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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:00:39 UTC

Update Date

2021-09-26 23:07:42 UTC

HMDB ID

HMDB0254014

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Leonurine

Description

Leonurine, also known as norboldine or SCM-198, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Reaction with sulfuric acid produces syringic acid. Leonurine can be synthesized starting from eudesmic acid. Protection with ethyl chloroformate followed by reaction with thionyl chloride SOCl2 and then tetrahydrofuran yields 4-carboethoxysyringic acid 4-chloro-1-butyl ester. Leonurine is a pseudoalkaloid that has been isolated fromLeonotis leonurus,Leonotis nepetifolia, Leonotis artemisia, Leonurus cardiaca (Motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae. Leonurine is a very strong basic compound (based on its pKa). The chloride is then converted to an amino group via a Gabriel synthesis with potassium pthalimide) followed by hydrazinolysis (Ing–Manske procedure). Leonurine is easily extracted into water. The final step is reaction of the amine with S-methylisothiourea hemisulfate salt. This compound has been identified in human blood as reported by (PMID: 31557052 ). Leonurine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Leonurine 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

HMDB0254014
     RDKit          3D
Leonurine
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.3747   -3.0675    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899   -1.8712    1.7333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6531   -0.6712    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415   -0.5050    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    0.7091    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    0.8799   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    1.9663   -1.0912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.2174   -0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116   -0.0874   -1.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -1.4417   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314   -1.4215   -2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2539   -0.4458   -1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296   -0.8280    0.0614 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -0.0221    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0863    1.2428    0.9313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3100   -0.6185    1.6037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753    1.7983    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    1.6710    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9452    2.7566    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397    4.0049    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675    0.4322    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817    0.3243    1.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190   -3.9072    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -3.2575    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705   -3.1605    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826   -1.3392    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    0.3403   -2.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9303    0.6368   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -2.1335   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870   -1.7397   -0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -2.4406   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2712   -1.1941   -3.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262   -0.4835   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    0.6003   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -1.6641    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265    1.6735    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5363   -0.3774    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8931   -1.3445    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    2.7505   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5106    4.2087    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424    4.8187    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    3.9911   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735   -0.5663    2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
  9 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
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 22 43  1  0
M  END

  Mrv1533004151514192D          

 22 22  0  0  0  0            999 V2000
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   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
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    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
   -2.8579   -0.0000    0.0000 O   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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   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
    4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254014

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1O)C(=O)OCCCCNC(N)=N

> <INCHI_IDENTIFIER>
InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17)

> <INCHI_KEY>
WNGSUWLDMZFYNZ-UHFFFAOYSA-N

> <FORMULA>
C14H21N3O5

> <MOLECULAR_WEIGHT>
311.338

> <EXACT_MASS>
311.148120788

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.9543249639307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-carbamimidamidobutyl 4-hydroxy-3,5-dimethoxybenzoate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.5960715919111994

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.420821783494894

> <JCHEM_PKA_STRONGEST_BASIC>
12.06839126773934

> <JCHEM_POLAR_SURFACE_AREA>
126.89

> <JCHEM_REFRACTIVITY>
91.16500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leonurine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254014
     RDKit          3D
Leonurine
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.3747   -3.0675    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899   -1.8712    1.7333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6531   -0.6712    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415   -0.5050    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    0.7091    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    0.8799   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    1.9663   -1.0912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.2174   -0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116   -0.0874   -1.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -1.4417   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314   -1.4215   -2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2539   -0.4458   -1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296   -0.8280    0.0614 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -0.0221    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0863    1.2428    0.9313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3100   -0.6185    1.6037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753    1.7983    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    1.6710    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9452    2.7566    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397    4.0049    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675    0.4322    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817    0.3243    1.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190   -3.9072    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -3.2575    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705   -3.1605    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826   -1.3392    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    0.3403   -2.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9303    0.6368   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -2.1335   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870   -1.7397   -0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -2.4406   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2712   -1.1941   -3.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262   -0.4835   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    0.6003   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -1.6641    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265    1.6735    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5363   -0.3774    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8931   -1.3445    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    2.7505   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5106    4.2087    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424    4.8187    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    3.9911   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735   -0.5663    2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
  9 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
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       8.002   4.620   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       6.668   2.310   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0254014
HETATM    1  C1  UNL     1      -3.375  -3.067   1.695  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.090  -1.871   1.733  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.653  -0.671   1.206  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.442  -0.505   0.569  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.040   0.709   0.056  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.765   0.880  -0.613  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.367   1.966  -1.091  1.00  0.00           O  
HETATM    8  O3  UNL     1       0.068  -0.217  -0.735  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.312  -0.087  -1.378  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.978  -1.442  -1.352  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.331  -1.422  -2.020  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.254  -0.446  -1.325  1.00  0.00           C  
HETATM   13  N1  UNL     1       4.430  -0.828   0.061  1.00  0.00           N  
HETATM   14  C10 UNL     1       5.266  -0.022   0.866  1.00  0.00           C  
HETATM   15  N2  UNL     1       5.086   1.243   0.931  1.00  0.00           N  
HETATM   16  N3  UNL     1       6.310  -0.618   1.604  1.00  0.00           N  
HETATM   17  C11 UNL     1      -2.875   1.798   0.181  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.097   1.671   0.813  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.945   2.757   0.946  1.00  0.00           O  
HETATM   20  C13 UNL     1      -4.540   4.005   0.422  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.468   0.432   1.318  1.00  0.00           C  
HETATM   22  O5  UNL     1      -5.682   0.324   1.941  1.00  0.00           O  
HETATM   23  H1  UNL     1      -4.119  -3.907   1.648  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.742  -3.257   2.571  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.770  -3.161   0.753  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.783  -1.339   0.464  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.235   0.340  -2.393  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.930   0.637  -0.784  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.340  -2.133  -1.935  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.087  -1.740  -0.308  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.773  -2.441  -1.856  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.271  -1.194  -3.093  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.226  -0.483  -1.872  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.868   0.600  -1.420  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.968  -1.664   0.480  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.327   1.673   0.394  1.00  0.00           H  
HETATM   37  H15 UNL     1       6.536  -0.377   2.589  1.00  0.00           H  
HETATM   38  H16 UNL     1       6.893  -1.344   1.140  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.539   2.750  -0.232  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.511   4.209   0.812  1.00  0.00           H  
HETATM   41  H19 UNL     1      -5.242   4.819   0.690  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.473   3.991  -0.686  1.00  0.00           H  
HETATM   43  H21 UNL     1      -5.974  -0.566   2.316  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   17   17
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35
CONECT   14   15   15   16
CONECT   15   36
CONECT   16   37   38
CONECT   17   18   39
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   40   41   42
CONECT   21   22
CONECT   22   43
END

HMDB0254014
     RDKit          3D
Leonurine
 43 43  0  0  0  0  0  0  0  0999 V2000
   -3.3747   -3.0675    1.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899   -1.8712    1.7333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6531   -0.6712    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415   -0.5050    0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    0.7091    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    0.8799   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    1.9663   -1.0912 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.2174   -0.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3116   -0.0874   -1.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9784   -1.4417   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314   -1.4215   -2.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2539   -0.4458   -1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296   -0.8280    0.0614 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -0.0221    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0863    1.2428    0.9313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3100   -0.6185    1.6037 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753    1.7983    0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0973    1.6710    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9452    2.7566    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5397    4.0049    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675    0.4322    1.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6817    0.3243    1.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190   -3.9072    1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -3.2575    2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705   -3.1605    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826   -1.3392    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351    0.3403   -2.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9303    0.6368   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -2.1335   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870   -1.7397   -0.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -2.4406   -1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2712   -1.1941   -3.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262   -0.4835   -1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    0.6003   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -1.6641    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3265    1.6735    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5363   -0.3774    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8931   -1.3445    1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5387    2.7505   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5106    4.2087    0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2424    4.8187    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4730    3.9911   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735   -0.5663    2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 14 16  1  0
  5 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
  9 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
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Norboldine	Kegg
SCM-198	MeSH
4-Guanidino-N-butyl syringate	MeSH
4-Carbamimidamidobutyl 4-hydroxy-3,5-dimethoxybenzoic acid	Generator

