Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014511

Secondary Accession Numbers

HMDB14511

Metabolite Identification

Common Name

Levonorgestrel

Description

Levonorgestrel, also known as microlut or norplant, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, levonorgestrel is considered to be a steroid lipid molecule. Levonorgestrel is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Levonorgestrel is a potentially toxic compound.

Structure

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

367
  Mrv1652305271900192D          

 27 30  0  0  1  0            999 V2000
    6.6263    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.5186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0993   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.7189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799    0.7700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3614    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -1.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3849    1.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5482    1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2165    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.9628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.0236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -0.0647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 22  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 24  1  6  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 25  1  1  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 26  1  6  0  0  0
  7 12  1  0  0  0  0
  7 19  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 27  1  1  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 21  2  0  0  0  0
 17 20  1  0  0  0  0
 19 23  3  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
M  END

HMDB0014511
     RDKit          3D
Levonorgestrel
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.6199    1.9156   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627    0.9884    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858   -0.1503    0.6865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8496   -1.3472    0.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508   -0.1124    2.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733   -0.4826    2.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508    0.2322    1.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4454   -0.1099    0.9428 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3375    0.3366    2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    0.3059    1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261    0.1037    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072   -0.0833    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -0.2848   -1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138   -1.0862   -1.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215    0.4713   -2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354    0.8315   -1.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1605    0.0916   -0.7549 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8606    0.6921   -0.2635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1207    0.7752   -1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561    0.8133   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -0.2016    0.0989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4690   -1.5558   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -1.9539   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2111    2.7257   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5127   -1.5863    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345    0.9251    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6550   -0.8747    2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5085   -1.5612    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.1611    3.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.3316    1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6272   -1.2001    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292    1.3727    2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.3080    2.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    1.2290    2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383   -0.5653    2.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -0.0843    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9916   -0.1332   -3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6011    1.3981   -2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    0.5715   -2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649    1.9282   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9307   -0.9659   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179    1.7241    0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877    1.7219   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438   -0.0369   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    0.6900   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847    1.8363   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5530   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -2.3409    0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -2.2809   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -2.8674   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -1.1243   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  6
 18 42  1  1
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

367
  Mrv1652305271900192D          

 27 30  0  0  1  0            999 V2000
    6.6263    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.5186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0993   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.7189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799    0.7700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3614    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -1.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3849    1.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5482    1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2165    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.9628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.0236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -0.0647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  2 22  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 14  1  1  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 24  1  6  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 25  1  1  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 26  1  6  0  0  0
  7 12  1  0  0  0  0
  7 19  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 27  1  1  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 21  2  0  0  0  0
 17 20  1  0  0  0  0
 19 23  3  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014511

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
WWYNJERNGUHSAO-XUDSTZEESA-N

> <FORMULA>
C21H28O2

> <MOLECULAR_WEIGHT>
312.4458

> <EXACT_MASS>
312.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.751894765209784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.6617966023333337

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.27817248474075

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.909290746374914

> <JCHEM_PKA_STRONGEST_BASIC>
-1.526003464744241

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
92.0255

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014511
     RDKit          3D
Levonorgestrel
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.6199    1.9156   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627    0.9884    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858   -0.1503    0.6865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8496   -1.3472    0.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508   -0.1124    2.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733   -0.4826    2.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508    0.2322    1.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4454   -0.1099    0.9428 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3375    0.3366    2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    0.3059    1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261    0.1037    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072   -0.0833    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -0.2848   -1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138   -1.0862   -1.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215    0.4713   -2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354    0.8315   -1.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1605    0.0916   -0.7549 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8606    0.6921   -0.2635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1207    0.7752   -1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561    0.8133   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -0.2016    0.0989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4690   -1.5558   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -1.9539   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2111    2.7257   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5127   -1.5863    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345    0.9251    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6550   -0.8747    2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5085   -1.5612    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.1611    3.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.3316    1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6272   -1.2001    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292    1.3727    2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.3080    2.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    1.2290    2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383   -0.5653    2.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -0.0843    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9916   -0.1332   -3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6011    1.3981   -2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    0.5715   -2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649    1.9282   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9307   -0.9659   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179    1.7241    0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877    1.7219   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438   -0.0369   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    0.6900   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847    1.8363   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5530   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -2.3409    0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -2.2809   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -2.8674   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -1.1243   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  6
 18 42  1  1
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 367                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      12.369   2.903   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.733   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.385   0.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.385  -0.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.052  -1.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.718  -0.572   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.842   1.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.052   1.738   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.842  -1.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.718   0.968   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.317  -1.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.741   0.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.076  -2.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.385   2.508   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.693  -3.759   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.304  -2.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -0.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.052   3.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.090   2.340   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.429  -1.297   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.864  -3.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.417  -2.968   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.337   3.243   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      11.516  -1.797   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      11.123  -1.950   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       9.785   0.044   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       7.340  -0.121   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   22                                                            
CONECT    3    4    7    8   14                                             
CONECT    4    3    5    9   24                                             
CONECT    5    4    6   13   25                                             
CONECT    6    5   10   11   26                                             
CONECT    7    1    3   12   19                                             
CONECT    8    3   10                                                       
CONECT    9    4   12                                                       
CONECT   10    6    8                                                       
CONECT   11    6   16   17   27                                             
CONECT   12    7    9                                                       
CONECT   13    5   15                                                       
CONECT   14    3   18                                                       
CONECT   15   13   16                                                       
CONECT   16   11   15   21                                                  
CONECT   17   11   20                                                       
CONECT   18   14                                                            
CONECT   19    7   23                                                       
CONECT   20   17   22                                                       
CONECT   21   16   22                                                       
CONECT   22    2   20   21                                                  
CONECT   23   19                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0014511
HETATM    1  C1  UNL     1      -4.620   1.916  -0.211  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.963   0.988   0.196  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.186  -0.150   0.687  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.850  -1.347   0.388  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.051  -0.112   2.198  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.573  -0.483   2.407  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.951   0.232   1.275  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.445  -0.110   0.943  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.338   0.337   2.085  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.791   0.306   1.782  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.126   0.104   0.348  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.407  -0.083   0.037  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.776  -0.285  -1.358  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.714  -1.086  -1.629  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.022   0.471  -2.388  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.635   0.832  -1.974  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.161   0.092  -0.755  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.861   0.692  -0.263  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.121   0.775  -1.354  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.556   0.813  -0.972  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.825  -0.202   0.099  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.469  -1.556  -0.415  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.440  -1.954  -1.476  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.211   2.726  -0.584  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.513  -1.586   1.081  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.235   0.925   2.589  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.655  -0.875   2.697  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.509  -1.561   2.276  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.239  -0.161   3.409  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.040   1.332   1.363  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.627  -1.200   0.827  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.029   1.373   2.400  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.083  -0.308   2.961  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.300   1.229   2.149  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.238  -0.565   2.327  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.164  -0.084   0.834  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.992  -0.133  -3.319  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.601   1.398  -2.673  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.915   0.572  -2.799  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.565   1.928  -1.865  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.931  -0.966  -1.022  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.118   1.724   0.110  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.088   1.722  -1.937  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.044  -0.037  -2.122  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.177   0.690  -1.876  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.785   1.836  -0.564  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.461  -1.553  -0.857  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.484  -2.341   0.370  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.911  -2.281  -2.420  1.00  0.00           H  
HETATM   50  H27 UNL     1      -3.041  -2.867  -1.190  1.00  0.00           H  
HETATM   51  H28 UNL     1      -3.106  -1.124  -1.815  1.00  0.00           H  
CONECT    1    2    2    2   24
CONECT    2    3
CONECT    3    4    5   21
CONECT    4   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   21   30
CONECT    8    9   18   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   12   17
CONECT   12   13   36
CONECT   13   14   14   15
CONECT   15   16   37   38
CONECT   16   17   39   40
CONECT   17   18   41
CONECT   18   19   42
CONECT   19   20   43   44
CONECT   20   21   45   46
CONECT   21   22
CONECT   22   23   47   48
CONECT   23   49   50   51
END

HMDB0014511
     RDKit          3D
Levonorgestrel
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.6199    1.9156   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627    0.9884    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858   -0.1503    0.6865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8496   -1.3472    0.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508   -0.1124    2.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733   -0.4826    2.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508    0.2322    1.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4454   -0.1099    0.9428 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3375    0.3366    2.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912    0.3059    1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261    0.1037    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072   -0.0833    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -0.2848   -1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7138   -1.0862   -1.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215    0.4713   -2.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6354    0.8315   -1.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1605    0.0916   -0.7549 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8606    0.6921   -0.2635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1207    0.7752   -1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5561    0.8133   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252   -0.2016    0.0989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4690   -1.5558   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -1.9539   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2111    2.7257   -0.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5127   -1.5863    1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345    0.9251    2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6550   -0.8747    2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5085   -1.5612    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -0.1611    3.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.3316    1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6272   -1.2001    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292    1.3727    2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828   -0.3080    2.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3002    1.2290    2.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383   -0.5653    2.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -0.0843    0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9916   -0.1332   -3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6011    1.3981   -2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    0.5715   -2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649    1.9282   -1.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9307   -0.9659   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179    1.7241    0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877    1.7219   -1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438   -0.0369   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    0.6900   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847    1.8363   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5530   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -2.3409    0.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -2.2809   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -2.8674   -1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063   -1.1243   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  6
 18 42  1  1
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one	ChEBI
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one	ChEBI
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one	ChEBI
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one	ChEBI
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one	ChEBI
17-alpha-Ethynyl-13-ethyl-19-nortestosterone	ChEBI
17-Ethynyl-18-methyl-19-nortestosterone	ChEBI
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol	ChEBI
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one	ChEBI
17alpha-Ethynyl-18-homo-19-nortestosterone	ChEBI
18-Methyl-17-alpha-ethynyl-19-nortestosterone	ChEBI
18-Methylnorethisterone	ChEBI
D(-)-Norgestrel	ChEBI
Jadelle	ChEBI
Levonelle	ChEBI
Levonorgestrelum	ChEBI
Levonova	ChEBI
Microlut	ChEBI
Microluton	ChEBI
Microval	ChEBI
Mirena	ChEBI
NorLevo	ChEBI
Plan b	ChEBI
Postinor	ChEBI
(+-)-Norgestrel	Kegg
Ovrette	Kegg
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one	Generator
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one	Generator
13-b-Ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one	Generator
13-Β-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one	Generator
13-Ethyl-17-a-ethynyl-17-b-hydroxy-4-gonen-3-one	Generator
13-Ethyl-17-α-ethynyl-17-β-hydroxy-4-gonen-3-one	Generator
13-Ethyl-17-a-ethynylgon-4-en-17-b-ol-3-one	Generator
13-Ethyl-17-α-ethynylgon-4-en-17-β-ol-3-one	Generator
17-a-Ethinyl-13-b-ethyl-17-b-hydroxy-4-estren-3-one	Generator
17-Α-ethinyl-13-β-ethyl-17-β-hydroxy-4-estren-3-one	Generator
17-a-Ethynyl-13-ethyl-19-nortestosterone	Generator
17-Α-ethynyl-13-ethyl-19-nortestosterone	Generator
17a-Ethynyl-13b-ethyl-3-oxo-4-estren-17b-ol	Generator
17Α-ethynyl-13β-ethyl-3-oxo-4-estren-17β-ol	Generator
17a-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one	Generator
17Α-ethynyl-17-hydroxy-18-methylestr-4-en-3-one	Generator
17a-Ethynyl-18-homo-19-nortestosterone	Generator
17Α-ethynyl-18-homo-19-nortestosterone	Generator
18-Methyl-17-a-ethynyl-19-nortestosterone	Generator
18-Methyl-17-α-ethynyl-19-nortestosterone	Generator
Levonorgestrel alcala brand	HMDB
Levonorgestrel hexal brand	HMDB
Norplant	HMDB
Paladin brand OF levonorgestrel	HMDB
Vikela	HMDB
Wyeth brand OF levonorgestrel	HMDB
Duofem	HMDB
L-Norgestrel	HMDB
Aventis pharma brand OF levonorgestrel	HMDB
Berlex brand OF levonorgestrel	HMDB
HRA brand 1 OF levonorgestrel	HMDB
Hexal brand OF levonorgestrel	HMDB
Levonorgestrel paladin brand	HMDB
Levonorgestrel wyeth brand	HMDB
Norplant 2	HMDB
Alcala brand OF levonorgestrel	HMDB
Capronor	HMDB
Cerazet	HMDB
D-Norgestrel	HMDB
HRA brand 2 OF levonorgestrel	HMDB
Norplant-2	HMDB
Schering brand 3 OF levonorgestrel	HMDB
L Norgestrel	HMDB
D Norgestrel	HMDB
Levonorgestrel berlex brand	HMDB
Norgeston	HMDB
Norplant2	HMDB
Schering brand 1 OF levonorgestrel	HMDB
Schering brand 2 OF levonorgestrel	HMDB
Women's capital brand OF levonorgestrel	HMDB
Levonorgestrel	MeSH

Chemical Formula

C₂₁H₂₈O₂

Average Molecular Weight

312.4458

Monoisotopic Molecular Weight

312.20893014

IUPAC Name

(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

797-63-7

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

InChI Key

WWYNJERNGUHSAO-XUDSTZEESA-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-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Ynone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:6443 )
3-oxo Delta(4)-steroid (CHEBI:6443 )
17beta-hydroxy steroid (CHEBI:6443 )
Pregnane and derivatives [Fig] (C08153 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08153 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030119 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014511)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	240 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0058 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	178.634	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001174

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0058 g/L	ALOGPS
logP	3.25	ALOGPS
logP	3.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	17.91	ChemAxon
pKa (Strongest Basic)	-1.5	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	1	ChemAxon
Refractivity	92.03 m³·mol⁻¹	ChemAxon
Polarizability	36.75 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]+	175.546	31661259
DarkChem	[M-H]-	175.423	31661259
DeepCCS	[M-2H]-	209.677	30932474
DeepCCS	[M+Na]+	183.905	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.1	32859911
AllCCS	[M+NH4]+	182.7	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	185.1	32859911
AllCCS	[M+Na-2H]-	185.3	32859911
AllCCS	[M+HCOO]-	185.6	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.	7.6 minutes	32390414
Predicted by Siyang on May 30, 2022	16.7629 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2577.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	423.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	469.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	804.1 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	751.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1460.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	473.2 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	1485.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	291.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	497.3 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	15.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levonorgestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3776.6	Standard polar	33892256
Levonorgestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2716.4	Standard non polar	33892256
Levonorgestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2765.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levonorgestrel,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC	2867.1	Semi standard non polar	33892256
Levonorgestrel,1TMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	2760.1	Semi standard non polar	33892256
Levonorgestrel,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	2837.5	Semi standard non polar	33892256
Levonorgestrel,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	2914.3	Standard non polar	33892256
Levonorgestrel,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3258.3	Standard polar	33892256
Levonorgestrel,1TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC	3128.6	Semi standard non polar	33892256
Levonorgestrel,1TBDMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3025.5	Semi standard non polar	33892256
Levonorgestrel,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3345.5	Semi standard non polar	33892256
Levonorgestrel,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3383.2	Standard non polar	33892256
Levonorgestrel,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC	3436.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
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	Taking drug identified by DrugBank entry DB00367	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00367	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00367

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

12560

KEGG Compound ID

C08153

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levonorgestrel

METLIN ID

Not Available

PubChem Compound

13109

PDB ID

Not Available

ChEBI ID

6443

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

Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771 ]
Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. [PubMed:10715364 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). FDA label.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. 3-oxo-5-alpha-steroid 4-dehydrogenase 1

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A1
Uniprot ID:: P18405
Molecular weight:: 29458.18

References

Hammond GL, Rabe T, Wagner JD: Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. Am J Obstet Gynecol. 2001 Aug;185(2 Suppl):S24-31. [PubMed:11521119 ]
Rabe T, Kowald A, Ortmann J, Rehberger-Schneider S: Inhibition of skin 5 alpha-reductase by oral contraceptive progestins in vitro. Gynecol Endocrinol. 2000 Aug;14(4):223-30. [PubMed:11075290 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Shields-Botella J, Duc I, Duranti E, Puccio F, Bonnet P, Delansorne R, Paris J: An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. J Steroid Biochem Mol Biol. 2003 Nov;87(2-3):111-22. [PubMed:14672731 ]
Freyberger A, Witters H, Weimer M, Lofink W, Berckmans P, Ahr HJ: Screening for (anti)androgenic properties using a standard operation protocol based on the human stably transfected androgen sensitive PALM cell line. First steps towards validation. Reprod Toxicol. 2010 Aug;30(1):9-17. doi: 10.1016/j.reprotox.2009.10.002. Epub 2009 Oct 27. [PubMed:19836445 ]
Freyberger A, Weimer M, Tran HS, Ahr HJ: Assessment of a recombinant androgen receptor binding assay: initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):2-8. doi: 10.1016/j.reprotox.2009.10.001. Epub 2009 Oct 13. [PubMed:19833195 ]
Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [PubMed:3139361 ]

Enzyme Details

5. Progesterone receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:: PGR
Uniprot ID:: P06401
Molecular weight:: 98980.0

References

Maruo T, Ohara N, Matsuo H, Xu Q, Chen W, Sitruk-Ware R, Johansson ED: Effects of levonorgestrel-releasing IUS and progesterone receptor modulator PRM CDB-2914 on uterine leiomyomas. Contraception. 2007 Jun;75(6 Suppl):S99-103. Epub 2007 Mar 21. [PubMed:17531625 ]
Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894 ]
Hompes PG, Mijatovic V: Endometriosis: the way forward. Gynecol Endocrinol. 2007 Jan;23(1):5-12. [PubMed:17484506 ]
Creinin MD, Schlaff W, Archer DF, Wan L, Frezieres R, Thomas M, Rosenberg M, Higgins J: Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstet Gynecol. 2006 Nov;108(5):1089-97. [PubMed:17077229 ]
Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

6. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Vereide AB, Kaino T, Sager G, Arnes M, Orbo A: Effect of levonorgestrel IUD and oral medroxyprogesterone acetate on glandular and stromal progesterone receptors (PRA and PRB), and estrogen receptors (ER-alpha and ER-beta) in human endometrial hyperplasia. Gynecol Oncol. 2006 May;101(2):214-23. Epub 2005 Dec 1. [PubMed:16325240 ]
Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894 ]
Abdel-Aleem H, Shaaban OM, Amin AF, Abdel-Aleem AM: Tamoxifen treatment of bleeding irregularities associated with Norplant use. Contraception. 2005 Dec;72(6):432-7. Epub 2005 Aug 9. [PubMed:16307966 ]
Sun D, Yan C, Jacobson A, Jiang H, Carroll MA, Huang A: Contribution of epoxyeicosatrienoic acids to flow-induced dilation in arteries of male ERalpha knockout mice: role of aromatase. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1239-46. Epub 2007 Jul 18. [PubMed:17634204 ]
Vijayanathan V, Venkiteswaran S, Nair SK, Verma A, Thomas TJ, Zhu BT, Thomas T: Physiologic levels of 2-methoxyestradiol interfere with nongenomic signaling of 17beta-estradiol in human breast cancer cells. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2038-48. [PubMed:16609013 ]

Showing metabocard for Levonorgestrel (HMDB0014511)

MOL for HMDB0014511 (Levonorgestrel)

3D MOL for HMDB0014511 (Levonorgestrel)

3D SDF for HMDB0014511 (Levonorgestrel)

3D-SDF for HMDB0014511 (Levonorgestrel)

PDB for HMDB0014511 (Levonorgestrel)

3D PDB for HMDB0014511 (Levonorgestrel)

SMILES for HMDB0014511 (Levonorgestrel)

INCHI for HMDB0014511 (Levonorgestrel)

Structure for HMDB0014511 (Levonorgestrel)

3D Structure for HMDB0014511 (Levonorgestrel)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

References