NP-MRD: Showing NP-Card for Hydroxy-gamma-isosanshool (NP0086486)

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Record Information

Version

2.0

Created at

2022-04-29 06:46:31 UTC

Updated at

2022-04-29 06:46:31 UTC

NP-MRD ID

NP0086486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxy-gamma-isosanshool

Description

N-(2-Hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide, also known as hydroxy-g-isosanshool, belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Thus, N-(2-hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide is considered to be a fatty amide lipid molecule. N-(2-Hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, N-(2-Hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide has been detected, but not quantified in, herbs and spices. Hydroxy-gamma-isosanshool is found in Zanthoxylum bungeanum and Zanthoxylum spp.. This could make N-(2-hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 47  0  0  0  0  0  0  0  0999 V2000
   10.5377    0.8732   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0661    0.8705   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3086    0.0257    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9034    0.0704    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7584    0.1054    0.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3263    0.1659    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5864   -0.6270    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1270   -0.6058    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846   -1.9602    0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064   -1.7936    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303   -0.6351    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850   -0.5096    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6373    0.6669    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456    0.9777    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3876    2.1429   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0307    0.0281    0.6545 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4219    0.4377    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9143    0.5680   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0457   -0.8612   -1.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3132    1.2021   -0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1961    1.3648   -1.6814 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0072    0.6180   -1.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8580    1.8970   -0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9479    0.1872    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5284    1.5330   -1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9159   -0.6051    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7902   -1.0016    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9133    1.1875   -0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7742    0.7745   -0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495   -1.2557    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.0128    1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -0.0390   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761   -2.6028    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -2.3805   -0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6495   -2.6878    0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516    0.2634    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6943   -1.3767    0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9221    1.5023    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7325   -0.9206    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5896    1.4002    1.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0371   -0.3256    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4967   -1.4157   -0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0437   -1.2709   -1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7079   -0.8864   -2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2129    2.2399   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6901    1.1946    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9507    0.6391   -1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746    0.8377   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
M  END


  Mrv0541 02241211012D          

 21 20  0  0  0  0            999 V2000
   -5.0038    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5742    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5740    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038    0.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199   -0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199   -1.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934   -0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8358   -1.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(2,3)21/h4-9,12-15,21H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8+,13-12+,15-14+

> <INCHI_KEY>
CRPPMKFSMRODIQ-FMBIJHKPSA-N

> <FORMULA>
C18H27NO2

> <MOLECULAR_WEIGHT>
289.4125

> <EXACT_MASS>
289.204179113

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.19815368682261

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,8E,10E,12E)-N-(2-hydroxy-2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

> <ALOGPS_LOGP>
4.44

> <JCHEM_LOGP>
3.3413654436666667

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.333732493124614

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.97472917763524

> <JCHEM_PKA_STRONGEST_BASIC>
2.144002283158103

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
95.50949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,8E,10E,12E)-N-(2-hydroxy-2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -9.340   0.932   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.006   1.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.672   0.932   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.337   1.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.003   0.932   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.669   1.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   0.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.701   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.932   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.669   1.701   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.003   0.932   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.337   1.701   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.671   0.932   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.006   1.701   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       9.340   0.932   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       8.006   3.243   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.340  -0.611   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.250  -1.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.250  -3.243   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.708  -1.701   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.160  -2.791   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   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
Hydroxy-g-isosanshool	HMDB

Chemical Formula

C₁₈H₂₇NO₂

Average Mass

289.4125 Da

Monoisotopic Mass

289.20418 Da

IUPAC Name

(2E,4E,8E,10E,12E)-N-(2-hydroxy-2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

Traditional Name

(2E,4E,8E,10E,12E)-N-(2-hydroxy-2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)(C)O

InChI Identifier

InChI=1S/C18H27NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(2,3)21/h4-9,12-15,21H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8+,13-12+,15-14+

InChI Key

CRPPMKFSMRODIQ-FMBIJHKPSA-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
Zanthoxylum bungeanum	LOTUS Database	35616633
Zanthoxylum spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Tertiary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.44	ALOGPS
logP	3.34	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.97	ChemAxon
pKa (Strongest Basic)	2.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	95.51 m³·mol⁻¹	ChemAxon
Polarizability	36.2 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

HMDB0031183

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003202

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

14135316

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hydroxy-gamma-isosanshool (NP0086486)

MOL for NP0086486 (Hydroxy-gamma-isosanshool)

3D MOL for NP0086486 (Hydroxy-gamma-isosanshool)

3D SDF for NP0086486 (Hydroxy-gamma-isosanshool)

3D-SDF for NP0086486 (Hydroxy-gamma-isosanshool)

PDB for NP0086486 (Hydroxy-gamma-isosanshool)

3D PDB for NP0086486 (Hydroxy-gamma-isosanshool)

SMILES for NP0086486 (Hydroxy-gamma-isosanshool)

INCHI for NP0086486 (Hydroxy-gamma-isosanshool)

Structure for NP0086486 (Hydroxy-gamma-isosanshool)

3D Structure for NP0086486 (Hydroxy-gamma-isosanshool)