NP-MRD: Showing NP-Card for 5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol (NP0290035)

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Record Information

Version

2.0

Created at

2022-09-09 20:31:01 UTC

Updated at

2022-09-09 20:31:02 UTC

NP-MRD ID

NP0290035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol

Description

5-(2R-hydroxy-tridecyl)resorcinol belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. 5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol is found in Ardisia virens. Based on a literature review very few articles have been published on 5-(2r-hydroxy-tridecyl)resorcinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 54 54  0  0  0  0  0  0  0  0999 V2000
    6.2164   -1.6083    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8972   -0.6183    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5721    0.8040    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1871    1.2339    0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1154    0.5805    0.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.2896    0.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    0.7036    1.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3699    1.3839    0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906    1.2400   -0.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218   -0.1923   -1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0909   -0.9625   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4741   -0.4545   -0.6325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8913   -0.4127   -1.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230   -1.3790    0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8239   -0.9514    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6497   -1.3999   -1.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9554   -0.9781   -1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7496   -1.4593   -2.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4803   -0.0828   -0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592    0.3757    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1933    1.2639    1.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3503   -0.0590    0.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7870   -1.1384    1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708   -2.1968    0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0014   -2.3299    1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6834   -0.9033   -1.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0141   -0.7671    0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2514    1.4528   -0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8671    1.0814    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9196    1.0535   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0724    2.3541    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1880    0.7015    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9693   -0.5004    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7050    1.1393   -0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8772    2.3558    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6280   -0.3910    0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015    0.7577    2.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    2.4893    0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205    0.9447    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218    1.8329   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033    1.7443   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639   -0.6740   -0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911   -0.2037   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920   -0.9547    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9978   -2.0373   -0.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5347    0.5513   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079    0.4464   -2.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670   -1.3411    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2703   -2.4346   -0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2827   -2.0979   -1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3859   -2.1039   -2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5035    0.2371   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1354    2.2781    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7465    0.3368    1.7474 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 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  1
 13 47  1  0
 14 48  1  0
 14 49  1  0
 16 50  1  0
 18 51  1  0
 19 52  1  0
 21 53  1  0
 22 54  1  0
M  END


  Mrv1652309092222312D          

 22 22  0  0  1  0            999 V2000
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 C   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  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC[C@@H](O)CC1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H32O3/c1-2-3-4-5-6-7-8-9-10-11-17(20)12-16-13-18(21)15-19(22)14-16/h13-15,17,20-22H,2-12H2,1H3/t17-/m1/s1

> <INCHI_KEY>
YXRFSHKHPSTTQE-QGZVFWFLSA-N

> <FORMULA>
C19H32O3

> <MOLECULAR_WEIGHT>
308.462

> <EXACT_MASS>
308.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63458030278074

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(2R)-2-hydroxytridecyl]benzene-1,3-diol

> <JCHEM_LOGP>
5.827642015000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.758113428236893

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.305318180406852

> <JCHEM_PKA_STRONGEST_BASIC>
-2.745818493421341

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
91.9425

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2R)-2-hydroxytridecyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.340 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.674 -13.860   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      24.006 -18.480   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+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   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₂O₃

Average Mass

308.4620 Da

Monoisotopic Mass

308.23514 Da

IUPAC Name

5-[(2R)-2-hydroxytridecyl]benzene-1,3-diol

Traditional Name

5-[(2R)-2-hydroxytridecyl]benzene-1,3-diol

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC[C@@H](O)CC1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C19H32O3/c1-2-3-4-5-6-7-8-9-10-11-17(20)12-16-13-18(21)15-19(22)14-16/h13-15,17,20-22H,2-12H2,1H3/t17-/m1/s1

InChI Key

YXRFSHKHPSTTQE-QGZVFWFLSA-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
Ardisia virens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	5.83	ChemAxon
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	91.94 m³·mol⁻¹	ChemAxon
Polarizability	38.63 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

113386088

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102163924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol (NP0290035)

MOL for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

3D MOL for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

3D SDF for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

3D-SDF for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

PDB for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

3D PDB for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

SMILES for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

INCHI for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

Structure for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)

3D Structure for NP0290035 (5-[(2r)-2-hydroxytridecyl]benzene-1,3-diol)