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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 16:49:34 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005886

Secondary Accession Numbers

HMDB05886

Metabolite Identification

Common Name

19-Noretiocholanolone

Description

19-noretiocholanolone (19-NE) is one of the two main indicators used to prove the illegal use of nandrolone by humans. Recent studies showed that 19-NE can be endogenously produced in some individuals. The mediated cases observed over the last years generated some questions about the appropriateness of the official International Olympic Committee cutoff level, which is 2 ng/mL of 19-NA in male urine samples. In 1997, in France, quite a few sportsmen had concentrations of nandrolone metabolites very close to the IOC cut off limit (2ng/ml). At that time, a debate took place about the capability of the human male body to produce by itself these metabolites without any intake of nandrolone or related compounds. The International Football Federation (FIFA) was very concerned with this problem, especially because the World Cup was about to start in France. Concentrations of 19- noretiocholanolone after a game are generally higher than those before games. Recent studies demonstrated the endogenous production of these compounds in man at concentrations very close to the threshold of the International Olympic Committee (IOC), i.e. 2 ng/ml. Because the possibility of reaching or exceeding this fateful limit is difficult to exclude, a complementary biochemical parameter is necessary for the differentiation of endogenous 19-NE production from residues resulting from nandrolone consumption. (PMID: 11888015 , 11755174 ).

Structure

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


  Mrv0541 02231220312D          

 25 28  0  0  1  0            999 V2000
   10.7891   -9.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7891  -10.4031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5035  -10.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2180  -10.4031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2180   -9.5781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5035   -9.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9325  -10.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6469  -10.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6469   -9.5781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9325   -9.1656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3614   -9.1656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3614   -8.3406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6469   -7.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9325   -8.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1461   -9.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6310   -8.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1461   -8.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0745  -10.8156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4477   -7.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4010   -7.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9325   -9.9906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2180   -8.7531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6469   -8.7531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4477   -9.9861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2238  -11.2751    0.0000 H   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  2  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  1  0  0  0
M  END

HMDB0005886
     RDKit          3D
19-Noretiocholanolone
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.0215   -1.2204    0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -0.2512   -0.2300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2539   -0.9262   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -1.4231   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276   -0.3600   -0.5194 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3338   -0.9797   -0.1321 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1771   -1.1097   -1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363   -1.2268   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630   -0.2734   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1951    1.0384   -0.4968 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960   -0.4549    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574   -0.1587    0.9477 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7302    1.3083    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730    1.6125    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.4043    0.6437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9077    0.8951    0.1347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7377    1.7121    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    1.8013    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853    0.5031   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9904    0.1127   -1.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -2.2359    0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1148   -1.3359    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -0.9288    1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -1.8192   -1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -0.1959   -2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157   -1.7919   -2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.3261   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    0.3713   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -1.9883    0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -0.2580   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -2.0228   -1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -0.9915   -2.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -2.2610   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245   -0.5723    0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0522    1.2894   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -1.4803    1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.3078    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -0.3886    1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9598    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9037    1.4913   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    1.9086    2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.4672    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.1887    1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362    1.4595   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    2.7118    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    1.2203    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015    2.0098    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256    2.5848   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
M  END


  Mrv0541 02231220312D          

 25 28  0  0  1  0            999 V2000
   10.7891   -9.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7891  -10.4031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5035  -10.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2180  -10.4031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2180   -9.5781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5035   -9.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9325  -10.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6469  -10.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6469   -9.5781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9325   -9.1656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3614   -9.1656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3614   -8.3406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6469   -7.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9325   -8.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1461   -9.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6310   -8.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1461   -8.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0745  -10.8156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4477   -7.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4010   -7.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9325   -9.9906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2180   -8.7531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6469   -8.7531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4477   -9.9861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2238  -11.2751    0.0000 H   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  2  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
  4 25  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0005886

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-16,19H,2-10H2,1H3/t11-,12-,13+,14-,15-,16+,18+/m1/s1

> <INCHI_KEY>
UOUIARGWRPHDBX-DHMVHTBWSA-N

> <FORMULA>
C18H28O2

> <MOLECULAR_WEIGHT>
276.4137

> <EXACT_MASS>
276.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.65389844431155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
3.4672374166666673

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.961848391949154

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.309468849649495

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3512379990436725

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
79.33379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0005886
     RDKit          3D
19-Noretiocholanolone
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.0215   -1.2204    0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -0.2512   -0.2300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2539   -0.9262   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -1.4231   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276   -0.3600   -0.5194 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3338   -0.9797   -0.1321 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1771   -1.1097   -1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363   -1.2268   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630   -0.2734   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1951    1.0384   -0.4968 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960   -0.4549    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574   -0.1587    0.9477 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7302    1.3083    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730    1.6125    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.4043    0.6437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9077    0.8951    0.1347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7377    1.7121    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    1.8013    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853    0.5031   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9904    0.1127   -1.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -2.2359    0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1148   -1.3359    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -0.9288    1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -1.8192   -1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -0.1959   -2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157   -1.7919   -2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.3261   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    0.3713   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -1.9883    0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -0.2580   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -2.0228   -1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -0.9915   -2.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -2.2610   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245   -0.5723    0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0522    1.2894   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -1.4803    1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.3078    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -0.3886    1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9598    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9037    1.4913   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    1.9086    2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.4672    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.1887    1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362    1.4595   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    2.7118    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    1.2203    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015    2.0098    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256    2.5848   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      20.140 -17.879   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.140 -19.419   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.473 -20.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.807 -19.419   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.807 -17.879   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.473 -17.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.141 -20.189   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.474 -19.419   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.474 -17.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.141 -17.109   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.808 -17.109   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.808 -15.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.474 -14.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.141 -15.569   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.273 -17.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.178 -16.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.273 -15.093   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.806 -20.189   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      26.969 -14.038   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.749 -13.629   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      24.141 -18.649   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      22.807 -16.339   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      25.474 -16.339   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      26.969 -18.641   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      22.818 -21.047   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   25                                             
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20                                                  
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0005886
HETATM    1  C1  UNL     1      -3.022  -1.220   0.911  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.839  -0.251  -0.230  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.254  -0.926  -1.421  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.877  -1.423  -1.062  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.028  -0.360  -0.519  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.334  -0.980  -0.132  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.177  -1.110  -1.368  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.636  -1.227  -1.108  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.163  -0.273  -0.085  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.195   1.038  -0.497  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.396  -0.455   1.205  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.957  -0.159   0.948  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.730   1.308   0.679  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.273   1.612   0.936  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.615   0.404   0.644  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.908   0.895   0.135  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.738   1.712   1.041  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.035   1.801   0.215  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.085   0.503  -0.500  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.990   0.113  -1.193  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.703  -2.236   0.592  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.115  -1.336   1.169  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.525  -0.929   1.835  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.850  -1.819  -1.711  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.157  -0.196  -2.232  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.416  -1.792  -2.004  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.919  -2.326  -0.392  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.213   0.371  -1.330  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.109  -1.988   0.309  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.934  -0.258  -2.044  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.845  -2.023  -1.907  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.170  -0.991  -2.075  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.944  -2.261  -0.860  1.00  0.00           H  
HETATM   34  H14 UNL     1       5.224  -0.572   0.127  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.052   1.289  -0.887  1.00  0.00           H  
HETATM   36  H16 UNL     1       3.536  -1.480   1.567  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.780   0.308   1.913  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.398  -0.389   1.898  1.00  0.00           H  
HETATM   39  H19 UNL     1       2.336   1.960   1.317  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.904   1.491  -0.406  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.129   1.909   2.014  1.00  0.00           H  
HETATM   42  H22 UNL     1      -0.037   2.467   0.320  1.00  0.00           H  
HETATM   43  H23 UNL     1      -0.646  -0.189   1.553  1.00  0.00           H  
HETATM   44  H24 UNL     1      -1.736   1.459  -0.805  1.00  0.00           H  
HETATM   45  H25 UNL     1      -2.298   2.712   1.158  1.00  0.00           H  
HETATM   46  H26 UNL     1      -2.972   1.220   1.997  1.00  0.00           H  
HETATM   47  H27 UNL     1      -4.902   2.010   0.837  1.00  0.00           H  
HETATM   48  H28 UNL     1      -3.826   2.585  -0.555  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   16   19
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   15   28
CONECT    6    7   12   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   11   34
CONECT   10   35
CONECT   11   12   36   37
CONECT   12   13   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43
CONECT   16   17   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   20
END

HMDB0005886
     RDKit          3D
19-Noretiocholanolone
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.0215   -1.2204    0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8388   -0.2512   -0.2300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2539   -0.9262   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770   -1.4231   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276   -0.3600   -0.5194 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3338   -0.9797   -0.1321 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1771   -1.1097   -1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363   -1.2268   -1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630   -0.2734   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1951    1.0384   -0.4968 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960   -0.4549    1.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574   -0.1587    0.9477 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7302    1.3083    0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730    1.6125    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150    0.4043    0.6437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9077    0.8951    0.1347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7377    1.7121    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353    1.8013    0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853    0.5031   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9904    0.1127   -1.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -2.2359    0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1148   -1.3359    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -0.9288    1.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -1.8192   -1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -0.1959   -2.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157   -1.7919   -2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.3261   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    0.3713   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -1.9883    0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9341   -0.2580   -2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -2.0228   -1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -0.9915   -2.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9445   -2.2610   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2245   -0.5723    0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0522    1.2894   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -1.4803    1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803    0.3078    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -0.3886    1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    1.9598    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9037    1.4913   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    1.9086    2.0145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.4672    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.1887    1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362    1.4595   -0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2984    2.7118    1.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720    1.2203    1.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9015    2.0098    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256    2.5848   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  6 29  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  1
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
19-Norandrosterone, (3alpha,5alpha)-isomer	MeSH
19-Norandrosterone, (3beta,5beta)-isomer	MeSH
19-Norandrosterone, (3beta,5alpha,8alpha,9beta,10alpha,13alpha,14beta)-isomer	MeSH
19-Norandrosterone, (3alpha,5beta)-isomer	MeSH
19-Norandrosterone, (3beta)-isomer	MeSH
19-Norandrosterone, (3beta,5alpha)-isomer	MeSH
2,2,3,4,4,-D5-19-Nor-5alpha-androsterone	MeSH
19-Norandrosterone	MeSH
19-Noreoiandrosterone	MeSH
3-Hydroxyestran-17-one	MeSH
(3a,5b)-3-Hydroxy-estran-17-one	HMDB
19-Noretiocholan-3a-ol-17-one	HMDB
3a-Hydroxy-5b-estran-17-one	HMDB
5b-Estran-3a-ol-17-one	HMDB
19-Noretiocholanolone	MeSH

Chemical Formula

C₁₈H₂₈O₂

Average Molecular Weight

276.4137

Monoisotopic Molecular Weight

276.20893014

IUPAC Name

(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one

Traditional Name

(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one

CAS Registry Number

33036-33-8

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[H]

InChI Identifier

InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-16,19H,2-10H2,1H3/t11-,12-,13+,14-,15-,16+,18+/m1/s1

InChI Key

UOUIARGWRPHDBX-DHMVHTBWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
17-oxosteroid
Oxosteroid
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0005886)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 15867559)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0005886)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005886)

Source

Endogenous

Endogenous (HMDB: HMDB0005886)

Animal

Animal (HMDB: HMDB0005886)

Exogenous

Food

Food (HMDB: HMDB0005886)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0005886)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0005886)

Molecular messenger

Hormone (HMDB: HMDB0005886)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0005886)

Physical Properties

State

Solid

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	0.011 g/L	ALOGPS
logP	3.34	ALOGPS
logP	3.47	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.31	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.33 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.551	31661259
DarkChem	[M-H]-	161.997	31661259
DeepCCS	[M-2H]-	202.079	30932474
DeepCCS	[M+Na]+	177.102	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.81 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0686 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2464.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	385.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	621.3 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	583.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1222.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	441.6 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	1425.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	297.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	368.7 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	56.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
19-Noretiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[H]	3052.5	Standard polar	33892256
19-Noretiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[H]	2378.7	Standard non polar	33892256
19-Noretiocholanolone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[H]	2551.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
19-Noretiocholanolone,1TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC[C@@H](O[Si](C)(C)C)C[C@H]4CC[C@H]3[C@@H]1CCC2=O	2530.3	Semi standard non polar	33892256
19-Noretiocholanolone,1TMS,isomer #2	C[C@]12CC[C@@H]3[C@H]4CC[C@@H](O)C[C@H]4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2535.4	Semi standard non polar	33892256
19-Noretiocholanolone,2TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC[C@@H](O[Si](C)(C)C)C[C@H]4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2535.9	Semi standard non polar	33892256
19-Noretiocholanolone,2TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC[C@@H](O[Si](C)(C)C)C[C@H]4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2515.8	Standard non polar	33892256
19-Noretiocholanolone,2TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC[C@@H](O[Si](C)(C)C)C[C@H]4CC[C@H]3[C@@H]1CC=C2O[Si](C)(C)C	2904.7	Standard polar	33892256
19-Noretiocholanolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H]2[C@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@H]23)C1	2789.5	Semi standard non polar	33892256
19-Noretiocholanolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@@H]4[C@H]3CC[C@]12C	2811.2	Semi standard non polar	33892256
19-Noretiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]4[C@H]3CC[C@]12C	3082.1	Semi standard non polar	33892256
19-Noretiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]4[C@H]3CC[C@]12C	2775.7	Standard non polar	33892256
19-Noretiocholanolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]4[C@H]3CC[C@]12C	3147.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 19-Noretiocholanolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l2-0390000000-3e9d3cc01211fe3f2e0c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 19-Noretiocholanolone GC-MS (1 TMS) - 70eV, Positive	splash10-0g1r-2269000000-927e4978162cfa2c72d4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 19-Noretiocholanolone 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 - 19-Noretiocholanolone 10V, Positive-QTOF	splash10-0a6r-0090000000-cbc92b8361a51e9f9374	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 20V, Positive-QTOF	splash10-05r0-0390000000-8f98ba1efcc73acea899	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 40V, Positive-QTOF	splash10-0f92-5980000000-22ddcd9c3181e54f339e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 10V, Negative-QTOF	splash10-004i-0090000000-020f4653853c30d0fb3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 20V, Negative-QTOF	splash10-004i-0090000000-fbcac4cd1c51b535f3d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 40V, Negative-QTOF	splash10-0a4m-1190000000-8e893b5bd8d4088c8a09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 10V, Positive-QTOF	splash10-004i-0090000000-7c08ae4a5c8bc21486d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 20V, Positive-QTOF	splash10-0zi1-2980000000-16396bb89df457c641e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 40V, Positive-QTOF	splash10-0ktb-2900000000-ee34ac41106cf13a9a3d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 10V, Negative-QTOF	splash10-004i-0090000000-4d3066b364d5c97a28e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 20V, Negative-QTOF	splash10-004i-0090000000-4d3066b364d5c97a28e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 19-Noretiocholanolone 40V, Negative-QTOF	splash10-00fr-0090000000-e73157a0418447ebbe85	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Detected and Quantified	0.0025 (0.000047-0.005) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15867559	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

FDB023785

KNApSAcK ID

Not Available

Chemspider ID

19347817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

19-Noretiocholanolone

METLIN ID

Not Available

PubChem Compound

14009228

PDB ID

Not Available

ChEBI ID

36412

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Counsell, R. E. Isomeric estrane derivatives. Tetrahedron (1961), 15 202-11.

Material Safety Data Sheet (MSDS)

Not Available

General References

Le BB, Bryand F, Gaudin I, Monteau F, Poulain F, Andre F: Endogenous nandrolone metabolites in human urine. Two-year monitoring of male professional soccer players. J Anal Toxicol. 2002 Jan-Feb;26(1):43-7. [PubMed:11888015 ]
Le Bizec B, Bryand F, Gaudin I, Monteau F, Poulain F, Andre F: Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin. Steroids. 2002 Feb;67(2):105-10. [PubMed:11755174 ]

Showing metabocard for 19-Noretiocholanolone (HMDB0005886)

MOL for HMDB0005886 (19-Noretiocholanolone)

3D MOL for HMDB0005886 (19-Noretiocholanolone)

3D SDF for HMDB0005886 (19-Noretiocholanolone)

3D-SDF for HMDB0005886 (19-Noretiocholanolone)

PDB for HMDB0005886 (19-Noretiocholanolone)

3D PDB for HMDB0005886 (19-Noretiocholanolone)

SMILES for HMDB0005886 (19-Noretiocholanolone)

INCHI for HMDB0005886 (19-Noretiocholanolone)

Structure for HMDB0005886 (19-Noretiocholanolone)

3D Structure for HMDB0005886 (19-Noretiocholanolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra