NP-MRD: Showing NP-Card for Abiraterone Acetate (NP0139777)

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Record Information

Version

2.0

Created at

2022-06-29 20:10:06 UTC

Updated at

2022-06-29 20:10:06 UTC

NP-MRD ID

NP0139777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Abiraterone Acetate

Description

Abiraterone acetate, also known as zytiga, 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. Abiraterone Acetate was first documented in 2004 (PMID: 15150570). Abiraterone acetate is a strong basic compound (based on its pKa) (PMID: 16809076) (PMID: 18645193) (PMID: 18957947) (PMID: 19189435).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004221606342D          

 33 37  0  0  1  0            999 V2000
    8.6072    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469    2.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8642    3.0334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148    1.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 17  1  1  0  0  0  0
 18  5  1  0  0  0  0
 18 16  2  0  0  0  0
 19  6  2  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  2  0  0  0  0
 22 18  1  0  0  0  0
 23  9  1  0  0  0  0
 23 21  1  0  0  0  0
 24 11  1  0  0  0  0
 24 21  1  0  0  0  0
 25  2  1  6  0  0  0
 25 12  1  0  0  0  0
 25 19  1  0  0  0  0
 25 24  1  0  0  0  0
 26  3  1  6  0  0  0
 26 13  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 14  2  0  0  0  0
 27 16  1  0  0  0  0
 28 17  2  0  0  0  0
 29 17  1  0  0  0  0
 20 29  1  6  0  0  0
 20 30  1  1  0  0  0
 21 31  1  6  0  0  0
 23 32  1  1  0  0  0
 24 33  1  1  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    8.1690    1.2444    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838    0.9575    1.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6007    0.7423    2.3183 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7017    0.9147    0.2733 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    0.6495    0.6371 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5414    1.9004    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249    1.7092    0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4742    0.4959    0.1295 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4643    0.6998   -1.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635   -0.6535    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.7411    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -1.9591    1.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390   -1.1432    0.6339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7698   -1.0623    1.0090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5071   -2.3040    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9004   -1.8791    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -0.9142   -0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0527   -0.3085   -0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.5684   -1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2166    1.0729   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4136    0.6967   -1.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4655   -0.1622   -0.5108 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3092   -0.6401   -0.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.5794   -0.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9809   -1.3852   -1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909    0.8431   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980    1.2996    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.3319    0.7607 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7790   -0.5523   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1128    1.7176   -0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7294    1.8496    1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6767    0.2614    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3579    0.4788    1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    2.2745   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9753    2.6864    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1077    1.5355    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555    2.6172    0.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491    0.8140   -1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0654    1.5687   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065   -0.1789   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718   -2.5754    1.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2981   -3.0378    1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4613   -1.7081    2.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053   -1.4507   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -0.2842    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4882   -2.4897    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -3.1698    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653   -2.3348    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    0.8792   -2.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1847    1.7538   -2.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3643    1.0822   -1.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3633   -1.3249    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8847   -1.4176   -2.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529   -2.4242   -1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2084   -0.8900   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    1.4630   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8903    1.0343   -1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4360    2.1364   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273    1.7828    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2434    0.4248    1.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3590   -1.4324    0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -0.4840   -1.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 23  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 17 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10 29  1  0
 29  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 24 14  1  0
  8 28  1  0
 13 14  1  0
  8 10  1  0
 19 18  1  0
 14 45  1  1
 15 46  1  0
 15 47  1  0
 16 48  1  0
 23 52  1  0
 21 51  1  0
 20 50  1  0
 19 49  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  1
 13 44  1  6
 12 42  1  0
 12 43  1  0
 11 41  1  0
 29 61  1  0
 29 62  1  0
  5 33  1  1
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1572004221606342D          

 33 37  0  0  1  0            999 V2000
    8.6072    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640    2.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469    2.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8642    3.0334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148    1.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7314   -0.5086    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  4  1  0  0  0  0
 17  1  1  0  0  0  0
 18  5  1  0  0  0  0
 18 16  2  0  0  0  0
 19  6  2  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  2  0  0  0  0
 22 18  1  0  0  0  0
 23  9  1  0  0  0  0
 23 21  1  0  0  0  0
 24 11  1  0  0  0  0
 24 21  1  0  0  0  0
 25  2  1  6  0  0  0
 25 12  1  0  0  0  0
 25 19  1  0  0  0  0
 25 24  1  0  0  0  0
 26  3  1  6  0  0  0
 26 13  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 14  2  0  0  0  0
 27 16  1  0  0  0  0
 28 17  2  0  0  0  0
 29 17  1  0  0  0  0
 20 29  1  6  0  0  0
 20 30  1  1  0  0  0
 21 31  1  6  0  0  0
 23 32  1  1  0  0  0
 24 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0139777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC=C(C3=CN=CC=C3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@]([H])(CC[C@]12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1

> <INCHI_KEY>
UVIQSJCZCSLXRZ-UBUQANBQSA-N

> <FORMULA>
C26H33NO2

> <MOLECULAR_WEIGHT>
391.555

> <EXACT_MASS>
391.251129307

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.62927185598708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,13-dien-5-yl acetate

> <ALOGPS_LOGP>
5.63

> <JCHEM_LOGP>
4.406418321000001

> <ALOGPS_LOGS>
-5.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.810035290371082

> <JCHEM_POLAR_SURFACE_AREA>
39.19

> <JCHEM_REFRACTIVITY>
116.45389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,13-dien-5-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      16.067   1.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.487   2.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.493   4.025   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.452   2.809   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.088   5.452   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.558   4.447   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.551   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.978   3.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.986   0.406   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       1.613   5.662   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      14.028   2.854   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      12.565  -0.949   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.509  -1.043   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.978   1.583   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.017  -0.136   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    5   14                                                       
CONECT    5    4   18                                                       
CONECT    6    7   19                                                       
CONECT    7    6   21                                                       
CONECT    8    9   22                                                       
CONECT    9    8   23                                                       
CONECT   10   12   20                                                       
CONECT   11   13   24                                                       
CONECT   12   10   25                                                       
CONECT   13   11   26                                                       
CONECT   14    4   27                                                       
CONECT   15   19   20                                                       
CONECT   16   18   27                                                       
CONECT   17    1   28   29                                                  
CONECT   18    5   16   22                                                  
CONECT   19    6   15   25                                                  
CONECT   20   10   15   29   30                                             
CONECT   21    7   23   24   31                                             
CONECT   22    8   18   26                                                  
CONECT   23    9   21   26   32                                             
CONECT   24   11   21   25   33                                             
CONECT   25    2   12   19   24                                             
CONECT   26    3   13   22   23                                             
CONECT   27   14   16                                                       
CONECT   28   17                                                            
CONECT   29   17   20                                                       
CONECT   30   20                                                            
CONECT   31   21                                                            
CONECT   32   23                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(3beta)-17-(Pyridin-3-yl)androsta-5,16-dien-3-yl acetate	ChEBI
17-(3-Pyridyl)-5,16-androstadien-3beta-acetate	ChEBI
Zytiga	ChEBI
(3b)-17-(Pyridin-3-yl)androsta-5,16-dien-3-yl acetate	Generator
(3b)-17-(Pyridin-3-yl)androsta-5,16-dien-3-yl acetic acid	Generator
(3beta)-17-(Pyridin-3-yl)androsta-5,16-dien-3-yl acetic acid	Generator
(3Β)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetate	Generator
(3Β)-17-(pyridin-3-yl)androsta-5,16-dien-3-yl acetic acid	Generator
17-(3-Pyridyl)-5,16-androstadien-3b-acetate	Generator
17-(3-Pyridyl)-5,16-androstadien-3b-acetic acid	Generator
17-(3-Pyridyl)-5,16-androstadien-3beta-acetic acid	Generator
17-(3-Pyridyl)-5,16-androstadien-3β-acetate	Generator
17-(3-Pyridyl)-5,16-androstadien-3β-acetic acid	Generator
Abiraterone acetic acid	Generator
[(3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetic acid	Generator
Abiraterone acetate	MeSH

Chemical Formula

C₂₆H₃₃NO₂

Average Mass

391.5550 Da

Monoisotopic Mass

391.25113 Da

IUPAC Name

(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,13-dien-5-yl acetate

Traditional Name

(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,13-dien-5-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC=C(C3=CN=CC=C3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@]([H])(CC[C@]12C)OC(C)=O

InChI Identifier

InChI=1S/C26H33NO2/c1-17(28)29-20-10-12-25(2)19(15-20)6-7-21-23-9-8-22(18-5-4-14-27-16-18)26(23,3)13-11-24(21)25/h4-6,8,14,16,20-21,23-24H,7,9-13,15H2,1-3H3/t20-,21-,23-,24-,25-,26+/m0/s1

InChI Key

UVIQSJCZCSLXRZ-UBUQANBQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Androstane-skeleton
Delta-5-steroid
Pyridine
Heteroaromatic compound
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridines (CHEBI:68639 )
sterol ester (CHEBI:68639 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.63	ALOGPS
logP	4.41	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	4.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.45 m³·mol⁻¹	ChemAxon
Polarizability	46.63 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DBSALT001173

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Abiraterone acetate

METLIN ID

Not Available

PubChem Compound

9821849

PDB ID

Not Available

ChEBI ID

68639

Good Scents ID

Not Available

References

General References

O'Donnell A, Judson I, Dowsett M, Raynaud F, Dearnaley D, Mason M, Harland S, Robbins A, Halbert G, Nutley B, Jarman M: Hormonal impact of the 17alpha-hydroxylase/C(17,20)-lyase inhibitor abiraterone acetate (CB7630) in patients with prostate cancer. Br J Cancer. 2004 Jun 14;90(12):2317-25. doi: 10.1038/sj.bjc.6601879. [PubMed:15150570 ]
Martins V, Asad Y, Wilsher N, Raynaud F: A validated liquid chromatographic-tandem mass spectroscopy method for the quantification of abiraterone acetate and abiraterone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Nov 7;843(2):262-7. doi: 10.1016/j.jchromb.2006.06.010. Epub 2006 Jun 30. [PubMed:16809076 ]
Attard G, Reid AH, Yap TA, Raynaud F, Dowsett M, Settatree S, Barrett M, Parker C, Martins V, Folkerd E, Clark J, Cooper CS, Kaye SB, Dearnaley D, Lee G, de Bono JS: Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven. J Clin Oncol. 2008 Oct 1;26(28):4563-71. doi: 10.1200/JCO.2007.15.9749. Epub 2008 Jul 21. [PubMed:18645193 ]
Antonarakis ES, Eisenberger MA: Is abiraterone acetate well tolerated and effective in the treatment of castration-resistant prostate cancer? Nat Clin Pract Oncol. 2009 Jan;6(1):12-3. doi: 10.1038/ncponc1262. Epub 2008 Oct 28. [PubMed:18957947 ]
Schalken JA: Words of wisdom. Re: phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration- resistant prostate cancer commonly remains hormone driven. Eur Urol. 2008 Dec;54(6):1438-9. doi: 10.1016/j.eururo.2008.08.043. [PubMed:19189435 ]

Showing NP-Card for Abiraterone Acetate (NP0139777)

MOL for NP0139777 (Abiraterone Acetate)

3D MOL for NP0139777 (Abiraterone Acetate)

3D SDF for NP0139777 (Abiraterone Acetate)

3D-SDF for NP0139777 (Abiraterone Acetate)

PDB for NP0139777 (Abiraterone Acetate)

3D PDB for NP0139777 (Abiraterone Acetate)

SMILES for NP0139777 (Abiraterone Acetate)

INCHI for NP0139777 (Abiraterone Acetate)

Structure for NP0139777 (Abiraterone Acetate)

3D Structure for NP0139777 (Abiraterone Acetate)