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

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014495

Secondary Accession Numbers

HMDB14495

Metabolite Identification

Common Name

Megestrol

Description

Megestrol, also known as magestin or megeron, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, megestrol is considered to be a steroid lipid molecule. Megestrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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


  Mrv0541 09041213522D          

 27 30  0  0  1  0            999 V2000
    1.8036   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    1.2211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4100    0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0189    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0189   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    1.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    2.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    2.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 19  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
  5  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
  2  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 22  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 19 20  1  6  0  0  0
 22 21  2  0  0  0  0
  6 23  1  1  0  0  0
  3 24  1  6  0  0  0
  3 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END

HMDB0014495
     RDKit          3D
Megestrol
 52 55  0  0  0  0  0  0  0  0999 V2000
   -5.2243   -1.0018    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2212    0.0582    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080    1.0889    1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603   -0.1477   -0.2481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2710   -1.3959   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.9656   -1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210    1.6715   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.5598   -0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3553    0.8925   -0.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0691    1.5219   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622    1.2546   -1.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128    0.3268   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -0.0803   -1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513   -1.0069   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9772   -1.7312   -1.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.0873    0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828   -1.2215    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -0.1104    0.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4843    1.1054    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460   -0.4334   -0.1946 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355   -1.1866    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199   -1.3349    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -0.0237    0.3105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6977    0.8627    1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9154   -1.7306    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1839   -0.5146    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4844   -1.5812    0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5132   -2.0625   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4723   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1045    1.6487   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    2.0633   -2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9756    2.5209   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -0.2074   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    1.5873    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149    2.2107   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.7310   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701    0.2376   -2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507   -1.9594    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370   -0.1274    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289   -1.2261    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384   -2.2272    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    1.1228    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232    1.0374    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378    2.0571    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -1.0244   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -0.7304    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -2.2006    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -2.0003   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.8139    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    0.9009    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    1.9019    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3032    0.3677    2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 11 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  6
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
M  END


  Mrv0541 09041213522D          

 27 30  0  0  1  0            999 V2000
    1.8036   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    1.2211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4100    0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0189    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0189   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    1.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    2.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202    2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    2.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 19  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
  5  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
  2  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 22  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 19 20  1  6  0  0  0
 22 21  2  0  0  0  0
  6 23  1  1  0  0  0
  3 24  1  6  0  0  0
  3 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014495

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4-5,12,16-18,24H,6-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

> <INCHI_KEY>
JBVNBBXAMBZTMQ-CEGNMAFCSA-N

> <FORMULA>
C21H28O3

> <MOLECULAR_WEIGHT>
328.4452

> <EXACT_MASS>
328.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.31424938276417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.0392576210000004

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.611049556584735

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.699101045727993

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8052039166501226

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
95.22189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
megestrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014495
     RDKit          3D
Megestrol
 52 55  0  0  0  0  0  0  0  0999 V2000
   -5.2243   -1.0018    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2212    0.0582    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080    1.0889    1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603   -0.1477   -0.2481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2710   -1.3959   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.9656   -1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210    1.6715   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.5598   -0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3553    0.8925   -0.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0691    1.5219   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622    1.2546   -1.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128    0.3268   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -0.0803   -1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513   -1.0069   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9772   -1.7312   -1.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.0873    0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828   -1.2215    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -0.1104    0.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4843    1.1054    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460   -0.4334   -0.1946 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355   -1.1866    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199   -1.3349    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -0.0237    0.3105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6977    0.8627    1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9154   -1.7306    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1839   -0.5146    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4844   -1.5812    0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5132   -2.0625   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4723   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1045    1.6487   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    2.0633   -2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9756    2.5209   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -0.2074   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    1.5873    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149    2.2107   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.7310   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701    0.2376   -2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507   -1.9594    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370   -0.1274    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289   -1.2261    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384   -2.2272    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    1.1228    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232    1.0374    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378    2.0571    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -1.0244   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -0.7304    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -2.2006    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -2.0003   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.8139    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    0.9009    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    1.9019    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3032    0.3677    2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 11 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  6
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
M  END

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       3.367  -0.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.568  -2.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.367   2.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.568   2.573   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.272   1.033   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.099  -0.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.765   1.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.765  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.099  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.433   0.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.433  -2.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.766  -0.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.568  -0.507   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.568   1.033   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.765   0.263   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.765  -1.277   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       1.902   1.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.902   3.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.902   0.263   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       1.902  -1.277   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      -6.100  -2.817   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.766  -2.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.099   1.033   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.700   3.049   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.367   3.819   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.278   4.908   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.700   4.589   0.000  0.00  0.00           O+0
CONECT    1   19    5                                                       
CONECT    2   13    8                                                       
CONECT    3   17    5   24   25                                             
CONECT    4   17    7                                                       
CONECT    5    1    3                                                       
CONECT    6   15    9   10   23                                             
CONECT    7   15    4                                                       
CONECT    8    2    9                                                       
CONECT    9    6   11    8                                                  
CONECT   10    6   12                                                       
CONECT   11    9   22                                                       
CONECT   12   10   22                                                       
CONECT   13   19   15    2   14                                             
CONECT   14   13                                                            
CONECT   15   13    6    7   16                                             
CONECT   16   15                                                            
CONECT   17   19    3    4   18                                             
CONECT   18   17                                                            
CONECT   19   13   17    1   20                                             
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   11   12   21                                                  
CONECT   23    6                                                            
CONECT   24    3                                                            
CONECT   25    3   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0014495
HETATM    1  C1  UNL     1      -5.224  -1.002   0.973  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.221   0.058   0.728  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.308   1.089   1.356  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.160  -0.148  -0.248  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.271  -1.396  -0.835  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.286   0.966  -1.298  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.921   1.672  -1.291  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.035   0.560  -0.884  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.355   0.892  -0.524  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.069   1.522  -1.662  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.362   1.255  -1.928  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.113   0.327  -1.096  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.300  -0.080  -1.484  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.051  -1.007  -0.655  1.00  0.00           C  
HETATM   15  O3  UNL     1       5.977  -1.731  -1.082  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.688  -1.087   0.777  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.183  -1.221   0.851  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.472  -0.110   0.164  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.484   1.105   1.100  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.046  -0.433  -0.195  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.336  -1.187   0.885  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.120  -1.335   0.623  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.771  -0.024   0.310  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.698   0.863   1.514  1.00  0.00           C  
HETATM   25  H1  UNL     1      -4.915  -1.731   1.746  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.184  -0.515   1.296  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.484  -1.581   0.065  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.513  -2.062  -0.145  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.354   0.472  -2.282  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.105   1.649  -1.081  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.690   2.063  -2.314  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.976   2.521  -0.614  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.031  -0.207  -1.676  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.460   1.587   0.333  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.515   2.211  -2.281  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.852   1.731  -2.766  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.770   0.238  -2.408  1.00  0.00           H  
HETATM   38  H14 UNL     1       5.151  -1.959   1.281  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.037  -0.127   1.239  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.929  -1.226   1.941  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.938  -2.227   0.442  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.474   1.123   1.599  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.723   1.037   1.878  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.438   2.057   0.507  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.049  -1.024  -1.130  1.00  0.00           H  
HETATM   46  H22 UNL     1       0.553  -0.730   1.891  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.784  -2.201   0.930  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.249  -2.000  -0.254  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.580  -1.814   1.532  1.00  0.00           H  
HETATM   50  H26 UNL     1      -0.672   0.901   1.883  1.00  0.00           H  
HETATM   51  H27 UNL     1      -2.039   1.902   1.329  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.303   0.368   2.314  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5    6   23
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   23   33
CONECT    9   10   20   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   18
CONECT   13   14   37
CONECT   14   15   15   16
CONECT   16   17   38   39
CONECT   17   18   40   41
CONECT   18   19   20
CONECT   19   42   43   44
CONECT   20   21   45
CONECT   21   22   46   47
CONECT   22   23   48   49
CONECT   23   24
CONECT   24   50   51   52
END

HMDB0014495
     RDKit          3D
Megestrol
 52 55  0  0  0  0  0  0  0  0999 V2000
   -5.2243   -1.0018    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2212    0.0582    0.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080    1.0889    1.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1603   -0.1477   -0.2481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2710   -1.3959   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    0.9656   -1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210    1.6715   -1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.5598   -0.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3553    0.8925   -0.5236 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0691    1.5219   -1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622    1.2546   -1.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128    0.3268   -1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -0.0803   -1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513   -1.0069   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9772   -1.7312   -1.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.0873    0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1828   -1.2215    0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -0.1104    0.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4843    1.1054    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460   -0.4334   -0.1946 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3355   -1.1866    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199   -1.3349    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705   -0.0237    0.3105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6977    0.8627    1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9154   -1.7306    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1839   -0.5146    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4844   -1.5812    0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5132   -2.0625   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    0.4723   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1045    1.6487   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    2.0633   -2.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9756    2.5209   -0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313   -0.2074   -1.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4604    1.5873    0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149    2.2107   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.7310   -2.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701    0.2376   -2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507   -1.9594    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370   -0.1274    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289   -1.2261    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9384   -2.2272    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    1.1228    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232    1.0374    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378    2.0571    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488   -1.0244   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -0.7304    1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -2.2006    0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -2.0003   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.8139    1.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    0.9009    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    1.9019    1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3032    0.3677    2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 11 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  6
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione	ChEBI
Magestin	ChEBI
Megeron	ChEBI
Megestrolum	ChEBI
Niagestin	ChEBI
Ovaban	ChEBI
Ovarid	ChEBI
Volidan	ChEBI
Megestrol acetate	HMDB
Megestrolo	HMDB
Megestryl acetate	HMDB
MGA	HMDB
17-Hydroxy-6-dehydroprogesterone, (9beta,10alpha)-isomer	HMDB
17-Hydroxy-6-dehydroprogesterone	HMDB
17-HDHPG	HMDB

Chemical Formula

C₂₁H₂₈O₃

Average Molecular Weight

328.4452

Monoisotopic Molecular Weight

328.203844762

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one

Traditional Name

megestrol

CAS Registry Number

3562-63-8

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H28O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4-5,12,16-18,24H,6-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

JBVNBBXAMBZTMQ-CEGNMAFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:6722 )
3-oxo Delta(4)-steroid (CHEBI:6722 )
20-oxo steroid (CHEBI:6722 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030177 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218.0 - 220.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.022 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	2.91	ALOGPS
logP	3.04	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.22 m³·mol⁻¹	ChemAxon
Polarizability	37.31 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]+	179.805	31661259
DarkChem	[M-H]-	174.319	31661259
DeepCCS	[M-2H]-	213.68	30932474
DeepCCS	[M+Na]+	188.37	30932474
AllCCS	[M+H]+	181.6	32859911
AllCCS	[M+H-H2O]+	178.7	32859911
AllCCS	[M+NH4]+	184.3	32859911
AllCCS	[M+Na]+	185.1	32859911
AllCCS	[M-H]-	188.3	32859911
AllCCS	[M+Na-2H]-	188.6	32859911
AllCCS	[M+HCOO]-	189.0	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.	6.31 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3723 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2669.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	385.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	666.4 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	654.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1405.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.9 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	1454.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	277.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	448.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Megestrol	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	3842.0	Standard polar	33892256
Megestrol	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	2739.7	Standard non polar	33892256
Megestrol	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	2996.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Megestrol,1TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3070.0	Semi standard non polar	33892256
Megestrol,1TMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3006.3	Semi standard non polar	33892256
Megestrol,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	2964.6	Semi standard non polar	33892256
Megestrol,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3065.6	Semi standard non polar	33892256
Megestrol,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2880.5	Standard non polar	33892256
Megestrol,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3328.5	Standard polar	33892256
Megestrol,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3039.7	Semi standard non polar	33892256
Megestrol,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	2836.7	Standard non polar	33892256
Megestrol,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3440.5	Standard polar	33892256
Megestrol,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2969.9	Semi standard non polar	33892256
Megestrol,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2843.2	Standard non polar	33892256
Megestrol,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3451.3	Standard polar	33892256
Megestrol,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3045.9	Semi standard non polar	33892256
Megestrol,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2912.0	Standard non polar	33892256
Megestrol,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3420.6	Standard polar	33892256
Megestrol,1TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3326.9	Semi standard non polar	33892256
Megestrol,1TBDMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3265.6	Semi standard non polar	33892256
Megestrol,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3237.5	Semi standard non polar	33892256
Megestrol,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3577.3	Semi standard non polar	33892256
Megestrol,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3336.8	Standard non polar	33892256
Megestrol,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3550.4	Standard polar	33892256
Megestrol,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3575.5	Semi standard non polar	33892256
Megestrol,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3339.2	Standard non polar	33892256
Megestrol,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3660.1	Standard polar	33892256
Megestrol,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3496.8	Semi standard non polar	33892256
Megestrol,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3267.2	Standard non polar	33892256
Megestrol,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3687.0	Standard polar	33892256
Megestrol,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3796.2	Semi standard non polar	33892256
Megestrol,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3526.0	Standard non polar	33892256
Megestrol,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3682.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Megestrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052o-3692000000-273ed2697dc747b07877	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Megestrol GC-MS (1 TMS) - 70eV, Positive	splash10-009l-5569000000-92c478c5541ca3cdb49d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Megestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 10V, Positive-QTOF	splash10-004i-0129000000-91e7aae3dcf4681023d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 20V, Positive-QTOF	splash10-01ti-0394000000-3a1e1148d707633d1893	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 40V, Positive-QTOF	splash10-014s-2940000000-35c10eae302be7284ec8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 10V, Negative-QTOF	splash10-004i-0019000000-c7b233401fe84cccc004	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 20V, Negative-QTOF	splash10-004r-0097000000-6b5af6858dc62dd2e876	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 40V, Negative-QTOF	splash10-0n2i-0091000000-8a487c18d41b7b41e85f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 10V, Negative-QTOF	splash10-004i-0019000000-f0d17e74dd87aa6f0a01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 20V, Negative-QTOF	splash10-004i-0049000000-5c51a1c8838c7592f1ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 40V, Negative-QTOF	splash10-015i-0091000000-caf99973cbd8b1d9964c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 10V, Positive-QTOF	splash10-004i-0019000000-927a758547b25409a106	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 20V, Positive-QTOF	splash10-0cfu-0942000000-783008fe6e6e6a07d8f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Megestrol 40V, Positive-QTOF	splash10-0596-5960000000-a807ceaf72ed64e8caf1	2021-09-23	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 DB00351	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00351	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2338340

KEGG Compound ID

C07120

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Megestrol

METLIN ID

Not Available

PubChem Compound

3080587

PDB ID

Not Available

ChEBI ID

6722

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

Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. [PubMed:19434889 ]
Orme LM, Bond JD, Humphrey MS, Zacharin MR, Downie PA, Jamsen KM, Mitchell SL, Robinson JM, Grapsas NA, Ashley DM: Megestrol acetate in pediatric oncology patients may lead to severe, symptomatic adrenal suppression. Cancer. 2003 Jul 15;98(2):397-405. [PubMed:12872362 ]
Pascual Lopez A, Roque i Figuls M, Urrutia Cuchi G, Berenstein EG, Almenar Pasies B, Balcells Alegre M, Herdman M: Systematic review of megestrol acetate in the treatment of anorexia-cachexia syndrome. J Pain Symptom Manage. 2004 Apr;27(4):360-9. [PubMed:15050664 ]
Berenstein EG, Ortiz Z: Megestrol acetate for the treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004310. [PubMed:15846706 ]
Rao GG, Miller DS: Hormonal therapy in epithelial ovarian cancer. Expert Rev Anticancer Ther. 2006 Jan;6(1):43-7. [PubMed:16375643 ]
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

Vadivelu S, Sharer L, Schulder M: Regression of multiple intracranial meningiomas after cessation of long-term progesterone agonist therapy. J Neurosurg. 2010 May;112(5):920-4. doi: 10.3171/2009.8.JNS09201. [PubMed:19731987 ]
Mokbel K: Focus on anastrozole and breast cancer. Curr Med Res Opin. 2003;19(8):683-8. [PubMed:14687437 ]
Wentling GK, Sevin BU, Geiger XJ, Bridges MD: Benign metastasizing leiomyoma responsive to megestrol: case report and review of the literature. Int J Gynecol Cancer. 2005 Nov-Dec;15(6):1213-7. [PubMed:16343217 ]
Gruber T, Dare AO, Balos LL, Lele S, Fenstermaker RA: Multiple meningiomas arising during long-term therapy with the progesterone agonist megestrol acetate. Case report. J Neurosurg. 2004 Feb;100(2):328-31. [PubMed:15086241 ]
Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. [PubMed:19434889 ]
Wermers RA, Hurley DL, Kearns AE: Osteoporosis associated with megestrol acetate. Mayo Clin Proc. 2004 Dec;79(12):1557-61. [PubMed:15595341 ]
Wiedemann K, Hirschmann M, Knaudt K, Rupprecht R, Seier FE, Holsboer F: Sleep endocrine effects of megestrol acetate in healthy men. J Neuroendocrinol. 1998 Sep;10(9):719-27. [PubMed:9744490 ]
Lamberts SW, Uitterlinden P, Bons EG, Verleun T: Comparison of the actions of RU 38486 and megestrol acetate in the model of a transplantable adrenocorticotropin- and prolactin-secreting rat pituitary tumor. Cancer Res. 1985 Mar;45(3):1015-9. [PubMed:2982481 ]
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

Wang L, Yang CP, Horwitz SB, Trail PA, Casazza AM: Reversal of the human and murine multidrug-resistance phenotype with megestrol acetate. Cancer Chemother Pharmacol. 1994;34(2):96-102. [PubMed:8194172 ]

Showing metabocard for Megestrol (HMDB0014495)

MOL for HMDB0014495 (Megestrol)

3D MOL for HMDB0014495 (Megestrol)

3D SDF for HMDB0014495 (Megestrol)

3D-SDF for HMDB0014495 (Megestrol)

PDB for HMDB0014495 (Megestrol)

3D PDB for HMDB0014495 (Megestrol)

SMILES for HMDB0014495 (Megestrol)

INCHI for HMDB0014495 (Megestrol)

Structure for HMDB0014495 (Megestrol)

3D Structure for HMDB0014495 (Megestrol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References