Chemical Formula

C₁₄H₂₁N₃O₅

Average Molecular Weight

311.338

Monoisotopic Molecular Weight

311.148120788

IUPAC Name

4-carbamimidamidobutyl 4-hydroxy-3,5-dimethoxybenzoate

Traditional Name

leonurine

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C(=O)OCCCCNC(N)=N

InChI Identifier

InChI=1S/C14H21N3O5/c1-20-10-7-9(8-11(21-2)12(10)18)13(19)22-6-4-3-5-17-14(15)16/h7-8,18H,3-6H2,1-2H3,(H4,15,16,17)

InChI Key

WNGSUWLDMZFYNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Phenol
Carboxylic acid ester
Guanidine
Carboximidamide
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

trihydroxybenzoic acid (CHEBI:80843 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	0.9	ALOGPS
logP	0.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	12.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	91.16 m³·mol⁻¹	ChemAxon
Polarizability	32.95 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.641	30932474
DeepCCS	[M-H]-	166.283	30932474
DeepCCS	[M-2H]-	199.169	30932474
DeepCCS	[M+Na]+	174.734	30932474
AllCCS	[M+H]+	171.4	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	173.7	32859911
AllCCS	[M+HCOO]-	174.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leonurine	COC1=CC(=CC(OC)=C1O)C(=O)OCCCCNC(N)=N	4415.5	Standard polar	33892256
Leonurine	COC1=CC(=CC(OC)=C1O)C(=O)OCCCCNC(N)=N	2748.5	Standard non polar	33892256
Leonurine	COC1=CC(=CC(OC)=C1O)C(=O)OCCCCNC(N)=N	2984.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leonurine,2TMS,isomer #1	COC1=CC(C(=O)OCCCCNC(=N)N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3077.5	Semi standard non polar	33892256
Leonurine,2TMS,isomer #1	COC1=CC(C(=O)OCCCCNC(=N)N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2671.8	Standard non polar	33892256
Leonurine,2TMS,isomer #1	COC1=CC(C(=O)OCCCCNC(=N)N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4591.4	Standard polar	33892256
Leonurine,2TMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2893.1	Semi standard non polar	33892256
Leonurine,2TMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2693.1	Standard non polar	33892256
Leonurine,2TMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4632.5	Standard polar	33892256
Leonurine,2TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(N)=N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2840.9	Semi standard non polar	33892256
Leonurine,2TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(N)=N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2564.6	Standard non polar	33892256
Leonurine,2TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(N)=N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4655.5	Standard polar	33892256
Leonurine,2TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2995.9	Semi standard non polar	33892256
Leonurine,2TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2864.2	Standard non polar	33892256
Leonurine,2TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	4681.6	Standard polar	33892256
Leonurine,2TMS,isomer #5	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N[Si](C)(C)C)=CC(OC)=C1O	2975.9	Semi standard non polar	33892256
Leonurine,2TMS,isomer #5	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N[Si](C)(C)C)=CC(OC)=C1O	2660.9	Standard non polar	33892256
Leonurine,2TMS,isomer #5	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N[Si](C)(C)C)=CC(OC)=C1O	4757.1	Standard polar	33892256
Leonurine,2TMS,isomer #6	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	3062.9	Semi standard non polar	33892256
Leonurine,2TMS,isomer #6	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2866.3	Standard non polar	33892256
Leonurine,2TMS,isomer #6	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	4591.8	Standard polar	33892256
Leonurine,2TMS,isomer #7	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2855.3	Semi standard non polar	33892256
Leonurine,2TMS,isomer #7	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2657.5	Standard non polar	33892256
Leonurine,2TMS,isomer #7	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	4743.6	Standard polar	33892256
Leonurine,3TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2922.9	Semi standard non polar	33892256
Leonurine,3TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2776.1	Standard non polar	33892256
Leonurine,3TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4126.9	Standard polar	33892256
Leonurine,3TMS,isomer #2	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2913.1	Semi standard non polar	33892256
Leonurine,3TMS,isomer #2	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2483.6	Standard non polar	33892256
Leonurine,3TMS,isomer #2	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4238.9	Standard polar	33892256
Leonurine,3TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2965.8	Semi standard non polar	33892256
Leonurine,3TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2819.8	Standard non polar	33892256
Leonurine,3TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4067.2	Standard polar	33892256
Leonurine,3TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2829.3	Semi standard non polar	33892256
Leonurine,3TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2495.0	Standard non polar	33892256
Leonurine,3TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	4414.3	Standard polar	33892256
Leonurine,3TMS,isomer #5	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2869.6	Semi standard non polar	33892256
Leonurine,3TMS,isomer #5	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2668.4	Standard non polar	33892256
Leonurine,3TMS,isomer #5	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	4179.1	Standard polar	33892256
Leonurine,3TMS,isomer #6	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2899.3	Semi standard non polar	33892256
Leonurine,3TMS,isomer #6	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	3018.8	Standard non polar	33892256
Leonurine,3TMS,isomer #6	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	4164.0	Standard polar	33892256
Leonurine,3TMS,isomer #7	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2899.9	Semi standard non polar	33892256
Leonurine,3TMS,isomer #7	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2730.9	Standard non polar	33892256
Leonurine,3TMS,isomer #7	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	4160.0	Standard polar	33892256
Leonurine,4TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2866.2	Semi standard non polar	33892256
Leonurine,4TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2482.9	Standard non polar	33892256
Leonurine,4TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3768.1	Standard polar	33892256
Leonurine,4TMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2900.3	Semi standard non polar	33892256
Leonurine,4TMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2916.0	Standard non polar	33892256
Leonurine,4TMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3785.7	Standard polar	33892256
Leonurine,4TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2888.6	Semi standard non polar	33892256
Leonurine,4TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2522.7	Standard non polar	33892256
Leonurine,4TMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3773.7	Standard polar	33892256
Leonurine,4TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2891.1	Semi standard non polar	33892256
Leonurine,4TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2792.3	Standard non polar	33892256
Leonurine,4TMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	3645.9	Standard polar	33892256
Leonurine,5TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2932.7	Semi standard non polar	33892256
Leonurine,5TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	2652.1	Standard non polar	33892256
Leonurine,5TMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3309.6	Standard polar	33892256
Leonurine,2TBDMS,isomer #1	COC1=CC(C(=O)OCCCCNC(=N)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3551.5	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #1	COC1=CC(C(=O)OCCCCNC(=N)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3037.2	Standard non polar	33892256
Leonurine,2TBDMS,isomer #1	COC1=CC(C(=O)OCCCCNC(=N)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4379.6	Standard polar	33892256
Leonurine,2TBDMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3394.2	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3047.4	Standard non polar	33892256
Leonurine,2TBDMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4568.8	Standard polar	33892256
Leonurine,2TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(N)=N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3351.1	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(N)=N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2926.1	Standard non polar	33892256
Leonurine,2TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(N)=N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4594.2	Standard polar	33892256
Leonurine,2TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3471.2	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3182.2	Standard non polar	33892256
Leonurine,2TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4383.4	Standard polar	33892256
Leonurine,2TBDMS,isomer #5	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3482.5	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #5	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3019.8	Standard non polar	33892256
Leonurine,2TBDMS,isomer #5	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4377.3	Standard polar	33892256
Leonurine,2TBDMS,isomer #6	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3536.6	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #6	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3194.2	Standard non polar	33892256
Leonurine,2TBDMS,isomer #6	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4347.7	Standard polar	33892256
Leonurine,2TBDMS,isomer #7	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3343.1	Semi standard non polar	33892256
Leonurine,2TBDMS,isomer #7	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	2988.5	Standard non polar	33892256
Leonurine,2TBDMS,isomer #7	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4593.1	Standard polar	33892256
Leonurine,3TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3633.5	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3239.9	Standard non polar	33892256
Leonurine,3TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4104.4	Standard polar	33892256
Leonurine,3TBDMS,isomer #2	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3610.4	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #2	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2964.2	Standard non polar	33892256
Leonurine,3TBDMS,isomer #2	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4093.7	Standard polar	33892256
Leonurine,3TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3663.0	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3286.7	Standard non polar	33892256
Leonurine,3TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4059.4	Standard polar	33892256
Leonurine,3TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3555.2	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	2973.3	Standard non polar	33892256
Leonurine,3TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4443.2	Standard polar	33892256
Leonurine,3TBDMS,isomer #5	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3539.1	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #5	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3097.5	Standard non polar	33892256
Leonurine,3TBDMS,isomer #5	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4051.3	Standard polar	33892256
Leonurine,3TBDMS,isomer #6	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3629.3	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #6	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3456.5	Standard non polar	33892256
Leonurine,3TBDMS,isomer #6	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4102.2	Standard polar	33892256
Leonurine,3TBDMS,isomer #7	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3578.4	Semi standard non polar	33892256
Leonurine,3TBDMS,isomer #7	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3173.4	Standard non polar	33892256
Leonurine,3TBDMS,isomer #7	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4032.7	Standard polar	33892256
Leonurine,4TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3717.0	Semi standard non polar	33892256
Leonurine,4TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3084.4	Standard non polar	33892256
Leonurine,4TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3869.1	Standard polar	33892256
Leonurine,4TBDMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3823.7	Semi standard non polar	33892256
Leonurine,4TBDMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3493.0	Standard non polar	33892256
Leonurine,4TBDMS,isomer #2	COC1=CC(C(=O)OCCCCN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3896.5	Standard polar	33892256
Leonurine,4TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3735.3	Semi standard non polar	33892256
Leonurine,4TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3154.5	Standard non polar	33892256
Leonurine,4TBDMS,isomer #3	COC1=CC(C(=O)OCCCCNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3849.8	Standard polar	33892256
Leonurine,4TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3782.0	Semi standard non polar	33892256
Leonurine,4TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3377.3	Standard non polar	33892256
Leonurine,4TBDMS,isomer #4	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3769.4	Standard polar	33892256
Leonurine,5TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3977.9	Semi standard non polar	33892256
Leonurine,5TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3411.4	Standard non polar	33892256
Leonurine,5TBDMS,isomer #1	COC1=CC(C(=O)OCCCCN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3622.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6910000000-d0598564604cec2b53b7	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonurine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonurine 10V, Positive-QTOF	splash10-03di-0049000000-f423f32eb2aa773e968e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonurine 20V, Positive-QTOF	splash10-0w94-1592000000-75a63f25a21ad3006b5d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonurine 40V, Positive-QTOF	splash10-0536-9810000000-91571e72dd6cefef3e5d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonurine 10V, Negative-QTOF	splash10-03di-0169000000-98441eae3ff283561758	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonurine 20V, Negative-QTOF	splash10-0fri-0190000000-4c09ce3bb6e69b2a2f71	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonurine 40V, Negative-QTOF	splash10-05di-4893000000-3267b234cec5c25b1117	2021-10-12	Wishart Lab	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

C16985

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Leonurine

METLIN ID

Not Available

PubChem Compound

161464

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 Leonurine (HMDB0254014)

MOL for HMDB0254014 (Leonurine)

3D MOL for HMDB0254014 (Leonurine)

3D SDF for HMDB0254014 (Leonurine)

3D-SDF for HMDB0254014 (Leonurine)

PDB for HMDB0254014 (Leonurine)

3D PDB for HMDB0254014 (Leonurine)

SMILES for HMDB0254014 (Leonurine)

INCHI for HMDB0254014 (Leonurine)

Structure for HMDB0254014 (Leonurine)

3D Structure for HMDB0254014 (Leonurine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra