   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   26   27                                                  
CONECT   25   23                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-tetracosansaeure	ChEBI
2-Hydroxylignoceric acid	ChEBI
2-Hydroxytetraeicosanoic acid	ChEBI
2-Hydroxytetraicosanoic acid	ChEBI
Acide cerebronique	ChEBI
Cerebronsaeure	ChEBI
2-Hydroxylignocerate	Generator
2-Hydroxytetraeicosanoate	Generator
2-Hydroxytetraicosanoate	Generator
Cerebronate	Generator
a-Hydroxylignoceric acid	HMDB
D-Cerebronic acid	HMDB
Phrenosic acid	HMDB
Phrenosinic acid	HMDB
DL-Cerebronate	Generator
Cerebronic acid	MeSH

Chemical Formula

C₂₄H₄₈O₃

Average Mass

384.6361 Da

Monoisotopic Mass

384.36035 Da

IUPAC Name

2-hydroxytetracosanoic acid

Traditional Name

cerebronic acid

CAS Registry Number

544-57-0

SMILES

CCCCCCCCCCCCCCCCCCCCCCC(O)C(O)=O

InChI Identifier

InChI=1S/C24H48O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(25)24(26)27/h23,25H,2-22H2,1H3,(H,26,27)

InChI Key

MSUOLNSQHLHDAS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Allamanda cathartica	LOTUS Database	35616633
Aplysina archeri	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Callyspongia fallax	LOTUS Database	35616633
Cervicornia cuspidifera	LOTUS Database	35616633
Myrmekioderma rea	LOTUS Database	35616633
Smenospongia aurea	LOTUS Database	35616633
Tripneustes ventricosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxy fatty acid (CHEBI:61302 )
straight-chain fatty acid (CHEBI:61302 )
very long-chain fatty acid (CHEBI:61302 )
Hydroxy fatty acids (LMFA01050080 )

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	9.03	ALOGPS
logP	8.94	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	115.38 m³·mol⁻¹	ChemAxon
Polarizability	52.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039540

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102430

PDB ID

Not Available

ChEBI ID

61302

Good Scents ID

Not Available

References

General References

Sandhir R, Khan M, Singh I: Identification of the pathway of alpha-oxidation of cerebronic acid in peroxisomes. Lipids. 2000 Oct;35(10):1127-33. doi: 10.1007/s11745-000-0628-5. [PubMed:11104019 ]
Murad S, Kishimoto Y: Alpha hydroxylation of lignoceric acid to cerebronic acid during brain development. Diminished hydroxylase activity in myelin-deficient mouse mutants. J Biol Chem. 1975 Aug 10;250(15):5841-6. [PubMed:1150661 ]

Showing NP-Card for Cerebronic acid (NP0049442)

MOL for NP0049442 (Cerebronic acid)

3D MOL for NP0049442 (Cerebronic acid)

3D SDF for NP0049442 (Cerebronic acid)

3D-SDF for NP0049442 (Cerebronic acid)

PDB for NP0049442 (Cerebronic acid)

3D PDB for NP0049442 (Cerebronic acid)

SMILES for NP0049442 (Cerebronic acid)

INCHI for NP0049442 (Cerebronic acid)

Structure for NP0049442 (Cerebronic acid)

3D Structure for NP0049442 (Cerebronic acid)