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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:04 UTC

Update Date

2021-09-14 14:57:39 UTC

HMDB ID

HMDB0060543

Secondary Accession Numbers

HMDB60543

Metabolite Identification

Common Name

6-Hydroxyetodolac

Description

6-Hydroxyetodolac belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. 6-Hydroxyetodolac is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060543
     RDKit          3D
6-Hydroxyetodolac
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.9486    1.9956    2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338    1.7716    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    0.3859    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0223   -0.5382    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -1.8524   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7674   -2.7807   -0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.2084   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214   -1.2846   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -1.3957   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001   -0.1282   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098    0.6679    0.0051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910    0.0047    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.1116   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019    1.2205   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682    1.4470   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7708    0.4086    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    1.5780    1.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    2.4779    1.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    1.7304    2.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523   -0.9941   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -2.2028   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039   -2.5259   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    1.5152    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    3.0971    2.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7693    1.5572    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738    2.4767    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4137    1.9537    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0481   -0.2679    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -3.7439   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.2248   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5091    1.7040    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.1145   -1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    0.7662   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    0.4369   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    2.1043   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    1.8286   -2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    0.4721    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -0.5104    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195    1.0783    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -2.2150    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -2.9726   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7348   -2.5685   -2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -3.4905   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 13 20  1  0
 20 21  1  0
 21 22  1  0
 12  3  1  0
 12  8  2  0
 22  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

[NO NAME]
  Mrv0541 04181210332D          
Created with ChemWriter - http://chemwriter.com
 22 24  0  0  0  0            999 V2000
    6.2901   -0.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7108    1.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2851   -0.3619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053    0.4231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7102    0.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726   -0.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6178   -0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1828   -1.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5294    0.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3168    0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0246   -1.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5380   -0.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004    0.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1360    1.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278   -1.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1043    0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546    0.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860   -1.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8363   -1.9365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 12  1  0  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4  6  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 15  1  0  0  0  0
 10 17  1  0  0  0  0
 11 13  1  0  0  0  0
 11 16  2  0  0  0  0
 13 14  2  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060543

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO4/c1-3-10-7-11(19)8-13-12-5-6-22-17(4-2,9-14(20)21)16(12)18-15(10)13/h7-8,18-19H,3-6,9H2,1-2H3,(H,20,21)

> <INCHI_KEY>
GQHWDDBALZVXBU-UHFFFAOYSA-N

> <FORMULA>
C17H21NO4

> <MOLECULAR_WEIGHT>
303.3529

> <EXACT_MASS>
303.147058165

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.01808155689937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{1,8-diethyl-6-hydroxy-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.1399610859999996

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.597565172035466

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4511251474345785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.212879002327254

> <JCHEM_POLAR_SURFACE_AREA>
82.55

> <JCHEM_REFRACTIVITY>
83.13820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{1,8-diethyl-6-hydroxy-3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060543
     RDKit          3D
6-Hydroxyetodolac
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.9486    1.9956    2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338    1.7716    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    0.3859    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0223   -0.5382    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -1.8524   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7674   -2.7807   -0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.2084   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214   -1.2846   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -1.3957   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001   -0.1282   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098    0.6679    0.0051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910    0.0047    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.1116   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019    1.2205   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682    1.4470   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7708    0.4086    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    1.5780    1.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    2.4779    1.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    1.7304    2.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523   -0.9941   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -2.2028   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039   -2.5259   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    1.5152    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    3.0971    2.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7693    1.5572    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738    2.4767    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4137    1.9537    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0481   -0.2679    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -3.7439   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.2248   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5091    1.7040    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.1145   -1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    0.7662   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    0.4369   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    2.1043   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    1.8286   -2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    0.4721    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -0.5104    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195    1.0783    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -2.2150    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -2.9726   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7348   -2.5685   -2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -3.4905   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 13 20  1  0
 20 21  1  0
 21 22  1  0
 12  3  1  0
 12  8  2  0
 22  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 18-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-12         0                                  
HETATM    1  O   UNK     0      11.742  -0.941   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      14.393   1.870   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.599  -0.676   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.850   0.790   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      10.659   0.242   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.096  -0.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.620  -1.580   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.675  -2.788   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.322   1.745   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.791   1.286   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.080  -1.580   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.246  -2.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.604  -0.115   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.041   0.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.454   2.788   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.025  -2.788   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.261   0.827   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.582   1.712   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.958  -0.941   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.454  -2.467   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.079   2.050   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.428  -3.615   0.000  0.00  0.00           O+0
CONECT    1    5   12                                                       
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4    6   13                                                       
CONECT    5    1    6    9   10                                             
CONECT    6    4    5    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7   12                                                       
CONECT    9    5   15                                                       
CONECT   10    5   17                                                       
CONECT   11    7   13   16                                                  
CONECT   12    1    8                                                       
CONECT   13    4   11   14                                                  
CONECT   14   13   18   19                                                  
CONECT   15    9                                                            
CONECT   16   11   20                                                       
CONECT   17    2    3   10                                                  
CONECT   18   14   21                                                       
CONECT   19   14   20                                                       
CONECT   20   16   19   22                                                  
CONECT   21   18                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060543
HETATM    1  C1  UNL     1      -2.949   1.996   2.153  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.334   1.772   0.703  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.982   0.386   0.307  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.022  -0.538   0.233  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.740  -1.852  -0.129  1.00  0.00           C  
HETATM    6  O1  UNL     1      -4.767  -2.781  -0.206  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.437  -2.208  -0.407  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.421  -1.285  -0.329  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.051  -1.396  -0.566  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.500  -0.128  -0.342  1.00  0.00           C  
HETATM   11  N1  UNL     1      -0.510   0.668   0.005  1.00  0.00           N  
HETATM   12  C10 UNL     1      -1.691   0.005   0.025  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.939   0.112  -0.531  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.102   1.221  -1.611  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.568   1.447  -1.796  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.771   0.409   0.647  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.537   1.578   1.451  1.00  0.00           C  
HETATM   18  O2  UNL     1       1.725   2.478   1.239  1.00  0.00           O  
HETATM   19  O3  UNL     1       3.314   1.730   2.615  1.00  0.00           O  
HETATM   20  O4  UNL     1       2.552  -0.994  -1.176  1.00  0.00           O  
HETATM   21  C16 UNL     1       2.230  -2.203  -0.602  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.804  -2.526  -0.987  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.963   1.515   2.315  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.916   3.097   2.325  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.769   1.557   2.765  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.774   2.477   0.052  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.414   1.954   0.519  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.048  -0.268   0.444  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.552  -3.744  -0.475  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.238  -3.225  -0.685  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.509   1.704   0.241  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.556   2.114  -1.324  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.692   0.766  -2.532  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.075   0.437  -1.767  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.963   2.104  -1.022  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.703   1.829  -2.838  1.00  0.00           H  
HETATM   37  H15 UNL     1       3.842   0.472   0.252  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.802  -0.510   1.291  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.020   1.078   2.902  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.247  -2.215   0.506  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.940  -2.973  -1.001  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.735  -2.569  -2.119  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.471  -3.491  -0.543  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    4   12
CONECT    4    5   28
CONECT    5    6    7    7
CONECT    6   29
CONECT    7    8   30
CONECT    8    9   12   12
CONECT    9   10   10   22
CONECT   10   11   13
CONECT   11   12   31
CONECT   13   14   16   20
CONECT   14   15   32   33
CONECT   15   34   35   36
CONECT   16   17   37   38
CONECT   17   18   18   19
CONECT   19   39
CONECT   20   21
CONECT   21   22   40   41
CONECT   22   42   43
END

HMDB0060543
     RDKit          3D
6-Hydroxyetodolac
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.9486    1.9956    2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3338    1.7716    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    0.3859    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0223   -0.5382    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -1.8524   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7674   -2.7807   -0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -2.2084   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4214   -1.2846   -0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -1.3957   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001   -0.1282   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098    0.6679    0.0051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6910    0.0047    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9393    0.1116   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1019    1.2205   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682    1.4470   -1.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7708    0.4086    0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    1.5780    1.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    2.4779    1.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    1.7304    2.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5523   -0.9941   -1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -2.2028   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039   -2.5259   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    1.5152    2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9156    3.0971    2.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7693    1.5572    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7738    2.4767    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4137    1.9537    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0481   -0.2679    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -3.7439   -0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2375   -3.2248   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5091    1.7040    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.1145   -1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    0.7662   -2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    0.4369   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    2.1043   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028    1.8286   -2.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    0.4721    0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -0.5104    1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0195    1.0783    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -2.2150    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -2.9726   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7348   -2.5685   -2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -3.4905   -0.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 13 20  1  0
 20 21  1  0
 21 22  1  0
 12  3  1  0
 12  8  2  0
 22  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₄

Average Molecular Weight

303.3529

Monoisotopic Molecular Weight

303.147058165

IUPAC Name

2-{1,8-diethyl-6-hydroxy-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

Traditional Name

{1,8-diethyl-6-hydroxy-3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

CAS Registry Number

Not Available

SMILES

CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C1

InChI Identifier

InChI=1S/C17H21NO4/c1-3-10-7-11(19)8-13-12-5-6-22-17(4-2,9-14(20)21)16(12)18-15(10)13/h7-8,18-19H,3-6,9H2,1-2H3,(H,20,21)

InChI Key

GQHWDDBALZVXBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060543)
Liver (HMDB: HMDB0060543)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0060543)

Excreta

Urine (HMDB: HMDB0060543)

Cellular substructure

Cytoplasm (HMDB: HMDB0060543)
Membrane (HMDB: HMDB0060543)

Process

Not Available

Role

Not Available

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	0.17 g/L	ALOGPS
logP	2.7	ALOGPS
logP	3.14	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.14 m³·mol⁻¹	ChemAxon
Polarizability	33.02 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]+	170.947	31661259
DarkChem	[M-H]-	172.154	31661259
DeepCCS	[M+H]+	180.015	30932474
DeepCCS	[M-H]-	177.657	30932474
DeepCCS	[M-2H]-	210.544	30932474
DeepCCS	[M+Na]+	186.108	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.9	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	177.3	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxyetodolac	CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C1	4050.7	Standard polar	33892256
6-Hydroxyetodolac	CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C1	2531.1	Standard non polar	33892256
6-Hydroxyetodolac	CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC(O)=C1	2858.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Hydroxyetodolac,1TMS,isomer #1	CCC1=CC(O)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C	2678.8	Semi standard non polar	33892256
6-Hydroxyetodolac,1TMS,isomer #2	CCC1=CC(O[Si](C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O	2733.5	Semi standard non polar	33892256
6-Hydroxyetodolac,1TMS,isomer #3	CCC1=CC(O)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O	2764.8	Semi standard non polar	33892256
6-Hydroxyetodolac,2TMS,isomer #1	CCC1=CC(O[Si](C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C	2710.9	Semi standard non polar	33892256
6-Hydroxyetodolac,2TMS,isomer #2	CCC1=CC(O)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C	2719.0	Semi standard non polar	33892256
6-Hydroxyetodolac,2TMS,isomer #3	CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O	2801.5	Semi standard non polar	33892256
6-Hydroxyetodolac,3TMS,isomer #1	CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C	2785.9	Semi standard non polar	33892256
6-Hydroxyetodolac,3TMS,isomer #1	CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C	2637.3	Standard non polar	33892256
6-Hydroxyetodolac,3TMS,isomer #1	CCC1=CC(O[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C	2855.7	Standard polar	33892256
6-Hydroxyetodolac,1TBDMS,isomer #1	CCC1=CC(O)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C	2944.7	Semi standard non polar	33892256
6-Hydroxyetodolac,1TBDMS,isomer #2	CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O	2983.2	Semi standard non polar	33892256
6-Hydroxyetodolac,1TBDMS,isomer #3	CCC1=CC(O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O	2971.8	Semi standard non polar	33892256
6-Hydroxyetodolac,2TBDMS,isomer #1	CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1[NH]C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C	3157.8	Semi standard non polar	33892256
6-Hydroxyetodolac,2TBDMS,isomer #2	CCC1=CC(O)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C	3133.7	Semi standard non polar	33892256
6-Hydroxyetodolac,2TBDMS,isomer #3	CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O	3192.3	Semi standard non polar	33892256
6-Hydroxyetodolac,3TBDMS,isomer #1	CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C	3339.1	Semi standard non polar	33892256
6-Hydroxyetodolac,3TBDMS,isomer #1	CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C	3224.4	Standard non polar	33892256
6-Hydroxyetodolac,3TBDMS,isomer #1	CCC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=C2CCOC1(CC)CC(=O)O[Si](C)(C)C(C)(C)C	3155.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyetodolac GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-4390000000-28acab85523823eedbdc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyetodolac GC-MS (2 TMS) - 70eV, Positive	splash10-00lr-2126900000-0e248492895b2eea8859	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyetodolac GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Hydroxyetodolac 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 - 6-Hydroxyetodolac 10V, Positive-QTOF	splash10-000i-0092000000-7d39a27e28deeba32770	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Positive-QTOF	splash10-0k9l-0290000000-e8a5307b083be332bacb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Positive-QTOF	splash10-0c09-1910000000-7a1083d040220cfda613	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 10V, Negative-QTOF	splash10-0pb9-0095000000-061349fb9a57097cdbba	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Negative-QTOF	splash10-0k9x-0091000000-c4910da12bf690da91c2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Negative-QTOF	splash10-00di-0890000000-8f1d7a5126d1f40a5a13	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 10V, Positive-QTOF	splash10-0udr-0079000000-6c0f3c7e90749e496671	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Positive-QTOF	splash10-0zg3-0092000000-f29c01cc188f2ad88391	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Positive-QTOF	splash10-0550-0950000000-694bd08d8a43c121852d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 10V, Negative-QTOF	splash10-0udi-0019000000-41e8b9873576a95f56d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 20V, Negative-QTOF	splash10-0zfr-0097000000-4761ff4c13eef5bdf7cc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Hydroxyetodolac 40V, Negative-QTOF	splash10-0udl-5598000000-c2d358ad89e2fc68a8b4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

METLIN ID

Not Available

PubChem Compound

14146232

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 6-Hydroxyetodolac (HMDB0060543)

MOL for HMDB0060543 (6-Hydroxyetodolac)

3D MOL for HMDB0060543 (6-Hydroxyetodolac)

3D SDF for HMDB0060543 (6-Hydroxyetodolac)

3D-SDF for HMDB0060543 (6-Hydroxyetodolac)

PDB for HMDB0060543 (6-Hydroxyetodolac)

3D PDB for HMDB0060543 (6-Hydroxyetodolac)

SMILES for HMDB0060543 (6-Hydroxyetodolac)

INCHI for HMDB0060543 (6-Hydroxyetodolac)

Structure for HMDB0060543 (6-Hydroxyetodolac)

3D Structure for HMDB0060543 (6-Hydroxyetodolac)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra