NP-MRD: Showing NP-Card for Phellogenic acid (NP0047064)

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Record Information

Version

2.0

Created at

2022-03-17 20:34:01 UTC

Updated at

2022-03-17 20:34:01 UTC

NP-MRD ID

NP0047064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phellogenic acid

Description

Phellogenic acid, also known as 1,22-docosanedioate or felogenate, 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. Phellogenic acid is found in Pinus radiata. Phellogenic acid was first documented in 2005 (PMID: 15716582). Phellogenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 19783438).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241223362D          

 26 25  0  0  0  0            999 V2000
   -0.0795   -1.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -1.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654   -1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236   -1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654    1.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    2.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213    2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795    2.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    1.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422    1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4011    1.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 25  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  2  0  0  0  0
 23 26  1  0  0  0  0
M  END

  Mrv0541 02241223362D          

 26 25  0  0  0  0            999 V2000
   -0.0795   -1.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -1.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0848   -2.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654   -1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236   -1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1654    1.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5236    1.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3631    2.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7213    2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795    2.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    1.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422    1.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    0.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4011    1.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 25  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  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  2  0  0  0  0
 23 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047064

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H42O4/c23-21(24)19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22(25)26/h1-20H2,(H,23,24)(H,25,26)

> <INCHI_KEY>
DGXRZJSPDXZJFG-UHFFFAOYSA-N

> <FORMULA>
C22H42O4

> <MOLECULAR_WEIGHT>
370.5665

> <EXACT_MASS>
370.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
48.266861633105954

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
docosanedioic acid

> <ALOGPS_LOGP>
7.48

> <JCHEM_LOGP>
7.603753002666665

> <ALOGPS_LOGS>
-6.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.253049650892543

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650989659564581

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
106.35499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.148  -1.870   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.148  -0.374   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.495   0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.844  -0.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.844  -1.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.191  -2.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.191  -4.265   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.844  -5.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.495  -4.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.148  -5.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197  -4.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.544  -5.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.892  -4.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.042  -2.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.844  -1.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.995  -0.374   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.191   0.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.042   2.021   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.844   2.919   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.544   4.266   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.346   5.014   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.148   4.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.448   3.068   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.945   2.769   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.197   0.374   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.749   2.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
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   26                                                  
CONECT   24   23                                                            
CONECT   25    2                                                            
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

View in JSmol

Synonyms

Value	Source
1,20-Eicosanedicarboxylic acid	ChEBI
1,20-Icosanedicarboxylic acid	ChEBI
1,22-Docosanedioic acid	ChEBI
Felogenic acid	ChEBI
1,20-Eicosanedicarboxylate	Generator
1,20-Icosanedicarboxylate	Generator
1,22-Docosanedioate	Generator
Felogenate	Generator
Phellogenate	Generator
Phellogenic acid	ChEBI
Docosanedioic acid	Generator

Chemical Formula

C₂₂H₄₂O₄

Average Mass

370.5665 Da

Monoisotopic Mass

370.30831 Da

IUPAC Name

docosanedioic acid

Traditional Name

docosanedioic acid

CAS Registry Number

505-56-6

SMILES

OC(=O)CCCCCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C22H42O4/c23-21(24)19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20-22(25)26/h1-20H2,(H,23,24)(H,25,26)

InChI Key

DGXRZJSPDXZJFG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pinus radiata	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:76319 )
Dicarboxylic acids (LMFA01170037 )

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	7.48	ALOGPS
logP	7.6	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	106.36 m³·mol⁻¹	ChemAxon
Polarizability	48.27 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007134

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19625

BioCyc ID

CPD-13101

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

244872

PDB ID

Not Available

ChEBI ID

76319

Good Scents ID

Not Available

References

General References

Bao B, Dang HT, Zhang P, Hong J, Lee CO, Cho HY, Jung JH: Bicyclic alpha,omega-dicarboxylic acid derivatives from a colonial tunicate of the family Polyclinidae. Bioorg Med Chem Lett. 2009 Nov 1;19(21):6205-8. doi: 10.1016/j.bmcl.2009.08.094. Epub 2009 Sep 3. [PubMed:19783438 ]
Sanders RJ, Ofman R, Valianpour F, Kemp S, Wanders RJ: Evidence for two enzymatic pathways for omega-oxidation of docosanoic acid in rat liver microsomes. J Lipid Res. 2005 May;46(5):1001-8. doi: 10.1194/jlr.M400510-JLR200. Epub 2005 Feb 16. [PubMed:15716582 ]

Showing NP-Card for Phellogenic acid (NP0047064)

MOL for NP0047064 (Phellogenic acid)

3D MOL for NP0047064 (Phellogenic acid)

3D SDF for NP0047064 (Phellogenic acid)

3D-SDF for NP0047064 (Phellogenic acid)

PDB for NP0047064 (Phellogenic acid)

3D PDB for NP0047064 (Phellogenic acid)

SMILES for NP0047064 (Phellogenic acid)

INCHI for NP0047064 (Phellogenic acid)

Structure for NP0047064 (Phellogenic acid)

3D Structure for NP0047064 (Phellogenic acid)