Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (1) Show 6 proteins XML

enzymes (5)transporters (1) Show 6 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014855

Secondary Accession Numbers

HMDB14855

Metabolite Identification

Common Name

Norethindrone

Description

Norethindrone, also known as 19-norethisterone or norcolut, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, norethindrone is considered to be a steroid. Norethindrone is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on Norethindrone.

Structure

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

717
  Mrv1652305271900242D          

 26 29  0  0  1  0            999 V2000
    6.6263    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0993    0.5186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.7189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799    0.7700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3614    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -1.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5482    1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2165    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.9628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.0236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -0.0647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 23  1  6  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 14  1  1  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 24  1  1  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 25  1  6  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
  9 12  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 26  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  2  0  0  0  0
 17 19  1  0  0  0  0
 18 22  3  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END

HMDB0014855
     RDKit          3D
Norethindrone
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.7505    2.7474   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864    1.5607   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788    0.1228   -0.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3665   -0.5720   -0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5206   -0.2752    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069   -0.6041    1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -0.0155    0.8940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0919   -0.5922    0.6654 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8831   -0.9171    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -1.5309    1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.5154    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -0.0667    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950    0.9284    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371    1.7116    0.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    0.9701   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.0780   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.0540   -0.6738 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7972    0.4568   -0.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0556    1.0190   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    0.3666   -1.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171   -0.3156   -0.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0552   -1.8331   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8770    3.7947   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9671   -1.0748   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    0.6041    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448   -1.1719    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -0.0356    2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -1.6532    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354    1.0878    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777   -1.5199    0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655   -1.7381    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -0.0821    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -1.7734    2.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -2.4091    0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463   -0.4213    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297    1.8528   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.0102   -1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504    1.0823   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    2.0696   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189   -0.8715   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    1.2837    0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    1.0013   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526    2.1213   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -0.3788   -2.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0800    1.1186   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821   -2.1085   -0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515   -2.3889    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -2.0686   -1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  6
 18 41  1  1
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
M  END

717
  Mrv1652305271900242D          

 26 29  0  0  1  0            999 V2000
    6.6263    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0993    0.5186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.7189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8799    0.7700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3614    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -1.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5482    1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2165    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.9628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.0236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323   -0.0647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  1  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 23  1  6  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 14  1  1  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 24  1  1  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 25  1  6  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
  9 12  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 26  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  2  0  0  0  0
 17 19  1  0  0  0  0
 18 22  3  0  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014855

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

> <INCHI_KEY>
VIKNJXKGJWUCNN-XGXHKTLJSA-N

> <FORMULA>
C20H26O2

> <MOLECULAR_WEIGHT>
298.4192

> <EXACT_MASS>
298.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.59020487980803

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.2172279373333335

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.27829748806947

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.594932036943536

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6634024140734995

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
87.4245

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.68e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014855
     RDKit          3D
Norethindrone
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.7505    2.7474   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864    1.5607   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788    0.1228   -0.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3665   -0.5720   -0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5206   -0.2752    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069   -0.6041    1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -0.0155    0.8940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0919   -0.5922    0.6654 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8831   -0.9171    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -1.5309    1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.5154    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -0.0667    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950    0.9284    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371    1.7116    0.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    0.9701   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.0780   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.0540   -0.6738 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7972    0.4568   -0.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0556    1.0190   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    0.3666   -1.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171   -0.3156   -0.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0552   -1.8331   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8770    3.7947   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9671   -1.0748   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    0.6041    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448   -1.1719    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -0.0356    2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -1.6532    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354    1.0878    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777   -1.5199    0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655   -1.7381    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -0.0821    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -1.7734    2.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -2.4091    0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463   -0.4213    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297    1.8528   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.0102   -1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504    1.0823   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    2.0696   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189   -0.8715   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    1.2837    0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    1.0013   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526    2.1213   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -0.3788   -2.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0800    1.1186   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821   -2.1085   -0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515   -2.3889    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -2.0686   -1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  6
 18 41  1  1
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 717                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      12.369   2.903   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.733   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.385  -0.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.385   0.968   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.052  -1.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.718  -0.572   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.052   1.738   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.842   1.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.842  -1.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.718   0.968   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.317  -1.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.741   0.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.076  -2.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.385   2.508   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.693  -3.759   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.304  -2.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -0.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.090   2.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.429  -1.297   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.864  -3.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.417  -2.968   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.337   3.243   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      11.516  -1.797   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      11.123  -1.950   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       9.785   0.044   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       7.340  -0.121   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   21                                                            
CONECT    3    4    5    9   23                                             
CONECT    4    3    7    8   14                                             
CONECT    5    3    6   13   24                                             
CONECT    6    5   10   11   25                                             
CONECT    7    4   10                                                       
CONECT    8    1    4   12   18                                             
CONECT    9    3   12                                                       
CONECT   10    6    7                                                       
CONECT   11    6   16   17   26                                             
CONECT   12    8    9                                                       
CONECT   13    5   15                                                       
CONECT   14    4                                                            
CONECT   15   13   16                                                       
CONECT   16   11   15   20                                                  
CONECT   17   11   19                                                       
CONECT   18    8   22                                                       
CONECT   19   17   21                                                       
CONECT   20   16   21                                                       
CONECT   21    2   19   20                                                  
CONECT   22   18                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26   11                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0014855
HETATM    1  C1  UNL     1      -3.751   2.747  -0.321  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.586   1.561  -0.202  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.379   0.123  -0.035  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.366  -0.572  -0.734  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.521  -0.275   1.433  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.107  -0.604   1.913  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.250  -0.016   0.894  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.092  -0.592   0.665  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.883  -0.917   1.882  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.203  -1.531   1.394  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.853  -0.515   0.530  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.026  -0.067   0.873  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.695   0.928   0.053  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.537   1.712   0.562  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.338   0.970  -1.389  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.807   1.078  -1.401  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.156  -0.054  -0.674  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.797   0.457  -0.197  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.056   1.019  -1.259  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.354   0.367  -1.520  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.017  -0.316  -0.403  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.055  -1.833  -0.613  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.877   3.795  -0.425  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.967  -1.075  -0.149  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.938   0.604   1.967  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.145  -1.172   1.557  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.978  -0.036   2.880  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.982  -1.653   2.156  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.235   1.088   0.989  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.078  -1.520   0.023  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.366  -1.738   2.419  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.056  -0.082   2.560  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.825  -1.773   2.257  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.934  -2.409   0.775  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.546  -0.421   1.785  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.730   1.853  -1.900  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.670   0.010  -1.826  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.550   1.082  -2.497  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.567   2.070  -0.989  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.019  -0.871  -1.427  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.053   1.284   0.532  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.537   1.001  -2.217  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.253   2.121  -1.099  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.235  -0.379  -2.363  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.080   1.119  -1.951  1.00  0.00           H  
HETATM   46  H24 UNL     1      -3.082  -2.109  -0.929  1.00  0.00           H  
HETATM   47  H25 UNL     1      -1.752  -2.389   0.268  1.00  0.00           H  
HETATM   48  H26 UNL     1      -1.350  -2.069  -1.436  1.00  0.00           H  
CONECT    1    2    2    2   23
CONECT    2    3
CONECT    3    4    5   21
CONECT    4   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   21   29
CONECT    8    9   18   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   17
CONECT   12   13   35
CONECT   13   14   14   15
CONECT   15   16   36   37
CONECT   16   17   38   39
CONECT   17   18   40
CONECT   18   19   41
CONECT   19   20   42   43
CONECT   20   21   44   45
CONECT   21   22
CONECT   22   46   47   48
END

