NP-MRD: Showing NP-Card for Hydroxy-Œ±-sanshool (NP0136955)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-30 16:37:13 UTC

Updated at

2022-05-30 16:37:13 UTC

NP-MRD ID

NP0136955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxy-Œ±-sanshool

Description

Hydroxy-alpha-sanshool 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, hydroxy-alpha-sanshool is considered to be a fatty amide lipid molecule. Hydroxy-alpha-sanshool is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hydroxy-alpha sanshool is a molecule found in plants from the genus Zanthoxylum. The term sanshool in the compound's name is derived from the Japanese term for the Sichuan pepper, sanshō (山椒) (literally, mountain pepper), to which was appended the suffix -ol, indicating an alcohol. Outside of the human body, Hydroxy-alpha-sanshool has been detected, but not quantified in, herbs and spices. This could make hydroxy-alpha-sanshool a potential biomarker for the consumption of these foods. Hydroxy-alpha sanshool excites D-hair afferent nerve fibers, a distinct subset of the sensitive light touch receptors in the skin, and targets novel populations of Aβ and C-fiber nerve fibers. The chemical structure of hydroxy-alpha sanshool is similar to that of capsaicin, but the mechanism of action by which it induces nerve sensations have been a matter of debate. It is believed to be responsible for the numbing and tingling sensation caused by eating food cooked with Sichuan peppercorns. Hydroxy-Œ±-sanshool is found in Zanthoxylum bungeanum. Although the compound is an agonist at the pain-integration channels TRPV1 and TRPA1 as capsaicin, newer evidence suggests that the tandem pore domain potassium channels KCNK3, KCNK9, and KCNK18 are primarily responsible for sanshool's effects.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 43  0  0  0  0  0  0  0  0999 V2000
    7.9973   -1.5829   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8959   -0.1773    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7216    0.4266    0.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5172   -0.2509   -0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3222    0.3216   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267   -0.3480   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9779    0.2420   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546    1.6145   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    1.5470    0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196    0.9384    0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827    1.5442    0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9497    0.9033    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1127    1.6425    0.3426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0336   -0.2627   -0.2225 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -1.0871   -0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4852   -0.6266   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9251   -0.4298    0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4269   -1.7218   -1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7652    0.5524   -1.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5038   -1.6229   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0296   -1.9371   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3761   -2.1910    0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8054    0.3024    0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6683    1.4512    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6032   -1.2702   -0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    1.3294    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -1.4036   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.3401   -1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002    2.2136    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2628    2.2105   -1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146    0.8847    1.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321    2.5628    1.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278   -0.0814    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058    2.5537    0.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974    2.1349    1.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -1.3127   -1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0563   -2.1211   -0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6471   -1.2399    1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -0.5613    1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4871    0.5103    1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3990   -1.2244   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5136   -2.4708   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9973   -2.1713   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7573    0.5486   -1.4059 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  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
M  END


  Mrv0541 05061304492D          

 19 18  0  0  0  0            999 V2000
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  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  2  0  0  0  0
 15 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+

> <INCHI_KEY>
LHFKHAVGGJJQFF-JRNWQWJGSA-N

> <FORMULA>
C16H25NO2

> <MOLECULAR_WEIGHT>
263.3752

> <EXACT_MASS>
263.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.04834034218719

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.6337538973333334

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.035121126665373

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.493271092456638

> <JCHEM_PKA_STRONGEST_BASIC>
4.954677333239283

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
85.7126

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.860   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.090   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.550   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.780   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -3.437   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
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                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15                                                       
CONECT   14   16   17                                                       
CONECT   15   13   17   18                                                  
CONECT   16    2    3   14   19                                             
CONECT   17   14   15                                                       
CONECT   18   15                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
Hydroxy-a-sanshool	Generator
Hydroxy-α-sanshool	Generator

Chemical Formula

C₁₆H₂₅NO₂

Average Mass

263.3752 Da

Monoisotopic Mass

263.18853 Da

IUPAC Name

(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

Traditional Name

(Z,2E,6Z,8E,10Z)-N-(2-hydroxy-2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

CAS Registry Number

Not Available

SMILES

C\C=C/C=C/C=C\CC\C=C\C(\O)=N\CC(C)(C)O

InChI Identifier

InChI=1S/C16H25NO2/c1-4-5-6-7-8-9-10-11-12-13-15(18)17-14-16(2,3)19/h4-9,12-13,19H,10-11,14H2,1-3H3,(H,17,18)/b5-4-,7-6+,9-8-,13-12+

InChI Key

LHFKHAVGGJJQFF-JRNWQWJGSA-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
Zanthoxylum bungeanum	LOTUS Database	35616633

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	4.28	ALOGPS
logP	3.63	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.71 m³·mol⁻¹	ChemAxon
Polarizability	32.05 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

HMDB0029567

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000722

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydroxy alpha sanshool

METLIN ID

Not Available

PubChem Compound

46870578

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hydroxy-Œ±-sanshool (NP0136955)

MOL for NP0136955 (Hydroxy-Œ±-sanshool)

3D MOL for NP0136955 (Hydroxy-Œ±-sanshool)

3D SDF for NP0136955 (Hydroxy-Œ±-sanshool)

3D-SDF for NP0136955 (Hydroxy-Œ±-sanshool)

PDB for NP0136955 (Hydroxy-Œ±-sanshool)

3D PDB for NP0136955 (Hydroxy-Œ±-sanshool)

SMILES for NP0136955 (Hydroxy-Œ±-sanshool)

INCHI for NP0136955 (Hydroxy-Œ±-sanshool)

Structure for NP0136955 (Hydroxy-Œ±-sanshool)

3D Structure for NP0136955 (Hydroxy-Œ±-sanshool)