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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:19:02 UTC

Update Date

2022-03-07 02:56:20 UTC

HMDB ID

HMDB0039777

Secondary Accession Numbers

HMDB39777

Metabolite Identification

Common Name

Orcein

Description

Once used as a food colouring but now banned throughout the EC Cudbear is a dye extracted from orchil lichens that produces colours in the purple range. It can be used to dye wool and silk, without the use of mordant. Cudbear was the first dye to be invented in modern times, and one of the few dyes to be credited to a named individual. Orcinol is extracted from archil lichen, Rocella tinctoria. It is then converted to orcein by ammonia and air. Orcein is a reddish-brown dye, orchil is a purple-blue dye. Orcein is also used as a stain in microscopy to visualize elastic fibers,Hepatitis B surface antigens and copper associated proteins. It is a mixture of phenoxazone derivates - hydroxyorceins, aminoorceins, and aminoorceinimines.

Structure

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


  Mrv0541 02241220502D          

 37 41  0  0  0  0            999 V2000
   -0.9866    0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0485   -0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3034   -1.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7514   -1.8746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444   -1.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.7470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 34  1  0  0  0  0
 10 35  1  0  0  0  0
  6 36  1  0  0  0  0
  4 37  1  0  0  0  0
M  END

HMDB0039777
     RDKit          3D
Orcein
 61 65  0  0  0  0  0  0  0  0999 V2000
   -1.4774   -1.2346   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9973    1.2658   -2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5782    0.5051   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9502   -0.1788    0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2829   -0.1810    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9664   -0.8577    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7431   -1.5873    1.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    1.9524    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    2.4029    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858    2.7411    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677    2.2383    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
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 21  2  1  0
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 37 61  1  0
M  END


  Mrv0541 02241220502D          

 37 41  0  0  0  0            999 V2000
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   -1.2415   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0485   -0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0285   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 35  1  0  0  0  0
  6 36  1  0  0  0  0
  4 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039777

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC(O)=C1NC1=C(C)C2=C3C(OC2=CC1=O)=CC(=O)C(NC1=C(O)C=C(O)C=C1C)=C3C

> <INCHI_IDENTIFIER>
InChI=1S/C28H24N2O7/c1-11-5-15(31)7-17(33)25(11)29-27-13(3)23-21(9-19(27)35)37-22-10-20(36)28(14(4)24(22)23)30-26-12(2)6-16(32)8-18(26)34/h5-10,29-34H,1-4H3

> <INCHI_KEY>
VPEASJIRGSVXBF-UHFFFAOYSA-N

> <FORMULA>
C28H24N2O7

> <MOLECULAR_WEIGHT>
500.4994

> <EXACT_MASS>
500.158351132

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
53.16057015779707

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,12-bis[(2,4-dihydroxy-6-methylphenyl)amino]-3,13-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1,3,6,9,12-pentaene-5,11-dione

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.173290822333333

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.67819023582024

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.096198912255247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.363691485980933

