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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:53:50 UTC

Update Date

2021-09-26 23:00:11 UTC

HMDB ID

HMDB0249385

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-

Description

Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate, also known as regroton, belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004161519462D          

 44 49  0  0  0  0            999 V2000
    2.0210   -2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0151   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 42 43  1  0  0  0  0
 41 44  2  0  0  0  0
 33 44  1  0  0  0  0
M  END

HMDB0249385
     RDKit          3D
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy...
 84 89  0  0  0  0  0  0  0  0999 V2000
   -2.4612    2.6199   -2.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    1.9102   -1.7285 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0916    0.0163   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
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 44 84  1  0
M  END


  Mrv1533004161519462D          

 44 49  0  0  0  0            999 V2000
    2.0210   -2.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7655   -4.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4165   -4.6766    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
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  6 24  1  0  0  0  0
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  3 25  1  0  0  0  0
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 26 27  2  0  0  0  0
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  4 30  1  0  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
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 41 44  2  0  0  0  0
 33 44  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249385

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C(CC2CN3CCC4=C(NC5=CC(OC)=CC=C45)C3CC2C1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3

> <INCHI_KEY>
QEVHRUUCFGRFIF-UHFFFAOYSA-N

> <FORMULA>
C33H40N2O9

> <MOLECULAR_WEIGHT>
608.688

> <EXACT_MASS>
608.273380876

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
66.35245357703664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
3.531495942666668

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.29011270611733

> <JCHEM_PKA_STRONGEST_BASIC>
7.015256831722955

> <JCHEM_POLAR_SURFACE_AREA>
117.78000000000002

> <JCHEM_REFRACTIVITY>
161.41849999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249385
     RDKit          3D
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy...
 84 89  0  0  0  0  0  0  0  0999 V2000
   -2.4612    2.6199   -2.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    1.9102   -1.7285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261    0.6954   -2.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    0.2408   -3.2695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    0.0163   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -0.3392    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2787   -0.5844   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750   -0.6073    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5106   -0.6640    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3801   -1.7088    0.6375 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5897   -1.1785    0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8159   -1.7662    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9194   -0.9714   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0051    0.2045    0.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1858   -1.7649    0.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9270    3.0132   -3.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6834    2.5312    1.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    1.9040    2.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0545   -0.3688    2.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161    1.4029    2.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2014    1.9618   -3.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
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 44 84  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       3.773  -3.794   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.265  -5.248   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.762  -7.869   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.041  -5.827   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      18.433  -6.484   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.804  -4.387   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.286  -3.507   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.794  -2.054   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.249  -8.156   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.741  -9.610   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.746 -10.776   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.228  -9.897   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.280 -11.350   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.793 -11.637   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.302 -13.091   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.815 -13.378   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.799 -10.470   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.312 -10.757   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.820 -12.211   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.291  -9.017   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.296  -7.850   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.788  -6.396   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.777  -8.730   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   11   14                                                  
CONECT   22   12    8   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    6   25                                                  
CONECT   25   24    3   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30    4   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   44                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   33                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

COMPND    HMDB0249385
HETATM    1  C1  UNL     1      -2.461   2.620  -2.562  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.564   1.910  -1.728  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.026   0.695  -2.145  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.350   0.241  -3.269  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.092   0.016  -1.210  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.823  -0.339   0.023  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.279  -0.584  -0.204  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.075  -0.607   1.078  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.511  -0.664   0.795  1.00  0.00           C  
HETATM   10  N1  UNL     1      -5.380  -1.709   0.638  1.00  0.00           N  
HETATM   11  C8  UNL     1      -6.590  -1.179   0.393  1.00  0.00           C  
HETATM   12  C9  UNL     1      -7.816  -1.766   0.160  1.00  0.00           C  
HETATM   13  C10 UNL     1      -8.919  -0.971  -0.066  1.00  0.00           C  
HETATM   14  O3  UNL     1     -10.163  -1.571  -0.302  1.00  0.00           O  
HETATM   15  C11 UNL     1     -10.273  -2.981  -0.304  1.00  0.00           C  
HETATM   16  C12 UNL     1      -8.791   0.413  -0.059  1.00  0.00           C  
HETATM   17  C13 UNL     1      -7.584   1.023   0.170  1.00  0.00           C  
HETATM   18  C14 UNL     1      -6.498   0.197   0.393  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.192   0.527   0.646  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.418   1.785   0.783  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.403   1.671   1.863  1.00  0.00           C  
HETATM   22  N2  UNL     1      -2.751   0.428   1.980  1.00  0.00           N  
HETATM   23  C18 UNL     1      -1.360   0.501   2.336  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.530   0.673   1.090  1.00  0.00           C  
HETATM   25  C20 UNL     1       0.953   0.450   1.429  1.00  0.00           C  
HETATM   26  C21 UNL     1       1.768   0.918   0.262  1.00  0.00           C  
HETATM   27  O4  UNL     1       3.005   0.204   0.210  1.00  0.00           O  
HETATM   28  C22 UNL     1       4.232   0.806   0.449  1.00  0.00           C  
HETATM   29  O5  UNL     1       4.238   2.028   0.720  1.00  0.00           O  
HETATM   30  C23 UNL     1       5.498   0.091   0.400  1.00  0.00           C  
HETATM   31  C24 UNL     1       5.561  -1.260   0.104  1.00  0.00           C  
HETATM   32  C25 UNL     1       6.780  -1.895   0.071  1.00  0.00           C  
HETATM   33  O6  UNL     1       6.905  -3.236  -0.217  1.00  0.00           O  
HETATM   34  C26 UNL     1       5.835  -4.101  -0.507  1.00  0.00           C  
HETATM   35  C27 UNL     1       7.920  -1.169   0.335  1.00  0.00           C  
HETATM   36  O7  UNL     1       9.186  -1.765   0.315  1.00  0.00           O  
HETATM   37  C28 UNL     1       9.658  -2.309   1.522  1.00  0.00           C  
HETATM   38  C29 UNL     1       7.878   0.183   0.634  1.00  0.00           C  
HETATM   39  O8  UNL     1       9.059   0.895   0.900  1.00  0.00           O  
HETATM   40  C30 UNL     1       8.969   2.264   1.199  1.00  0.00           C  
HETATM   41  C31 UNL     1       6.651   0.799   0.662  1.00  0.00           C  
HETATM   42  C32 UNL     1       1.088   0.931  -1.051  1.00  0.00           C  
HETATM   43  O9  UNL     1       0.750   2.234  -1.413  1.00  0.00           O  
HETATM   44  C33 UNL     1       1.449   2.612  -2.554  1.00  0.00           C  
HETATM   45  H1  UNL     1      -1.927   3.013  -3.462  1.00  0.00           H  
HETATM   46  H2  UNL     1      -3.348   2.013  -2.816  1.00  0.00           H  
HETATM   47  H3  UNL     1      -2.817   3.519  -2.005  1.00  0.00           H  
HETATM   48  H4  UNL     1       0.193  -0.944  -1.731  1.00  0.00           H  
HETATM   49  H5  UNL     1      -0.381  -1.311   0.407  1.00  0.00           H  
HETATM   50  H6  UNL     1      -2.753   0.066  -0.965  1.00  0.00           H  
HETATM   51  H7  UNL     1      -2.364  -1.627  -0.635  1.00  0.00           H  
HETATM   52  H8  UNL     1      -2.794  -1.583   1.577  1.00  0.00           H  
HETATM   53  H9  UNL     1      -5.142  -2.739   0.698  1.00  0.00           H  
HETATM   54  H10 UNL     1      -7.919  -2.845   0.155  1.00  0.00           H  
HETATM   55  H11 UNL     1      -9.530  -3.409  -1.015  1.00  0.00           H  
HETATM   56  H12 UNL     1     -11.308  -3.247  -0.645  1.00  0.00           H  
HETATM   57  H13 UNL     1     -10.096  -3.371   0.722  1.00  0.00           H  
HETATM   58  H14 UNL     1      -9.674   1.007  -0.241  1.00  0.00           H  
HETATM   59  H15 UNL     1      -7.443   2.102   0.185  1.00  0.00           H  
HETATM   60  H16 UNL     1      -4.009   2.140  -0.168  1.00  0.00           H  
HETATM   61  H17 UNL     1      -5.148   2.589   1.100  1.00  0.00           H  
HETATM   62  H18 UNL     1      -2.683   2.531   1.726  1.00  0.00           H  
HETATM   63  H19 UNL     1      -3.902   1.904   2.842  1.00  0.00           H  
HETATM   64  H20 UNL     1      -1.054  -0.369   2.937  1.00  0.00           H  
HETATM   65  H21 UNL     1      -1.216   1.403   2.963  1.00  0.00           H  
HETATM   66  H22 UNL     1      -0.626   1.724   0.758  1.00  0.00           H  
HETATM   67  H23 UNL     1       1.067  -0.660   1.500  1.00  0.00           H  
HETATM   68  H24 UNL     1       1.225   0.910   2.383  1.00  0.00           H  
HETATM   69  H25 UNL     1       2.058   1.982   0.518  1.00  0.00           H  
HETATM   70  H26 UNL     1       4.652  -1.776  -0.095  1.00  0.00           H  
HETATM   71  H27 UNL     1       6.287  -5.014  -0.984  1.00  0.00           H  
HETATM   72  H28 UNL     1       5.299  -4.466   0.389  1.00  0.00           H  
HETATM   73  H29 UNL     1       5.180  -3.563  -1.224  1.00  0.00           H  
HETATM   74  H30 UNL     1      10.500  -1.736   1.954  1.00  0.00           H  
HETATM   75  H31 UNL     1      10.025  -3.345   1.347  1.00  0.00           H  
HETATM   76  H32 UNL     1       8.865  -2.390   2.305  1.00  0.00           H  
HETATM   77  H33 UNL     1       8.340   2.442   2.117  1.00  0.00           H  
HETATM   78  H34 UNL     1       8.553   2.796   0.341  1.00  0.00           H  
HETATM   79  H35 UNL     1       9.988   2.637   1.479  1.00  0.00           H  
HETATM   80  H36 UNL     1       6.643   1.863   0.900  1.00  0.00           H  
HETATM   81  H37 UNL     1       1.837   0.586  -1.811  1.00  0.00           H  
HETATM   82  H38 UNL     1       1.139   3.668  -2.800  1.00  0.00           H  
HETATM   83  H39 UNL     1       2.550   2.526  -2.432  1.00  0.00           H  
HETATM   84  H40 UNL     1       1.201   1.962  -3.437  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   42   48
CONECT    6    7   24   49
CONECT    7    8   50   51
CONECT    8    9   22   52
CONECT    9   10   19   19
CONECT   10   11   53
CONECT   11   12   12   18
CONECT   12   13   54
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   55   56   57
CONECT   16   17   58
CONECT   17   18   18   59
CONECT   18   19
CONECT   19   20
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23
CONECT   23   24   64   65
CONECT   24   25   66
CONECT   25   26   67   68
CONECT   26   27   42   69
CONECT   27   28
CONECT   28   29   29   30
CONECT   30   31   31   41
CONECT   31   32   70
CONECT   32   33   35   35
CONECT   33   34
CONECT   34   71   72   73
CONECT   35   36   38
CONECT   36   37
CONECT   37   74   75   76
CONECT   38   39   41   41
CONECT   39   40
CONECT   40   77   78   79
CONECT   41   80
CONECT   42   43   81
CONECT   43   44
CONECT   44   82   83   84
END

HMDB0249385
     RDKit          3D
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy...
 84 89  0  0  0  0  0  0  0  0999 V2000
   -2.4612    2.6199   -2.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    1.9102   -1.7285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261    0.6954   -2.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    0.2408   -3.2695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    0.0163   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -0.3392    0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2787   -0.5844   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0750   -0.6073    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5106   -0.6640    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3801   -1.7088    0.6375 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5897   -1.1785    0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8159   -1.7662    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9194   -0.9714   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1628   -1.5706   -0.3015 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2733   -2.9813   -0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7915    0.4127   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5838    1.0228    0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4983    0.1971    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1916    0.5268    0.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.7853    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4032    1.6711    1.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    0.4284    1.9803 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598    0.5015    2.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    0.6731    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9528    0.4501    1.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682    0.9180    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0051    0.2045    0.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2315    0.8063    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2379    2.0284    0.7195 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4975    0.0908    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -1.2602    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7801   -1.8951    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9049   -3.2361   -0.2173 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8348   -4.1012   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9196   -1.1690    0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1858   -1.7649    0.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6578   -2.3085    1.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8778    0.1826    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0588    0.8953    0.8995 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9688    2.2637    1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6511    0.7989    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    0.9313   -1.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    2.2336   -1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4485    2.6119   -2.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270    3.0132   -3.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    2.0132   -2.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166    3.5191   -2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934   -0.9437   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3807   -1.3107    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    0.0660   -0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640   -1.6271   -0.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942   -1.5831    1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419   -2.7386    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9190   -2.8445    0.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5299   -3.4094   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3079   -3.2466   -0.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0959   -3.3709    0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6736    1.0068   -0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4434    2.1023    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0087    2.1402   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1484    2.5895    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    2.5312    1.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    1.9040    2.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0545   -0.3688    2.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2161    1.4029    2.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    1.7237    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0674   -0.6596    1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254    0.9102    2.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581    1.9817    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6521   -1.7765   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2872   -5.0141   -0.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993   -4.4663    0.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802   -3.5626   -1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5003   -1.7361    1.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0248   -3.3449    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8648   -2.3898    2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396    2.4420    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5531    2.7959    0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9876    2.6368    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6431    1.8630    0.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368    0.5861   -1.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385    3.6683   -2.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500    2.5258   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2014    1.9618   -3.4367 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
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 41 30  1  0
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 18 11  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  5 48  1  0
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  7 50  1  0
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  8 52  1  0
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 42 81  1  0
 44 82  1  0
 44 83  1  0
 44 84  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid	Generator
Regroton	MeSH

Chemical Formula

C₃₃H₄₀N₂O₉

Average Molecular Weight

608.688

Monoisotopic Molecular Weight

608.273380876

IUPAC Name

methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

methyl 6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

CAS Registry Number

Not Available

SMILES

COC1C(CC2CN3CCC4=C(NC5=CC(OC)=CC=C45)C3CC2C1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3

InChI Key

QEVHRUUCFGRFIF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Pyridoindole
Beta-carboline
Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
Benzoate ester
3-alkylindole
Indole
Indole or derivatives
Benzoic acid or derivatives
Benzoyl
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
Pyrrole
Methyl ester
Heteroaromatic compound
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxylic acid ester
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Azacycle
Dialkyl ether
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.05	ALOGPS
logP	3.53	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.29	ChemAxon
pKa (Strongest Basic)	7.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.78 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	161.42 m³·mol⁻¹	ChemAxon
Polarizability	66.35 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	276.093	30932474
DeepCCS	[M+Na]+	251.58	30932474
AllCCS	[M+H]+	241.9	32859911
AllCCS	[M+H-H2O]+	241.0	32859911
AllCCS	[M+NH4]+	242.7	32859911
AllCCS	[M+Na]+	243.0	32859911
AllCCS	[M-H]-	230.2	32859911
AllCCS	[M+Na-2H]-	232.5	32859911
AllCCS	[M+HCOO]-	235.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-	COC1C(CC2CN3CCC4=C(NC5=CC(OC)=CC=C45)C3CC2C1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1	5487.4	Standard polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-	COC1C(CC2CN3CCC4=C(NC5=CC(OC)=CC=C45)C3CC2C1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1	4585.3	Standard non polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-	COC1C(CC2CN3CCC4=C(NC5=CC(OC)=CC=C45)C3CC2C1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1	4855.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-,1TMS,isomer #1	COC(=O)C1C2CC3C4=C(CCN3CC2CC(OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C	4680.5	Semi standard non polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-,1TMS,isomer #1	COC(=O)C1C2CC3C4=C(CCN3CC2CC(OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C	4448.7	Standard non polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-,1TMS,isomer #1	COC(=O)C1C2CC3C4=C(CCN3CC2CC(OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C	6316.7	Standard polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-,1TBDMS,isomer #1	COC(=O)C1C2CC3C4=C(CCN3CC2CC(OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	4799.7	Semi standard non polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-,1TBDMS,isomer #1	COC(=O)C1C2CC3C4=C(CCN3CC2CC(OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	4588.0	Standard non polar	33892256
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-,1TBDMS,isomer #1	COC(=O)C1C2CC3C4=C(CCN3CC2CC(OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	6279.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 25V, Positive-QTOF	splash10-052b-0319207000-1f1643a232b68af4618a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0000009000-dc556162a143019fcb9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Negative-QTOF	splash10-0a4i-0000039000-b460e2b3cffcf3429ac0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 20V, Positive-QTOF	splash10-0a4i-0002009000-31a816ea4ed6be57b049	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 50V, Positive-QTOF	splash10-006t-0944000000-80c745fc7d4619349f51	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0201109000-cf941042733f29a4abde	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 20V, Positive-QTOF	splash10-0a4i-0000009000-ed4716b519bb3cd3eaa8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 10V, Positive-QTOF	splash10-0a4i-0000009000-41363d0e6063ad2d2933	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 30V, Positive-QTOF	splash10-0a4j-0305109000-38c4bffd9bdf805d084e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 40V, Positive-QTOF	splash10-0002-0928000000-626886d83d9209b38581	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0006-0211090000-15151eec3004a4fbf9bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0201109000-b89d40f15a1ee8d090d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-014i-0920000000-8bad2ea47d7ede06b2ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0006-0311090000-7bf27a18c8b6e6d9d1a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0002-0925504000-d0b81de77576b016baf8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0000009000-cecdd73c9cd05e895bf0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 35V, Positive-QTOF	splash10-0002-0108920000-4d1d7b9e7ba13a433d00	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0000039000-299cfd0c181629a056df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 15V, Positive-QTOF	splash10-0a4i-0000009000-83e006221548d14fe566	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0000039000-edd664b1321b158e6878	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-014i-0911000000-bf3f013ed7b518897566	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0000009000-f246e5f3cea1e34ba6c7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 30V, Positive-QTOF	splash10-0a4j-0305109000-ae2fbf7ab6dd0ed6c1f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 50V, Positive-QTOF	splash10-006t-0944000000-fd474bec6ca35de72b20	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- 6V, Positive-QTOF	splash10-0a4i-0110039000-55301d4c893e15d7fe98	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

5052

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)- (HMDB0249385)

MOL for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

3D MOL for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

3D SDF for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

3D-SDF for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

PDB for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

3D PDB for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

SMILES for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

INCHI for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

Structure for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

3D Structure for HMDB0249385 (Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra