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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:17:09 UTC

Update Date

2021-09-26 22:55:11 UTC

HMDB ID

HMDB0246253

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3alpha-Hydroxynorethynodrel

Description

3alpha-Hydroxynorethynodrel belongs to the class of organic compounds known as 17-hydroxysteroids. These are steroids carrying a hydroxyl group at the 17-position of the steroid backbone. Based on a literature review very few articles have been published on 3alpha-Hydroxynorethynodrel. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3alpha-hydroxynorethynodrel is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3alpha-Hydroxynorethynodrel 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

HMDB0246253
     RDKit          3D
3alpha-Hydroxynorethynodrel
 50 53  0  0  0  0  0  0  0  0999 V2000
   -5.2979    1.5110    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5379    0.7106    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.2708    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.4428    1.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9032   -0.5484   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -0.7580   -1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -0.7085   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -0.5467   -1.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.8986   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -1.9141   -0.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -0.7503   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323    0.3959   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    1.6351    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1028    1.4513    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7360    0.2784   -0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0584    0.1745    0.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -0.9329    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    0.4107   -0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0239    0.1844    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079    0.2799    1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    0.3403    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    1.6896   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    2.2080    1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601   -2.1290    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.4590   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117    0.3386   -1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507   -1.7526   -2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3697   -0.0067   -2.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786   -1.6795   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -0.1208   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -2.4334   -0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -2.4650   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048   -1.9455   -1.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -2.8263   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    2.0709   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446    2.3355    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1425    1.2366    1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7155    2.3348    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    0.4965   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5636    0.8617   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246   -1.8400   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946   -0.8962    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.4279   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4102   -0.7632    1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283    1.0021    1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383    1.0895    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -0.6716    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    1.8323   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    2.4436    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    2.0203   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
M  END


  Mrv1652309112101172D          

 22 25  0  0  0  0            999 V2000
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093   -0.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  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
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 10 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246253

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4=C3CCC(O)C4)C1CCC2(O)C#C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,14,16-18,21-22H,4-12H2,2H3

> <INCHI_KEY>
XSQAQKNJHGGMRV-UHFFFAOYSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.647833554015875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-ene-5,14-diol

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.6063241646666673

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.21661922177883

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.594918997214442

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2058418439393837

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
88.2093

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-ene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246253
     RDKit          3D
3alpha-Hydroxynorethynodrel
 50 53  0  0  0  0  0  0  0  0999 V2000
   -5.2979    1.5110    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5379    0.7106    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.2708    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.4428    1.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9032   -0.5484   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -0.7580   -1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -0.7085   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -0.5467   -1.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.8986   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -1.9141   -0.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -0.7503   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323    0.3959   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    1.6351    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1028    1.4513    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7360    0.2784   -0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0584    0.1745    0.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -0.9329    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    0.4107   -0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0239    0.1844    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079    0.2799    1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    0.3403    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    1.6896   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    2.2080    1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601   -2.1290    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.4590   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117    0.3386   -1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507   -1.7526   -2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3697   -0.0067   -2.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786   -1.6795   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -0.1208   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -2.4334   -0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -2.4650   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048   -1.9455   -1.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -2.8263   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    2.0709   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446    2.3355    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1425    1.2366    1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7155    2.3348    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    0.4965   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5636    0.8617   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246   -1.8400   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946   -0.8962    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.4279   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4102   -0.7632    1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283    1.0021    1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383    1.0895    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -0.6716    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    1.8323   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    2.4436    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    2.0203   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  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       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.357  -0.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.777  -1.455   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.163  -1.787   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    2   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14    6   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0246253
HETATM    1  C1  UNL     1      -5.298   1.511   1.306  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.538   0.711   0.825  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.626  -0.271   0.264  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.567  -1.443   1.012  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.903  -0.548  -1.204  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.556  -0.758  -1.865  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.623  -0.709  -0.717  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.180  -0.547  -1.033  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.468  -1.899  -1.019  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.953  -1.914  -0.984  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.554  -0.750  -0.285  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.932   0.396  -0.113  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.740   1.635   0.014  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.103   1.451   0.568  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.736   0.278  -0.195  1.00  0.00           C  
HETATM   16  O2  UNL     1       6.058   0.175   0.211  1.00  0.00           O  
HETATM   17  C15 UNL     1       3.938  -0.933   0.237  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.460   0.411  -0.055  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.024   0.184   1.356  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.508   0.280   1.491  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.217   0.340   0.162  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.365   1.690  -0.407  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.965   2.208   1.747  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.060  -2.129   0.485  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.511  -1.459  -1.275  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.412   0.339  -1.639  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.551  -1.753  -2.399  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.370  -0.007  -2.653  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.779  -1.680  -0.152  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.028  -0.121  -2.051  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.089  -2.433  -0.109  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.064  -2.465  -1.886  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.405  -1.945  -1.997  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.290  -2.826  -0.450  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.854   2.071  -1.020  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.145   2.336   0.639  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.143   1.237   1.645  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.715   2.335   0.298  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.622   0.497  -1.270  1.00  0.00           H  
HETATM   40  H18 UNL     1       6.564   0.862  -0.291  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.425  -1.840  -0.139  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.895  -0.896   1.349  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.131   1.428  -0.348  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.410  -0.763   1.717  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.428   1.002   1.975  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.838   1.090   2.181  1.00  0.00           H  
HETATM   47  H25 UNL     1      -1.852  -0.672   1.984  1.00  0.00           H  
HETATM   48  H26 UNL     1      -1.971   1.832  -1.430  1.00  0.00           H  
HETATM   49  H27 UNL     1      -1.936   2.444   0.319  1.00  0.00           H  
HETATM   50  H28 UNL     1      -3.446   2.020  -0.478  1.00  0.00           H  
CONECT    1    2    2    2   23
CONECT    2    3
CONECT    3    4    5   21
CONECT    4   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   21   29
CONECT    8    9   18   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   17
CONECT   12   13   18
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   17   39
CONECT   16   40
CONECT   17   41   42
CONECT   18   19   43
CONECT   19   20   44   45
CONECT   20   21   46   47
CONECT   21   22
CONECT   22   48   49   50
END

HMDB0246253
     RDKit          3D
3alpha-Hydroxynorethynodrel
 50 53  0  0  0  0  0  0  0  0999 V2000
   -5.2979    1.5110    1.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5379    0.7106    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.2708    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.4428    1.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9032   -0.5484   -1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5556   -0.7580   -1.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6226   -0.7085   -0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -0.5467   -1.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.8986   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -1.9141   -0.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -0.7503   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323    0.3959   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405    1.6351    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1028    1.4513    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7360    0.2784   -0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0584    0.1745    0.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381   -0.9329    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600    0.4107   -0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0239    0.1844    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079    0.2799    1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    0.3403    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    1.6896   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9653    2.2080    1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601   -2.1290    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.4590   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117    0.3386   -1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507   -1.7526   -2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3697   -0.0067   -2.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7786   -1.6795   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281   -0.1208   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -2.4334   -0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -2.4650   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048   -1.9455   -1.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -2.8263   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8541    2.0709   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446    2.3355    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1425    1.2366    1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7155    2.3348    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    0.4965   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5636    0.8617   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246   -1.8400   -0.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8946   -0.8962    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.4279   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4102   -0.7632    1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4283    1.0021    1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8383    1.0895    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515   -0.6716    1.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    1.8323   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    2.4436    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    2.0203   -0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3a-Hydroxynorethynodrel	Generator
3Α-hydroxynorethynodrel	Generator

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.442

Monoisotopic Molecular Weight

300.208930142

IUPAC Name

14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-ene-5,14-diol

Traditional Name

14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-ene-5,14-diol

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=C3CCC(O)C4)C1CCC2(O)C#C

InChI Identifier

InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,14,16-18,21-22H,4-12H2,2H3

InChI Key

XSQAQKNJHGGMRV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 17-hydroxysteroids. These are steroids carrying a hydroxyl group at the 17-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

17-hydroxysteroids

Alternative Parents

Substituents

17-hydroxysteroid
3-hydroxysteroid
Ynone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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 (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	2.48	ALOGPS
logP	2.61	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	17.59	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.21 m³·mol⁻¹	ChemAxon
Polarizability	35.65 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]-	206.823	30932474
DeepCCS	[M+Na]+	182.388	30932474
AllCCS	[M+H]+	178.5	32859911
AllCCS	[M+H-H2O]+	175.4	32859911
AllCCS	[M+NH4]+	181.4	32859911
AllCCS	[M+Na]+	182.2	32859911
AllCCS	[M-H]-	182.5	32859911
AllCCS	[M+Na-2H]-	182.7	32859911
AllCCS	[M+HCOO]-	183.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	14.6497 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2359.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	326.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	380.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	710.9 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	670.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1228.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	425.1 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	1434.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	410.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	508.1 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	49.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3alpha-Hydroxynorethynodrel	CC12CCC3C(CCC4=C3CCC(O)C4)C1CCC2(O)C#C	3178.4	Standard polar	33892256
3alpha-Hydroxynorethynodrel	CC12CCC3C(CCC4=C3CCC(O)C4)C1CCC2(O)C#C	2546.6	Standard non polar	33892256
3alpha-Hydroxynorethynodrel	CC12CCC3C(CCC4=C3CCC(O)C4)C1CCC2(O)C#C	2631.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fv-0290000000-7fa624a6353e0574a35f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Hydroxynorethynodrel GC-MS (TBDMS_2_1) - 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 - 3alpha-Hydroxynorethynodrel 10V, Positive-QTOF	splash10-001i-0091000000-ae968119802dc4129db7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Hydroxynorethynodrel 20V, Positive-QTOF	splash10-0aor-0891000000-a256ef5d5b54d0935034	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Hydroxynorethynodrel 40V, Positive-QTOF	splash10-014i-3690000000-88f62e0be0cb2ce5f8ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Hydroxynorethynodrel 10V, Negative-QTOF	splash10-0002-0090000000-344a11f406f20d02412c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Hydroxynorethynodrel 20V, Negative-QTOF	splash10-0002-0090000000-ff35c63074d1061c47aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Hydroxynorethynodrel 40V, Negative-QTOF	splash10-0002-1290000000-4d67baf6d611f05b7fe5	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

222461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

253812

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 3alpha-Hydroxynorethynodrel (HMDB0246253)

MOL for HMDB0246253 (3alpha-Hydroxynorethynodrel)

3D MOL for HMDB0246253 (3alpha-Hydroxynorethynodrel)

3D SDF for HMDB0246253 (3alpha-Hydroxynorethynodrel)

3D-SDF for HMDB0246253 (3alpha-Hydroxynorethynodrel)

PDB for HMDB0246253 (3alpha-Hydroxynorethynodrel)

3D PDB for HMDB0246253 (3alpha-Hydroxynorethynodrel)

SMILES for HMDB0246253 (3alpha-Hydroxynorethynodrel)

INCHI for HMDB0246253 (3alpha-Hydroxynorethynodrel)

Structure for HMDB0246253 (3alpha-Hydroxynorethynodrel)

3D Structure for HMDB0246253 (3alpha-Hydroxynorethynodrel)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra