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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:58 UTC

Update Date

2022-03-07 02:57:14 UTC

HMDB ID

HMDB0042010

Secondary Accession Numbers

HMDB42010

Metabolite Identification

Common Name

Rutaecarpine

Description

Rutaecarpine, also known as rhetine, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Based on a literature review very few articles have been published on Rutaecarpine.

Structure

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

HMDB0042010
     RDKit          3D
Rutaecarpine
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.8137   -2.4710    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533   -1.3780    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -0.4531   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6264   -0.7257   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414    0.2170   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999    1.4310   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    1.6631   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182    0.7429   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4950    0.9696   -0.5202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.0618   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -1.1189    0.4020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -2.1395    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -1.8702    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310   -0.5633    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330    0.3601   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    1.4559   -0.4954 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302    1.2548   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    2.0553   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108    1.6038   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3490    0.3500    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.4660    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -0.0023    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566   -1.6719    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -0.0103   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    2.1398   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6062   -1.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -3.1002    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4650   -2.3287    1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.6566    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -2.0848    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0919    2.3063   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7943    3.0225   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573    2.2529   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3455   -0.0224    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310   -1.4299    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 22 14  1  0
  8  3  1  0
 15 10  1  0
 22 17  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv0541 09131211532D          

 22 26  0  0  0  0            999 V2000
    5.6934   -0.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106   -0.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6252   -1.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5384   -1.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0155   -0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721   -0.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791   -1.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721   -1.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2363    0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258    0.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2693   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5085   -0.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384   -0.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2012   -1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106   -0.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701   -0.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -0.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768    0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3982   -1.3663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -1.1325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874    0.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    1.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 20 17  2  0  0  0  0
 21 10  1  0  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042010

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1N2CCC3=C(NC4=CC=CC=C34)C2=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2

> <INCHI_KEY>
ACVGWSKVRYFWRP-UHFFFAOYSA-N

> <FORMULA>
C18H13N3O

> <MOLECULAR_WEIGHT>
287.3153

> <EXACT_MASS>
287.105862053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.598989626217012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.9099426283333334

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.441172910157633

> <JCHEM_PKA_STRONGEST_BASIC>
2.417666908355677

> <JCHEM_POLAR_SURFACE_AREA>
48.46

> <JCHEM_REFRACTIVITY>
87.2307

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rutaecarpine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0042010
     RDKit          3D
Rutaecarpine
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.8137   -2.4710    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533   -1.3780    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -0.4531   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6264   -0.7257   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414    0.2170   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999    1.4310   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    1.6631   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182    0.7429   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4950    0.9696   -0.5202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.0618   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -1.1189    0.4020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -2.1395    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -1.8702    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310   -0.5633    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330    0.3601   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    1.4559   -0.4954 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302    1.2548   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    2.0553   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108    1.6038   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3490    0.3500    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.4660    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -0.0023    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566   -1.6719    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -0.0103   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    2.1398   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6062   -1.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -3.1002    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4650   -2.3287    1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.6566    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -2.0848    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0919    2.3063   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7943    3.0225   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573    2.2529   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3455   -0.0224    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310   -1.4299    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 22 14  1  0
  8  3  1  0
 15 10  1  0
 22 17  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      10.628  -0.883   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.513  -1.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.500  -2.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.005  -2.707   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.362  -0.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.508  -0.086   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.108  -3.075   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.508  -2.994   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.041   1.387   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.528   1.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.969  -0.662   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.549  -0.067   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.005  -0.373   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.842  -2.197   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.513  -1.827   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.544  -1.234   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.031  -0.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.010   0.794   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.343  -2.550   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       3.026  -2.114   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       3.523   0.507   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       1.502   2.247   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1   11                                                       
CONECT    6    2   13                                                       
CONECT    7    3   14                                                       
CONECT    8    4   15                                                       
CONECT    9   10   12                                                       
CONECT   10    9   21                                                       
CONECT   11    5   12   14                                                  
CONECT   12    9   11   16                                                  
CONECT   13    6   15   18                                                  
CONECT   14    7   11   19                                                  
CONECT   15    8   13   20                                                  
CONECT   16   12   17   19                                                  
CONECT   17   16   20   21                                                  
CONECT   18   13   21   22                                                  
CONECT   19   14   16                                                       
CONECT   20   15   17                                                       
CONECT   21   10   17   18                                                  
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0042010
HETATM    1  O1  UNL     1      -2.814  -2.471   0.839  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.353  -1.378   0.410  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.275  -0.453  -0.053  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.626  -0.726  -0.041  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.541   0.217  -0.512  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.100   1.431  -0.993  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.742   1.663  -0.987  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.818   0.743  -0.526  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.495   0.970  -0.520  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.594   0.062  -0.066  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.033  -1.119   0.402  1.00  0.00           N  
HETATM   12  C9  UNL     1      -0.159  -2.140   0.909  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.285  -1.870   0.874  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.731  -0.563   0.366  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.833   0.360  -0.089  1.00  0.00           C  
HETATM   16  N3  UNL     1       1.526   1.456  -0.495  1.00  0.00           N  
HETATM   17  C13 UNL     1       2.830   1.255  -0.313  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.930   2.055  -0.565  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.211   1.604  -0.279  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.349   0.350   0.257  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.249  -0.466   0.515  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.008  -0.002   0.227  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.957  -1.672   0.335  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.598  -0.010  -0.497  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.833   2.140  -1.351  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.366   2.606  -1.359  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.394  -3.100   0.346  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.465  -2.329   1.989  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.767  -2.657   0.221  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.724  -2.085   1.888  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.092   2.306  -0.885  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.794   3.022  -0.980  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.057   2.253  -0.487  1.00  0.00           H  
HETATM   34  H12 UNL     1       6.345  -0.022   0.488  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.431  -1.430   0.933  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4    8
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   10   10
CONECT   10   11   15
CONECT   11   12
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   14   15   15   22
CONECT   15   16
CONECT   16   17   31
CONECT   17   18   18   22
CONECT   18   19   32
CONECT   19   20   20   33
CONECT   20   21   34
CONECT   21   22   22   35
END

HMDB0042010
     RDKit          3D
Rutaecarpine
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.8137   -2.4710    0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533   -1.3780    0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -0.4531   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6264   -0.7257   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414    0.2170   -0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0999    1.4310   -0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7417    1.6631   -0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182    0.7429   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4950    0.9696   -0.5202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.0618   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332   -1.1189    0.4020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587   -2.1395    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -1.8702    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310   -0.5633    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330    0.3601   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265    1.4559   -0.4954 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302    1.2548   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    2.0553   -0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108    1.6038   -0.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3490    0.3500    0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2491   -0.4660    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081   -0.0023    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9566   -1.6719    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -0.0103   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8332    2.1398   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6062   -1.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -3.1002    0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4650   -2.3287    1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.6566    0.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -2.0848    1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0919    2.3063   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7943    3.0225   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573    2.2529   -0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3455   -0.0224    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310   -1.4299    0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 22 14  1  0
  8  3  1  0
 15 10  1  0
 22 17  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rutecarpine	Kegg
Rhetine	HMDB
Rutacarpine	HMDB
Rutaecarpin	HMDB

Chemical Formula

C₁₈H₁₃N₃O

Average Molecular Weight

287.3153

Monoisotopic Molecular Weight

287.105862053

IUPAC Name

3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(10),4,6,8,15,17,19-octaen-14-one

Traditional Name

rutaecarpine

CAS Registry Number

84-26-4

SMILES

O=C1N2CCC3=C(NC4=CC=CC=C34)C2=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2

InChI Key

ACVGWSKVRYFWRP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Diazanaphthalene
Pyridopyrimidine
3-alkylindole
Quinazoline
Indole
Pyrimidone
Pyridine
Benzenoid
Pyrimidine
Heteroaromatic compound
Pyrrole
Lactam
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-carbolines (CHEBI:8922 )
Quinazoline alkaloids (C09238 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0042010)

Source

Exogenous

Exogenous (HMDB: HMDB0042010)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260 °C	Not Available
Boiling Point	209.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	0.792 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.91	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.44	ChemAxon
pKa (Strongest Basic)	2.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.23 m³·mol⁻¹	ChemAxon
Polarizability	31.6 Å³	ChemAxon
Number of Rings	5	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]+	162.404	31661259
DarkChem	[M-H]-	166.431	31661259
DeepCCS	[M-2H]-	202.031	30932474
DeepCCS	[M+Na]+	177.596	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	170.1	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	172.8	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	170.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.87 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1783 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2263.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	425.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	238.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	657.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	655.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1118.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	593.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1537.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	431.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	254.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rutaecarpine	O=C1N2CCC3=C(NC4=CC=CC=C34)C2=NC2=CC=CC=C12	3592.3	Standard polar	33892256
Rutaecarpine	O=C1N2CCC3=C(NC4=CC=CC=C34)C2=NC2=CC=CC=C12	2909.4	Standard non polar	33892256
Rutaecarpine	O=C1N2CCC3=C(NC4=CC=CC=C34)C2=NC2=CC=CC=C12	3267.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rutaecarpine,1TMS,isomer #1	C[Si](C)(C)N1C2=C(CCN3C2=NC2=CC=CC=C2C3=O)C2=CC=CC=C21	3277.8	Semi standard non polar	33892256
Rutaecarpine,1TMS,isomer #1	C[Si](C)(C)N1C2=C(CCN3C2=NC2=CC=CC=C2C3=O)C2=CC=CC=C21	3031.1	Standard non polar	33892256
Rutaecarpine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=C(CCN3C2=NC2=CC=CC=C2C3=O)C2=CC=CC=C21	3506.1	Semi standard non polar	33892256
Rutaecarpine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=C(CCN3C2=NC2=CC=CC=C2C3=O)C2=CC=CC=C21	3217.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rutaecarpine GC-MS (Non-derivatized) - 70eV, Positive	splash10-060c-1950000000-170810115c540e84065f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutaecarpine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rutaecarpine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rutaecarpine LC-ESI-qTof , Positive-QTOF	splash10-052f-3940000000-801d2bb05abdf7c5e1c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rutaecarpine , positive-QTOF	splash10-000i-2590000000-35e86b6a012fc59ccba2	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 10V, Positive-QTOF	splash10-000i-0090000000-7216478e0bcf8b7414bf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 20V, Positive-QTOF	splash10-000i-0090000000-a55d58939f3dc921a64e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 40V, Positive-QTOF	splash10-00di-1290000000-f81b4a6cb037ef0ab2f9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 10V, Negative-QTOF	splash10-000i-0090000000-2aab935e401188894dcc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 20V, Negative-QTOF	splash10-000i-0090000000-7386e507d82bbd167adf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 40V, Negative-QTOF	splash10-0cdl-2980000000-8c470c4e6c0579dbb5f5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 10V, Negative-QTOF	splash10-000i-0090000000-f1cb3da485a341921559	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 20V, Negative-QTOF	splash10-000i-0090000000-f1cb3da485a341921559	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 40V, Negative-QTOF	splash10-0540-0490000000-f1b550307cc9e948fca5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 10V, Positive-QTOF	splash10-000i-0090000000-d7d6c33fb0d677140f4f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 20V, Positive-QTOF	splash10-000i-0090000000-d7d6c33fb0d677140f4f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rutaecarpine 40V, Positive-QTOF	splash10-01p9-0390000000-d4d444033da1f6e647ed	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

Not Available

KNApSAcK ID

C00001766

Chemspider ID

59175

KEGG Compound ID

C09238

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rutecarpine

METLIN ID

Not Available

PubChem Compound

65752

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1476971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Rutaecarpine (HMDB0042010)

MOL for HMDB0042010 (Rutaecarpine)

3D MOL for HMDB0042010 (Rutaecarpine)

3D SDF for HMDB0042010 (Rutaecarpine)

3D-SDF for HMDB0042010 (Rutaecarpine)

PDB for HMDB0042010 (Rutaecarpine)

3D PDB for HMDB0042010 (Rutaecarpine)

SMILES for HMDB0042010 (Rutaecarpine)

INCHI for HMDB0042010 (Rutaecarpine)

Structure for HMDB0042010 (Rutaecarpine)

3D Structure for HMDB0042010 (Rutaecarpine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra