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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015092

Secondary Accession Numbers

HMDB15092

Metabolite Identification

Common Name

Norgestimate

Description

Norgestimate is only found in individuals that have used or taken this drug. It is a form of progesterone, which is a female hormone important for the regulation of ovulation and menstruation. Norgestimate is used with estradiol to treat the symptoms of menopause.Norgestimate binds to androgen and progestogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Norgestimate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

Structure

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

957
  Mrv0541 02231215082D          

 31 34  0  0  1  0            999 V2000
    8.7053    0.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5431   -0.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0940   -1.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069   -2.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2563   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5418   -1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8274   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0369    0.3753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5418    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0369   -0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5184   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766   -1.1193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5550   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142   -2.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699   -1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7834    1.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5418    1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298   -1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2982   -2.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4583    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5298    1.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1266    1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3262   -1.3575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1159   -1.4392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3989   -0.3712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893   -0.4595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 25  1  0  0  0  0
  2 25  2  0  0  0  0
  3  4  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 28  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 29  1  1  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
  8 30  1  6  0  0  0
  9 13  1  0  0  0  0
  9 20  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 14 31  1  1  0  0  0
 15 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 23  2  0  0  0  0
 19 22  1  0  0  0  0
 20 26  3  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0015092
     RDKit          3D
Norgestimate
 58 61  0  0  0  0  0  0  0  0999 V2000
   -2.2473    2.5305   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    1.5964   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    0.4647   -0.2076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0292   -0.1780   -0.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3223   -0.7615   -1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6354   -1.4466   -2.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607   -0.7212   -2.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1837    1.0382    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    1.2604    1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.8073    0.7791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4811    0.4442    1.2068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1692    1.6541    1.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372    2.2357    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    1.2154    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939    1.5875    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859    0.5530   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066    0.8545   -1.0377 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268   -0.1448   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8951   -0.8732   -0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213   -0.9783   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.1658    0.2201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1881   -0.0162   -0.0785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5202   -1.2174   -0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987   -0.8794   -1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661   -0.3323    0.1161 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9485   -1.4208    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724   -2.3926    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    3.3604   -2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8344   -1.3419   -3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4512   -0.9090   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -2.4966   -1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7704    0.2907    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681    1.9543    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    2.3747    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6948    0.7578    2.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    1.6050    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346   -0.3826    1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    2.4734    1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479    1.4381    2.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8165    2.8566    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8366    2.9319    1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641    2.5976    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9569   -0.4540   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265   -1.5373   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405   -1.1118    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.5644   -1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422   -2.0351   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7340   -0.6372    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    0.8230   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -1.5661   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -2.0342    0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124   -1.8072   -1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -0.1311   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162   -2.0025    1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2777   -1.0250    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852   -3.2939    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -2.0611    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -2.7865   -0.3448 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 26 27  1  0
 25  3  1  0
 25 10  1  0
 22 11  1  0
 21 14  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  6
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
M  END

957
  Mrv0541 02231215082D          

 31 34  0  0  1  0            999 V2000
    8.7053    0.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5431   -0.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0940   -1.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8069   -2.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2563   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5418   -1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8274   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0369    0.3753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5418    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0369   -0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5184   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766   -1.1193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5550   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2563    0.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8142   -2.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699   -1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3119   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7834    1.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5418    1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298   -1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2982   -2.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4583    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5298    1.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1266    1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3262   -1.3575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1159   -1.4392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3989   -0.3712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893   -0.4595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 25  1  0  0  0  0
  2 25  2  0  0  0  0
  3  4  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 28  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 29  1  1  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
  8 30  1  6  0  0  0
  9 13  1  0  0  0  0
  9 20  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 14 31  1  1  0  0  0
 15 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 23  2  0  0  0  0
 19 22  1  0  0  0  0
 20 26  3  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015092

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1

> <INCHI_KEY>
KIQQMECNKUGGKA-NMYWJIRASA-N

> <FORMULA>
C23H31NO3

> <MOLECULAR_WEIGHT>
369.4971

> <EXACT_MASS>
369.230393863

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
42.82406406020445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
4.112401798666667

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.46612800448324

> <JCHEM_PKA_STRONGEST_BASIC>
3.1146409641686694

> <JCHEM_POLAR_SURFACE_AREA>
58.89

> <JCHEM_REFRACTIVITY>
104.9987

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norgestimate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015092
     RDKit          3D
Norgestimate
 58 61  0  0  0  0  0  0  0  0999 V2000
   -2.2473    2.5305   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    1.5964   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    0.4647   -0.2076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0292   -0.1780   -0.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3223   -0.7615   -1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6354   -1.4466   -2.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607   -0.7212   -2.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1837    1.0382    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    1.2604    1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.8073    0.7791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4811    0.4442    1.2068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1692    1.6541    1.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372    2.2357    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    1.2154    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939    1.5875    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859    0.5530   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066    0.8545   -1.0377 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268   -0.1448   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8951   -0.8732   -0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213   -0.9783   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.1658    0.2201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1881   -0.0162   -0.0785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5202   -1.2174   -0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987   -0.8794   -1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661   -0.3323    0.1161 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9485   -1.4208    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724   -2.3926    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    3.3604   -2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8344   -1.3419   -3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4512   -0.9090   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -2.4966   -1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7704    0.2907    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681    1.9543    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    2.3747    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6948    0.7578    2.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    1.6050    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346   -0.3826    1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    2.4734    1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479    1.4381    2.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8165    2.8566    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8366    2.9319    1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641    2.5976    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9569   -0.4540   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265   -1.5373   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405   -1.1118    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.5644   -1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422   -2.0351   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7340   -0.6372    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    0.8230   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -1.5661   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -2.0342    0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124   -1.8072   -1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -0.1311   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162   -2.0025    1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2777   -1.0250    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852   -3.2939    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -2.0611    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -2.7865   -0.3448 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 26 27  1  0
 25  3  1  0
 25 10  1  0
 22 11  1  0
 21 14  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  6
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 957                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.250   1.604   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      17.814  -0.557   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.909  -3.694   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.240  -4.470   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      13.545   0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.545  -1.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.211  -2.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.878  -1.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.002   0.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.211   1.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.002  -1.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.878   0.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.901  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.476  -2.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.236  -3.683   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.545   1.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.853  -4.495   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.464  -3.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.049  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.529   2.166   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.211   2.541   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.589  -2.034   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.023  -4.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.576  -3.705   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.655   0.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.056   3.631   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.903   1.878   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      13.676  -2.534   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      13.283  -2.687   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      11.945  -0.693   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       9.500  -0.858   0.000  0.00  0.00           H+0
CONECT    1    9   25                                                       
CONECT    2   25                                                            
CONECT    3    4                                                            
CONECT    4    3   24                                                       
CONECT    5    6    9   10   16                                             
CONECT    6    5    7   11   28                                             
CONECT    7    6    8   15   29                                             
CONECT    8    7   12   14   30                                             
CONECT    9    1    5   13   20                                             
CONECT   10    5   12                                                       
CONECT   11    6   13                                                       
CONECT   12    8   10                                                       
CONECT   13    9   11                                                       
CONECT   14    8   18   19   31                                             
CONECT   15    7   17                                                       
CONECT   16    5   21                                                       
CONECT   17   15   18                                                       
CONECT   18   14   17   23                                                  
CONECT   19   14   22                                                       
CONECT   20    9   26                                                       
CONECT   21   16                                                            
CONECT   22   19   24                                                       
CONECT   23   18   24                                                       
CONECT   24    4   22   23                                                  
CONECT   25    1    2   27                                                  
CONECT   26   20                                                            
CONECT   27   25                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31   14                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0015092
HETATM    1  C1  UNL     1      -2.247   2.530  -1.773  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.532   1.596  -1.075  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.880   0.465  -0.208  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.029  -0.178  -0.588  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.322  -0.762  -1.792  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.635  -1.447  -2.058  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.461  -0.721  -2.705  1.00  0.00           O  
HETATM    8  C6  UNL     1      -3.184   1.038   1.213  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.820   1.260   1.822  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.880   0.807   0.779  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.481   0.444   1.207  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.169   1.654   1.755  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.237   2.236   0.891  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.170   1.215   0.360  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.394   1.587   0.048  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.286   0.553  -0.473  1.00  0.00           C  
HETATM   17  N1  UNL     1       6.407   0.854  -1.038  1.00  0.00           N  
HETATM   18  O3  UNL     1       7.227  -0.145  -1.520  1.00  0.00           O  
HETATM   19  C15 UNL     1       4.895  -0.873  -0.351  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.421  -0.978  -0.767  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.637  -0.166   0.220  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.188  -0.016  -0.079  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.520  -1.217  -0.628  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.899  -0.879  -1.029  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.666  -0.332   0.116  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.949  -1.421   1.132  1.00  0.00           C  
HETATM   27  C23 UNL     1      -2.972  -2.393   0.662  1.00  0.00           C  
HETATM   28  H1  UNL     1      -2.003   3.360  -2.407  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.834  -1.342  -3.136  1.00  0.00           H  
HETATM   30  H3  UNL     1      -6.451  -0.909  -1.523  1.00  0.00           H  
HETATM   31  H4  UNL     1      -5.623  -2.497  -1.714  1.00  0.00           H  
HETATM   32  H5  UNL     1      -3.770   0.291   1.774  1.00  0.00           H  
HETATM   33  H6  UNL     1      -3.768   1.954   1.084  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.759   2.375   2.016  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.695   0.758   2.803  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.802   1.605   0.011  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.535  -0.383   1.940  1.00  0.00           H  
HETATM   38  H11 UNL     1       0.443   2.473   1.978  1.00  0.00           H  
HETATM   39  H12 UNL     1       1.648   1.438   2.755  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.816   2.857   0.056  1.00  0.00           H  
HETATM   41  H14 UNL     1       2.837   2.932   1.507  1.00  0.00           H  
HETATM   42  H15 UNL     1       4.764   2.598   0.156  1.00  0.00           H  
HETATM   43  H16 UNL     1       7.957  -0.454  -0.862  1.00  0.00           H  
HETATM   44  H17 UNL     1       5.526  -1.537  -0.942  1.00  0.00           H  
HETATM   45  H18 UNL     1       4.941  -1.112   0.745  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.332  -0.564  -1.786  1.00  0.00           H  
HETATM   47  H20 UNL     1       3.142  -2.035  -0.681  1.00  0.00           H  
HETATM   48  H21 UNL     1       2.734  -0.637   1.224  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.078   0.823  -0.813  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.104  -1.566  -1.512  1.00  0.00           H  
HETATM   51  H24 UNL     1       0.592  -2.034   0.115  1.00  0.00           H  
HETATM   52  H25 UNL     1      -1.412  -1.807  -1.396  1.00  0.00           H  
HETATM   53  H26 UNL     1      -0.834  -0.131  -1.836  1.00  0.00           H  
HETATM   54  H27 UNL     1      -1.016  -2.002   1.331  1.00  0.00           H  
HETATM   55  H28 UNL     1      -2.278  -1.025   2.096  1.00  0.00           H  
HETATM   56  H29 UNL     1      -2.885  -3.294   1.341  1.00  0.00           H  
HETATM   57  H30 UNL     1      -4.023  -2.061   0.782  1.00  0.00           H  
HETATM   58  H31 UNL     1      -2.850  -2.787  -0.345  1.00  0.00           H  
CONECT    1    2    2    2   28
CONECT    2    3
CONECT    3    4    8   25
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   29   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   25   36
CONECT   11   12   22   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   15   21
CONECT   15   16   42
CONECT   16   17   17   19
CONECT   17   18
CONECT   18   43
CONECT   19   20   44   45
CONECT   20   21   46   47
CONECT   21   22   48
CONECT   22   23   49
CONECT   23   24   50   51
CONECT   24   25   52   53
CONECT   25   26
CONECT   26   27   54   55
CONECT   27   56   57   58
END

HMDB0015092
     RDKit          3D
Norgestimate
 58 61  0  0  0  0  0  0  0  0999 V2000
   -2.2473    2.5305   -1.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    1.5964   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    0.4647   -0.2076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0292   -0.1780   -0.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3223   -0.7615   -1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6354   -1.4466   -2.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607   -0.7212   -2.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1837    1.0382    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203    1.2604    1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    0.8073    0.7791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4811    0.4442    1.2068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1692    1.6541    1.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372    2.2357    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1704    1.2154    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939    1.5875    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859    0.5530   -0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066    0.8545   -1.0377 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268   -0.1448   -1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8951   -0.8732   -0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4213   -0.9783   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.1658    0.2201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1881   -0.0162   -0.0785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5202   -1.2174   -0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987   -0.8794   -1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661   -0.3323    0.1161 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9485   -1.4208    1.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724   -2.3926    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    3.3604   -2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8344   -1.3419   -3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4512   -0.9090   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6228   -2.4966   -1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7704    0.2907    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681    1.9543    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7590    2.3747    2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6948    0.7578    2.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    1.6050    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346   -0.3826    1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    2.4734    1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479    1.4381    2.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8165    2.8566    0.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8366    2.9319    1.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7641    2.5976    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9569   -0.4540   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5265   -1.5373   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9405   -1.1118    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315   -0.5644   -1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1422   -2.0351   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7340   -0.6372    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    0.8230   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -1.5661   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -2.0342    0.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4124   -1.8072   -1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -0.1311   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0162   -2.0025    1.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2777   -1.0250    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8852   -3.2939    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -2.0611    0.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8499   -2.7865   -0.3448 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 26 27  1  0
 25  3  1  0
 25 10  1  0
 22 11  1  0
 21 14  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  1
 22 49  1  6
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 27 58  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 oxime acetate (ester)	ChEBI
(17alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime	ChEBI
D-13beta-Ethyl-17alpha-ethynyl-17beta-acetoxygon-4-en-3-one oxime	ChEBI
Dexnorgestrel acetime	ChEBI
Norgestimato	ChEBI
Norgestimatum	ChEBI
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one oxime acetate (ester)	Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one oxime acetic acid (ester)	Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetic acid (ester)	Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetate (ester)	Generator
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one oxime acetic acid (ester)	Generator
(17a)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime	Generator
(17Α)-17-(acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime	Generator
D-13b-Ethyl-17a-ethynyl-17b-acetoxygon-4-en-3-one oxime	Generator
D-13Β-ethyl-17α-ethynyl-17β-acetoxygon-4-en-3-one oxime	Generator
Norgestimic acid	Generator
Norgestrel oxime acetate	HMDB

Chemical Formula

C₂₃H₃₁NO₃

Average Molecular Weight

369.4971

Monoisotopic Molecular Weight

369.230393863

IUPAC Name

(1S,2R,5E,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-(hydroxyimino)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate

Traditional Name

norgestimate

CAS Registry Number

35189-28-7

SMILES

[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O

InChI Identifier

InChI=1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1

InChI Key

KIQQMECNKUGGKA-NMYWJIRASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
Estrane-skeleton
Delta-4-steroid
Ynone
Ketoxime
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxime
Acetylide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:50815 )
steroid ester (CHEBI:50815 )
ketoxime (CHEBI:50815 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	216 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0053 g/L	Not Available
LogP	4.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	197.597	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001204

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0053 g/L	ALOGPS
logP	3.8	ALOGPS
logP	4.11	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	3.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105 m³·mol⁻¹	ChemAxon
Polarizability	42.82 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]+	189.772	31661259
DarkChem	[M-H]-	180.561	31661259
DeepCCS	[M-2H]-	223.685	30932474
DeepCCS	[M+Na]+	197.663	30932474
AllCCS	[M+H]+	193.2	32859911
AllCCS	[M+H-H2O]+	190.7	32859911
AllCCS	[M+NH4]+	195.5	32859911
AllCCS	[M+Na]+	196.1	32859911
AllCCS	[M-H]-	194.6	32859911
AllCCS	[M+Na-2H]-	195.2	32859911
AllCCS	[M+HCOO]-	196.0	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.	7.17 minutes	32390414
Predicted by Siyang on May 30, 2022	20.3734 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3022.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	531.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	243.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	236.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	540.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	989.5 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	908.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1789.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	549.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1770.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	624.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	503.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	543.0 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	12.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norgestimate	[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O	4333.3	Standard polar	33892256
Norgestimate	[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O	2841.8	Standard non polar	33892256
Norgestimate	[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CC\C(C=C3CC[C@@]21[H])=N/O	3001.7	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 - Norgestimate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2698000000-7e02d6124cbf30e8be87	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norgestimate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norgestimate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norgestimate 20V, Positive-QTOF	splash10-00di-0009000000-b5b2b147e5ce033804a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norgestimate 10V, Positive-QTOF	splash10-00di-0009000000-1bb2450b5dc4140f5e93	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norgestimate 30V, Positive-QTOF	splash10-00di-0209000000-c0873e43f4129a09814d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norgestimate 40V, Positive-QTOF	splash10-00di-0922000000-9b40bb72db6c044b370c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norgestimate 40V, Positive-QTOF	splash10-00di-0922000000-59c3543a046f1a654729	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norgestimate 50V, Positive-QTOF	splash10-05i3-0910000000-6a2449a24f6efdf10513	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 10V, Positive-QTOF	splash10-00di-0009000000-cda4a2de67f83fe17601	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 20V, Positive-QTOF	splash10-03di-0129000000-e3b5fba490277d952c9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 40V, Positive-QTOF	splash10-0006-6491000000-51d7c89ce72eb09d3993	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 10V, Negative-QTOF	splash10-016r-1009000000-2b5a8cbd62430bb58add	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 20V, Negative-QTOF	splash10-05r0-2009000000-05bf9254a578ac3a1a11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 40V, Negative-QTOF	splash10-0a4i-4029000000-76a6829838c24ac7bd2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 10V, Positive-QTOF	splash10-03di-0019000000-ffdfef9c7bc973ccee83	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 20V, Positive-QTOF	splash10-001i-0293000000-fcd7c087298d41406df8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 40V, Positive-QTOF	splash10-01qa-0930000000-01441e5a4930cf72a343	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 10V, Negative-QTOF	splash10-014i-3009000000-8b4cc4a89faf8b738f0e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 20V, Negative-QTOF	splash10-0a4i-0049000000-27e791a48fed12ec9d0a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norgestimate 40V, Negative-QTOF	splash10-0zfs-2049000000-4e6f026ed6781f5b8b3b	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 DB00957	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00957	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00957

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5022837

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norgestimate

METLIN ID

Not Available

PubChem Compound

6540478

PDB ID

Not Available

ChEBI ID

50815

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

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. 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

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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. 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 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Lindenmaier H, Becker M, Haefeli WE, Weiss J: Interaction of progestins with the human multidrug resistance-associated protein 2 (MRP2). Drug Metab Dispos. 2005 Nov;33(11):1576-9. Epub 2005 Jul 27. [PubMed:16049127 ]

Showing metabocard for Norgestimate (HMDB0015092)

MOL for HMDB0015092 (Norgestimate)

3D MOL for HMDB0015092 (Norgestimate)

3D SDF for HMDB0015092 (Norgestimate)

3D-SDF for HMDB0015092 (Norgestimate)

PDB for HMDB0015092 (Norgestimate)

3D PDB for HMDB0015092 (Norgestimate)

SMILES for HMDB0015092 (Norgestimate)

INCHI for HMDB0015092 (Norgestimate)

Structure for HMDB0015092 (Norgestimate)

3D Structure for HMDB0015092 (Norgestimate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References