HMDB0014855
     RDKit          3D
Norethindrone
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.7505    2.7474   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864    1.5607   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788    0.1228   -0.0354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3665   -0.5720   -0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5206   -0.2752    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1069   -0.6041    1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -0.0155    0.8940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0919   -0.5922    0.6654 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8831   -0.9171    1.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034   -1.5309    1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -0.5154    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -0.0667    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6950    0.9284    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371    1.7116    0.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    0.9701   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    1.0780   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.0540   -0.6738 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7972    0.4568   -0.1967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0556    1.0190   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    0.3666   -1.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171   -0.3156   -0.4026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0552   -1.8331   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8770    3.7947   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9671   -1.0748   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9385    0.6041    1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448   -1.1719    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -0.0356    2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -1.6532    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354    1.0878    0.9886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777   -1.5199    0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3655   -1.7381    2.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -0.0821    2.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -1.7734    2.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -2.4091    0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5463   -0.4213    1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297    1.8528   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.0102   -1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504    1.0823   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    2.0696   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189   -0.8715   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    1.2837    0.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    1.0013   -2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2526    2.1213   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349   -0.3788   -2.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0800    1.1186   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821   -2.1085   -0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515   -2.3889    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -2.0686   -1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  1
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  6
 18 41  1  1
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(17alpha)-17-Ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one	ChEBI
17-alpha-Ethynyl-17-hydroxy-4-estren-3-one	ChEBI
17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one	ChEBI
17-alpha-Ethynyl-19-nortestosterone	ChEBI
17-alpha-Ethynyl-4-estren-17-ol-3-one	ChEBI
17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one	ChEBI
17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one	ChEBI
17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one	ChEBI
17alpha-Ethinyl-19-nortestosterone	ChEBI
17alpha-Ethinylestra-4-en-17beta-ol-3-one	ChEBI
17alpha-Ethynyl-17-hydroxy-4-estren-3-one	ChEBI
17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one	ChEBI
17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-one	ChEBI
17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one	ChEBI
17alpha-Ethynyl-19-nortestosterone	ChEBI
17alpha-Ethynyl-4-estren-17-ol-3-one	ChEBI
17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one	ChEBI
19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one	ChEBI
19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one	ChEBI
19-Nor-17-alpha-ethynyltestosterone	ChEBI
19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one	ChEBI
19-Nor-17alpha-ethynylandrosten-17beta-ol-3-one	ChEBI
19-Nor-17alpha-ethynyltestosterone	ChEBI
19-Nor-ethindrone	ChEBI
19-Norethisterone	ChEBI
4-Estren-17alpha-ethynyl-17beta-ol-3-one	ChEBI
Camila	ChEBI
Conludag	ChEBI
Micronor	ChEBI
Micronovum	ChEBI
Mini-pe	ChEBI
Mini-pill	ChEBI
Norcolut	ChEBI
Norethisteron	ChEBI
Norethisteronum	ChEBI
Noretisterona	ChEBI
Noriday	ChEBI
Norluten	ChEBI
Norlutin	ChEBI
Primolut-N	ChEBI
Utovlan	ChEBI
Norethisterone	Kegg
(17a)-17-Ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one	Generator
(17Α)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one	Generator
17-a-Ethynyl-17-hydroxy-4-estren-3-one	Generator
17-Α-ethynyl-17-hydroxy-4-estren-3-one	Generator
17-a-Ethynyl-19-norandrost-4-en-17-b-ol-3-one	Generator
17-Α-ethynyl-19-norandrost-4-en-17-β-ol-3-one	Generator
17-a-Ethynyl-19-nortestosterone	Generator
17-Α-ethynyl-19-nortestosterone	Generator
17-a-Ethynyl-4-estren-17-ol-3-one	Generator
17-Α-ethynyl-4-estren-17-ol-3-one	Generator
17-b-Hydroxy-19-norpregn-4-en-20-yn-3-one	Generator
17-Β-hydroxy-19-norpregn-4-en-20-yn-3-one	Generator
17-Hydroxy-19-nor-17-a-pregn-4-en-20-yn-3-one	Generator
17-Hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one	Generator
17-Hydroxy-19-nor-17a-pregn-4-en-20-yn-3-one	Generator
17-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one	Generator
17a-Ethinyl-19-nortestosterone	Generator
17Α-ethinyl-19-nortestosterone	Generator
17a-Ethinylestra-4-en-17b-ol-3-one	Generator
17Α-ethinylestra-4-en-17β-ol-3-one	Generator
17a-Ethynyl-17-hydroxy-4-estren-3-one	Generator
17Α-ethynyl-17-hydroxy-4-estren-3-one	Generator
17a-Ethynyl-17b-hydroxy-19-norandrost-4-en-3-one	Generator
17Α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one	Generator
17a-Ethynyl-19-nor-4-androsten-17b-ol-3-one	Generator
17Α-ethynyl-19-nor-4-androsten-17β-ol-3-one	Generator
17a-Ethynyl-19-norandrost-4-en-17b-ol-3-one	Generator
17Α-ethynyl-19-norandrost-4-en-17β-ol-3-one	Generator
17a-Ethynyl-19-nortestosterone	Generator
17Α-ethynyl-19-nortestosterone	Generator
17a-Ethynyl-4-estren-17-ol-3-one	Generator
17Α-ethynyl-4-estren-17-ol-3-one	Generator
17b-Hydroxy-19-norpregn-4-en-20-yn-3-one	Generator
17Β-hydroxy-19-norpregn-4-en-20-yn-3-one	Generator
19-Nor-17-a-ethynyl-17-b-hydroxy-4-androsten-3-one	Generator
19-Nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-one	Generator
19-Nor-17-a-ethynylandrosten-17-b-ol-3-one	Generator
19-Nor-17-α-ethynylandrosten-17-β-ol-3-one	Generator
19-Nor-17-a-ethynyltestosterone	Generator
19-Nor-17-α-ethynyltestosterone	Generator
19-Nor-17a-ethynyl-17b-hydroxy-4-androsten-3-one	Generator
19-Nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one	Generator
19-Nor-17a-ethynylandrosten-17b-ol-3-one	Generator
19-Nor-17α-ethynylandrosten-17β-ol-3-one	Generator
19-Nor-17a-ethynyltestosterone	Generator
19-Nor-17α-ethynyltestosterone	Generator
4-Estren-17a-ethynyl-17b-ol-3-one	Generator
4-Estren-17α-ethynyl-17β-ol-3-one	Generator
(17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one	HMDB
17-alpha-Ethynyl-17-beta-hydroxy-4-estren-3-one	HMDB
17-Ethinyl-19-nor-testosterone	HMDB
17-Ethynyl-17-hydroxyestr-4-en-3-one (acd/name 4.0)	HMDB
17-Ethynyl-17beta-hydroxyestr-4-en-3-one	HMDB
17-Ethynyl-19-nortestosterone	HMDB
17-Hydroxy-(17alpha)-19-norpregn-4-en-20-yn-3-one	HMDB
17-Hydroxy-17-alpha-19-norpregn-4-en-20-yn-3-one	HMDB
17alpha-Ethinyl-17alpha-ethinyl-19-nortestosterone	HMDB
17alpha-Ethynyl-17-hydroxy-estr-4-en-3-one	HMDB
17alpha-Ethynyl-17-hydroxyest-4-en-3-one	HMDB
17alpha-Ethynyl-17beta-hydroxyestr-4-en-3-one	HMDB
17alpha-Ethynyl-3-oxo-4-estren-17beta-ol	HMDB
17alpha-Pregn-4-en-20-yn-3-one	HMDB
17beta-Hydroxy-17alpha-ethynylestr-4-en-3-one	HMDB
19-Nor-17-ethinyltestosterone	HMDB
19-Norethinyltestosterone	HMDB
Anhydrohydroxynorprogesterone	HMDB
Anovule	HMDB
Conludaf	HMDB
ENT	HMDB
Ethinyl-19-nortestosterone	HMDB
Ethinylnortestosterone	HMDB
Ethynylnortestosterone	HMDB
Gestest	HMDB
Menzol	HMDB
Micronett	HMDB
Minovlar	HMDB
NET	HMDB
Nor-q.d.	HMDB
Nor-QD	HMDB
Noralutin	HMDB
Noresthisterone	HMDB
Norethyndron	HMDB
Norethynodrone	HMDB
Norfor	HMDB
Norgestin	HMDB
Norlutate	HMDB
Norluton	HMDB
Normapause	HMDB
Norpregneninlone	HMDB
Norpregneninolone	HMDB
Primolut N	HMDB
Proluteasi	HMDB
Utovlar	HMDB
Conceplan	HMDB
Nor QD	HMDB
Norethindrone, (1 beta)-isomer	HMDB
Norcolute	HMDB
Monogest	HMDB
NorQD	HMDB
Norethindrone	ChEBI

Chemical Formula

C₂₀H₂₆O₂

Average Molecular Weight

298.4192

Monoisotopic Molecular Weight

298.193280076

IUPAC Name

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

Traditional Name

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

CAS Registry Number

68-22-4

SMILES

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

InChI Identifier

InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

InChI Key

VIKNJXKGJWUCNN-XGXHKTLJSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:7627 )
tertiary alcohol (CHEBI:7627 )
3-oxo Delta(4)-steroid (CHEBI:7627 )
17beta-hydroxy steroid (CHEBI:7627 )
Pregnane and derivatives [Fig] (C05028 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05028 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030097 )

Ontology

Not Available

Exogenous (HMDB: HMDB0014855)

Food

Pulse

Bean

Scarlet bean (FooDB: FOOD00132)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0067 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	174.376	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001173

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0067 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.22	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.59	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.42 m³·mol⁻¹	ChemAxon
Polarizability	34.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.004	31661259
DarkChem	[M-H]-	169.759	31661259
DeepCCS	[M-2H]-	207.581	30932474
DeepCCS	[M+Na]+	181.797	30932474
AllCCS	[M+H]+	175.8	32859911
AllCCS	[M+H-H2O]+	172.7	32859911
AllCCS	[M+NH4]+	178.7	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	182.2	32859911
AllCCS	[M+Na-2H]-	182.2	32859911
AllCCS	[M+HCOO]-	182.3	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.	7.03 minutes	32390414
Predicted by Siyang on May 30, 2022	16.476 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2502.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	437.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	773.7 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	757.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1409.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.8 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	1454.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	315.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	532.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	24.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norethindrone	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3732.9	Standard polar	33892256
Norethindrone	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2625.2	Standard non polar	33892256
Norethindrone	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2691.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norethindrone,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C	2782.7	Semi standard non polar	33892256
Norethindrone,1TMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	2645.4	Semi standard non polar	33892256
Norethindrone,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	2746.8	Semi standard non polar	33892256
Norethindrone,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	2814.7	Standard non polar	33892256
Norethindrone,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	3117.4	Standard polar	33892256
Norethindrone,1TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C	3046.0	Semi standard non polar	33892256
Norethindrone,1TBDMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	2926.7	Semi standard non polar	33892256
Norethindrone,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	3263.0	Semi standard non polar	33892256
Norethindrone,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	3286.2	Standard non polar	33892256
Norethindrone,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21C	3312.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norethindrone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00w9-0690000000-7050c3192b843aecc482	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norethindrone GC-MS (1 TMS) - 70eV, Positive	splash10-052f-1369000000-cfce41c0dca4a0c3cd9c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norethindrone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01rt-4950000000-fcbe8bf03b1aa103152b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone LC-ESI-qTof , Positive-QTOF	splash10-0002-0391000000-ae51cc90bb8f2161f149	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone LC-ESI-qTof , Positive-QTOF	splash10-0j59-2494000000-76c71f96c07e87ef8962	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOF	splash10-0a5c-3900000000-4b2a5d95e4b6d50f16fc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOF	splash10-00ea-0790000000-60d1a1a37c0ba98d6a4a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone LC-ESI-ITFT , positive-QTOF	splash10-00e9-0890000000-5d3b8210450a1c43b119	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone , positive-QTOF	splash10-0002-0391000000-ae51cc90bb8f2161f149	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone , positive-QTOF	splash10-0ar0-3920000000-e31fa7c9e871f2e39846	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 30V, Positive-QTOF	splash10-001j-0930000000-9c2fc72a1b360913fb56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 40V, Positive-QTOF	splash10-005c-0910000000-ef775abfdf43d67a4225	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 80V, Positive-QTOF	splash10-0a5c-3900000000-11a6390c5bc543829135	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 20V, Positive-QTOF	splash10-0002-0391000000-7b2e411df9eccc111c8e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 10V, Positive-QTOF	splash10-0002-0091000000-3a83c5fc59fdaea61231	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 55V, Positive-QTOF	splash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 35V, Positive-QTOF	splash10-00ea-0790000000-1844e6f664d23868bbab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 50V, Positive-QTOF	splash10-004l-0900000000-623cab7c657eda4d2f5f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 15V, Positive-QTOF	splash10-0002-0090000000-412f7f0b9259fe759372	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 55V, Positive-QTOF	splash10-00e9-0890000000-d8c560fa1ac40e4ba22f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norethindrone 45V, Positive-QTOF	splash10-0a59-2910000000-7b16e32a71f6c1df6d1e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norethindrone 10V, Positive-QTOF	splash10-0002-0090000000-ec79e2d15a020c198dde	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norethindrone 20V, Positive-QTOF	splash10-001m-0290000000-b8f5efd6d7713f50f65c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norethindrone 40V, Positive-QTOF	splash10-0l5l-2980000000-14cb82df2a3c251f955e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norethindrone 10V, Negative-QTOF	splash10-0002-0090000000-eab48ea9142da299d923	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norethindrone 20V, Negative-QTOF	splash10-0002-0090000000-64471e6cc8b0f3e495b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norethindrone 40V, Negative-QTOF	splash10-00l6-0090000000-ccad820f0e5b5559e8e8	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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 DB00717	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00717	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00717

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5994

KEGG Compound ID

C05028

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norethisterone

METLIN ID

Not Available

PubChem Compound

6230

PDB ID

Not Available

ChEBI ID

7627

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)

Download (PDF)

General References

Knox SA, Viney RC, Gu Y, Hole AR, Fiebig DG, Street DJ, Haas MR, Weisberg E, Bateson D: The effect of adverse information and positive promotion on women's preferences for prescribed contraceptive products. Soc Sci Med. 2013 Apr;83:70-80. doi: 10.1016/j.socscimed.2012.12.025. Epub 2013 Jan 5. [PubMed:23351426 ]
Karkar A: Pregnancy and contraceptive issues in renal transplant recipients. Saudi J Kidney Dis Transpl. 2008 Mar;19(2):165-73. [PubMed:18310862 ]
Debski R, Kotarski J, Paszkowski T, Pawelczyk L, Skrzypulec V, Tomaszewski J: [The statement of Polish Gynecological Society experts on oral use of contraceptive 75 microg desogestrel minipill in different clinical cases--state of art in 2008]. Ginekol Pol. 2009 Jan;80(1):63-75. [PubMed:19323063 ]
Rabe T, Grunwald K, Runnebaum B: [Future prospects in contraception]. Arch Gynecol Obstet. 1995;257(1-4):541-7. [PubMed:8579440 ]
Tscherne G: [Benefits and risks of hormonal contraception]. Gynakol Geburtshilfliche Rundsch. 1992;32(3):174-6. [PubMed:1467664 ]
Spornitz UM: The functional morphology of the human endometrium and decidua. Adv Anat Embryol Cell Biol. 1992;124:1-99. [PubMed:1561944 ]
Kovacs G: Progestogen-only pills and bleeding disturbances. Hum Reprod. 1996 Oct;11 Suppl 2:20-3. [PubMed:8982741 ]
Lauritzen C: [Prevention of conception in adolescence]. Ther Umsch. 1994 May;51(5):314-24. [PubMed:8016756 ]
Authors unspecified: Emergency contraception hot line launched. Reprod Freedom News. 1996 Feb 23;5(4):7. [PubMed:12290778 ]
Authors unspecified: Maximizing the use of the progestin minipill. Contracept Technol Update. 1999 Feb;20(2):19-21. [PubMed:12294591 ]
Dorea JG, Miazaki ES: The effects of oral contraceptive use on iron and copper concentrations in breast milk. Fertil Steril. 1999 Aug;72(2):297-301. [PubMed:10438999 ]
Benagiano G, Bastianelli C, Farris M: Hormonal contraception: state of the art and future perspectives. Minerva Ginecol. 2007 Jun;59(3):241-70. [PubMed:17576403 ]
Benagiano G, Primiero FM: Seventy-five microgram desogestrel minipill, a new perspective in estrogen-free contraception. Ann N Y Acad Sci. 2003 Nov;997:163-73. [PubMed:14644823 ]
Authors unspecified: Is Cerazette the minipill of choice? Drug Ther Bull. 2003 Sep;41(9):68-9. [PubMed:14531209 ]
Benagiano G, Bastianelli C, Farris M: Contraception today. Ann N Y Acad Sci. 2006 Dec;1092:1-32. [PubMed:17308130 ]
Helleday J, Siwers B, Ritzen EM, Carlstrom K: Subnormal androgen and elevated progesterone levels in women treated for congenital virilizing 21-hydroxylase deficiency. J Clin Endocrinol Metab. 1993 Apr;76(4):933-6. [PubMed:8473408 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). FDA label . .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

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

Enzyme Details

3. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

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

Enzyme Details

4. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

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

Enzyme Details

5. Progesterone receptor

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

References

Mendoza-Rodriguez CA, Camacho-Arroyo I, Garcia GA, Cerbon MA: Variations of progesterone receptor and c-fos gene expression in the rat uterus after treatment with norethisterone and its A-ring reduced metabolites. Contraception. 1999 May;59(5):339-43. [PubMed:10494488 ]
Madauss KP, Deng SJ, Austin RJ, Lambert MH, McLay I, Pritchard J, Short SA, Stewart EL, Uings IJ, Williams SP: Progesterone receptor ligand binding pocket flexibility: crystal structures of the norethindrone and mometasone furoate complexes. J Med Chem. 2004 Jun 17;47(13):3381-7. [PubMed:15189034 ]
Garcia-Becerra R, Cooney AJ, Borja-Cacho E, Lemus AE, Perez-Palacios G, Larrea F: Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins. J Steroid Biochem Mol Biol. 2004 Jun;91(1-2):21-7. [PubMed:15261304 ]
Mirkin S, Wong BC, Archer DF: Effect of 17 beta-estradiol, progesterone, synthetic progestins, tibolone, and tibolone metabolites on vascular endothelial growth factor mRNA in breast cancer cells. Fertil Steril. 2005 Aug;84(2):485-91. [PubMed:16084894 ]
Pasapera AM, Cerbon MA, Castro I, Gutierrez R, Camacho-Arroyo I, Garcia GA, Perez-Palacios G: Norethisterone metabolites modulate the uteroglobin and progesterone receptor gene expression in prepubertal rabbits. Biol Reprod. 1995 Feb;52(2):426-32. [PubMed:7711211 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871 ]

Showing metabocard for Norethindrone (HMDB0014855)

MOL for HMDB0014855 (Norethindrone)

3D MOL for HMDB0014855 (Norethindrone)

3D SDF for HMDB0014855 (Norethindrone)

3D-SDF for HMDB0014855 (Norethindrone)

PDB for HMDB0014855 (Norethindrone)

3D PDB for HMDB0014855 (Norethindrone)

SMILES for HMDB0014855 (Norethindrone)

INCHI for HMDB0014855 (Norethindrone)

Structure for HMDB0014855 (Norethindrone)

3D Structure for HMDB0014855 (Norethindrone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References

Transporters

References