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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:47:36 UTC

Update Date

2021-09-26 22:57:35 UTC

HMDB ID

HMDB0247722

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Di-deacetyl adrogolide

Description

Di-deacetyl adrogolide belongs to the class of organic compounds known as thienoquinolines. These are heterocyclic compounds containing a thiophene ring fused to a quinoline. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Based on a literature review very few articles have been published on Di-deacetyl adrogolide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Di-deacetyl adrogolide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Di-deacetyl adrogolide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247722
     RDKit          3D
Di-deacetyl adrogolide
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.1950    1.0213    1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8516    1.1376    0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    1.5577   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    0.5044   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240    0.4526   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -0.6287   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2455   -1.5233   -1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544   -0.8779   -1.8810 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165   -2.8002   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -3.1597   -0.6199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2189   -2.0314   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -2.4603    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495   -1.4917    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164   -0.1088    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.8101    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    2.0536    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5620    2.9954    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    2.3595   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412    3.6093   -0.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2794    1.4296   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.2103    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386   -0.9060    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484    1.0544    2.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.7936    1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127    0.0089    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0980   -0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7582    1.7466    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    1.6165   -1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    2.5137   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537    1.2355    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044   -2.5719   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -3.6042   -1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -3.2398    0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -1.6512   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3121   -2.4925   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808   -3.4832    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984   -1.6823    1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.6315    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.5509    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183    2.7329    0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709    4.3049   -0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544    1.7137   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897   -1.1665    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  8  4  1  0
 22 11  1  0
 22  6  1  0
 21 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
M  END


  Mrv1652309112102472D          

 22 25  0  0  0  0            999 V2000
    5.4079   -1.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284   -0.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247   -0.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090   -0.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745    0.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070    1.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1943    0.5270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6446    1.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497    2.3752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2171    1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795    1.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4470    0.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -0.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195    0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7897    2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222    2.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7506   -0.3465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6393   -1.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 16 21  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247722

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC1=CC2=C(CNC3CCC4=CC(O)=C(O)C=C4C23)S1

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3

> <INCHI_KEY>
REHAKLRYABHSQJ-UHFFFAOYSA-N

> <FORMULA>
C18H21NO2S

> <MOLECULAR_WEIGHT>
315.43

> <EXACT_MASS>
315.129300094

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.480594801345106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-propyl-14-thia-11-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,13(17),15-pentaene-4,5-diol

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.8768156077614435

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.926181990979845

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.76111916431108

> <JCHEM_PKA_STRONGEST_BASIC>
9.029448432767166

> <JCHEM_POLAR_SURFACE_AREA>
52.489999999999995

> <JCHEM_REFRACTIVITY>
89.79599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-propyl-14-thia-11-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,13(17),15-pentaene-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247722
     RDKit          3D
Di-deacetyl adrogolide
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.1950    1.0213    1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8516    1.1376    0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    1.5577   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    0.5044   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240    0.4526   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -0.6287   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2455   -1.5233   -1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544   -0.8779   -1.8810 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165   -2.8002   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -3.1597   -0.6199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2189   -2.0314   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -2.4603    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495   -1.4917    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164   -0.1088    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.8101    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    2.0536    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5620    2.9954    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    2.3595   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412    3.6093   -0.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2794    1.4296   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.2103    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386   -0.9060    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484    1.0544    2.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.7936    1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127    0.0089    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0980   -0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7582    1.7466    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    1.6165   -1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    2.5137   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537    1.2355    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044   -2.5719   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -3.6042   -1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -3.2398    0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -1.6512   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3121   -2.4925   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808   -3.4832    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984   -1.6823    1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.6315    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.5509    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183    2.7329    0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709    4.3049   -0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544    1.7137   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897   -1.1665    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  8  4  1  0
 22 11  1  0
 22  6  1  0
 21 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      10.095  -3.198   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.386  -1.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.848  -1.761   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.139  -0.393   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.617  -0.163   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.366   1.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.733   2.065   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       7.829   0.984   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       6.803   3.604   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.506   4.434   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.139   3.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.068   2.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.701   1.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.631  -0.060   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.263  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.034   0.062   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.036   1.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.404   2.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.474   3.847   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.841   4.555   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.401  -0.647   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.193  -2.307   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   11                                                       
CONECT   21   16                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0247722
HETATM    1  C1  UNL     1       4.195   1.021   1.544  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.852   1.138   0.190  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.856   1.558  -0.865  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.775   0.504  -0.915  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.624   0.453  -0.213  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.789  -0.629  -0.446  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.245  -1.523  -1.370  1.00  0.00           C  
HETATM    8  S1  UNL     1       2.754  -0.878  -1.881  1.00  0.00           S  
HETATM    9  C8  UNL     1       0.517  -2.800  -1.755  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.340  -3.160  -0.620  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.219  -2.031  -0.485  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.468  -2.460   0.246  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.849  -1.492   1.345  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.716  -0.109   0.802  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.734   0.810   0.876  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.530   2.054   0.326  1.00  0.00           C  
HETATM   17  O1  UNL     1      -4.562   2.995   0.397  1.00  0.00           O  
HETATM   18  C15 UNL     1      -2.326   2.359  -0.283  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.141   3.609  -0.828  1.00  0.00           O  
HETATM   20  C16 UNL     1      -1.279   1.430  -0.364  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.493   0.210   0.182  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.539  -0.906   0.201  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.948   1.054   2.335  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.450   1.794   1.740  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.713   0.009   1.606  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.182   0.098  -0.102  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.758   1.747   0.195  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.363   1.617  -1.835  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.366   2.514  -0.568  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.354   1.235   0.548  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.104  -2.572  -2.641  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.225  -3.604  -1.907  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.280  -3.240   0.219  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.506  -1.651  -1.513  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.312  -2.492  -0.473  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.381  -3.483   0.674  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.898  -1.682   1.637  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.138  -1.632   2.178  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.676   0.551   1.359  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.418   2.733   0.847  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.871   4.305  -0.789  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.354   1.714  -0.874  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.390  -1.167   1.281  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5    5    8
CONECT    5    6   30
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    9   10   31   32
CONECT   10   11   33
CONECT   11   12   22   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   15   15   21
CONECT   15   16   39
CONECT   16   17   18   18
CONECT   17   40
CONECT   18   19   20
CONECT   19   41
CONECT   20   21   21   42
CONECT   21   22
CONECT   22   43
END

HMDB0247722
     RDKit          3D
Di-deacetyl adrogolide
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.1950    1.0213    1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8516    1.1376    0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8562    1.5577   -0.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753    0.5044   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6240    0.4526   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -0.6287   -0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2455   -1.5233   -1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544   -0.8779   -1.8810 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5165   -2.8002   -1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396   -3.1597   -0.6199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2189   -2.0314   -0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -2.4603    0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8495   -1.4917    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164   -0.1088    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.8101    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    2.0536    0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5620    2.9954    0.3970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    2.3595   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1412    3.6093   -0.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2794    1.4296   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    0.2103    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386   -0.9060    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9484    1.0544    2.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.7936    1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127    0.0089    1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0980   -0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7582    1.7466    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    1.6165   -1.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655    2.5137   -0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537    1.2355    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044   -2.5719   -2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -3.6042   -1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -3.2398    0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -1.6512   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3121   -2.4925   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808   -3.4832    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8984   -1.6823    1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.6315    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760    0.5509    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183    2.7329    0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709    4.3049   -0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544    1.7137   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897   -1.1665    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
  8  4  1  0
 22 11  1  0
 22  6  1  0
 21 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₂S

Average Molecular Weight

315.43

Monoisotopic Molecular Weight

315.129300094

IUPAC Name

15-propyl-14-thia-11-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,13(17),15-pentaene-4,5-diol

Traditional Name

15-propyl-14-thia-11-azatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-2,4,6,13(17),15-pentaene-4,5-diol

CAS Registry Number

Not Available

SMILES

CCCC1=CC2=C(CNC3CCC4=CC(O)=C(O)C=C4C23)S1

InChI Identifier

InChI=1S/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3

InChI Key

REHAKLRYABHSQJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienoquinolines. These are heterocyclic compounds containing a thiophene ring fused to a quinoline. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Thienoquinolines

Alternative Parents

Substituents

Thienoquinoline
Benzoquinoline
Tetralin
2,3,5-trisubstituted thiophene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Heteroaromatic compound
Thiophene
Secondary amine
Secondary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	3.4	ALOGPS
logP	3.88	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.8 m³·mol⁻¹	ChemAxon
Polarizability	35.48 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	209.051	30932474
DeepCCS	[M+Na]+	184.528	30932474
AllCCS	[M+H]+	176.1	32859911
AllCCS	[M+H-H2O]+	172.9	32859911
AllCCS	[M+NH4]+	179.0	32859911
AllCCS	[M+Na]+	179.9	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	182.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.3372 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.92 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	799.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	174.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	135.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	142.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	352.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	315.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	627.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	759.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	307.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	932.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	373.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	118.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Di-deacetyl adrogolide	CCCC1=CC2=C(CNC3CCC4=CC(O)=C(O)C=C4C23)S1	4080.8	Standard polar	33892256
Di-deacetyl adrogolide	CCCC1=CC2=C(CNC3CCC4=CC(O)=C(O)C=C4C23)S1	2878.8	Standard non polar	33892256
Di-deacetyl adrogolide	CCCC1=CC2=C(CNC3CCC4=CC(O)=C(O)C=C4C23)S1	3104.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Di-deacetyl adrogolide,3TMS,isomer #1	CCCC1=CC2=C(CN([Si](C)(C)C)C3CCC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4C23)S1	2970.7	Semi standard non polar	33892256
Di-deacetyl adrogolide,3TMS,isomer #1	CCCC1=CC2=C(CN([Si](C)(C)C)C3CCC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4C23)S1	3054.5	Standard non polar	33892256
Di-deacetyl adrogolide,3TMS,isomer #1	CCCC1=CC2=C(CN([Si](C)(C)C)C3CCC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4C23)S1	3226.2	Standard polar	33892256
Di-deacetyl adrogolide,3TBDMS,isomer #1	CCCC1=CC2=C(CN([Si](C)(C)C(C)(C)C)C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4C23)S1	3537.9	Semi standard non polar	33892256
Di-deacetyl adrogolide,3TBDMS,isomer #1	CCCC1=CC2=C(CN([Si](C)(C)C(C)(C)C)C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4C23)S1	3750.2	Standard non polar	33892256
Di-deacetyl adrogolide,3TBDMS,isomer #1	CCCC1=CC2=C(CN([Si](C)(C)C(C)(C)C)C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4C23)S1	3538.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f9f-2931000000-5cf15dbf9ec78d443ca5	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-deacetyl adrogolide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	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 - Di-deacetyl adrogolide 10V, Negative-QTOF	splash10-03di-0009000000-54e03750a37a34c097b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-deacetyl adrogolide 20V, Negative-QTOF	splash10-03di-0009000000-84e7e5a70584a67fbca5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-deacetyl adrogolide 40V, Negative-QTOF	splash10-01ot-0290000000-9e1fb391a5b1fb6c02d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-deacetyl adrogolide 10V, Positive-QTOF	splash10-014i-0009000000-1f349adb3b34dd311c26	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-deacetyl adrogolide 20V, Positive-QTOF	splash10-014i-0009000000-d130a6df81ce57039ce9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-deacetyl adrogolide 40V, Positive-QTOF	splash10-001r-0980000000-a375819318ae08c4b5b2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

64879862

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44212156

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Di-deacetyl adrogolide (HMDB0247722)

MOL for HMDB0247722 (Di-deacetyl adrogolide)

3D MOL for HMDB0247722 (Di-deacetyl adrogolide)

3D SDF for HMDB0247722 (Di-deacetyl adrogolide)

3D-SDF for HMDB0247722 (Di-deacetyl adrogolide)

PDB for HMDB0247722 (Di-deacetyl adrogolide)

3D PDB for HMDB0247722 (Di-deacetyl adrogolide)

SMILES for HMDB0247722 (Di-deacetyl adrogolide)

INCHI for HMDB0247722 (Di-deacetyl adrogolide)

Structure for HMDB0247722 (Di-deacetyl adrogolide)

3D Structure for HMDB0247722 (Di-deacetyl adrogolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra