Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:31 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030219

Secondary Accession Numbers

HMDB30219

Metabolite Identification

Common Name

Heptaphylline

Description

Heptaphylline 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 very few articles have been published on Heptaphylline.

Structure

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

HMDB0030219
     RDKit          3D
Heptaphylline
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.4886   -1.8647   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7384   -0.8511   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.2923    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -0.9887    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -0.0397    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473    0.4715    0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5423    1.4224   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.8689   -1.1340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5717    1.9265   -1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    2.9232   -2.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337    3.3283   -3.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    1.4592   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    0.5087   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389    0.0166    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2468   -0.8921    1.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024   -0.9778    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -1.7275    1.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -1.6081    1.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335   -0.7284    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3971    0.0296    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0655   -0.1075    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2593   -2.3226   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -1.3821   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8107   -2.7140   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347    0.3087    0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5230    0.2128    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508    1.2690    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -1.8703   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.5461    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860    0.7888    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768    2.5553   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    3.3260   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.8458   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.4503    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.4190    2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644   -2.1815    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3771   -0.6048    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7356    0.7227   -0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061305052D          

 21 23  0  0  0  0            999 V2000
   -0.3053   -2.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643   -2.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8573   -2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    1.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 10  2  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030219

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C2NC3=CC=CC=C3C2=CC(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO2/c1-11(2)7-8-14-17-15(9-12(10-20)18(14)21)13-5-3-4-6-16(13)19-17/h3-7,9-10,19,21H,8H2,1-2H3

> <INCHI_KEY>
ICYHRFZZQCYWNF-UHFFFAOYSA-N

> <FORMULA>
C18H17NO2

> <MOLECULAR_WEIGHT>
279.3331

> <EXACT_MASS>
279.125928793

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.61880327231107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
4.878389711666667

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.053795596263868

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.875894139747321

> <JCHEM_PKA_STRONGEST_BASIC>
-6.071583430236028

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
86.2799

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heptaphylline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030219
     RDKit          3D
Heptaphylline
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.4886   -1.8647   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7384   -0.8511   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.2923    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -0.9887    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -0.0397    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473    0.4715    0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5423    1.4224   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.8689   -1.1340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5717    1.9265   -1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    2.9232   -2.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337    3.3283   -3.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    1.4592   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    0.5087   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389    0.0166    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2468   -0.8921    1.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024   -0.9778    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -1.7275    1.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -1.6081    1.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335   -0.7284    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3971    0.0296    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0655   -0.1075    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2593   -2.3226   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -1.3821   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8107   -2.7140   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347    0.3087    0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5230    0.2128    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508    1.2690    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -1.8703   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.5461    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860    0.7888    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768    2.5553   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    3.3260   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.8458   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.4503    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.4190    2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644   -2.1815    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3771   -0.6048    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7356    0.7227   -0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  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      -0.570  -5.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.107  -4.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.124  -2.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.727   3.059   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.600  -3.944   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -2.234   2.739   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   16                                                       
CONECT    7    8   11                                                       
CONECT    8    7   14                                                       
CONECT    9   12   15                                                       
CONECT   10   12   20                                                       
CONECT   11    1    2    7                                                  
CONECT   12    9   10   18                                                  
CONECT   13    5   15   16                                                  
CONECT   14    8   17   18                                                  
CONECT   15    9   13   17                                                  
CONECT   16    6   13   19                                                  
CONECT   17   14   15   19                                                  
CONECT   18   12   14   21                                                  
CONECT   19   16   17                                                       
CONECT   20   10                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030219
HETATM    1  C1  UNL     1       4.489  -1.865  -0.868  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.738  -0.851  -0.088  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.470   0.292   0.491  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.455  -0.989   0.102  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.632  -0.040   0.855  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.447   0.471   0.165  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.542   1.422  -0.823  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.804   1.869  -1.134  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.572   1.927  -1.494  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.466   2.923  -2.529  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.534   3.328  -3.090  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.828   1.459  -1.161  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.943   0.509  -0.176  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.839   0.017   0.481  1.00  0.00           C  
HETATM   15  N1  UNL     1      -1.247  -0.892   1.385  1.00  0.00           N  
HETATM   16  C13 UNL     1      -2.602  -0.978   1.304  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.548  -1.727   1.972  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.900  -1.608   1.675  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.334  -0.728   0.695  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.397   0.030   0.017  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.065  -0.108   0.330  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.259  -2.323  -0.207  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.954  -1.382  -1.747  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.811  -2.714  -1.152  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.535   0.309   0.164  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.523   0.213   1.618  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.051   1.269   0.200  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.964  -1.870  -0.332  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.266  -0.546   1.797  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.286   0.789   1.256  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.977   2.555  -1.834  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.487   3.326  -2.832  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.702   1.846  -1.678  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.673  -1.450   2.045  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.265  -2.419   2.736  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.664  -2.182   2.181  1.00  0.00           H  
HETATM   37  H16 UNL     1      -6.377  -0.605   0.433  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.736   0.723  -0.755  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    4
CONECT    3   25   26   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7    7   14
CONECT    7    8    9
CONECT    8   31
CONECT    9   10   12   12
CONECT   10   11   11   32
CONECT   12   13   33
CONECT   13   14   14   21
CONECT   14   15
CONECT   15   16   34
CONECT   16   17   17   21
CONECT   17   18   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   21   38
END

HMDB0030219
     RDKit          3D
Heptaphylline
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.4886   -1.8647   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7384   -0.8511   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    0.2923    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -0.9887    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -0.0397    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473    0.4715    0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5423    1.4224   -0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8040    1.8689   -1.1340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5717    1.9265   -1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    2.9232   -2.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5337    3.3283   -3.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    1.4592   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    0.5087   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389    0.0166    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2468   -0.8921    1.3851 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024   -0.9778    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -1.7275    1.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9002   -1.6081    1.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335   -0.7284    0.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3971    0.0296    0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0655   -0.1075    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2593   -2.3226   -0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -1.3821   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8107   -2.7140   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347    0.3087    0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5230    0.2128    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0508    1.2690    0.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639   -1.8703   -0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2664   -0.5461    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860    0.7888    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9768    2.5553   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    3.3260   -2.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.8458   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.4503    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.4190    2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6644   -2.1815    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3771   -0.6048    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7356    0.7227   -0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
 21 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-1-(3-methyl-2-butenyl)-9H-carbazole-3-carboxaldehyde, 9ci	HMDB
3-Formyl-2-hydroxy-1-prenylcarbazole	HMDB
Heptaphylline	MeSH

Chemical Formula

C₁₈H₁₇NO₂

Average Molecular Weight

279.3331

Monoisotopic Molecular Weight

279.125928793

IUPAC Name

2-hydroxy-1-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde

Traditional Name

heptaphylline

CAS Registry Number

17750-35-5

SMILES

CC(C)=CCC1=C2NC3=CC=CC=C3C2=CC(C=O)=C1O

InChI Identifier

InChI=1S/C18H17NO2/c1-11(2)7-8-14-17-15(9-12(10-20)18(14)21)13-5-3-4-6-16(13)19-17/h3-7,9-10,19,21H,8H2,1-2H3

InChI Key

ICYHRFZZQCYWNF-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
Hydroxyindole
Indole
Aryl-aldehyde
Benzenoid
Pyrrole
Vinylogous acid
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Aldehyde
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazoles (CHEBI:69927 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030219)

Cellular substructure

Membrane (HMDB: HMDB0030219)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030219)

Source

Endogenous

Endogenous (HMDB: HMDB0030219)

Plant

Plant (HMDB: HMDB0030219)

Exogenous

Food

Food (HMDB: HMDB0030219)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	171 - 172 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.037 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	0.0047 g/L	ALOGPS
logP	3.85	ALOGPS
logP	4.88	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.28 m³·mol⁻¹	ChemAxon
Polarizability	31.62 Å³	ChemAxon
Number of Rings	3	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]+	165.923	31661259
DarkChem	[M-H]-	162.357	31661259
DeepCCS	[M+H]+	164.188	30932474
DeepCCS	[M-H]-	161.83	30932474
DeepCCS	[M-2H]-	194.908	30932474
DeepCCS	[M+Na]+	170.281	30932474
AllCCS	[M+H]+	165.1	32859911
AllCCS	[M+H-H2O]+	161.4	32859911
AllCCS	[M+NH4]+	168.5	32859911
AllCCS	[M+Na]+	169.5	32859911
AllCCS	[M-H]-	169.3	32859911
AllCCS	[M+Na-2H]-	168.5	32859911
AllCCS	[M+HCOO]-	167.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heptaphylline	CC(C)=CCC1=C2NC3=CC=CC=C3C2=CC(C=O)=C1O	3796.8	Standard polar	33892256
Heptaphylline	CC(C)=CCC1=C2NC3=CC=CC=C3C2=CC(C=O)=C1O	2904.2	Standard non polar	33892256
Heptaphylline	CC(C)=CCC1=C2NC3=CC=CC=C3C2=CC(C=O)=C1O	2848.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heptaphylline,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C=O)=CC2=C1[NH]C1=CC=CC=C12	2863.5	Semi standard non polar	33892256
Heptaphylline,1TMS,isomer #2	CC(C)=CCC1=C(O)C(C=O)=CC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2805.2	Semi standard non polar	33892256
Heptaphylline,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C=O)=CC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2872.9	Semi standard non polar	33892256
Heptaphylline,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C(C=O)=CC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2707.5	Standard non polar	33892256
Heptaphylline,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=CC2=C1[NH]C1=CC=CC=C12	3086.8	Semi standard non polar	33892256
Heptaphylline,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C(C=O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3003.3	Semi standard non polar	33892256
Heptaphylline,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3234.7	Semi standard non polar	33892256
Heptaphylline,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	3089.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Heptaphylline GC-MS (Non-derivatized) - 70eV, Positive	splash10-03du-3090000000-24bcccb0e4fda147e94f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptaphylline GC-MS (1 TMS) - 70eV, Positive	splash10-000i-7069000000-e4c82aa741d4e5b1a20c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptaphylline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptaphylline 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 - Heptaphylline 10V, Positive-QTOF	splash10-001i-0090000000-1932c6fb6b7291767f20	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 20V, Positive-QTOF	splash10-00e9-0090000000-30fa73e6d950b8656207	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 40V, Positive-QTOF	splash10-0gi3-9760000000-19b6becfb32c6689b7e5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 10V, Negative-QTOF	splash10-004i-0090000000-261ef446492f540d04c1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 20V, Negative-QTOF	splash10-004i-0090000000-338a9ce8fe47276a83bc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 40V, Negative-QTOF	splash10-0bt9-1790000000-2e7af0d4d31e6aa049fa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 10V, Positive-QTOF	splash10-00e9-0090000000-b23ce656ba30369a4c20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 20V, Positive-QTOF	splash10-00e9-0190000000-8b517ed02c047661e105	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 40V, Positive-QTOF	splash10-0abd-0890000000-8f900141f7fcd1edfc61	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 10V, Negative-QTOF	splash10-004i-0090000000-50cc1ea4c83b57b666b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 20V, Negative-QTOF	splash10-002b-0190000000-b45ee88216310204a2e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptaphylline 40V, Negative-QTOF	splash10-00l6-0950000000-699dc493b7692e3bbcdc	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

FDB002038

KNApSAcK ID

C00025172

Chemspider ID

4476663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318015

PDB ID

Not Available

ChEBI ID

1178408

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818061

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 Heptaphylline (HMDB0030219)

MOL for HMDB0030219 (Heptaphylline)

3D MOL for HMDB0030219 (Heptaphylline)

3D SDF for HMDB0030219 (Heptaphylline)

3D-SDF for HMDB0030219 (Heptaphylline)

PDB for HMDB0030219 (Heptaphylline)

3D PDB for HMDB0030219 (Heptaphylline)

SMILES for HMDB0030219 (Heptaphylline)

INCHI for HMDB0030219 (Heptaphylline)

Structure for HMDB0030219 (Heptaphylline)

3D Structure for HMDB0030219 (Heptaphylline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra