NP-MRD: Showing NP-Card for dl-9-hydroxy stearic acid (NP0168137)

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Record Information

Version

2.0

Created at

2022-09-03 03:51:48 UTC

Updated at

2022-09-03 03:51:48 UTC

NP-MRD ID

NP0168137

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dl-9-hydroxy stearic acid

Description

9-Hydroxyoctadecanoic acid, also known as 9-hydroxystearate or 18:0(9-OH), 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. dl-9-hydroxy stearic acid is found in Jodina rhombifolia. dl-9-hydroxy stearic acid was first documented in 2004 (PMID: 14715257). 9-Hydroxyoctadecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 15716589) (PMID: 16487928) (PMID: 16702808) (PMID: 17234448).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 57 56  0  0  0  0  0  0  0  0999 V2000
   -7.9427    0.7714   -2.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4187    0.5363   -1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2875   -0.8378   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077   -1.4509   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0428   -0.9407    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    0.3913   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4477    0.7445    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3281   -0.2292    1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301    0.1243    2.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2195    1.4377    2.1191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7036    2.4655    2.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0661    1.6029    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823    0.5741    0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726    0.8055   -0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.1964   -0.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0242   -0.1001    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787   -1.0846    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653   -0.8123   -0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1200   -1.7625   -0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8781   -2.9486   -1.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3880   -1.2877   -0.6488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2691    0.1504   -2.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4968    0.6160   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0090    1.8510   -2.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2430    1.3325   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9359    0.7788   -2.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8029   -1.5112   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241   -0.9336   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4096   -1.6561   -1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2341   -2.5321   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713   -1.6860   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702   -1.0385    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7600    0.4074   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1249    1.2127   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476    0.8742    1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    1.7327    0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -1.2641    1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7573   -0.3741    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162    0.1276    3.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.7239    2.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300    1.5933    3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    3.3139    1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    2.5959    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    1.5811    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8403   -0.4574    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614    0.7257    1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316    0.7211   -1.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4501    1.8112   -0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5722   -1.2040   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6004   -0.1033   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760    0.9369    0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139   -0.3436    1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8576   -0.9823    1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7871   -2.1312    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886    0.2420   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3783   -1.0031   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6560   -0.3238   -0.6528 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  1
 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  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 21 57  1  0
M  END

  Mrv0541 04111415172D          

 21 20  0  0  0  0            999 V2000
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    4.8908    0.0000 O   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
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    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
   13.4724    6.1283    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
   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
   15.6158    4.8908    0.0000 O   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
   17.0447    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
   18.4737    5.7158    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
   19.9026    5.7158    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
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  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
 11 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
M  END
> <DATABASE_ID>
NP0168137

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC(O)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)

> <INCHI_KEY>
RKHXDCVAPIMDMG-UHFFFAOYSA-N

> <FORMULA>
C18H36O3

> <MOLECULAR_WEIGHT>
300.4766

> <EXACT_MASS>
300.266445018

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.40307073590938

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-hydroxyoctadecanoic acid

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
5.759001580666666

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.484172992642115

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615326145544296

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2748235273973116

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
87.9551

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DL-9-hydroxy stearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-APR-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-APR-14         0                                  
HETATM    1  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.146  11.439   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.480   9.129   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      19.814  11.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.147  10.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.481  11.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.815  10.669   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      26.482  10.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.816  11.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.149  10.669   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      29.149   9.129   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      30.483  11.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.817  10.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.151  11.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.484  10.669   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.818  11.439   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.152  10.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.485  11.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.819  10.669   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.153  11.439   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    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   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxystearic acid	ChEBI
9-Hydroxystearate	Generator
9-Hydroxyoctadecanoate	Generator
DL-9-Hydroxy stearate	HMDB
9-Hydroxystearic acid, (R)-isomer	HMDB
9-Hydroxystearic acid, (S)-isomer	HMDB
18:0(9-OH)	HMDB
9-hydroxystearic acid	HMDB
9-DL-Hydroxystearic acid	HMDB
9-hydroxyoctadecanoic acid	SMPDB, ChEMBL

Chemical Formula

C₁₈H₃₆O₃

Average Mass

300.4766 Da

Monoisotopic Mass

300.26645 Da

IUPAC Name

9-hydroxyoctadecanoic acid

Traditional Name

DL-9-hydroxy stearic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC(O)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H36O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)

InChI Key

RKHXDCVAPIMDMG-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
Jodina rhombifolia	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
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

Other Octadecanoids (LMFA02000127 )

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	6.6	ALOGPS
logP	5.76	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-1.3	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	16	ChemAxon
Refractivity	87.96 m³·mol⁻¹	ChemAxon
Polarizability	39.4 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

HMDB0061661

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

9570127

PDB ID

Not Available

ChEBI ID

136638

Good Scents ID

Not Available

References

General References

Calonghi N, Cappadone C, Pagnotta E, Farruggia G, Buontempo F, Boga C, Brusa GL, Santucci MA, Masotti L: 9-Hydroxystearic acid upregulates p21(WAF1) in HT29 cancer cells. Biochem Biophys Res Commun. 2004 Jan 30;314(1):138-42. doi: 10.1016/j.bbrc.2003.12.066. [PubMed:14715257 ]
Calonghi N, Cappadone C, Pagnotta E, Boga C, Bertucci C, Fiori J, Tasco G, Casadio R, Masotti L: Histone deacetylase 1: a target of 9-hydroxystearic acid in the inhibition of cell growth in human colon cancer. J Lipid Res. 2005 Aug;46(8):1596-603. doi: 10.1194/jlr.M400424-JLR200. Epub 2005 Feb 16. [PubMed:15716589 ]
Calonghi N, Pagnotta E, Parolin C, Tognoli C, Boga C, Masotti L: 9-Hydroxystearic acid interferes with EGF signalling in a human colon adenocarcinoma. Biochem Biophys Res Commun. 2006 Apr 7;342(2):585-8. doi: 10.1016/j.bbrc.2006.02.008. Epub 2006 Feb 10. [PubMed:16487928 ]
Pagnotta E, Calonghi N, Boga C, Masotti L: N-methylformamide and 9-hydroxystearic acid: two anti-proliferative and differentiating agents with different modes of action in colon cancer cells. Anticancer Drugs. 2006 Jun;17(5):521-6. doi: 10.1097/00001813-200606000-00005. [PubMed:16702808 ]
Calonghi N, Pagnotta E, Parolin C, Molinari C, Boga C, Dal Piaz F, Brusa GL, Santucci MA, Masotti L: Modulation of apoptotic signalling by 9-hydroxystearic acid in osteosarcoma cells. Biochim Biophys Acta. 2007 Feb;1771(2):139-46. doi: 10.1016/j.bbalip.2006.11.012. Epub 2006 Dec 13. [PubMed:17234448 ]
LOTUS database [Link]

Showing NP-Card for dl-9-hydroxy stearic acid (NP0168137)

MOL for NP0168137 (dl-9-hydroxy stearic acid)

3D MOL for NP0168137 (dl-9-hydroxy stearic acid)

3D SDF for NP0168137 (dl-9-hydroxy stearic acid)

3D-SDF for NP0168137 (dl-9-hydroxy stearic acid)

PDB for NP0168137 (dl-9-hydroxy stearic acid)

3D PDB for NP0168137 (dl-9-hydroxy stearic acid)

SMILES for NP0168137 (dl-9-hydroxy stearic acid)

INCHI for NP0168137 (dl-9-hydroxy stearic acid)

Structure for NP0168137 (dl-9-hydroxy stearic acid)

3D Structure for NP0168137 (dl-9-hydroxy stearic acid)