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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015658

Secondary Accession Numbers

HMDB15658

Metabolite Identification

Common Name

Norelgestromin

Description

Norelgestromin is only found in individuals that have used or taken this drug. It is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch. Norelgestromin inhibits estrone sulfatase, which converts sulfated steroid precursors to estrogen during pregnancy. Norgelgestromin/ethinylestradiol suppresses follicular development, induces changes to the endometrium, which decreases chances of implantation and thickens the cervical mucus, impeding sperm swimming into the uterus. It also has similar agonisting binding affinities as its parent compound, Norgestimate, for progesterone and estrogen receptors.

Structure

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

HMDB0015658
     RDKit          3D
Norelgestromin
 53 56  0  0  0  0  0  0  0  0999 V2000
   -5.3186    0.1759    1.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4083   -0.3886    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3007   -1.0521    0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -2.1303    1.2180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -1.4050   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3058   -1.1682   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -0.9421   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -0.6803   -0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199    0.4941   -1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    0.1697   -2.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -0.0079   -0.7336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059    0.4461   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888    0.2909    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9878    0.7533    0.6536 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175    1.4064   -0.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -0.4142    1.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -0.1346    1.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1948   -0.6652    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.6979    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.3252    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    0.1242    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290   -0.0408    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7707    1.1420   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867    2.3396   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1147    0.6844    2.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -2.0977    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4262   -0.8399   -1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731   -2.4909   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3949   -0.4096   -2.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503   -2.1365   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574   -1.9463   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -1.5972   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    0.7229   -2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    1.3979   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3940    1.0670   -2.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631   -0.7308   -2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4409    0.9332   -1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    2.3501   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.0200    2.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -1.5071    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038    0.9105    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380   -0.7800    2.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -1.7350    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028   -1.7000    0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5143    0.1169    2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    1.3568    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883   -0.8605    2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468    0.8488    2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3410    0.8414   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.4999    0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    2.6155    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    3.2615   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    2.3044   -1.7196 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  2  3
 14 15  1  0
 13 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  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 22  7  1  0
 19  8  1  0
 18 11  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
M  END


  Mrv0541 02241212482D          

 24 27  0  0  0  0            999 V2000
    3.8598    2.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484    1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3093    1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089    1.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -0.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   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
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  4  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 17 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015658

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC12CCC3C(CCC4=CC(CCC34)=NO)C1CCC2(O)C#C

> <INCHI_IDENTIFIER>
InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3

> <INCHI_KEY>
ISHXLNHNDMZNMC-UHFFFAOYSA-N

> <FORMULA>
C21H29NO2

> <MOLECULAR_WEIGHT>
327.4605

> <EXACT_MASS>
327.219829177

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.53210007724397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.671276388333333

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.909290746374918

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.466128004560874

> <JCHEM_PKA_STRONGEST_BASIC>
3.1152818968924207

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
95.84719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orthra evra

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015658
     RDKit          3D
Norelgestromin
 53 56  0  0  0  0  0  0  0  0999 V2000
   -5.3186    0.1759    1.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4083   -0.3886    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3007   -1.0521    0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -2.1303    1.2180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -1.4050   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3058   -1.1682   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -0.9421   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -0.6803   -0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199    0.4941   -1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    0.1697   -2.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -0.0079   -0.7336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059    0.4461   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888    0.2909    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9878    0.7533    0.6536 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175    1.4064   -0.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -0.4142    1.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -0.1346    1.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1948   -0.6652    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.6979    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.3252    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    0.1242    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290   -0.0408    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7707    1.1420   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867    2.3396   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1147    0.6844    2.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -2.0977    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4262   -0.8399   -1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731   -2.4909   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3949   -0.4096   -2.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503   -2.1365   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574   -1.9463   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -1.5972   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    0.7229   -2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    1.3979   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3940    1.0670   -2.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631   -0.7308   -2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4409    0.9332   -1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    2.3501   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.0200    2.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -1.5071    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038    0.9105    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380   -0.7800    2.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -1.7350    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028   -1.7000    0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5143    0.1169    2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    1.3568    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883   -0.8605    2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468    0.8488    2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3410    0.8414   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.4999    0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    2.6155    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    3.2615   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    2.3044   -1.7196 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  2  3
 14 15  1  0
 13 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  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 22  7  1  0
 19  8  1  0
 18 11  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       7.205   4.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.397   1.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.357   2.399   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.777   2.995   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.163   3.328   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.811  -0.678   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -1.698   0.228   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -2.222  -1.221   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   11                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3   12   14                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15    7   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    6   17                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0015658
HETATM    1  C1  UNL     1      -5.319   0.176   1.717  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.408  -0.389   1.185  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.301  -1.052   0.527  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.810  -2.130   1.218  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.600  -1.405  -0.913  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.306  -1.168  -1.708  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.350  -0.942  -0.602  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.049  -0.680  -0.840  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.520   0.494  -1.579  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.970   0.170  -2.011  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.753  -0.008  -0.734  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.006   0.446  -0.667  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.789   0.291   0.549  1.00  0.00           C  
HETATM   14  N1  UNL     1       5.988   0.753   0.654  1.00  0.00           N  
HETATM   15  O2  UNL     1       6.517   1.406  -0.428  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.247  -0.414   1.749  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.751  -0.135   1.756  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.195  -0.665   0.451  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.716  -0.698   0.551  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.100   0.325   1.438  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.377   0.124   1.569  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.129  -0.041   0.304  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.771   1.142  -0.270  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.987   2.340  -0.620  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.115   0.684   2.198  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.166  -2.098   2.137  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.426  -0.840  -1.338  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.873  -2.491  -0.953  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.395  -0.410  -2.474  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.050  -2.137  -2.205  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.357  -1.946  -0.026  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.489  -1.597  -1.329  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.013   0.723  -2.498  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.690   1.398  -0.916  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.394   1.067  -2.502  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.963  -0.731  -2.623  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.441   0.933  -1.525  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.208   2.350  -0.647  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.654  -0.020   2.693  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.377  -1.507   1.661  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.504   0.910   1.937  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.338  -0.780   2.565  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.564  -1.735   0.407  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.403  -1.700   0.971  1.00  0.00           H  
HETATM   45  H21 UNL     1       0.514   0.117   2.477  1.00  0.00           H  
HETATM   46  H22 UNL     1       0.427   1.357   1.234  1.00  0.00           H  
HETATM   47  H23 UNL     1      -1.488  -0.860   2.125  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.847   0.849   2.279  1.00  0.00           H  
HETATM   49  H25 UNL     1      -3.341   0.841  -1.200  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.618   1.500   0.399  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.150   2.615   0.015  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.656   3.262  -0.601  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.713   2.304  -1.720  1.00  0.00           H  
CONECT    1    2    2    2   25
CONECT    2    3
CONECT    3    4    5   22
CONECT    4   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   22   31
CONECT    8    9   19   32
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   12   18
CONECT   12   13   37
CONECT   13   14   14   16
CONECT   14   15
CONECT   15   38
CONECT   16   17   39   40
CONECT   17   18   41   42
CONECT   18   19   43
CONECT   19   20   44
CONECT   20   21   45   46
CONECT   21   22   47   48
CONECT   22   23
CONECT   23   24   49   50
CONECT   24   51   52   53
END

HMDB0015658
     RDKit          3D
Norelgestromin
 53 56  0  0  0  0  0  0  0  0999 V2000
   -5.3186    0.1759    1.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4083   -0.3886    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3007   -1.0521    0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -2.1303    1.2180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002   -1.4050   -0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3058   -1.1682   -1.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3496   -0.9421   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0488   -0.6803   -0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199    0.4941   -1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9695    0.1697   -2.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7527   -0.0079   -0.7336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059    0.4461   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888    0.2909    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9878    0.7533    0.6536 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5175    1.4064   -0.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -0.4142    1.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515   -0.1346    1.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1948   -0.6652    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.6979    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0999    0.3252    1.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3772    0.1242    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290   -0.0408    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7707    1.1420   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9867    2.3396   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1147    0.6844    2.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -2.0977    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4262   -0.8399   -1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731   -2.4909   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3949   -0.4096   -2.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0503   -2.1365   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574   -1.9463   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -1.5972   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0133    0.7229   -2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    1.3979   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3940    1.0670   -2.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631   -0.7308   -2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4409    0.9332   -1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    2.3501   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6538   -0.0200    2.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -1.5071    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038    0.9105    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380   -0.7800    2.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -1.7350    0.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028   -1.7000    0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5143    0.1169    2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    1.3568    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4883   -0.8605    2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468    0.8488    2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3410    0.8414   -1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    1.4999    0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    2.6155    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    3.2615   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    2.3044   -1.7196 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  2  3
 14 15  1  0
 13 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  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 22  7  1  0
 19  8  1  0
 18 11  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17-Deacetylnorgestimate	HMDB
LNGO	HMDB
Levonorgestrel oxime	HMDB
Levonorgestrel oxime, (3E,17alpha)-isomer	HMDB
Levonorgestrel oxime, (3Z,17alpha)-isomer	HMDB
Progestin norelgestromin	HMDB

Chemical Formula

C₂₁H₂₉NO₂

Average Molecular Weight

327.4605

Monoisotopic Molecular Weight

327.219829177

IUPAC Name

15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

Traditional Name

orthra evra

CAS Registry Number

53016-31-2

SMILES

CCC12CCC3C(CCC4=CC(CCC34)=NO)C1CCC2(O)C#C

InChI Identifier

InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3

InChI Key

ISHXLNHNDMZNMC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Delta-4-steroid
Ynone
Cyclic alcohol
Ketoxime
Tertiary alcohol
Oxime
Acetylide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
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: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015658)

Process

Not Available

Role

Not Available

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	0.006 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.67	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	3.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.85 m³·mol⁻¹	ChemAxon
Polarizability	38.53 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
DarkChem	[M+H]+	177.56	31661259
DarkChem	[M-H]-	171.197	31661259
DeepCCS	[M-2H]-	210.94	30932474
DeepCCS	[M+Na]+	186.505	30932474
AllCCS	[M+H]+	184.3	32859911
AllCCS	[M+H-H2O]+	181.4	32859911
AllCCS	[M+NH4]+	186.9	32859911
AllCCS	[M+Na]+	187.7	32859911
AllCCS	[M-H]-	187.1	32859911
AllCCS	[M+Na-2H]-	187.4	32859911
AllCCS	[M+HCOO]-	187.8	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.	5.58 minutes	32390414
Predicted by Siyang on May 30, 2022	17.2523 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2578.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	425.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	215.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	476.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	863.7 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	738.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1510.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	487.1 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	1530.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	511.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	445.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	339.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	567.6 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	19.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norelgestromin	CCC12CCC3C(CCC4=CC(CCC34)=NO)C1CCC2(O)C#C	4261.7	Standard polar	33892256
Norelgestromin	CCC12CCC3C(CCC4=CC(CCC34)=NO)C1CCC2(O)C#C	2806.2	Standard non polar	33892256
Norelgestromin	CCC12CCC3C(CCC4=CC(CCC34)=NO)C1CCC2(O)C#C	3074.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norelgestromin,1TMS,isomer #1	C#CC1(O[Si](C)(C)C)CCC2C3CCC4=CC(=NO)CCC4C3CCC21CC	2973.9	Semi standard non polar	33892256
Norelgestromin,1TBDMS,isomer #1	C#CC1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(=NO)CCC4C3CCC21CC	3211.9	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 - Norelgestromin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1591000000-d15c9fb4d4be46393c12	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norelgestromin GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-1459000000-c21d7ad1916eda54f442	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norelgestromin 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 - Norelgestromin 10V, Positive-QTOF	splash10-004i-0019000000-aa08354d41171a2e94d2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 20V, Positive-QTOF	splash10-01r2-0195000000-1f698646faea40b0ff22	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 40V, Positive-QTOF	splash10-07bf-5691000000-8713c690ec4c0dedbb0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 10V, Negative-QTOF	splash10-004i-0009000000-856211f15c7d2df57e00	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 20V, Negative-QTOF	splash10-004i-0029000000-0fbf66f0573d98dd247b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 40V, Negative-QTOF	splash10-0a59-3093000000-88fe0954b453600797c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 10V, Positive-QTOF	splash10-03e9-0049000000-bb736099f135ec98040d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 20V, Positive-QTOF	splash10-01q9-0394000000-d79abdaa7f1d7be949e4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 40V, Positive-QTOF	splash10-01rw-0890000000-2055bc9542a620a0aeb9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 10V, Negative-QTOF	splash10-004i-0009000000-ad4847b3b72e4c91ee0a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 20V, Negative-QTOF	splash10-004j-0049000000-6a932430636eca9316f6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norelgestromin 40V, Negative-QTOF	splash10-00kb-0191000000-181ebb18ff8c35e8eaa2	2021-10-11	Wishart Lab	View Spectrum

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 DB06713	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06713	21059682	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

11498267

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norelgestromin

METLIN ID

Not Available

PubChem Compound

13752005

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

Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [PubMed:11499185 ]
Abrams LS, Skee DM, Wong FA, Anderson NJ, Leese PT: Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. J Clin Pharmacol. 2001 Nov;41(11):1232-7. [PubMed:11697756 ]
Goa KL, Warner GT, Easthope SE: Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. Treat Endocrinol. 2003;2(3):191-206. [PubMed:15966567 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Steryl-sulfatase

General function:: Involved in catalytic activity
Specific function:: Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name:: STS
Uniprot ID:: P08842
Molecular weight:: 65491.72

References

Pasqualini JR, Chetrite GS: Recent insight on the control of enzymes involved in estrogen formation and transformation in human breast cancer. J Steroid Biochem Mol Biol. 2005 Feb;93(2-5):221-36. [PubMed:15860265 ]
Pasqualini JR, Caubel P, Friedman AJ, Philippe JC, Chetrite GS: Norelgestromin as selective estrogen enzyme modulator in human breast cancer cell lines. Effect on sulfatase activity in comparison to medroxyprogesterone acetate. J Steroid Biochem Mol Biol. 2003 Feb;84(2-3):193-8. [PubMed:12711003 ]
Pasqualini JR: The selective estrogen enzyme modulators in breast cancer: a review. Biochim Biophys Acta. 2004 Jun 7;1654(2):123-43. [PubMed:15172700 ]

Enzyme Details

2. 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

Henzl MR: Norgestimate. From the laboratory to three clinical indications. J Reprod Med. 2001 Jul;46(7):647-61. [PubMed:11499185 ]
Pasqualini JR: Breast cancer and steroid metabolizing enzymes: the role of progestogens. Maturitas. 2009 Dec;65 Suppl 1:S17-21. doi: 10.1016/j.maturitas.2009.11.006. Epub 2009 Dec 3. [PubMed:19962254 ]
London RS, Chapdelaine A, Upmalis D, Olson W, Smith J: Comparative contraceptive efficacy and mechanism of action of the norgestimate-containing triphasic oral contraceptive. Acta Obstet Gynecol Scand Suppl. 1992;156:9-14. [PubMed:1324557 ]
Graziottin A: A review of transdermal hormonal contraception : focus on the ethinylestradiol/norelgestromin contraceptive patch. Treat Endocrinol. 2006;5(6):359-65. [PubMed:17107221 ]
Kuhnz W, Fritzemeier KH, Hegele-Hartung C, Krattenmacher R: Comparative progestational activity of norgestimate, levonorgestrel-oxime and levonorgestrel in the rat and binding of these compounds to the progesterone receptor. Contraception. 1995 Feb;51(2):131-9. [PubMed:7750291 ]
Juchem M, Pollow K, Elger W, Hoffmann G, Mobus V: Receptor binding of norgestimate--a new orally active synthetic progestational compound. Contraception. 1993 Mar;47(3):283-94. [PubMed:8384965 ]

Enzyme Details

3. 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

Pasqualini JR: Differential effects of progestins on breast tissue enzymes. Maturitas. 2003 Dec 10;46 Suppl 1:S45-54. [PubMed:14670645 ]
Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. [PubMed:2175153 ]
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 ]

Showing metabocard for Norelgestromin (HMDB0015658)

MOL for HMDB0015658 (Norelgestromin)

3D MOL for HMDB0015658 (Norelgestromin)

3D SDF for HMDB0015658 (Norelgestromin)

3D-SDF for HMDB0015658 (Norelgestromin)

PDB for HMDB0015658 (Norelgestromin)

3D PDB for HMDB0015658 (Norelgestromin)

SMILES for HMDB0015658 (Norelgestromin)

INCHI for HMDB0015658 (Norelgestromin)

Structure for HMDB0015658 (Norelgestromin)

3D Structure for HMDB0015658 (Norelgestromin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References