NP-MRD: Showing NP-Card for β-hydroxyhexadecanoic acid (NP0289713)

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Record Information

Version

2.0

Created at

2022-09-09 20:02:13 UTC

Updated at

2022-09-09 20:02:13 UTC

NP-MRD ID

NP0289713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-hydroxyhexadecanoic acid

Description

3-Hydroxyhexadecanoic acid, also known as b-hydroxypalmitic acid or beta-hydroxyhexadecanoate, 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-Hydroxyhexadecanoic acid is a long-chain hydroxy fatty acid that is the 3-hydroxy derivative of palmitic acid. 3-Hydroxyhexadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. β-hydroxyhexadecanoic acid is found in Centaurea aspera and Hypericum perforatum. In humans, 3-hydroxyhexadecanoic acid is involved in fatty acid metabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -4.4620    2.5933   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102    1.2319   -1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8431    0.1126   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8829    0.0602    0.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.1083    1.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8554   -1.3790    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4927   -1.5669    1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999   -0.4277    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -0.6495    1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706   -1.9321    1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4744   -1.8671   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255   -0.7518   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -0.8849   -0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6326    0.2153   -1.0081 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9041   -0.0134   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1709    1.5803   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    2.5886   -1.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883    3.8152   -0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2145    2.2254   -1.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9976    2.6066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    3.3194   -0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1760    2.9999   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9387    1.0974   -1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942    1.1839   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8913    0.1755   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4574   -0.8403   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4812   -0.8488    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4007    0.9074    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255   -0.0381    2.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448    0.7536    0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -1.3850   -0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5006   -2.2609    0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130   -2.5626    1.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -1.5458    2.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5174   -0.2723   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387    0.4943    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5845   -0.7686    2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350    0.2125    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -2.8247    1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4047   -2.0049    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624   -1.8730   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9151   -2.8634   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -0.8186   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    0.1952   -0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8256   -0.9809    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352   -1.8379   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6943    0.1390   -2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0536   -1.0041   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228    1.6783    0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387    1.8046   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1637    2.3202   -1.5876 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
 14 16  1  0
 16 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  6
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END

  Mrv0541 09041213012D          

 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
   17.9506    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
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    4.1763    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
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  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>
NP0289713

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
CBWALJHXHCJYTE-UHFFFAOYSA-N

> <FORMULA>
C16H32O3

> <MOLECULAR_WEIGHT>
272.4235

> <EXACT_MASS>
272.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.81828652595447

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxyhexadecanoic acid

> <ALOGPS_LOGP>
5.75

> <JCHEM_LOGP>
5.025771710666666

> <ALOGPS_LOGS>
-4.69

> <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>
78.59909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-hydroxyhexadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   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   15                                                       
CONECT   14   15   16                                                       
CONECT   15   13   14   17                                                  
CONECT   16   14   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
beta-Hydroxyhexadecanoic acid	ChEBI
beta-Hydroxypalmitic acid	ChEBI
b-Hydroxyhexadecanoate	Generator
b-Hydroxyhexadecanoic acid	Generator
beta-Hydroxyhexadecanoate	Generator
Β-hydroxyhexadecanoate	Generator
Β-hydroxyhexadecanoic acid	Generator
b-Hydroxypalmitate	Generator
b-Hydroxypalmitic acid	Generator
beta-Hydroxypalmitate	Generator
Β-hydroxypalmitate	Generator
Β-hydroxypalmitic acid	Generator
3-Hydroxyhexadecanoate	Generator
16:0(3-OH)	HMDB
3-Hydroxypalmitic acid	HMDB
3-Hydroxypalmitic acid, (+-)-isomer	HMDB
3-Hydroxypalmitate	Generator

Chemical Formula

C₁₆H₃₂O₃

Average Mass

272.4235 Da

Monoisotopic Mass

272.23514 Da

IUPAC Name

3-hydroxyhexadecanoic acid

Traditional Name

β-hydroxyhexadecanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(O)CC(O)=O

InChI Identifier

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

InChI Key

CBWALJHXHCJYTE-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Centaurea aspera	LOTUS Database	35616633
Hypericum perforatum	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
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:37248 )
3-hydroxy fatty acid (CHEBI:37248 )
hydroxypalmitic acid (CHEBI:37248 )
Hydroxy fatty acids (LMFA01050188 )

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	5.75	ALOGPS
logP	5.03	ChemAxon
logS	-4.7	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	14	ChemAxon
Refractivity	78.6 m³·mol⁻¹	ChemAxon
Polarizability	34.82 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

HMDB0061658

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

301590

PDB ID

Not Available

ChEBI ID

37248

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for β-hydroxyhexadecanoic acid (NP0289713)

MOL for NP0289713 (β-hydroxyhexadecanoic acid)

3D MOL for NP0289713 (β-hydroxyhexadecanoic acid)

3D SDF for NP0289713 (β-hydroxyhexadecanoic acid)

3D-SDF for NP0289713 (β-hydroxyhexadecanoic acid)

PDB for NP0289713 (β-hydroxyhexadecanoic acid)

3D PDB for NP0289713 (β-hydroxyhexadecanoic acid)

SMILES for NP0289713 (β-hydroxyhexadecanoic acid)

INCHI for NP0289713 (β-hydroxyhexadecanoic acid)

Structure for NP0289713 (β-hydroxyhexadecanoic acid)

3D Structure for NP0289713 (β-hydroxyhexadecanoic acid)