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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:39 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030241

Secondary Accession Numbers

HMDB30241

Metabolite Identification

Common Name

Girinimbine

Description

Girinimbine, also known as NSC 94932, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Based on a literature review a significant number of articles have been published on Girinimbine.

Structure

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

HMDB0030241
     RDKit          3D
Girinimbine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -0.9609   -3.0630   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706   -1.7959   -0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -1.6878   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339   -0.5167   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.5273    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806    1.5819    0.6233 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9616    1.2200    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1113    1.9490    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3193    1.3079    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691    0.0060    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289   -0.7294   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.0770    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4751    0.4524    0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675   -0.7176   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -0.8054   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    0.2460    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.2145    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    0.6350   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.4852    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047    1.5774    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -3.1748   -0.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -3.1553   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213   -3.8862   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -2.5157   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350    2.5124    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    2.9602    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125    1.8771    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351   -0.4383   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2203   -1.7467   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4981    0.6992    1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -0.8096    2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -0.8379    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7853   -0.2284   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8812    1.4416   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    1.1094   -1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2321    2.3139    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    2.4989    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 14  2  1  0
 12  4  1  0
 20 13  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

  Mrv0541 05061305062D          

 20 23  0  0  0  0            999 V2000
    2.6777    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4665    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5058    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030241

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3

> <INCHI_KEY>
GAEQWKVGMHUUKO-UHFFFAOYSA-N

> <FORMULA>
C18H17NO

> <MOLECULAR_WEIGHT>
263.3337

> <EXACT_MASS>
263.131014171

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.801638238253393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazole

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
4.504930480666667

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.849801921735594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.919571545196121

> <JCHEM_POLAR_SURFACE_AREA>
25.02

> <JCHEM_REFRACTIVITY>
82.90680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030241
     RDKit          3D
Girinimbine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -0.9609   -3.0630   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706   -1.7959   -0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -1.6878   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339   -0.5167   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.5273    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806    1.5819    0.6233 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9616    1.2200    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1113    1.9490    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3193    1.3079    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691    0.0060    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289   -0.7294   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.0770    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4751    0.4524    0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675   -0.7176   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -0.8054   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    0.2460    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.2145    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    0.6350   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.4852    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047    1.5774    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -3.1748   -0.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -3.1553   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213   -3.8862   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -2.5157   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350    2.5124    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    2.9602    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125    1.8771    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351   -0.4383   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2203   -1.7467   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4981    0.6992    1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -0.8096    2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -0.8379    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7853   -0.2284   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8812    1.4416   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    1.1094   -1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2321    2.3139    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    2.4989    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 14  2  1  0
 12  4  1  0
 20 13  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.998   4.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.229  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.342   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.071   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.144   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.702   2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.849  -0.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.694  -0.606   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.156  -0.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.228   3.257   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.691   3.345   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.407   1.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.539   0.682   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.921   1.881   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.480  -0.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.076   0.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.846   2.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.464   0.858   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.039  -0.607   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       3.308   2.146   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   15                                                       
CONECT    8    9   13                                                       
CONECT    9    8   18                                                       
CONECT   10   11   14                                                       
CONECT   11    1   10   17                                                  
CONECT   12    6   14   15                                                  
CONECT   13    8   16   17                                                  
CONECT   14   10   12   16                                                  
CONECT   15    7   12   19                                                  
CONECT   16   13   14   19                                                  
CONECT   17   11   13   20                                                  
CONECT   18    2    3    9   20                                             
CONECT   19   15   16                                                       
CONECT   20   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0030241
HETATM    1  C1  UNL     1      -0.961  -3.063  -0.902  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.271  -1.796  -0.485  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.104  -1.688  -0.471  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.734  -0.517  -0.086  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.912   0.527   0.280  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.681   1.582   0.623  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.962   1.220   0.481  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.111   1.949   0.709  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.319   1.308   0.473  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.369   0.006   0.033  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.229  -0.729  -0.197  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.019  -0.077   0.042  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.475   0.452   0.276  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.068  -0.718  -0.109  1.00  0.00           C  
HETATM   15  O1  UNL     1      -2.448  -0.805  -0.117  1.00  0.00           O  
HETATM   16  C14 UNL     1      -3.289   0.246   0.251  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.125  -0.215   1.436  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.236   0.635  -0.887  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.610   1.485   0.659  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.305   1.577   0.669  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.941  -3.175  -0.385  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.041  -3.155  -1.985  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.321  -3.886  -0.498  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.725  -2.516  -0.760  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.335   2.512   0.943  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.057   2.960   1.051  1.00  0.00           H  
HETATM   27  H7  UNL     1       6.212   1.877   0.651  1.00  0.00           H  
HETATM   28  H8  UNL     1       6.335  -0.438  -0.132  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.220  -1.747  -0.540  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.498   0.699   1.944  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.499  -0.810   2.102  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.974  -0.838   1.093  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.785  -0.228  -1.272  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.881   1.442  -0.480  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.577   1.109  -1.672  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.232   2.314   0.948  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.788   2.499   0.972  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   14
CONECT    3    4   24
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7   25
CONECT    7    8    8   12
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   13   14   14   20
CONECT   14   15
CONECT   15   16
CONECT   16   17   18   19
CONECT   17   30   31   32
CONECT   18   33   34   35
CONECT   19   20   20   36
CONECT   20   37
END

HMDB0030241
     RDKit          3D
Girinimbine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -0.9609   -3.0630   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2706   -1.7959   -0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038   -1.6878   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339   -0.5167   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    0.5273    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806    1.5819    0.6233 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9616    1.2200    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1113    1.9490    0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3193    1.3079    0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691    0.0060    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289   -0.7294   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.0770    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4751    0.4524    0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675   -0.7176   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -0.8054   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    0.2460    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1246   -0.2145    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    0.6350   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.4852    0.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3047    1.5774    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -3.1748   -0.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0409   -3.1553   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213   -3.8862   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254   -2.5157   -0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350    2.5124    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574    2.9602    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2125    1.8771    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351   -0.4383   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2203   -1.7467   -0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4981    0.6992    1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -0.8096    2.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9741   -0.8379    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7853   -0.2284   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8812    1.4416   -0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    1.1094   -1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2321    2.3139    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    2.4989    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 14  2  1  0
 12  4  1  0
 20 13  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,11-Dihydro-3,3,5-trimethyl-pyrano(3,2-a)carbazole	HMDB
3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci	HMDB
Girinimbin	HMDB
NSC 94932	HMDB
Girinimbine	ChEMBL, MeSH

Chemical Formula

C₁₈H₁₇NO

Average Molecular Weight

263.3337

Monoisotopic Molecular Weight

263.131014171

IUPAC Name

3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazole

Traditional Name

3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole

CAS Registry Number

23095-44-5

SMILES

CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1

InChI Identifier

InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3

InChI Key

GAEQWKVGMHUUKO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Indole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazoles (CHEBI:69926 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030241)
Cell membrane (HMDB: HMDB0030241)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030241)

Source

Endogenous

Endogenous (HMDB: HMDB0030241)

Plant

Plant (HMDB: HMDB0030241)

Exogenous

Food

Food (HMDB: HMDB0030241)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030241)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.031 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00072 g/L	ALOGPS
logP	5.03	ALOGPS
logP	4.5	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	25.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.91 m³·mol⁻¹	ChemAxon
Polarizability	30.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	162.377	31661259
DarkChem	[M-H]-	161.066	31661259
DeepCCS	[M+H]+	167.4	30932474
DeepCCS	[M-H]-	165.042	30932474
DeepCCS	[M-2H]-	197.928	30932474
DeepCCS	[M+Na]+	173.493	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.6	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.2	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Girinimbine	CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1	3494.9	Standard polar	33892256
Girinimbine	CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1	2648.7	Standard non polar	33892256
Girinimbine	CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1	2522.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Girinimbine,1TMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C)C1=CC=CC=C21	2748.5	Semi standard non polar	33892256
Girinimbine,1TMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C)C1=CC=CC=C21	2263.5	Standard non polar	33892256
Girinimbine,1TBDMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2888.2	Semi standard non polar	33892256
Girinimbine,1TBDMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2481.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Girinimbine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0390000000-5b3fa9ed6294c6938516	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Girinimbine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Girinimbine 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 - Girinimbine LC-ESI-qTof , Positive-QTOF	splash10-00di-0900100000-c917ef851680fb36c083	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Girinimbine , positive-QTOF	splash10-00ec-0980000000-415281ebee755de18f7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Girinimbine , positive-QTOF	splash10-03l0-0390000000-3ba844380d4d94524dd8	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 10V, Positive-QTOF	splash10-03di-0090000000-25275313f14e4865c628	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 20V, Positive-QTOF	splash10-03di-0190000000-4a4710de5186aa728903	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 40V, Positive-QTOF	splash10-0pb9-4790000000-de7062d5462ff7edaa28	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 10V, Negative-QTOF	splash10-03di-0090000000-8a2e57223f0a86762359	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 20V, Negative-QTOF	splash10-03di-0190000000-4bd29e9c325d7dd06942	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 40V, Negative-QTOF	splash10-004l-1930000000-229d4c98ef86dd6b4a40	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 10V, Positive-QTOF	splash10-03di-0090000000-5e460ef1869ed61a8f64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 20V, Positive-QTOF	splash10-03di-0090000000-3298e75076d6764881e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 40V, Positive-QTOF	splash10-074i-0690000000-b1afe8c260a18e4077ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 10V, Negative-QTOF	splash10-03di-0090000000-897fd6fd89cc6eff86e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 20V, Negative-QTOF	splash10-03di-0090000000-897fd6fd89cc6eff86e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Girinimbine 40V, Negative-QTOF	splash10-0ht9-0290000000-c627f12e57f2fa923491	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002064

KNApSAcK ID

C00025171

Chemspider ID

87534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Girinimbine

METLIN ID

Not Available

PubChem Compound

96943

PDB ID

Not Available

ChEBI ID

1001644

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818271

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ko FN, Lee YS, Wu TS, Teng CM: Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia. Biochem Pharmacol. 1994 Jul 19;48(2):353-60. [PubMed:8053931 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Girinimbine (HMDB0030241)

MOL for HMDB0030241 (Girinimbine)

3D MOL for HMDB0030241 (Girinimbine)

3D SDF for HMDB0030241 (Girinimbine)

3D-SDF for HMDB0030241 (Girinimbine)

PDB for HMDB0030241 (Girinimbine)

3D PDB for HMDB0030241 (Girinimbine)

SMILES for HMDB0030241 (Girinimbine)

INCHI for HMDB0030241 (Girinimbine)

Structure for HMDB0030241 (Girinimbine)

3D Structure for HMDB0030241 (Girinimbine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra