NP-MRD: Showing NP-Card for 12s-hepe (NP0302405)

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Record Information

Version

2.0

Created at

2022-09-10 15:55:43 UTC

Updated at

2022-09-10 15:55:43 UTC

NP-MRD ID

NP0302405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12s-hepe

Description

12(S)-HEPE, also known as 12S-hepe, belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. Thus, 12(S)-hepe is considered to be an eicosanoid. 12s-hepe is found in Murrayella periclados. Based on a literature review very few articles have been published on 12(S)-HEPE.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 52  0  0  0  0  0  0  0  0999 V2000
   -6.3927    2.5129    1.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9840    1.3375    0.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3645    0.0580    0.7763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6923   -0.7675   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4374   -0.5864   -1.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -0.4868   -1.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -0.4936   -1.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7514   -0.6044    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890   -1.8316    0.5210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8652   -1.8138    1.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761   -2.0150   -0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317   -1.0792   -0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124   -1.3772   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352   -0.5027   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751    0.9031   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1314    1.6294   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051    1.2110    0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803   -0.1692    0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0239   -0.3161    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9362    0.5386    1.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3467    0.4187    0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6256   -0.3287   -0.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3558    1.1070    1.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4892    3.4649    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8680    2.6412    2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    2.2481    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0495    1.2735    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1150    1.4831   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4508   -0.2648    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3163   -1.6996    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9509    0.3748   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0600   -1.3358   -2.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0047   -0.3848   -3.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0360   -0.4034   -2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9826    0.2641    0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378   -0.3193    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410   -2.6974    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2705   -2.5983    2.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3728   -3.0254   -0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263   -0.0786   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -2.4405   -1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3623   -0.9096   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114    1.3962   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1884    1.2066   -0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9041    2.7514    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6315    1.9916    1.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.3611    1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9365   -0.9800    0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3726   -1.3619    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296    0.0275   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6217    1.6030    1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8883    0.1000    2.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2537    0.6904    1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  1
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 23 53  1  0
M  END


  Mrv1652309102217552D          

 23 22  0  0  1  0            999 V2000
    1.2375    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    6.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    4.8395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5230    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h3-4,7-11,13-14,17,19,21H,2,5-6,12,15-16,18H2,1H3,(H,22,23)/b4-3-,9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

> <INCHI_KEY>
MCRJLMXYVFDXLS-UOLHMMFFSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.457

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.285447305544295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,10E,12S,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoic acid

> <JCHEM_LOGP>
4.994438087333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720819929173768

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.88963064504959

> <JCHEM_PKA_STRONGEST_BASIC>
-1.60871350084006

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
102.5861

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12S-hepe

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.310   4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.644   6.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644   8.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   9.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310  10.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.976  11.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.357  10.574   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.357   9.034   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.976   8.264   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.691   8.264   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.691   6.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.025   5.954   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.977  -0.206   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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   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   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
12S-HEPE	ChEBI
12S-Hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoic acid	ChEBI
12S-Hydroxy-5Z,8Z,10E,14Z,17Z-eicosapentaenoate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4570 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(5Z,8Z,10E,12S,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoic acid

Traditional Name

12S-hepe

CAS Registry Number

Not Available

SMILES

CC\C=C/C\C=C/C[C@H](O)\C=C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h3-4,7-11,13-14,17,19,21H,2,5-6,12,15-16,18H2,1H3,(H,22,23)/b4-3-,9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

InChI Key

MCRJLMXYVFDXLS-UOLHMMFFSA-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
Murrayella periclados	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroxyeicosapentaenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy/hydroperoxyeicosapentaenoic acids (LMFA03070008 )

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	4.99	ChemAxon
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-1.6	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	13	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	37.29 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000416

Chemspider ID

4446313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283191

PDB ID

Not Available

ChEBI ID

88345

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12s-hepe (NP0302405)

MOL for NP0302405 (12s-hepe)

3D MOL for NP0302405 (12s-hepe)

3D SDF for NP0302405 (12s-hepe)

3D-SDF for NP0302405 (12s-hepe)

PDB for NP0302405 (12s-hepe)

3D PDB for NP0302405 (12s-hepe)

SMILES for NP0302405 (12s-hepe)

INCHI for NP0302405 (12s-hepe)

Structure for NP0302405 (12s-hepe)

3D Structure for NP0302405 (12s-hepe)