NP-MRD: Showing NP-Card for 9,10,18-Trihydroxyoctadecanoic acid (NP0047928)

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Record Information

Version

2.0

Created at

2022-03-17 20:48:14 UTC

Updated at

2022-03-17 20:48:14 UTC

NP-MRD ID

NP0047928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,10,18-Trihydroxyoctadecanoic acid

Description

Floionolic acid, also known as floionolate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. An omega-hydroxy fatty acid that is 18-hydroxyoctadecanoic acid carrying two additional hydroxy substituents at positions 9 and 10. Floionolic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Floionolic acid has been detected, but not quantified in, several different foods, such as buffalo currants, cupuaçus, evergreen huckleberries, common mushrooms, and loganberries. 9,10,18-Trihydroxyoctadecanoic acid is found in Pinus radiata. 9,10,18-Trihydroxyoctadecanoic acid was first documented in 1992 (PMID: 1567426). This could make floionolic acid a potential biomarker for the consumption of these foods (PMID: 17328933) (PMID: 11171237) (PMID: 16417304) (PMID: 18998700).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307422D          

 23 22  0  0  0  0            999 V2000
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4711    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCCCCCCCC(O)C(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O5/c19-15-11-7-2-1-4-8-12-16(20)17(21)13-9-5-3-6-10-14-18(22)23/h16-17,19-21H,1-15H2,(H,22,23)

> <INCHI_KEY>
OISFHODBOQNZAG-UHFFFAOYSA-N

> <FORMULA>
C18H36O5

> <MOLECULAR_WEIGHT>
332.4754

> <EXACT_MASS>
332.256274262

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.244684252444344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10,18-trihydroxyoctadecanoic acid

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.247419356999999

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.909717016038122

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6153254581459935

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922595168618003

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
91.24529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phloionolic 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      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.815  10.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.151  11.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.148  11.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.482  10.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.146  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.813  10.669   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      27.816  12.979   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      29.149   9.129   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      41.153  11.439   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      39.819   9.129   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1    8                                                       
CONECT    5    3    9                                                       
CONECT    6    3   10                                                       
CONECT    7    2   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   16                                                       
CONECT   13    9   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   17   20                                                  
CONECT   17   13   16   21                                                  
CONECT   18   14   22   23                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
9,10,18-Trihydroxy-octadecanoic acid	ChEBI
9,10,18-Trihydroxystearic acid	ChEBI
9,10,18-Trihydroxy-octadecanoate	Generator
9,10,18-Trihydroxystearate	Generator
Floionolate	Generator
Phloionolic acid	HMDB
Phloionolate	Generator
9,10,18-Trihydroxyoctadecanoate	Generator

Chemical Formula

C₁₈H₃₆O₅

Average Mass

332.4754 Da

Monoisotopic Mass

332.25627 Da

IUPAC Name

9,10,18-trihydroxyoctadecanoic acid

Traditional Name

phloionolic acid

CAS Registry Number

496-86-6

SMILES

OCCCCCCCCC(O)C(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H36O5/c19-15-11-7-2-1-4-8-12-16(20)17(21)13-9-5-3-6-10-14-18(22)23/h16-17,19-21H,1-15H2,(H,22,23)

InChI Key

OISFHODBOQNZAG-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
Prunus avium	FooDB	KNAPSACK
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Other Octadecanoids (LMFA02000147 )

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	3.63	ALOGPS
logP	3.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	91.25 m³·mol⁻¹	ChemAxon
Polarizability	41.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034295

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

5282938

PDB ID

Not Available

ChEBI ID

133325

Good Scents ID

Not Available

References

General References

Peschel S, Franke R, Schreiber L, Knoche M: Composition of the cuticle of developing sweet cherry fruit. Phytochemistry. 2007 Apr;68(7):1017-25. doi: 10.1016/j.phytochem.2007.01.008. Epub 2007 Feb 27. [PubMed:17328933 ]
Pinot F, Skrabs M, Compagnon V, Salaun JP, Benveniste I, Schreiber L, Durst F: omega-Hydroxylation of epoxy- and hydroxy-fatty acids by CYP94A1: possible involvement in plant defence. Biochem Soc Trans. 2000 Dec;28(6):867-70. [PubMed:11171237 ]
Pinot F, Salaun JP, Bosch H, Lesot A, Mioskowski C, Durst F: omega-Hydroxylation of Z9-octadecenoic, Z9,10-epoxystearic and 9,10-dihydroxystearic acids by microsomal cytochrome P450 systems from Vicia sativa. Biochem Biophys Res Commun. 1992 Apr 15;184(1):183-93. doi: 10.1016/0006-291x(92)91176-q. [PubMed:1567426 ]
Kallio H, Nieminen R, Tuomasjukka S, Hakala M: Cutin composition of five finnish berries. J Agric Food Chem. 2006 Jan 25;54(2):457-62. doi: 10.1021/jf0522659. [PubMed:16417304 ]
Tsubaki S, Iida H, Sakamoto M, Azuma J: Microwave heating of tea residue yields polysaccharides, polyphenols, and plant biopolyester. J Agric Food Chem. 2008 Dec 10;56(23):11293-9. doi: 10.1021/jf802253s. [PubMed:18998700 ]

Showing NP-Card for 9,10,18-Trihydroxyoctadecanoic acid (NP0047928)

MOL for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

3D MOL for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

3D SDF for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

3D-SDF for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

PDB for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

3D PDB for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

SMILES for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

INCHI for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

Structure for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)

3D Structure for NP0047928 (9,10,18-Trihydroxyoctadecanoic acid)