NP-MRD: Showing NP-Card for beta-Hydroxymyristic acid (NP0083910)

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Record Information

Version

2.0

Created at

2022-04-29 04:48:25 UTC

Updated at

2022-04-29 04:48:25 UTC

NP-MRD ID

NP0083910

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Hydroxymyristic acid

Description

3-Hydroxytetradecanoic acid, also known as 3-hydroxymyristic acid or beta-hydroxymyristate, 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. 3-Hydroxytetradecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxytetradecanoic acid exists in all living organisms, ranging from bacteria to humans. beta-Hydroxymyristic acid is found in Hypericum perforatum and Triticum aestivum . beta-Hydroxymyristic acid was first documented in 2014 (PMID: 24445207). 3-Hydroxytetradecanoic acid is a long-chain hydroxy fatty acid (PMID: 24946182).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.1825    0.3684   -1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3309   -0.8360   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761   -1.4137   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2941   -0.5532    0.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7879    0.7450    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    1.3988    1.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8217    0.5944    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502    0.3574    0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3274   -0.4540    1.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3239   -0.7343    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    0.5525   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723    0.3541   -1.5837 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2595   -0.3351   -2.6303 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0896   -0.3961   -1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285    0.2798   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4866    1.3708    0.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9745   -0.3323    0.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5793    1.2637   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8857    0.2758   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1753    0.5233   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8312   -1.6345   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0920   -0.6536    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2659   -2.4031    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4203   -1.7144   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4037   -1.1216    1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9153   -0.3284    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5852    1.5187    0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818    0.6599   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127    1.5733    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381    2.3717    1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    1.2217    2.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.3226    2.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4536    1.3357    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683   -0.2024   -0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664   -1.4056    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8916    0.0591    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8770   -1.3787   -0.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617   -1.3479    0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9963    1.0852   -0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1763    1.1929    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1854    1.3552   -1.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476   -1.3000   -2.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7935   -0.4324   -2.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8464   -1.4417   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000    0.2845    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END

  Mrv1652305171802452D          

 17 16  0  0  0  0            999 V2000
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    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
  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083910

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

> <INCHI_KEY>
ATRNZOYKSNPPBF-UHFFFAOYSA-N

> <FORMULA>
C14H28O3

> <MOLECULAR_WEIGHT>
244.3703

> <EXACT_MASS>
244.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.558238870709154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxytetradecanoic acid

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
4.136634380666667

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288670866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
69.3971

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-myristic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.197   8.002   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      27.197   6.462   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      28.530   8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      31.198   8.772   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      29.864   6.462   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   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-tetradecanoic acid	ChEBI
3-Hydroxymyristic acid	ChEBI
beta-Hydroxymyristic acid	ChEBI
beta-Hydroxytetradecanoic acid	ChEBI
3-Hydroxy-tetradecanoate	Generator
3-Hydroxymyristate	Generator
b-Hydroxymyristate	Generator
b-Hydroxymyristic acid	Generator
beta-Hydroxymyristate	Generator
Β-hydroxymyristate	Generator
Β-hydroxymyristic acid	Generator
b-Hydroxytetradecanoate	Generator
b-Hydroxytetradecanoic acid	Generator
beta-Hydroxytetradecanoate	Generator
Β-hydroxytetradecanoate	Generator
Β-hydroxytetradecanoic acid	Generator
3-Hydroxytetradecanoate	Generator
14:0(3-OH)	HMDB
beta-Hydroxymyristic acid, (R)-isomer	HMDB
3-Hydroxytetradecanoic acid	MeSH

Chemical Formula

C₁₄H₂₈O₃

Average Mass

244.3703 Da

Monoisotopic Mass

244.20384 Da

IUPAC Name

3-hydroxytetradecanoic acid

Traditional Name

3-hydroxy-myristic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC(O)CC(O)=O

InChI Identifier

InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

InChI Key

ATRNZOYKSNPPBF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypericum perforatum	LOTUS Database	35616633
Triticum aestivum	Plant	KNApSAcK

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
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:85148 )
3-hydroxy monocarboxylic acid (CHEBI:85148 )
3-hydroxy fatty acid (CHEBI:85148 )
Hydroxy fatty acids (LMFA01050175 )

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	4.69	ALOGPS
logP	4.14	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	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	12	ChemAxon
Refractivity	69.4 m³·mol⁻¹	ChemAxon
Polarizability	30.56 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

HMDB0061656

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

CPD-12808

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16064

PDB ID

Not Available

ChEBI ID

85148

Good Scents ID

Not Available

References

General References

Chen YS, Shieh WJ, Goldsmith CS, Metcalfe MG, Greer PW, Zaki SR, Chang HH, Chan H, Chen YL: Alteration of the phenotypic and pathogenic patterns of Burkholderia pseudomallei that persist in a soil environment. Am J Trop Med Hyg. 2014 Mar;90(3):469-79. doi: 10.4269/ajtmh.13-0051. Epub 2014 Jan 20. [PubMed:24445207 ]
Tonin AM, Amaral AU, Busanello EN, Gasparotto J, Gelain DP, Gregersen N, Wajner M: Mitochondrial bioenergetics deregulation caused by long-chain 3-hydroxy fatty acids accumulating in LCHAD and MTP deficiencies in rat brain: a possible role of mPTP opening as a pathomechanism in these disorders? Biochim Biophys Acta. 2014 Sep;1842(9):1658-67. doi: 10.1016/j.bbadis.2014.06.011. Epub 2014 Jun 16. [PubMed:24946182 ]

Showing NP-Card for beta-Hydroxymyristic acid (NP0083910)

MOL for NP0083910 (beta-Hydroxymyristic acid)

3D MOL for NP0083910 (beta-Hydroxymyristic acid)

3D SDF for NP0083910 (beta-Hydroxymyristic acid)

3D-SDF for NP0083910 (beta-Hydroxymyristic acid)

PDB for NP0083910 (beta-Hydroxymyristic acid)

3D PDB for NP0083910 (beta-Hydroxymyristic acid)

SMILES for NP0083910 (beta-Hydroxymyristic acid)

INCHI for NP0083910 (beta-Hydroxymyristic acid)

Structure for NP0083910 (beta-Hydroxymyristic acid)

3D Structure for NP0083910 (beta-Hydroxymyristic acid)