> <JCHEM_POLAR_SURFACE_AREA>
148.35

> <JCHEM_REFRACTIVITY>
146.30470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,12-bis[(2,4-dihydroxy-6-methylphenyl)amino]-3,13-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1,3,6,9,12-pentaene-5,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039777
     RDKit          3D
Orcein
 61 65  0  0  0  0  0  0  0  0999 V2000
   -1.4774   -1.2346   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.1538   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    0.6185   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.1491   -0.7981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2784   -0.1793   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2560    0.5019   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9973    1.2658   -2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5782    0.5051   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9502   -0.1788    0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2829   -0.1810    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9664   -0.8577    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407   -0.8664    0.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7431   -1.5873    1.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    1.9524    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    2.4029    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858    2.7411    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677    2.2383    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262    2.7601    1.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226    1.9260    1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799    0.7661    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889    0.9629    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797   -0.3206    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -1.4735   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755   -0.1781    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351   -1.1798    0.3578 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057   -0.9404    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -0.6103   -1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6524   -0.4858   -2.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0073   -0.3847   -1.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9662   -0.4940   -0.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3116   -0.2787   -0.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6110   -0.8203    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2928   -1.0440    1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9733   -1.3761    2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    1.0424    1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.2198    1.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746    2.1046    1.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048   -1.4382   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0288   -1.8689    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5305   -1.7630   -0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7589   -0.8041   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    1.1962   -2.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7184    1.0138   -3.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1767    2.3432   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3589    1.0453   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8554   -0.9333    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2554   -1.3957    2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7723   -1.6985    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    3.7179    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270   -2.3649   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218   -1.1751   -1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4098   -1.8314   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6276   -2.1822    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786   -1.4961   -2.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459    0.0447   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449    0.1016   -3.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2924   -0.1265   -2.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677    0.6087   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3487   -0.9120    1.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -1.4584    3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810    3.0355    2.0171 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 24 35  1  0
 35 36  2  0
 35 37  1  0
 21  2  1  0
 33 26  1  0
 12  5  1  0
 21 17  1  0
 37 19  2  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
 10 46  1  0
 11 47  1  0
 13 48  1  0
 16 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
 32 59  1  0
 34 60  1  0
 37 61  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.842   0.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.317  -0.570   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.824  -0.890   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.300  -2.355   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.269  -3.499   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.763  -3.179   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.287  -1.715   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.219  -1.394   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.846  -4.324   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.803  -4.828   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.557  -5.733   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.311  -4.828   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.774  -4.003   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.732  -4.324   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       8.894  -1.394   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      10.400  -1.715   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.431  -0.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.937  -0.890   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.413  -2.355   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.382  -3.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.876  -3.179   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.715  -4.711   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.919  -2.675   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.955   0.895   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.881  -0.754   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.232  -0.754   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.602  -4.711   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.806  -2.675   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    9   23                                                  
CONECT   23   22                                                            
CONECT   24   14   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   28                                                            
CONECT   33   26                                                            
CONECT   34   13                                                            
CONECT   35   10                                                            
CONECT   36    6                                                            
CONECT   37    4                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

COMPND    HMDB0039777
HETATM    1  C1  UNL     1      -1.477  -1.235  -0.675  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.638   0.154  -0.243  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.884   0.618  -0.328  1.00  0.00           C  
HETATM    4  N1  UNL     1      -3.928  -0.149  -0.798  1.00  0.00           N  
HETATM    5  C4  UNL     1      -5.278  -0.179  -0.357  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.256   0.502  -1.044  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.997   1.266  -2.309  1.00  0.00           C  
HETATM    8  C7  UNL     1      -7.578   0.505  -0.614  1.00  0.00           C  
HETATM    9  C8  UNL     1      -7.950  -0.179   0.520  1.00  0.00           C  
HETATM   10  O1  UNL     1      -9.283  -0.181   0.961  1.00  0.00           O  
HETATM   11  C9  UNL     1      -6.966  -0.858   1.201  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.641  -0.866   0.778  1.00  0.00           C  
HETATM   13  O2  UNL     1      -4.743  -1.587   1.551  1.00  0.00           O  
HETATM   14  C11 UNL     1      -3.152   1.952   0.189  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.316   2.403   0.118  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.086   2.741   0.774  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.868   2.238   0.830  1.00  0.00           C  
HETATM   18  O4  UNL     1       0.226   2.760   1.307  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.223   1.926   1.160  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.780   0.766   0.543  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.589   0.963   0.336  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.680  -0.321   0.238  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.368  -1.474  -0.617  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.975  -0.178   0.604  1.00  0.00           C  
HETATM   25  N2  UNL     1       3.935  -1.180   0.358  1.00  0.00           N  
HETATM   26  C20 UNL     1       5.306  -0.940   0.076  1.00  0.00           C  
HETATM   27  C21 UNL     1       5.679  -0.610  -1.206  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.652  -0.486  -2.259  1.00  0.00           C  
HETATM   29  C23 UNL     1       7.007  -0.385  -1.554  1.00  0.00           C  
HETATM   30  C24 UNL     1       7.966  -0.494  -0.598  1.00  0.00           C  
HETATM   31  O5  UNL     1       9.312  -0.279  -0.890  1.00  0.00           O  
HETATM   32  C25 UNL     1       7.611  -0.820   0.674  1.00  0.00           C  
HETATM   33  C26 UNL     1       6.293  -1.044   1.016  1.00  0.00           C  
HETATM   34  O6  UNL     1       5.973  -1.376   2.315  1.00  0.00           O  
HETATM   35  C27 UNL     1       3.420   1.042   1.261  1.00  0.00           C  
HETATM   36  O7  UNL     1       4.610   1.220   1.614  1.00  0.00           O  
HETATM   37  C28 UNL     1       2.475   2.105   1.526  1.00  0.00           C  
HETATM   38  H1  UNL     1      -1.205  -1.438  -1.691  1.00  0.00           H  
HETATM   39  H2  UNL     1      -1.029  -1.869   0.154  1.00  0.00           H  
HETATM   40  H3  UNL     1      -2.530  -1.763  -0.618  1.00  0.00           H  
HETATM   41  H4  UNL     1      -3.759  -0.804  -1.628  1.00  0.00           H  
HETATM   42  H5  UNL     1      -4.946   1.196  -2.601  1.00  0.00           H  
HETATM   43  H6  UNL     1      -6.718   1.014  -3.096  1.00  0.00           H  
HETATM   44  H7  UNL     1      -6.177   2.343  -2.042  1.00  0.00           H  
HETATM   45  H8  UNL     1      -8.359   1.045  -1.157  1.00  0.00           H  
HETATM   46  H9  UNL     1      -9.855  -0.933   0.587  1.00  0.00           H  
HETATM   47  H10 UNL     1      -7.255  -1.396   2.091  1.00  0.00           H  
HETATM   48  H11 UNL     1      -3.772  -1.699   1.404  1.00  0.00           H  
HETATM   49  H12 UNL     1      -2.273   3.718   1.158  1.00  0.00           H  
HETATM   50  H13 UNL     1       1.027  -2.365  -0.132  1.00  0.00           H  
HETATM   51  H14 UNL     1       0.922  -1.175  -1.591  1.00  0.00           H  
HETATM   52  H15 UNL     1       2.410  -1.831  -1.023  1.00  0.00           H  
HETATM   53  H16 UNL     1       3.628  -2.182   0.405  1.00  0.00           H  
HETATM   54  H17 UNL     1       4.379  -1.496  -2.642  1.00  0.00           H  
HETATM   55  H18 UNL     1       3.746   0.045  -1.878  1.00  0.00           H  
HETATM   56  H19 UNL     1       5.045   0.102  -3.108  1.00  0.00           H  
HETATM   57  H20 UNL     1       7.292  -0.126  -2.560  1.00  0.00           H  
HETATM   58  H21 UNL     1       9.768   0.609  -0.828  1.00  0.00           H  
HETATM   59  H22 UNL     1       8.349  -0.912   1.443  1.00  0.00           H  
HETATM   60  H23 UNL     1       6.676  -1.458   3.022  1.00  0.00           H  
HETATM   61  H24 UNL     1       2.781   3.035   2.017  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    3   21
CONECT    3    4   14
CONECT    4    5   41
CONECT    5    6    6   12
CONECT    6    7    8
CONECT    7   42   43   44
CONECT    8    9    9   45
CONECT    9   10   11
CONECT   10   46
CONECT   11   12   12   47
CONECT   12   13
CONECT   13   48
CONECT   14   15   15   16
CONECT   16   17   17   49
CONECT   17   18   21
CONECT   18   19
CONECT   19   20   37   37
CONECT   20   21   21   22
CONECT   22   23   24   24
CONECT   23   50   51   52
CONECT   24   25   35
CONECT   25   26   53
CONECT   26   27   27   33
CONECT   27   28   29
CONECT   28   54   55   56
CONECT   29   30   30   57
CONECT   30   31   32
CONECT   31   58
CONECT   32   33   33   59
CONECT   33   34
CONECT   34   60
CONECT   35   36   36   37
CONECT   37   61
END

HMDB0039777
     RDKit          3D
Orcein
 61 65  0  0  0  0  0  0  0  0999 V2000
   -1.4774   -1.2346   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.1538   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    0.6185   -0.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.1491   -0.7981 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2784   -0.1793   -0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2560    0.5019   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9973    1.2658   -2.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5782    0.5051   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9502   -0.1788    0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2829   -0.1810    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9664   -0.8577    1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407   -0.8664    0.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7431   -1.5873    1.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525    1.9524    0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    2.4029    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858    2.7411    0.7743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677    2.2383    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262    2.7601    1.3075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226    1.9260    1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799    0.7661    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889    0.9629    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797   -0.3206    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680   -1.4735   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755   -0.1781    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351   -1.1798    0.3578 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3057   -0.9404    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -0.6103   -1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6524   -0.4858   -2.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0073   -0.3847   -1.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9662   -0.4940   -0.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3116   -0.2787   -0.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6110   -0.8203    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2928   -1.0440    1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9733   -1.3761    2.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4198    1.0424    1.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.2198    1.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746    2.1046    1.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048   -1.4382   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0288   -1.8689    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5305   -1.7630   -0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7589   -0.8041   -1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460    1.1962   -2.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7184    1.0138   -3.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1767    2.3432   -2.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3589    1.0453   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8554   -0.9333    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2554   -1.3957    2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7723   -1.6985    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735    3.7179    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0270   -2.3649   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218   -1.1751   -1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4098   -1.8314   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6276   -2.1822    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786   -1.4961   -2.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7459    0.0447   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449    0.1016   -3.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2924   -0.1265   -2.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677    0.6087   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3487   -0.9120    1.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -1.4584    3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7810    3.0355    2.0171 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
  3 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 24 35  1  0
 35 36  2  0
 35 37  1  0
 21  2  1  0
 33 26  1  0
 12  5  1  0
 21 17  1  0
 37 19  2  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
 10 46  1  0
 11 47  1  0
 13 48  1  0
 16 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
 32 59  1  0
 34 60  1  0
 37 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PAcein	MeSH
C.I. natural red 28	HMDB
NSC 610930	ChEBI
Orcein	MeSH

Chemical Formula

C₂₈H₂₄N₂O₇

Average Molecular Weight

500.4994

Monoisotopic Molecular Weight

500.158351132

IUPAC Name

4,12-bis[(2,4-dihydroxy-6-methylphenyl)amino]-3,13-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1,3,6,9,12-pentaene-5,11-dione

Traditional Name

4,12-bis[(2,4-dihydroxy-6-methylphenyl)amino]-3,13-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1,3,6,9,12-pentaene-5,11-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1NC1=C(C)C2=C3C(OC2=CC1=O)=CC(=O)C(NC1=C(O)C=C(O)C=C1C)=C3C

InChI Identifier

InChI=1S/C28H24N2O7/c1-11-5-15(31)7-17(33)25(11)29-27-13(3)23-21(9-19(27)35)37-22-10-20(36)28(14(4)24(22)23)30-26-12(2)6-16(32)8-18(26)34/h5-10,29-34H,1-4H3

InChI Key

VPEASJIRGSVXBF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
P-aminophenol
O-aminophenol
Aminotoluene
Aniline or substituted anilines
Resorcinol
M-cresol
Aminophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Secondary ketimine
Furan
Azomethine
Cyclic ketone
Ketone
Ketimine
Oxacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039777)

Cellular substructure

Membrane (HMDB: HMDB0039777)

Source

Exogenous

Food

Food (HMDB: HMDB0039777)

Not Available

Nutrient (HMDB: HMDB0039777)

