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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:44 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030256

Secondary Accession Numbers

HMDB30256

Metabolite Identification

Common Name

Erysopine

Description

Erysopine belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof. Erysopine is a very strong basic compound (based on its pKa). Outside of the human body, erysopine has been detected, but not quantified in, green vegetables. This could make erysopine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030256
     RDKit          3D
Erysopine
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.1930    1.3325   -1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.4782   -0.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.9136   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541    1.2914    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    0.6409    2.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909   -0.5666    1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704   -1.6652    2.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.5803    1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -2.0717    0.1189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -2.5058   -0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -1.5139   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588   -0.3399   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    0.2843   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719    1.3729   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5984    2.0189   -0.2876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    1.8227    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7804    2.9313    1.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.1729    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.0826    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446   -0.6558    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -0.1499   -0.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    1.3793   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.8594   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567    2.3402   -1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.8602   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070    2.1740    1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    0.9280    3.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436   -1.8564    3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -3.6036    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -2.5848    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -3.0128   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973   -3.3371   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4622   -1.9759   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228   -1.1239   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -0.1033   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2879    1.7326   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0956    3.2340    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727    1.5426    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -1.0086   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886    0.2626   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21  3  1  0
 20  6  1  0
 20  9  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
M  END


  Mrv0541 02241216092D          

 21 24  0  0  0  0            999 V2000
   -0.7259   -1.6154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1809    0.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7259    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810    0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810    1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    1.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739    0.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809   -0.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739   -0.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3739   -1.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458   -1.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -1.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -0.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7259    1.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1809    1.6154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -1.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  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
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030256

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1CC23N(CC=C2C=C1)CCC1=C3C=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c1-21-13-3-2-12-5-7-18-6-4-11-8-15(19)16(20)9-14(11)17(12,18)10-13/h2-3,5,8-9,13,19-20H,4,6-7,10H2,1H3

> <INCHI_KEY>
GNBQGLMYBIWCOO-UHFFFAOYSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.51236155997894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2(7),3,5,12,14-pentaene-4,5-diol

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.361124672166971

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.804307041806474

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.681202835079231

> <JCHEM_PKA_STRONGEST_BASIC>
14.310280428301397

> <JCHEM_POLAR_SURFACE_AREA>
52.93000000000001

> <JCHEM_REFRACTIVITY>
83.47460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-methoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2(7),3,5,12,14-pentaene-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030256
     RDKit          3D
Erysopine
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.1930    1.3325   -1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.4782   -0.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.9136   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541    1.2914    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    0.6409    2.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909   -0.5666    1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704   -1.6652    2.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.5803    1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -2.0717    0.1189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -2.5058   -0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -1.5139   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588   -0.3399   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    0.2843   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719    1.3729   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5984    2.0189   -0.2876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    1.8227    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7804    2.9313    1.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.1729    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.0826    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446   -0.6558    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -0.1499   -0.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    1.3793   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.8594   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567    2.3402   -1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.8602   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070    2.1740    1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    0.9280    3.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436   -1.8564    3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -3.6036    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -2.5848    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -3.0128   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973   -3.3371   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4622   -1.9759   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228   -1.1239   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -0.1033   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2879    1.7326   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0956    3.2340    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727    1.5426    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -1.0086   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886    0.2626   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21  3  1  0
 20  6  1  0
 20  9  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.355  -3.015   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -4.071   0.002   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.699   0.754   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.355   0.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.151   0.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.151   2.261   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.205   3.015   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.565   2.261   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.565   0.754   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.071   0.754   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.071  -0.752   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.205   0.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.565  -0.752   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.565  -2.261   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.205  -3.015   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.151  -2.261   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.151  -0.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.355   3.015   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.699   2.261   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.071   3.015   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.725  -2.289   0.000  0.00  0.00           C+0
CONECT    1   16   21                                                       
CONECT    2    3                                                            
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10   13                                                       
CONECT   12    5    9   13   17                                             
CONECT   13   11   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16    1   15   17                                                  
CONECT   17   12   16                                                       
CONECT   18    6   19                                                       
CONECT   19    3   18   20                                                  
CONECT   20   19                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0030256
HETATM    1  C1  UNL     1       4.193   1.333  -1.521  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.551   0.478  -0.629  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.237   0.914  -0.332  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.254   1.291   1.081  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.644   0.641   2.063  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.891  -0.567   1.656  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.570  -1.665   2.306  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.203  -2.580   1.422  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.188  -2.072   0.119  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.642  -2.506  -0.936  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.509  -1.514  -1.594  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.859  -0.340  -0.759  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.085   0.284  -0.931  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.372   1.373  -0.135  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.598   2.019  -0.288  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.465   1.823   0.799  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.780   2.931   1.595  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.258   1.173   0.937  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.928   0.083   0.165  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.345  -0.656   0.265  1.00  0.00           C  
HETATM   21  C17 UNL     1       1.303  -0.150  -0.745  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.613   1.379  -2.483  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.163   0.859  -1.757  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.357   2.340  -1.099  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.105   1.860  -0.933  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.807   2.174   1.361  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.664   0.928   3.096  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.844  -1.856   3.345  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.215  -3.604   1.507  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.271  -2.585   1.604  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.001  -3.013  -1.704  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.297  -3.337  -0.543  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.462  -1.976  -1.946  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.023  -1.124  -2.514  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.766  -0.103  -1.676  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.288   1.733  -0.949  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.096   3.234   2.268  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.573   1.543   1.670  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.843  -1.009  -1.213  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.689   0.263  -1.601  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4   21   25
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    7   20
CONECT    7    8   28
CONECT    8    9   29   30
CONECT    9   10   20
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   13   19
CONECT   13   14   35
CONECT   14   15   16   16
CONECT   15   36
CONECT   16   17   18
CONECT   17   37
CONECT   18   19   19   38
CONECT   19   20
CONECT   20   21
CONECT   21   39   40
END

HMDB0030256
     RDKit          3D
Erysopine
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.1930    1.3325   -1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506    0.4782   -0.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.9136   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541    1.2914    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    0.6409    2.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909   -0.5666    1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5704   -1.6652    2.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032   -2.5803    1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -2.0717    0.1189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -2.5058   -0.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -1.5139   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588   -0.3399   -0.7589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0855    0.2843   -0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719    1.3729   -0.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5984    2.0189   -0.2876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    1.8227    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7804    2.9313    1.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.1729    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283    0.0826    0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446   -0.6558    0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -0.1499   -0.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    1.3793   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.8594   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567    2.3402   -1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.8602   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070    2.1740    1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    0.9280    3.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436   -1.8564    3.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2151   -3.6036    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2713   -2.5848    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -3.0128   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2973   -3.3371   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4622   -1.9759   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228   -1.1239   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -0.1033   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2879    1.7326   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0956    3.2340    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727    1.5426    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433   -1.0086   -1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886    0.2626   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21  3  1  0
 20  6  1  0
 20  9  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 21 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Erysopine	MeSH

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

IUPAC Name

16-methoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2(7),3,5,12,14-pentaene-4,5-diol

Traditional Name

16-methoxy-10-azatetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadeca-2(7),3,5,12,14-pentaene-4,5-diol

CAS Registry Number

545-68-6

SMILES

COC1CC23N(CC=C2C=C1)CCC1=C3C=C(O)C(O)=C1

InChI Identifier

InChI=1S/C17H19NO3/c1-21-13-3-2-12-5-7-18-6-4-11-8-15(19)16(20)9-14(11)17(12,18)10-13/h2-3,5,8-9,13,19-20H,4,6-7,10H2,1H3

InChI Key

GNBQGLMYBIWCOO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Erythrinane skeleton
Tetrahydroisoquinoline
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Pyrroline
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030256)
Cytoplasm (HMDB: HMDB0030256)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030256)

Source

Endogenous

Endogenous (HMDB: HMDB0030256)

Plant

Plant (HMDB: HMDB0030256)

Exogenous

Food

Food (HMDB: HMDB0030256)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	241 - 242 °C	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
Water Solubility	1.19 g/L	ALOGPS
logP	2.01	ALOGPS
logP	1.36	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	14.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.47 m³·mol⁻¹	ChemAxon
Polarizability	30.51 Å³	ChemAxon
Number of Rings	4	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
DarkChem	[M+H]+	167.758	31661259
DarkChem	[M-H]-	166.992	31661259
DeepCCS	[M-2H]-	206.092	30932474
DeepCCS	[M+Na]+	181.656	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	171.2	32859911
AllCCS	[M+Na]+	172.1	32859911
AllCCS	[M-H]-	173.1	32859911
AllCCS	[M+Na-2H]-	172.6	32859911
AllCCS	[M+HCOO]-	172.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erysopine	COC1CC23N(CC=C2C=C1)CCC1=C3C=C(O)C(O)=C1	4176.2	Standard polar	33892256
Erysopine	COC1CC23N(CC=C2C=C1)CCC1=C3C=C(O)C(O)=C1	2431.8	Standard non polar	33892256
Erysopine	COC1CC23N(CC=C2C=C1)CCC1=C3C=C(O)C(O)=C1	2728.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erysopine,1TMS,isomer #1	COC1C=CC2=CCN3CCC4=CC(O)=C(O[Si](C)(C)C)C=C4C23C1	2663.1	Semi standard non polar	33892256
Erysopine,1TMS,isomer #2	COC1C=CC2=CCN3CCC4=CC(O[Si](C)(C)C)=C(O)C=C4C23C1	2676.6	Semi standard non polar	33892256
Erysopine,2TMS,isomer #1	COC1C=CC2=CCN3CCC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4C23C1	2687.2	Semi standard non polar	33892256
Erysopine,1TBDMS,isomer #1	COC1C=CC2=CCN3CCC4=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C4C23C1	2905.8	Semi standard non polar	33892256
Erysopine,1TBDMS,isomer #2	COC1C=CC2=CCN3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C4C23C1	2924.0	Semi standard non polar	33892256
Erysopine,2TBDMS,isomer #1	COC1C=CC2=CCN3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4C23C1	3118.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Erysopine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0390000000-febafbb0abb2f10d1749	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erysopine GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-1009200000-901b69938ba671fa9305	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erysopine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Erysopine 10V, Positive-QTOF	splash10-000i-0090000000-fb4466c4d38b7fed0a40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 20V, Positive-QTOF	splash10-000i-0090000000-cb76bd5eaa186200b9d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 40V, Positive-QTOF	splash10-0h7i-4980000000-d55cf5c59b6c83aadd94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 10V, Negative-QTOF	splash10-001i-0090000000-d38882d4af2baa9ca271	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 20V, Negative-QTOF	splash10-001i-0090000000-d72639ada8031a9b09e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 40V, Negative-QTOF	splash10-0gb9-1190000000-183197ea773b494155d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 10V, Positive-QTOF	splash10-000i-0090000000-12d6d7cf9e71a6a9ec09	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 20V, Positive-QTOF	splash10-000i-0090000000-bfb3c9f046d14fad206f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 40V, Positive-QTOF	splash10-003r-0490000000-d8815fe798493fcf8dcb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 10V, Negative-QTOF	splash10-001i-0090000000-793f02ff50658d83401d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 20V, Negative-QTOF	splash10-001i-0090000000-e1520357fc2d7878a18c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erysopine 40V, Negative-QTOF	splash10-00pl-0190000000-cc76ecd5596766b6ae1d	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB002080

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

12308892

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Erysopine (HMDB0030256)

MOL for HMDB0030256 (Erysopine)

3D MOL for HMDB0030256 (Erysopine)

3D SDF for HMDB0030256 (Erysopine)

3D-SDF for HMDB0030256 (Erysopine)

PDB for HMDB0030256 (Erysopine)

3D PDB for HMDB0030256 (Erysopine)

SMILES for HMDB0030256 (Erysopine)

INCHI for HMDB0030256 (Erysopine)

Structure for HMDB0030256 (Erysopine)

3D Structure for HMDB0030256 (Erysopine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra