NP-MRD: Showing NP-Card for 2-Hydroxyhexadecanoic acid (NP0083752)

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Record Information

Version

2.0

Created at

2022-04-29 04:42:02 UTC

Updated at

2022-04-29 04:42:02 UTC

NP-MRD ID

NP0083752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxyhexadecanoic acid

Description

(R)-2-Hydroxyhexadecanoic acid, also known as 2-hydroxypalmitic acid, belongs to the class of organic compounds known as long-chain fatty acids. 2-Hydroxyhexadecanoic acid is found in Allamanda cathartica, Aplysina lacunosa, Averrhoa bilimbi , Suberites massa and Ulva pertusa. 2-Hydroxyhexadecanoic acid was first documented in 2014 (PMID: 25041144). These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms (R)-2-Hydroxyhexadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -8.1081   -0.1671   -0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9789   -0.0384   -1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7391    0.3826   -0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4572   -0.6814    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2494   -0.3811    1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0120   -0.2478    0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8593    0.0552    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174    0.1848    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338    0.4814    1.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864    0.6344    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -0.5872   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4037   -0.4396   -1.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5975   -0.1406   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8598   -0.0010   -1.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9957    0.3005   -0.0570 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7144    1.4699    0.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2406    0.3880   -0.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5762   -0.6387   -1.5123 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0345    1.4981   -0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0690   -0.0058   -0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0379   -1.2085    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9744    0.5210    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7536   -1.0219   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1838    0.7518   -2.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9356    0.5070   -1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8660    1.3400   -0.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3309   -1.6857   -0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3452   -0.7462    1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    0.5749    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847   -1.1647    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0520    0.6182   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548   -1.1267   -0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -0.7030    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046    1.0272    1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -0.7552   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8357    1.0048   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4012    1.4223    1.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6696   -0.3147    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    0.8351    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    1.5144   -0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3450   -0.9096   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -1.4416    0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309    0.3912   -1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5114   -1.3770   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7659   -1.0024    0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4288    0.7369    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8156    0.8310   -1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0049   -0.9354   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0305   -0.5383    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1769    2.0979    0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1907    2.1808   -0.2485 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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 19  1  0
 17 18  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 19 51  1  0
M  END


  Mrv1652305221920062D          

 19 18  0  0  0  0            999 V2000
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    4.1763    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 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083752

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15,17H,2-14H2,1H3,(H,18,19)

> <INCHI_KEY>
JGHSBPIZNUXPLA-UHFFFAOYSA-N

> <FORMULA>
C16H32O3

> <MOLECULAR_WEIGHT>
272.4235

> <EXACT_MASS>
272.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.12073784799544

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxyhexadecanoic acid

> <ALOGPS_LOGP>
5.55

> <JCHEM_LOGP>
5.385516856999999

> <ALOGPS_LOGS>
-4.85

> <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>
78.57579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy palmitic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.840  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.842   9.336   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      33.508  11.646   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      36.175  10.106   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      34.842   7.796   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   17                                                  
CONECT   16   15   18   19                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxypalmitic acid	ChEBI
2-Hydroxypalmitate	Generator
(R)-2-Hydroxyhexadecanoate	Generator
2-Hydroxyhexadecanoic acid, (+-)-isomer	MeSH
2-Hydroxyhexadecanoate	MeSH
2-Hydroxyhexadecanoic acid, (S)-isomer	MeSH
2-Hydroxyhexadecanoic acid, (R)-isomer	MeSH
alpha-Hydroxypalmitic acid	MeSH

Chemical Formula

C₁₆H₃₂O₃

Average Mass

272.4235 Da

Monoisotopic Mass

272.23514 Da

IUPAC Name

2-hydroxyhexadecanoic acid

Traditional Name

2-hydroxy palmitic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC(O)C(O)=O

InChI Identifier

InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15,17H,2-14H2,1H3,(H,18,19)

InChI Key

JGHSBPIZNUXPLA-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
Allamanda cathartica	LOTUS Database	35616633
Aplysina lacunosa	LOTUS Database	35616633
Averrhoa bilimbi	Plant	KNApSAcK
Suberites massa	LOTUS Database	35616633
Ulva pertusa	LOTUS Database	35616633

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:65101 )
2-hydroxy fatty acid (CHEBI:65101 )
Hydroxy fatty acids (LMFA01050047 )

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	5.55	ALOGPS
logP	5.39	ChemAxon
logS	-4.8	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	14	ChemAxon
Refractivity	78.58 m³·mol⁻¹	ChemAxon
Polarizability	35.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

FDB003058

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-8475

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92836

PDB ID

Not Available

ChEBI ID

65101

Good Scents ID

Not Available

References

General References

Lustgarten MS, Price LL, Chale A, Fielding RA: Metabolites related to gut bacterial metabolism, peroxisome proliferator-activated receptor-alpha activation, and insulin sensitivity are associated with physical function in functionally-limited older adults. Aging Cell. 2014 Oct;13(5):918-25. doi: 10.1111/acel.12251. Epub 2014 Jul 18. [PubMed:25041144 ]

Showing NP-Card for 2-Hydroxyhexadecanoic acid (NP0083752)

MOL for NP0083752 (2-Hydroxyhexadecanoic acid)

3D MOL for NP0083752 (2-Hydroxyhexadecanoic acid)

3D SDF for NP0083752 (2-Hydroxyhexadecanoic acid)

3D-SDF for NP0083752 (2-Hydroxyhexadecanoic acid)

PDB for NP0083752 (2-Hydroxyhexadecanoic acid)

3D PDB for NP0083752 (2-Hydroxyhexadecanoic acid)

SMILES for NP0083752 (2-Hydroxyhexadecanoic acid)

INCHI for NP0083752 (2-Hydroxyhexadecanoic acid)

Structure for NP0083752 (2-Hydroxyhexadecanoic acid)

3D Structure for NP0083752 (2-Hydroxyhexadecanoic acid)