Industrial application

Dye (HMDB: HMDB0039777)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	4.14	ALOGPS
logP	3.17	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146.3 m³·mol⁻¹	ChemAxon
Polarizability	53.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	215.194	31661259
DarkChem	[M-H]-	209.61	31661259
DeepCCS	[M+H]+	209.448	30932474
DeepCCS	[M-H]-	207.052	30932474
DeepCCS	[M-2H]-	240.191	30932474
DeepCCS	[M+Na]+	215.36	30932474
AllCCS	[M+H]+	219.3	32859911
AllCCS	[M+H-H2O]+	217.4	32859911
AllCCS	[M+NH4]+	221.0	32859911
AllCCS	[M+Na]+	221.5	32859911
AllCCS	[M-H]-	214.2	32859911
AllCCS	[M+Na-2H]-	214.6	32859911
AllCCS	[M+HCOO]-	215.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Orcein	CC1=CC(O)=CC(O)=C1NC1=C(C)C2=C3C(OC2=CC1=O)=CC(=O)C(NC1=C(O)C=C(O)C=C1C)=C3C	6887.5	Standard polar	33892256
Orcein	CC1=CC(O)=CC(O)=C1NC1=C(C)C2=C3C(OC2=CC1=O)=CC(=O)C(NC1=C(O)C=C(O)C=C1C)=C3C	2957.0	Standard non polar	33892256
Orcein	CC1=CC(O)=CC(O)=C1NC1=C(C)C2=C3C(OC2=CC1=O)=CC(=O)C(NC1=C(O)C=C(O)C=C1C)=C3C	5082.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Orcein,1TMS,isomer #1	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C)C=C4O)=C(C)C3=C12	4907.9	Semi standard non polar	33892256
Orcein,1TMS,isomer #2	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O)C=C4O[Si](C)(C)C)=C(C)C3=C12	4897.7	Semi standard non polar	33892256
Orcein,1TMS,isomer #3	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4639.0	Semi standard non polar	33892256
Orcein,2TMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C)C=C4O)=C(C)C3=C12	4739.6	Semi standard non polar	33892256
Orcein,2TMS,isomer #2	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O)C=C4O[Si](C)(C)C)=C(C)C3=C12	4739.3	Semi standard non polar	33892256
Orcein,2TMS,isomer #3	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)=C(C)C3=C12	4737.6	Semi standard non polar	33892256
Orcein,2TMS,isomer #4	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4544.8	Semi standard non polar	33892256
Orcein,2TMS,isomer #5	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4532.9	Semi standard non polar	33892256
Orcein,2TMS,isomer #6	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O)C=C4O[Si](C)(C)C)=C(C)C3=C12	4752.1	Semi standard non polar	33892256
Orcein,2TMS,isomer #7	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4560.7	Semi standard non polar	33892256
Orcein,2TMS,isomer #8	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4529.4	Semi standard non polar	33892256
Orcein,2TMS,isomer #9	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4344.0	Semi standard non polar	33892256
Orcein,3TMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)=C(C)C3=C12	4640.1	Semi standard non polar	33892256
Orcein,3TMS,isomer #10	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4268.4	Semi standard non polar	33892256
Orcein,3TMS,isomer #2	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4492.2	Semi standard non polar	33892256
Orcein,3TMS,isomer #3	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)=C(C)C3=C12	4634.3	Semi standard non polar	33892256
Orcein,3TMS,isomer #4	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4491.9	Semi standard non polar	33892256
Orcein,3TMS,isomer #5	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4454.1	Semi standard non polar	33892256
Orcein,3TMS,isomer #6	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4479.6	Semi standard non polar	33892256
Orcein,3TMS,isomer #7	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4438.1	Semi standard non polar	33892256
Orcein,3TMS,isomer #8	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4293.2	Semi standard non polar	33892256
Orcein,3TMS,isomer #9	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4472.7	Semi standard non polar	33892256
Orcein,4TMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)=C(C)C3=C12	4574.5	Semi standard non polar	33892256
Orcein,4TMS,isomer #2	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4463.2	Semi standard non polar	33892256
Orcein,4TMS,isomer #3	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4416.1	Semi standard non polar	33892256
Orcein,4TMS,isomer #4	CC1=C(N(C2=C(C)C=C(O[Si](C)(C)C)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O)[Si](C)(C)C)=C(C)C3=C12	4314.4	Semi standard non polar	33892256
Orcein,4TMS,isomer #5	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4412.6	Semi standard non polar	33892256
Orcein,4TMS,isomer #6	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4406.7	Semi standard non polar	33892256
Orcein,4TMS,isomer #7	CC1=C(N(C2=C(C)C=C(O[Si](C)(C)C)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4262.1	Semi standard non polar	33892256
Orcein,4TMS,isomer #8	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4232.8	Semi standard non polar	33892256
Orcein,4TMS,isomer #9	CC1=C(N(C2=C(C)C=C(O)C=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4245.6	Semi standard non polar	33892256
Orcein,5TMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4400.9	Semi standard non polar	33892256
Orcein,5TMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4477.6	Standard non polar	33892256
Orcein,5TMS,isomer #2	CC1=C(N(C2=C(C)C=C(O[Si](C)(C)C)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4289.0	Semi standard non polar	33892256
Orcein,5TMS,isomer #2	CC1=C(N(C2=C(C)C=C(O[Si](C)(C)C)C=C2O)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4441.1	Standard non polar	33892256
Orcein,5TMS,isomer #3	CC1=C(N(C2=C(C)C=C(O)C=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4251.6	Semi standard non polar	33892256
Orcein,5TMS,isomer #3	CC1=C(N(C2=C(C)C=C(O)C=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C)C=C4O[Si](C)(C)C)[Si](C)(C)C)=C(C)C3=C12	4457.3	Standard non polar	33892256
Orcein,1TBDMS,isomer #1	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O)=C(C)C3=C12	5082.5	Semi standard non polar	33892256
Orcein,1TBDMS,isomer #2	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5075.8	Semi standard non polar	33892256
Orcein,1TBDMS,isomer #3	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4827.7	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O)=C(C)C3=C12	5136.1	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #2	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5130.2	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #3	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5134.7	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #4	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4933.7	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #5	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4943.1	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #6	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5134.2	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #7	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4938.3	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #8	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4914.6	Semi standard non polar	33892256
Orcein,2TBDMS,isomer #9	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4746.6	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #1	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5226.1	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #10	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4846.5	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #2	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5063.7	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #3	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(NC4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5197.7	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #4	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5047.1	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #5	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5019.3	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #6	CC1=C(NC2=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5036.6	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #7	CC1=C(NC2=C(C)C=C(O)C=C2O)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5015.2	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #8	CC1=C(N(C2=C(C)C=C(O)C=C2O)[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C4O)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	4881.0	Semi standard non polar	33892256
Orcein,3TBDMS,isomer #9	CC1=C(NC2=C(C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(=O)C=C2OC3=CC(=O)C(N(C4=C(C)C=C(O)C=C4O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C3=C12	5019.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Orcein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-0632920000-123dd4ad3a506a96a39d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orcein GC-MS (2 TMS) - 70eV, Positive	splash10-00fs-2330029000-852e97f1e2e24eb53623	2017-10-06	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 - Orcein 10V, Positive-QTOF	splash10-0udi-0000190000-36b73a203923997d9ecc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 20V, Positive-QTOF	splash10-0udi-0225790000-14fd8705726174ab45bf	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 40V, Positive-QTOF	splash10-004i-1904400000-ab7844f6af08a959f022	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 10V, Negative-QTOF	splash10-0002-0000900000-04502af16d5e9088017c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 20V, Negative-QTOF	splash10-0002-0001900000-a135eb875b7008ed9040	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 40V, Negative-QTOF	splash10-004i-3900300000-0ede7f8faee4e358d05f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 10V, Positive-QTOF	splash10-0udi-0000090000-8aee1d79240e4c0d58aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 20V, Positive-QTOF	splash10-0udi-0202490000-8255fed7cac1bd77a92b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 40V, Positive-QTOF	splash10-00ei-0305900000-cf3c7de19607cd988dc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 10V, Negative-QTOF	splash10-0002-0001900000-93cbe327dbf43898f8ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 20V, Negative-QTOF	splash10-0002-0000900000-90727d3b11cb75be3caf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orcein 40V, Negative-QTOF	splash10-000i-1009400000-742fe1b2998d483ad751	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orcein

METLIN ID

Not Available

PubChem Compound

72685

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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

Showing metabocard for Orcein (HMDB0039777)

MOL for HMDB0039777 (Orcein)

3D MOL for HMDB0039777 (Orcein)

3D SDF for HMDB0039777 (Orcein)

3D-SDF for HMDB0039777 (Orcein)

PDB for HMDB0039777 (Orcein)

3D PDB for HMDB0039777 (Orcein)

SMILES for HMDB0039777 (Orcein)

INCHI for HMDB0039777 (Orcein)

Structure for HMDB0039777 (Orcein)

3D Structure for HMDB0039777 (Orcein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra