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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015446

Secondary Accession Numbers

HMDB15446

Metabolite Identification

Common Name

Mestranol

Description

Mestranol is only found in individuals that have used or taken this drug. It is the 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives. [PubChem]Mestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formulations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70%.Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).

Structure

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


  Mrv1652305271900202D          

 26 29  0  0  0  0            999 V2000
    7.7254    1.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3626   -1.9994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    0.5185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8116   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971   -0.7188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5921    0.7699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971    0.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5921   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    0.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0734    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1102   -1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -0.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -2.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2602    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -2.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0774    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0759    0.0864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3762   -1.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -1.1266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  1  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 22  1  1  0  0  0
  6 10  1  0  0  0  0
  6 16  1  6  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  3  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
  5 23  1  0  0  0  0
 23  9  1  0  0  0  0
 23 13  1  0  0  0  0
 23 24  1  6  0  0  0
  4 25  1  6  0  0  0
  2 26  1  0  0  0  0
M  END

HMDB0015446
     RDKit          3D
Mestranol
 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.1440    1.8312    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    0.9996    0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -0.0298   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6901    0.0793   -1.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -1.3789    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4946   -1.7122    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548   -0.4335    0.5941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2775   -0.5449    0.5460 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2339   -0.7388    1.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.0048    2.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585    0.1931    1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    0.0046    1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4471    0.2178    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    0.0261    0.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    0.2287   -1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    0.5972   -1.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759    0.7808   -1.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516    0.5714   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2819    0.7373   -0.0343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3140    1.0949   -1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    1.2973   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -0.0308   -0.7557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1322   -1.0592   -1.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2829    2.5611    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5410   -0.3684   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3046   -2.1551   -0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -1.2619    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602   -2.0860    1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030   -2.4562    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    0.2919    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0432   -1.3608   -0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274   -1.8336    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421   -0.4309    2.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    0.9883    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.5912    3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.2895    2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4138    1.2397   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -0.5837   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6952    0.2213   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    0.7367   -2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    1.0779   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    1.5985    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    0.2162   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.9830   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123    1.9907   -0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080    1.6900   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.7795   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -1.6147   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -0.5104   -2.7978 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  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  3  1  0
 22  7  1  0
 19  8  1  0
 18 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END


  Mrv1652305271900202D          

 26 29  0  0  0  0            999 V2000
    7.7254    1.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3626   -1.9994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    0.5185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8116   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971   -0.7188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5921    0.7699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971    0.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5921   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    0.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0734    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1102   -1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -0.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -2.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2602    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -2.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0774    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0759    0.0864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3762   -1.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -1.1266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497   -1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  1  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 22  1  1  0  0  0
  6 10  1  0  0  0  0
  6 16  1  6  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  3  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
  5 23  1  0  0  0  0
 23  9  1  0  0  0  0
 23 13  1  0  0  0  0
 23 24  1  6  0  0  0
  4 25  1  6  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015446

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

> <INCHI_KEY>
IMSSROKUHAOUJS-MJCUULBUSA-N

> <FORMULA>
C21H26O2

> <MOLECULAR_WEIGHT>
310.4299

> <EXACT_MASS>
310.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69513287062886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.043247144

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.594918895355708

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6634785376158088

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
91.85679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015446
     RDKit          3D
Mestranol
 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.1440    1.8312    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    0.9996    0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -0.0298   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6901    0.0793   -1.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -1.3789    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4946   -1.7122    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548   -0.4335    0.5941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2775   -0.5449    0.5460 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2339   -0.7388    1.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.0048    2.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585    0.1931    1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    0.0046    1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4471    0.2178    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    0.0261    0.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    0.2287   -1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    0.5972   -1.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759    0.7808   -1.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516    0.5714   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2819    0.7373   -0.0343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3140    1.0949   -1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    1.2973   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -0.0308   -0.7557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1322   -1.0592   -1.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2829    2.5611    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5410   -0.3684   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3046   -2.1551   -0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -1.2619    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602   -2.0860    1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030   -2.4562    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    0.2919    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0432   -1.3608   -0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274   -1.8336    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421   -0.4309    2.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    0.9883    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.5912    3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.2895    2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4138    1.2397   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -0.5837   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6952    0.2213   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    0.7367   -2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    1.0779   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    1.5985    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    0.2162   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.9830   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123    1.9907   -0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080    1.6900   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.7795   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -1.6147   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -0.5104   -2.7978 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  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  3  1  0
 22  7  1  0
 19  8  1  0
 18 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      14.421   2.902   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.410  -3.732   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.715   0.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.715  -0.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.381  -1.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.172   1.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.381   1.738   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.172  -1.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.048   0.968   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.070   0.198   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.406  -2.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.715   2.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.647  -1.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.023  -3.758   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.634  -2.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.419   1.729   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.219  -0.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.194  -3.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.760  -1.297   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747  -2.968   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.944   1.965   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      11.342   0.161   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      10.048  -0.572   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      10.036  -2.112   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      12.878  -2.103   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       3.079  -2.957   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   20   26                                                       
CONECT    3    4    6    7   12                                             
CONECT    4    3    5    8   25                                             
CONECT    5    4   11   22   23                                             
CONECT    6    1    3   10   16                                             
CONECT    7    3    9                                                       
CONECT    8    4   10                                                       
CONECT    9    7   23                                                       
CONECT   10    6    8                                                       
CONECT   11    5   14                                                       
CONECT   12    3                                                            
CONECT   13   15   17   23                                                  
CONECT   14   11   15                                                       
CONECT   15   13   14   18                                                  
CONECT   16    6   21                                                       
CONECT   17   13   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   20                                                       
CONECT   20    2   18   19                                                  
CONECT   21   16                                                            
CONECT   22    5                                                            
CONECT   23    5    9   13   24                                             
CONECT   24   23                                                            
CONECT   25    4                                                            
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0015446
HETATM    1  C1  UNL     1      -4.144   1.831   1.528  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.985   1.000   0.668  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.799  -0.030  -0.361  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.690   0.079  -1.392  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.908  -1.379   0.364  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.495  -1.712   0.816  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.755  -0.433   0.594  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.277  -0.545   0.546  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.234  -0.739   1.946  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.486  -0.005   2.277  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.358   0.193   1.093  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.725   0.005   1.177  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.447   0.218   0.009  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.819   0.026   0.102  1.00  0.00           O  
HETATM   15  C13 UNL     1       6.618   0.229  -1.060  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.861   0.597  -1.182  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.476   0.781  -1.237  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.752   0.571  -0.084  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.282   0.737  -0.034  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.314   1.095  -1.357  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.809   1.297  -1.149  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.364  -0.031  -0.756  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.132  -1.059  -1.812  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.283   2.561   2.306  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.541  -0.368  -1.115  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.305  -2.155  -0.328  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.542  -1.262   1.258  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.460  -2.086   1.843  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.103  -2.456   0.067  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.079   0.292   1.349  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.043  -1.361  -0.134  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.427  -1.834   2.068  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.542  -0.431   2.706  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.283   0.988   2.759  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.024  -0.591   3.069  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.153  -0.289   2.112  1.00  0.00           H  
HETATM   37  H14 UNL     1       6.414   1.240  -1.489  1.00  0.00           H  
HETATM   38  H15 UNL     1       6.347  -0.584  -1.766  1.00  0.00           H  
HETATM   39  H16 UNL     1       7.695   0.221  -0.811  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.513   0.737  -2.031  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.018   1.078  -2.171  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.096   1.598   0.672  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.230   0.216  -2.049  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.184   1.983  -1.740  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.912   1.991  -0.293  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.308   1.690  -2.042  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.990  -1.780  -1.904  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.197  -1.615  -1.732  1.00  0.00           H  
HETATM   49  H26 UNL     1      -2.090  -0.510  -2.798  1.00  0.00           H  
CONECT    1    2    2    2   24
CONECT    2    3
CONECT    3    4    5   22
CONECT    4   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   22   30
CONECT    8    9   19   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   12   18
CONECT   12   13   36
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   37   38   39
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   18   19
CONECT   19   20   42
CONECT   20   21   43   44
CONECT   21   22   45   46
CONECT   22   23
CONECT   23   47   48   49
END

HMDB0015446
     RDKit          3D
Mestranol
 49 52  0  0  0  0  0  0  0  0999 V2000
   -4.1440    1.8312    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    0.9996    0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -0.0298   -0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6901    0.0793   -1.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080   -1.3789    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4946   -1.7122    0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548   -0.4335    0.5941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2775   -0.5449    0.5460 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2339   -0.7388    1.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.0048    2.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585    0.1931    1.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7247    0.0046    1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4471    0.2178    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8190    0.0261    0.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    0.2287   -1.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    0.5972   -1.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759    0.7808   -1.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7516    0.5714   -0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2819    0.7373   -0.0343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3140    1.0949   -1.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088    1.2973   -1.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -0.0308   -0.7557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1322   -1.0592   -1.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2829    2.5611    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5410   -0.3684   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3046   -2.1551   -0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -1.2619    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602   -2.0860    1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1030   -2.4562    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0794    0.2919    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0432   -1.3608   -0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274   -1.8336    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421   -0.4309    2.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    0.9883    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -0.5912    3.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1531   -0.2895    2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4138    1.2397   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468   -0.5837   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6952    0.2213   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    0.7367   -2.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    1.0779   -2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963    1.5985    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    0.2162   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837    1.9830   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123    1.9907   -0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080    1.6900   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9900   -1.7795   -1.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -1.6147   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -0.5104   -2.7978 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  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  3  1  0
 22  7  1  0
 19  8  1  0
 18 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratriene	ChEBI
(+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene	ChEBI
17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol	ChEBI
3-Methoxy-17alpha-ethynylestradiol	ChEBI
3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol	ChEBI
Ethynylestradiol 3-methyl ether	ChEBI
Mestranolum	ChEBI
(+)-17a-Ethynyl-17b-hydroxy-3-methoxy-1,3,5(10)-estratriene	Generator
(+)-17Α-ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene	Generator
(+)-17a-Ethynyl-17b-hydroxy-3-methoxy-1,3,5(10)-oestratriene	Generator
(+)-17Α-ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-oestratriene	Generator
17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17b-ol	Generator
17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17β-ol	Generator
3-Methoxy-17a-ethynylestradiol	Generator
3-Methoxy-17α-ethynylestradiol	Generator
3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17b-ol	Generator
3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol	Generator
Ethinyl estradiol 3-methyl ether	HMDB
Ethinyl estradiol 3 methyl ether	HMDB

Chemical Formula

C₂₁H₂₆O₂

Average Molecular Weight

310.4299

Monoisotopic Molecular Weight

310.193280076

IUPAC Name

(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol

Traditional Name

(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol

CAS Registry Number

72-33-3

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3

InChI Identifier

InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

InChI Key

IMSSROKUHAOUJS-MJCUULBUSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Phenanthrene
Tetralin
Anisole
Alkyl aryl ether
Ynone
Benzenoid
Tertiary alcohol
Cyclic alcohol
Acetylide
Ether
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:6784 )
aromatic ether (CHEBI:6784 )
17beta-hydroxy steroid (CHEBI:6784 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015446)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0038 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0038 g/L	ALOGPS
logP	3.89	ALOGPS
logP	4.04	ChemAxon
logS	-4.9	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	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.86 m³·mol⁻¹	ChemAxon
Polarizability	36.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.468	31661259
DarkChem	[M-H]-	172.412	31661259
DeepCCS	[M-2H]-	218.078	30932474
DeepCCS	[M+Na]+	192.65	30932474
AllCCS	[M+H]+	179.1	32859911
AllCCS	[M+H-H2O]+	175.9	32859911
AllCCS	[M+NH4]+	182.0	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	185.6	32859911
AllCCS	[M+Na-2H]-	185.5	32859911
AllCCS	[M+HCOO]-	185.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.94 minutes	32390414
Predicted by Siyang on May 30, 2022	17.8466 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.43 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2557.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	502.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	471.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	911.9 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	849.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1599.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	543.5 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	1612.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	351.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	524.1 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mestranol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3	3673.8	Standard polar	33892256
Mestranol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3	2591.1	Standard non polar	33892256
Mestranol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C=C3	2681.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mestranol,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(OC)=CC=C4[C@H]3CC[C@@]21C	2777.7	Semi standard non polar	33892256
Mestranol,1TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(OC)=CC=C4[C@H]3CC[C@@]21C	3063.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mestranol GC-MS (Non-derivatized) - 70eV, Positive	splash10-008i-0790000000-4f67d1073f5d63b0e27d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mestranol GC-MS (1 TMS) - 70eV, Positive	splash10-0g4l-3559000000-e7deac0497bd25eac9e3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mestranol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01t9-1972000000-5e394201ba0e38e5391f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 10V, Positive-QTOF	splash10-03di-0149000000-c1a392ac6a255cba0e08	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 20V, Positive-QTOF	splash10-03dr-0592000000-0cc5cea78731703ef0b3	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 40V, Positive-QTOF	splash10-0k9f-3980000000-fe6e57c0238f233c2ba6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 10V, Negative-QTOF	splash10-0a4i-0009000000-85dc48ac6fb3820afe06	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 20V, Negative-QTOF	splash10-0a4i-0069000000-cd914e79f9bb96f842c3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 40V, Negative-QTOF	splash10-0f76-0090000000-84d635c97eb379340fca	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 10V, Positive-QTOF	splash10-03di-0029000000-cb3f205cf264d3c6ade0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 20V, Positive-QTOF	splash10-00ko-0970000000-461534673e7c6e28a398	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 40V, Positive-QTOF	splash10-072i-1940000000-132bc2499590ddce96ec	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 10V, Negative-QTOF	splash10-0a4i-0009000000-d834b990dbff0e00d266	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 20V, Negative-QTOF	splash10-0a4i-0049000000-cca49518a1592cc72782	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mestranol 40V, Negative-QTOF	splash10-0udi-0090000000-041fe496acbbddb615b1	2021-10-11	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 DB01357	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01357	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

DB01357

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00032009

Chemspider ID

6054

KEGG Compound ID

C07618

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mestranol

METLIN ID

Not Available

PubChem Compound

6291

PDB ID

Not Available

ChEBI ID

6784

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Schmider J, Greenblatt DJ, von Moltke LL, Karsov D, Vena R, Friedman HL, Shader RI: Biotransformation of mestranol to ethinyl estradiol in vitro: the role of cytochrome P-450 2C9 and metabolic inhibitors. J Clin Pharmacol. 1997 Mar;37(3):193-200. [PubMed:9089421 ]

Enzyme Details

2. Estrogen receptor

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

References

Dulos J, Vijn P, van Doorn C, Hofstra CL, Veening-Griffioen D, de Graaf J, Dijcks FA, Boots AM: Suppression of the inflammatory response in experimental arthritis is mediated via estrogen receptor alpha but not estrogen receptor beta. Arthritis Res Ther. 2010;12(3):R101. doi: 10.1186/ar3032. Epub 2010 May 24. [PubMed:20497523 ]
Cleuren AC, Van der Linden IK, De Visser YP, Wagenaar GT, Reitsma PH, Van Vlijmen BJ: 17alpha-Ethinylestradiol rapidly alters transcript levels of murine coagulation genes via estrogen receptor alpha. J Thromb Haemost. 2010 Aug;8(8):1838-46. doi: 10.1111/j.1538-7836.2010.03930.x. Epub 2010 May 27. [PubMed:20524981 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Mestranol (HMDB0015446)

MOL for HMDB0015446 (Mestranol)

3D MOL for HMDB0015446 (Mestranol)

3D SDF for HMDB0015446 (Mestranol)

3D-SDF for HMDB0015446 (Mestranol)

PDB for HMDB0015446 (Mestranol)

3D PDB for HMDB0015446 (Mestranol)

SMILES for HMDB0015446 (Mestranol)

INCHI for HMDB0015446 (Mestranol)

Structure for HMDB0015446 (Mestranol)

3D Structure for HMDB0015446 (Mestranol)

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