NP-MRD: Showing NP-Card for Dihydrocapsiate (NP0084528)

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Record Information

Version

2.0

Created at

2022-04-29 05:14:39 UTC

Updated at

2022-04-29 05:14:39 UTC

NP-MRD ID

NP0084528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrocapsiate

Description

Dihydrocapsiate, also known as capsiate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Dihydrocapsiate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydrocapsiate has been detected, but not quantified in, several different foods, such as fruits, green bell peppers, orange bell peppers, yellow bell peppers, and red bell peppers. Dihydrocapsiate is found in Capsicum annuum . This could make dihydrocapsiate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 50  0  0  0  0  0  0  0  0999 V2000
    8.2374    0.5391    1.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6339    1.5125    0.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3603    1.4307    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5288    0.3261    0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647    0.2688   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4331   -0.9266    0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791   -0.8577   -0.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783   -1.8989   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6316   -2.8759    0.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0713   -1.9241   -0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -1.5081    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773   -1.5523   -0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5856   -1.1300    0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8688   -1.2054   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0968   -0.8387    0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1683    0.5372    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0672    1.6156   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    0.7944    2.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8304    1.3199   -0.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428    2.4319   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068    2.4724   -0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7548    3.5662   -0.7658 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4732   -0.4000    1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6358    0.3205    2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1874    1.0009    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9469   -0.4562    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3790   -1.0332    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9627   -1.8394   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691   -1.2849   -1.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2765   -2.9676   -1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439   -0.4531    0.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0857   -2.1649    0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691   -2.5687   -1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -0.8677   -1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6054   -1.8451    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256   -0.0933    0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8173   -0.6713   -1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975   -2.2866   -0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9612   -0.9814   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2739   -1.5461    1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2277    0.6457    1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0419    1.7036   -0.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9525    2.6020    0.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2919    1.4386   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5148    1.5962    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245   -0.1171    2.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8419    1.2519    2.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    1.3032   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3206    3.2592   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4771    4.3577   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 19  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5  4  2  0
  4  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 50  1  0
 20 49  1  0
 19 48  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
  4 26  1  0
M  END


  Mrv0541 05061308042D          

 22 22  0  0  0  0            999 V2000
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  2  0  0  0  0
 21  3  1  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(COC(=O)CCCCCCC(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O4/c1-14(2)8-6-4-5-7-9-18(20)22-13-15-10-11-16(19)17(12-15)21-3/h10-12,14,19H,4-9,13H2,1-3H3

> <INCHI_KEY>
RBCYRZPENADQGZ-UHFFFAOYSA-N

> <FORMULA>
C18H28O4

> <MOLECULAR_WEIGHT>
308.4125

> <EXACT_MASS>
308.198759384

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.524587710069056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4-hydroxy-3-methoxyphenyl)methyl 8-methylnonanoate

> <ALOGPS_LOGP>
5.00

> <JCHEM_LOGP>
4.840751805

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.914333183815877

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890495145485763

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
87.25099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-hydroxy-3-methoxyphenyl)methyl 8-methylnonanoate

> <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       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -9.336   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -9.336   0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   21                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   14                                                       
CONECT    9    7   18                                                       
CONECT   10   11   15                                                       
CONECT   11   10   16                                                       
CONECT   12   15   17                                                       
CONECT   13   15   22                                                       
CONECT   14    1    2    8                                                  
CONECT   15   10   12   13                                                  
CONECT   16   11   17   19                                                  
CONECT   17   12   16   21                                                  
CONECT   18    9   20   22                                                  
CONECT   19   16                                                            
CONECT   20   18                                                            
CONECT   21    3   17                                                       
CONECT   22   13   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
Dihydrocapsiic acid	Generator
4-Hydroxy-3-methoxybenzyl 8-methylnonanoate	HMDB
Capsiate	HMDB
(4-Hydroxy-3-methoxyphenyl)methyl 8-methylnonanoic acid	Generator
Dihydrocapsiate	MeSH
Nonanoic acid, 8-methyl-, (4-hydroxy-3-methoxyphenyl)methyl ester	MeSH

Chemical Formula

C₁₈H₂₈O₄

Average Mass

308.4125 Da

Monoisotopic Mass

308.19876 Da

IUPAC Name

(4-hydroxy-3-methoxyphenyl)methyl 8-methylnonanoate

Traditional Name

(4-hydroxy-3-methoxyphenyl)methyl 8-methylnonanoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(COC(=O)CCCCCCC(C)C)=C1

InChI Identifier

InChI=1S/C18H28O4/c1-14(2)8-6-4-5-7-9-18(20)22-13-15-10-11-16(19)17(12-15)21-3/h10-12,14,19H,4-9,13H2,1-3H3

InChI Key

RBCYRZPENADQGZ-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, 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
Capsicum annuum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzyloxycarbonyl
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	ALOGPS
logP	4.84	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	87.25 m³·mol⁻¹	ChemAxon
Polarizability	36.52 Å³	ChemAxon
Number of Rings	1	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

HMDB0034781

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013334

KNApSAcK ID

Not Available

Chemspider ID

8049443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9873754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dihydrocapsiate (NP0084528)

MOL for NP0084528 (Dihydrocapsiate)

3D MOL for NP0084528 (Dihydrocapsiate)

3D SDF for NP0084528 (Dihydrocapsiate)

3D-SDF for NP0084528 (Dihydrocapsiate)

PDB for NP0084528 (Dihydrocapsiate)

3D PDB for NP0084528 (Dihydrocapsiate)

SMILES for NP0084528 (Dihydrocapsiate)

INCHI for NP0084528 (Dihydrocapsiate)

Structure for NP0084528 (Dihydrocapsiate)

3D Structure for NP0084528 (Dihydrocapsiate)