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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 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014961

Secondary Accession Numbers

HMDB14961

Metabolite Identification

Common Name

Ethynodiol Diacetate

Description

Ethynodiol Diacetate is only found in individuals that have used or taken this drug. It is a synthetic progestational hormone used alone or in combination with estrogens as an oral contraceptive. [PubChem]Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Ethynodiol Diacetate will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

Structure

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

823
  Mrv0541 02231215022D          

 32 35  0  0  1  0            999 V2000
    8.9774    0.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8152   -0.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693   -1.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5284    0.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5284   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8139   -1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0994   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3090    0.3753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8139    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3090   -0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0994    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487   -1.1193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7906   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8272   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5284    0.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3420   -1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0862   -2.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5840   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019   -1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0555    1.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703   -2.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951   -1.9846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7304    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8019    1.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3987    1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5983   -1.3575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3880   -1.4392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -0.3712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3614   -0.4595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 24  1  0  0  0  0
 23  2  1  1  0  0  0
  2 27  1  0  0  0  0
  3 24  2  0  0  0  0
  4 27  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 29  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 30  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 31  1  6  0  0  0
  9 14  1  0  0  0  0
  9 21  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  0  0  0  0
 13 32  1  1  0  0  0
 15 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  0  0  0  0
 19 20  1  0  0  0  0
 20 23  1  0  0  0  0
 21 25  3  0  0  0  0
 22 23  1  0  0  0  0
 24 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0014961
     RDKit          3D
Ethynodiol Diacetate
 60 63  0  0  0  0  0  0  0  0999 V2000
   -4.4898   -2.8220   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812   -1.6579   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305   -0.2094   -0.0826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6888    0.2295    0.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.4517    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8729    1.7385    2.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2396    2.4088    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    0.4494   -1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    1.1946   -1.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7677    0.1687   -1.1467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3598    0.4946   -0.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3433    1.1741   -2.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485    1.6920   -1.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4087    0.5437   -0.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337    0.6363   -0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -0.4459   -0.3771 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9630   -0.1545    0.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    0.1091    1.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    0.4048    2.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1580    0.0874    0.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388   -1.8132   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.8522   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -0.6951   -0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3546   -0.8462   -0.6737 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3123   -1.6455    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981   -1.6282    0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -0.2248    0.2110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8992    0.6077    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7721   -3.8300   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7145    2.3674    2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2277    0.8428    3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422    2.3690    3.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853   -0.2796   -2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8810    1.1072   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679    2.1805   -1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5440    1.2944   -2.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669   -0.7310   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    1.0776    0.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548    2.0263   -2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    0.4493   -2.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191    2.2853   -2.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    2.3441   -0.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2057    1.5530   -1.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -0.4050   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730    1.1142    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9030   -0.5525    3.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7878    0.9042    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949   -2.3373    0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6415   -2.4646   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -1.7730   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.8299   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788   -0.7349    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -1.3942   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.4563    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -2.7241    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1276   -2.2704   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1537   -2.0898    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    1.6576    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9908    0.1334    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6633    0.5473    2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  3  1  0
 27 10  1  0
 24 11  1  0
 23 14  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  1
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  6
 19 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  1
 24 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
M  END

823
  Mrv0541 02231215022D          

 32 35  0  0  1  0            999 V2000
    8.9774    0.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.3944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8152   -0.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693   -1.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5284    0.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5284   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8139   -1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0994   -0.7012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3090    0.3753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8139    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3090   -0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0994    0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3487   -1.1193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7906   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8272   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5284    0.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3420   -1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0862   -2.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5840   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019   -1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0555    1.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5703   -2.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951   -1.9846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7304    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8019    1.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3987    1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5983   -1.3575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3880   -1.4392    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -0.3712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3614   -0.4595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 24  1  0  0  0  0
 23  2  1  1  0  0  0
  2 27  1  0  0  0  0
  3 24  2  0  0  0  0
  4 27  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 29  1  6  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 30  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 31  1  6  0  0  0
  9 14  1  0  0  0  0
  9 21  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  0  0  0  0
 13 32  1  1  0  0  0
 15 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  0  0  0  0
 19 20  1  0  0  0  0
 20 23  1  0  0  0  0
 21 25  3  0  0  0  0
 22 23  1  0  0  0  0
 24 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014961

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1

> <INCHI_KEY>
ONKUMRGIYFNPJW-KIEAKMPYSA-N

> <FORMULA>
C24H32O4

> <MOLECULAR_WEIGHT>
384.5085

> <EXACT_MASS>
384.230059512

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
44.109316003685606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
3.6881402700000017

