NP-MRD: Showing NP-Card for alpha-Hydroxybehenic acid (NP0047024)

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Record Information

Version

2.0

Created at

2022-03-17 20:33:22 UTC

Updated at

2022-03-17 20:33:22 UTC

NP-MRD ID

NP0047024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Hydroxybehenic acid

Description

2(R)-hydroxydocosanoic acid, also known as a-hydroxybehenate or a-hydroxydocosanoate, 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. 2(R)-hydroxydocosanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2(R)-hydroxydocosanoic acid has been detected, but not quantified in, black elderberries. alpha-Hydroxybehenic acid is found in Amphimedon compressa, Aplysina lacunosa, Callyspongia fallax, Cervicornia cuspidifera, Malvaviscus arboreus, Myrmekioderma rea, Suberites massa, Tripneustes ventricosus and Verongula gigantea. This could make 2(R)-hydroxydocosanoic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04111415172D          

 25 24  0  0  0  0            999 V2000
   12.3750    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605    7.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750    6.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0895    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0895    8.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8039    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5184    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2329    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9474    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6618    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3763    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0908    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8052    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2342    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9487    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6631    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3776    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0921    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8065    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2355    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6644    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3789    7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047024

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(23)22(24)25/h21,23H,2-20H2,1H3,(H,24,25)

> <INCHI_KEY>
RPGJJWLCCOPDAZ-UHFFFAOYSA-N

> <FORMULA>
C22H44O3

> <MOLECULAR_WEIGHT>
356.583

> <EXACT_MASS>
356.329045274

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
48.040406610913706

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxydocosanoic acid

> <ALOGPS_LOGP>
8.57

> <JCHEM_LOGP>
8.052928847

> <ALOGPS_LOGS>
-6.47

> <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>
106.1818

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy behenic

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-APR-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-APR-14         0                                  
HETATM    1  C   UNK     0      23.100  13.337   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      21.766  14.107   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      23.100  11.797   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      24.434  14.107   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      24.434  15.647   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      25.767  13.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.101  14.107   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.435  13.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.768  14.107   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.102  13.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.436  14.107   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.769  13.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.103  14.107   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.437  13.337   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.771  14.107   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.104  13.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.438  14.107   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.772  13.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      43.105  14.107   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.439  13.337   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      45.773  14.107   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      47.106  13.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      48.440  14.107   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      49.774  13.337   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      51.107  14.107   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-22:0 fatty acid	ChEBI
alpha-Hydroxybehenic acid	ChEBI
alpha-Hydroxydocosanoic acid	ChEBI
a-Hydroxybehenate	Generator
a-Hydroxybehenic acid	Generator
alpha-Hydroxybehenate	Generator
Α-hydroxybehenate	Generator
Α-hydroxybehenic acid	Generator
a-Hydroxydocosanoate	Generator
a-Hydroxydocosanoic acid	Generator
alpha-Hydroxydocosanoate	Generator
Α-hydroxydocosanoate	Generator
Α-hydroxydocosanoic acid	Generator
2(R)-Hydroxydocosanoate	Generator

Chemical Formula

C₂₂H₄₄O₃

Average Mass

356.5830 Da

Monoisotopic Mass

356.32905 Da

IUPAC Name

2-hydroxydocosanoic acid

Traditional Name

2-hydroxy behenic

CAS Registry Number

13980-14-8

SMILES

CCCCCCCCCCCCCCCCCCCCC(O)C(O)=O

InChI Identifier

InChI=1S/C22H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(23)22(24)25/h21,23H,2-20H2,1H3,(H,24,25)

InChI Key

RPGJJWLCCOPDAZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amphimedon compressa	LOTUS Database	35616633
Aplysina lacunosa	LOTUS Database	35616633
Callyspongia fallax	LOTUS Database	35616633
Cervicornia cuspidifera	LOTUS Database	35616633
Malvaviscus arboreus	LOTUS Database	35616633
Myrmekioderma rea	LOTUS Database	35616633
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Suberites massa	LOTUS Database	35616633
Tripneustes ventricosus	LOTUS Database	35616633
Verongula gigantea	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

long-chain fatty acid (CHEBI:76980 )
2-hydroxy fatty acid (CHEBI:76980 )
Hydroxy fatty acids (LMFA01050077 )

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	8.57	ALOGPS
logP	8.05	ChemAxon
logS	-6.5	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	20	ChemAxon
Refractivity	106.18 m³·mol⁻¹	ChemAxon
Polarizability	48.04 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

HMDB0061660

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007024

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-9780

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193484

PDB ID

Not Available

ChEBI ID

76980

Good Scents ID

Not Available

References

General References

Showing NP-Card for alpha-Hydroxybehenic acid (NP0047024)

MOL for NP0047024 (alpha-Hydroxybehenic acid)

3D MOL for NP0047024 (alpha-Hydroxybehenic acid)

3D SDF for NP0047024 (alpha-Hydroxybehenic acid)

3D-SDF for NP0047024 (alpha-Hydroxybehenic acid)

PDB for NP0047024 (alpha-Hydroxybehenic acid)

3D PDB for NP0047024 (alpha-Hydroxybehenic acid)

SMILES for NP0047024 (alpha-Hydroxybehenic acid)

INCHI for NP0047024 (alpha-Hydroxybehenic acid)

Structure for NP0047024 (alpha-Hydroxybehenic acid)

3D Structure for NP0047024 (alpha-Hydroxybehenic acid)