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.728312793878715

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
106.62490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethynodiol diacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014961
     RDKit          3D
Ethynodiol Diacetate
 60 63  0  0  0  0  0  0  0  0999 V2000
   -4.4898   -2.8220   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812   -1.6579   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305   -0.2094   -0.0826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6888    0.2295    0.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.4517    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8729    1.7385    2.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2396    2.4088    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    0.4494   -1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    1.1946   -1.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7677    0.1687   -1.1467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3598    0.4946   -0.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3433    1.1741   -2.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485    1.6920   -1.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4087    0.5437   -0.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337    0.6363   -0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -0.4459   -0.3771 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9630   -0.1545    0.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    0.1091    1.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    0.4048    2.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1580    0.0874    0.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388   -1.8132   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.8522   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -0.6951   -0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3546   -0.8462   -0.6737 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3123   -1.6455    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981   -1.6282    0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -0.2248    0.2110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8992    0.6077    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7721   -3.8300   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7145    2.3674    2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2277    0.8428    3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422    2.3690    3.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853   -0.2796   -2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8810    1.1072   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679    2.1805   -1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5440    1.2944   -2.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669   -0.7310   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    1.0776    0.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548    2.0263   -2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    0.4493   -2.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191    2.2853   -2.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    2.3441   -0.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2057    1.5530   -1.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -0.4050   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730    1.1142    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9030   -0.5525    3.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7878    0.9042    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949   -2.3373    0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6415   -2.4646   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -1.7730   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.8299   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788   -0.7349    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -1.3942   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.4563    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -2.7241    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1276   -2.2704   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1537   -2.0898    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    1.6576    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9908    0.1334    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6633    0.5473    2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  3  1  0
 27 10  1  0
 24 11  1  0
 23 14  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  1
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  6
 19 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  1
 24 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 823                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.758   1.604   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.747  -4.470   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.322  -0.557   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.423  -2.154   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.053   0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.053  -1.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.719  -2.079   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.386  -1.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.510   0.701   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.719   1.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.510  -1.778   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.386   0.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.984  -2.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.409  -0.539   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.744  -3.683   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.053   1.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.972  -3.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.361  -4.495   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.557  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.097  -2.034   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.037   2.166   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.531  -4.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.084  -3.705   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.163   0.975   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.564   3.631   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.411   1.878   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.417  -3.694   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080  -4.459   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      14.183  -2.534   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      13.791  -2.687   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      12.453  -0.693   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      10.008  -0.858   0.000  0.00  0.00           H+0
CONECT    1    9   24                                                       
CONECT    2   23   27                                                       
CONECT    3   24                                                            
CONECT    4   27                                                            
CONECT    5    6    9   10   16                                             
CONECT    6    5    7   11   29                                             
CONECT    7    6    8   15   30                                             
CONECT    8    7   12   13   31                                             
CONECT    9    1    5   14   21                                             
CONECT   10    5   12                                                       
CONECT   11    6   14                                                       
CONECT   12    8   10                                                       
CONECT   13    8   17   19   32                                             
CONECT   14    9   11                                                       
CONECT   15    7   18                                                       
CONECT   16    5                                                            
CONECT   17   13   18   22                                                  
CONECT   18   15   17                                                       
CONECT   19   13   20                                                       
CONECT   20   19   23                                                       
CONECT   21    9   25                                                       
CONECT   22   17   23                                                       
CONECT   23    2   20   22                                                  
CONECT   24    1    3   26                                                  
CONECT   25   21                                                            
CONECT   26   24                                                            
CONECT   27    2    4   28                                                  
CONECT   28   27                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32   13                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0014961
HETATM    1  C1  UNL     1      -4.490  -2.822  -0.426  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.181  -1.658  -0.271  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.831  -0.209  -0.083  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.689   0.230   0.900  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.895   1.452   1.442  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.873   1.738   2.530  1.00  0.00           C  
HETATM    7  O2  UNL     1      -4.240   2.409   1.020  1.00  0.00           O  
HETATM    8  C6  UNL     1      -4.024   0.449  -1.424  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.693   1.195  -1.646  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.768   0.169  -1.147  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.360   0.495  -0.905  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.343   1.174  -2.055  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.648   1.692  -1.485  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.409   0.544  -0.937  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.734   0.636  -0.902  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.608  -0.446  -0.377  1.00  0.00           C  
HETATM   17  O3  UNL     1       4.963  -0.155   0.983  1.00  0.00           O  
HETATM   18  C15 UNL     1       6.270   0.109   1.361  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.606   0.405   2.763  1.00  0.00           C  
HETATM   20  O4  UNL     1       7.158   0.087   0.469  1.00  0.00           O  
HETATM   21  C17 UNL     1       4.039  -1.813  -0.534  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.621  -1.852  -1.003  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.804  -0.695  -0.428  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.355  -0.846  -0.674  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.312  -1.645   0.390  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.798  -1.628   0.409  1.00  0.00           C  
HETATM   27  C23 UNL     1      -2.372  -0.225   0.211  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.899   0.608   1.342  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.772  -3.830  -0.572  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.714   2.367   2.139  1.00  0.00           H  
HETATM   31  H3  UNL     1      -6.228   0.843   3.041  1.00  0.00           H  
HETATM   32  H4  UNL     1      -5.342   2.369   3.273  1.00  0.00           H  
HETATM   33  H5  UNL     1      -4.085  -0.280  -2.260  1.00  0.00           H  
HETATM   34  H6  UNL     1      -4.881   1.107  -1.487  1.00  0.00           H  
HETATM   35  H7  UNL     1      -2.668   2.181  -1.205  1.00  0.00           H  
HETATM   36  H8  UNL     1      -2.544   1.294  -2.760  1.00  0.00           H  
HETATM   37  H9  UNL     1      -1.867  -0.731  -1.801  1.00  0.00           H  
HETATM   38  H10 UNL     1      -0.147   1.078   0.011  1.00  0.00           H  
HETATM   39  H11 UNL     1      -0.255   2.026  -2.395  1.00  0.00           H  
HETATM   40  H12 UNL     1       0.595   0.449  -2.865  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.219   2.285  -2.212  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.375   2.344  -0.617  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.206   1.553  -1.278  1.00  0.00           H  
HETATM   44  H16 UNL     1       5.554  -0.405  -0.961  1.00  0.00           H  
HETATM   45  H17 UNL     1       7.473   1.114   2.782  1.00  0.00           H  
HETATM   46  H18 UNL     1       6.903  -0.552   3.266  1.00  0.00           H  
HETATM   47  H19 UNL     1       5.788   0.904   3.319  1.00  0.00           H  
HETATM   48  H20 UNL     1       4.095  -2.337   0.465  1.00  0.00           H  
HETATM   49  H21 UNL     1       4.642  -2.465  -1.224  1.00  0.00           H  
HETATM   50  H22 UNL     1       2.614  -1.773  -2.107  1.00  0.00           H  
HETATM   51  H23 UNL     1       2.185  -2.830  -0.717  1.00  0.00           H  
HETATM   52  H24 UNL     1       1.979  -0.735   0.676  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.228  -1.394  -1.653  1.00  0.00           H  
HETATM   54  H26 UNL     1       0.164  -1.456   1.392  1.00  0.00           H  
HETATM   55  H27 UNL     1      -0.020  -2.724   0.188  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.128  -2.270  -0.460  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.154  -2.090   1.344  1.00  0.00           H  
HETATM   58  H30 UNL     1      -1.693   1.658   1.148  1.00  0.00           H  
HETATM   59  H31 UNL     1      -0.991   0.133   1.844  1.00  0.00           H  
HETATM   60  H32 UNL     1      -2.663   0.547   2.164  1.00  0.00           H  
CONECT    1    2    2    2   29
CONECT    2    3
CONECT    3    4    8   27
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   30   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   27   37
CONECT   11   12   24   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   15   23
CONECT   15   16   43
CONECT   16   17   21   44
CONECT   17   18
CONECT   18   19   20   20
CONECT   19   45   46   47
CONECT   21   22   48   49
CONECT   22   23   50   51
CONECT   23   24   52
CONECT   24   25   53
CONECT   25   26   54   55
CONECT   26   27   56   57
CONECT   27   28
CONECT   28   58   59   60
END

HMDB0014961
     RDKit          3D
Ethynodiol Diacetate
 60 63  0  0  0  0  0  0  0  0999 V2000
   -4.4898   -2.8220   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812   -1.6579   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305   -0.2094   -0.0826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6888    0.2295    0.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8953    1.4517    1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8729    1.7385    2.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2396    2.4088    1.0197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0240    0.4494   -1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    1.1946   -1.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7677    0.1687   -1.1467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3598    0.4946   -0.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3433    1.1741   -2.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6485    1.6920   -1.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4087    0.5437   -0.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337    0.6363   -0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076   -0.4459   -0.3771 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9630   -0.1545    0.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2701    0.1091    1.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065    0.4048    2.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1580    0.0874    0.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0388   -1.8132   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.8522   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8037   -0.6951   -0.4276 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3546   -0.8462   -0.6737 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3123   -1.6455    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7981   -1.6282    0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -0.2248    0.2110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8992    0.6077    1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7721   -3.8300   -0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7145    2.3674    2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2277    0.8428    3.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3422    2.3690    3.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0853   -0.2796   -2.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8810    1.1072   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679    2.1805   -1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5440    1.2944   -2.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8669   -0.7310   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1466    1.0776    0.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548    2.0263   -2.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5952    0.4493   -2.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191    2.2853   -2.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    2.3441   -0.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2057    1.5530   -1.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5538   -0.4050   -0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4730    1.1142    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9030   -0.5525    3.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7878    0.9042    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949   -2.3373    0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6415   -2.4646   -1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -1.7730   -2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1852   -2.8299   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9788   -0.7349    0.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -1.3942   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.4563    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -2.7241    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1276   -2.2704   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1537   -2.0898    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6932    1.6576    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9908    0.1334    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6633    0.5473    2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27  3  1  0
 27 10  1  0
 24 11  1  0
 23 14  1  0
  1 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  1
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  6
 19 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  1
 24 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetate	ChEBI
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate	ChEBI
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetate	ChEBI
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate	ChEBI
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetate	ChEBI
3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene	ChEBI
3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yne	ChEBI
17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetate	Generator
17a-Ethynyl-19-norandrost-4-ene-3b,17-b-diol diacetic acid	Generator
17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetic acid	Generator
17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetate	Generator
17Α-ethynyl-19-norandrost-4-ene-3β,17-β-diol diacetic acid	Generator
17a-Ethynyl-3,17-dihydroxy-4-estrene diacetate	Generator
17a-Ethynyl-3,17-dihydroxy-4-estrene diacetic acid	Generator
17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetic acid	Generator
17Α-ethynyl-3,17-dihydroxy-4-estrene diacetate	Generator
17Α-ethynyl-3,17-dihydroxy-4-estrene diacetic acid	Generator
17a-Ethynyl-4-estrene-3b,17b-diol diacetate	Generator
17a-Ethynyl-4-estrene-3b,17b-diol diacetic acid	Generator
17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetic acid	Generator
17Α-ethynyl-4-estrene-3β,17β-diol diacetate	Generator
17Α-ethynyl-4-estrene-3β,17β-diol diacetic acid	Generator
17a-Ethynylestr-4-ene-3b,17b-diol acetate	Generator
17a-Ethynylestr-4-ene-3b,17b-diol acetic acid	Generator
17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetic acid	Generator
17Α-ethynylestr-4-ene-3β,17β-diol acetate	Generator
17Α-ethynylestr-4-ene-3β,17β-diol acetic acid	Generator
19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetate	Generator
19-Nor-17a-pregn-4-en-20-yne-3b,17-diol diacetic acid	Generator
19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetic acid	Generator
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetate	Generator
19-Nor-17α-pregn-4-en-20-yne-3β,17-diol diacetic acid	Generator
3b, 17b-Diacetoxy-17a-ethynyl-4-oestrene	Generator
3Β, 17β-diacetoxy-17α-ethynyl-4-oestrene	Generator
3b,17b-Diacetoxy-19-nor-17a-pregn-4-en-20-yne	Generator
3Β,17β-diacetoxy-19-nor-17α-pregn-4-en-20-yne	Generator
Ethynodiol diacetic acid	Generator
Ethinodiol diacetate	HMDB
Ethynodiol	HMDB
Etynodiol	HMDB
Ethyndiol diacetate	HMDB
Diacetate, ethyndiol	HMDB
Ethynodiol diacetate, (17 alpha)-isomer	HMDB
Femulen	HMDB
Continuin	HMDB
(3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diol diacetate	HMDB
Diacetate, ethynodiol	HMDB

Chemical Formula

C₂₄H₃₂O₄

Average Molecular Weight

384.5085

Monoisotopic Molecular Weight

384.230059512

IUPAC Name

(1S,2R,5S,10R,11S,14R,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl acetate

Traditional Name

ethynodiol diacetate

CAS Registry Number

297-76-7

SMILES

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

InChI Identifier

InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1

InChI Key

ONKUMRGIYFNPJW-KIEAKMPYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
Estrane-skeleton
Delta-4-steroid
Ynone
Dicarboxylic acid or derivatives
Carboxylic acid ester
Acetylide
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:31580 )
steroid ester (CHEBI:31580 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C12724 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030124 )

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: HMDB0014961)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.004 g/L	Not Available
LogP	5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.004 g/L	ALOGPS
logP	3.99	ALOGPS
logP	3.69	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.62 m³·mol⁻¹	ChemAxon
Polarizability	44.11 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]+	193.033	31661259
DarkChem	[M-H]-	187.399	31661259
DeepCCS	[M-2H]-	221.649	30932474
DeepCCS	[M+Na]+	195.822	30932474
AllCCS	[M+H]+	197.1	32859911
AllCCS	[M+H-H2O]+	194.7	32859911
AllCCS	[M+NH4]+	199.3	32859911
AllCCS	[M+Na]+	200.0	32859911
AllCCS	[M-H]-	197.4	32859911
AllCCS	[M+Na-2H]-	198.2	32859911
AllCCS	[M+HCOO]-	199.2	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.	8.79 minutes	32390414
Predicted by Siyang on May 30, 2022	20.2601 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3099.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	469.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	239.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	484.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	922.1 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	915.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1810.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	574.9 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	1853.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	578.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	328.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	465.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	19.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethynodiol Diacetate	[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](OC(C)=O)C=C3CC[C@@]21[H]	3466.2	Standard polar	33892256
Ethynodiol Diacetate	[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](OC(C)=O)C=C3CC[C@@]21[H]	2773.9	Standard non polar	33892256
Ethynodiol Diacetate	[H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](OC(C)=O)C=C3CC[C@@]21[H]	2783.0	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 - Ethynodiol Diacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0100-1194000000-36378317102183460fae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethynodiol Diacetate 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 - Ethynodiol Diacetate 10V, Positive-QTOF	splash10-002u-0019000000-a73cd21b30c9439d33be	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Positive-QTOF	splash10-004l-0079000000-136800a52b34f352d78e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Positive-QTOF	splash10-00e9-0290000000-2ea658e56bd9ec1ef885	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Negative-QTOF	splash10-000x-0009000000-85f53cde1cbdf66e3366	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Negative-QTOF	splash10-000x-2029000000-0187f016d0d4a58f5182	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Negative-QTOF	splash10-052e-7094000000-0495ab26817d2a5560a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Positive-QTOF	splash10-016r-0095000000-0d85902c71bc8262416e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Positive-QTOF	splash10-03fr-0193000000-f41b8945f2b34a40a819	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Positive-QTOF	splash10-0006-3940000000-741355bc9568273bd065	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 10V, Negative-QTOF	splash10-001i-0029000000-4a30e3513b9cdfbc7e7d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 20V, Negative-QTOF	splash10-053s-4091000000-8176c0956e97e17ec13c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethynodiol Diacetate 40V, Negative-QTOF	splash10-016u-2029000000-e5afd8ca7c979d5debd7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00823	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00823	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00823

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8913

KEGG Compound ID

C12724

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethynodiol_Diacetate

METLIN ID

Not Available

PubChem Compound

9270

PDB ID

Not Available

ChEBI ID

31580

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. Progesterone receptor

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

References

Tamaya T, Nioka S, Furuta N, Shimura T, Takano N: Contribution of functional groups of 19-nor-progestogens to binding to progesterone and estradiol-17beta receptors in rabbit uterus. Endocrinology. 1977 Jun;100(6):1579-84. [PubMed:858280 ]
Briggs MH: Contraceptive steroid binding to the human uterine progesterone-receptor. Curr Med Res Opin. 1975;3(2):95-8. [PubMed:166800 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Estrogen receptor

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

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kappus H, Bolt HM, Remmer H: Affinity of ethynyl-estradiol and mestranol for the uterine estrogen receptor and for the microsomal mixed function oxidase of the liver. J Steroid Biochem. 1973 Mar;4(2):121-8. [PubMed:4123746 ]

Showing metabocard for Ethynodiol Diacetate (HMDB0014961)

MOL for HMDB0014961 (Ethynodiol Diacetate)

3D MOL for HMDB0014961 (Ethynodiol Diacetate)

3D SDF for HMDB0014961 (Ethynodiol Diacetate)

3D-SDF for HMDB0014961 (Ethynodiol Diacetate)

PDB for HMDB0014961 (Ethynodiol Diacetate)

3D PDB for HMDB0014961 (Ethynodiol Diacetate)

SMILES for HMDB0014961 (Ethynodiol Diacetate)

INCHI for HMDB0014961 (Ethynodiol Diacetate)

Structure for HMDB0014961 (Ethynodiol Diacetate)

3D Structure for HMDB0014961 (Ethynodiol Diacetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References