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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015031

Secondary Accession Numbers

HMDB15031

Metabolite Identification

Common Name

Testolactone

Description

Testolactone, also known as teslac, belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Thus, testolactone is considered to be a steroid lipid molecule. Testolactone is a drug which is used for palliative treatment of advanced breast cancer in postmenopausal women. It works by blocking the production of estrogens, which helps prevent the growth of breast cancers that are stimulated by estrogens. Testolactone was first approved for medical use in the United States in 1970. Testolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Androstenedione, a 19-carbon steroid hormone produced in the adrenal glands and the gonads, is where estrone synthesis originates and is the source of estrogen in postmenopausal women. In vitro studies report that the aromatase inhibition may be noncompetitive and irreversible, and could possibly account for the persistence of this drug's effect on estrogen synthesis after drug withdrawal. However, it has been reported to still be marketed in the United States by Bristol-Myers Squibb under the brand name Teslac. Testolactone has also been used to postpone precocious puberty because of its ability to block estrogen production. In addition to its activity as an aromatase inhibitor, testolactone also reportedly possesses some anabolic activity and weak androgenic activity via binding to and activation of the androgen receptor (AR). Testolactone (INN, USAN) (brand name Teslac) is a non-selective, irreversible, steroidal aromatase inhibitor which is used as an antineoplastic drug to treat advanced-stage breast cancer.

Structure

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

HMDB0015031
     RDKit          3D
Testolactone
 46 49  0  0  0  0  0  0  0  0999 V2000
    2.3807   -0.8736   -1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001   -0.9480    0.0892 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2721   -2.0877    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -1.8774   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611   -0.6146    0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2147    0.5865    0.2149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3487    1.7450    0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8102    1.9492    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    0.7349    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8036    0.6085    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.5988    0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7130   -0.7051    1.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -1.6313   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7926   -1.4666   -0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.2846   -0.3238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7596    0.4263   -1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390    0.3132    0.6980 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4550    1.5316    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144    1.2445    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123   -0.0536    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4222   -0.1069    1.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713   -1.1582    0.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -0.0173   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -0.8622   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.8314   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.9979    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -3.0810    0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -2.7179    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0046   -1.9047   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753   -0.7734    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.7927   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1916    2.6907    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.6211    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    2.6808    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270    2.4420    1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012    1.3924    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -2.5278   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -2.2332   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    0.4367   -2.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.1404   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    1.4845   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822    0.1713    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2162    2.3283    1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9220   -0.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951    1.3047   -0.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4640    2.0864    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17  2  1  0
 22  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  6 31  1  6
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
M  END

  Mrv1652309172019012D          

 25 28  0  0  0  0            999 V2000
 9998.940110000.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8009 9998.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.078110001.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.219010001.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6525 9999.1536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.364510000.3880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0781 9999.1536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2277 9999.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5132 9999.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5132 9998.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2277 9998.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6527 9999.9737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9382 9999.5612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9382 9998.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6527 9998.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3672 9998.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3672 9999.5612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.364510001.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.650010000.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0790 9999.9810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.079010000.8061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.791110001.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7911 9999.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5056 9999.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.505610000.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10  2  2  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 25  1  0  0  0  0
 25  4  2  0  0  0  0
 22 21  1  0  0  0  0
 21  3  1  1  0  0  0
 20 23  1  0  0  0  0
 20  7  1  6  0  0  0
 11 14  2  0  0  0  0
  8 13  1  0  0  0  0
 13  1  1  1  0  0  0
 19 12  1  0  0  0  0
 12  5  1  6  0  0  0
 17 20  1  0  0  0  0
 17  6  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0015031

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1

> <INCHI_KEY>
BPEWUONYVDABNZ-DZBHQSCQSA-N

> <FORMULA>
C19H24O3

> <MOLECULAR_WEIGHT>
300.3921

> <EXACT_MASS>
300.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.415636812061166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
3.2313274366666658

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.836204178017976

> <JCHEM_PKA_STRONGEST_BASIC>
-4.998336720346294

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
85.79099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015031
     RDKit          3D
Testolactone
 46 49  0  0  0  0  0  0  0  0999 V2000
    2.3807   -0.8736   -1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001   -0.9480    0.0892 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2721   -2.0877    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -1.8774   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611   -0.6146    0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2147    0.5865    0.2149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3487    1.7450    0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8102    1.9492    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    0.7349    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8036    0.6085    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.5988    0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7130   -0.7051    1.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -1.6313   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7926   -1.4666   -0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.2846   -0.3238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7596    0.4263   -1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390    0.3132    0.6980 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4550    1.5316    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144    1.2445    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123   -0.0536    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4222   -0.1069    1.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713   -1.1582    0.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -0.0173   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -0.8622   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.8314   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.9979    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -3.0810    0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -2.7179    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0046   -1.9047   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753   -0.7734    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.7927   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1916    2.6907    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.6211    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    2.6808    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270    2.4420    1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012    1.3924    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -2.5278   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -2.2332   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    0.4367   -2.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.1404   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    1.4845   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822    0.1713    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2162    2.3283    1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9220   -0.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951    1.3047   -0.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4640    2.0864    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17  2  1  0
 22  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  6 31  1  6
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
M  END

HEADER    PROTEIN                                 17-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-20         0                                  
HETATM    1  C   UNK     0    8664.6888667.391   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8660.6958663.527   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8668.6798669.716   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.6758668.950   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8666.0188665.087   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8667.3478667.391   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8668.6798665.087   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8663.3588666.615   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0258665.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0258664.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3588663.535   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0188666.618   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6858665.848   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6858664.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.0188663.538   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.3528664.307   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3528665.848   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3478668.941   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0138668.171   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.6818666.631   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.6818668.171   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8670.0108668.941   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8670.0108665.861   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.3448666.631   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.3448668.171   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   10                                                            
CONECT    3   21                                                            
CONECT    4   25                                                            
CONECT    5   12                                                            
CONECT    6   17                                                            
CONECT    7   20                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    2                                                  
CONECT   11   10   14                                                       
CONECT   12   13   17   19    5                                             
CONECT   13   12   14    8    1                                             
CONECT   14   13   15   11                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   20    6                                             
CONECT   18   19   21                                                       
CONECT   19   18   12                                                       
CONECT   20   21   23    7   17                                             
CONECT   21   18   20   22    3                                             
CONECT   22   25   21                                                       
CONECT   23   24   20                                                       
CONECT   24   23   25                                                       
CONECT   25   24   22    4                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0015031
HETATM    1  C1  UNL     1       2.381  -0.874  -1.390  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.200  -0.948   0.089  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.272  -2.088   0.473  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.051  -1.877  -0.195  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.661  -0.615   0.339  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.215   0.587   0.215  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.349   1.745   0.951  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.810   1.949   0.844  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.605   0.735   0.550  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.804   0.609   1.063  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.558  -0.599   0.753  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.713  -0.705   1.256  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.991  -1.631  -0.103  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.793  -1.467  -0.594  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.986  -0.285  -0.324  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.760   0.426  -1.658  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.639   0.313   0.698  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.455   1.532   0.316  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.914   1.245   0.189  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.312  -0.054   0.784  1.00  0.00           C  
HETATM   21  O2  UNL     1       5.422  -0.107   1.379  1.00  0.00           O  
HETATM   22  O3  UNL     1       3.471  -1.158   0.675  1.00  0.00           O  
HETATM   23  H1  UNL     1       1.919  -0.017  -1.879  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.470  -0.862  -1.688  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.994  -1.831  -1.837  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.107  -1.998   1.571  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.719  -3.081   0.263  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.717  -2.718   0.111  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.005  -1.905  -1.298  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.875  -0.773   1.417  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.329   0.793  -0.890  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.192   2.691   0.652  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.095   1.621   2.041  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.008   2.681   0.033  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.227   2.442   1.772  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.201   1.392   1.696  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.594  -2.528  -0.312  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.379  -2.233  -1.225  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.764   0.437  -2.154  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.092  -0.140  -2.322  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.479   1.485  -1.528  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.582   0.171   1.787  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.216   2.328   1.059  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.038   1.922  -0.658  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.195   1.305  -0.883  1.00  0.00           H  
HETATM   46  H24 UNL     1       4.464   2.086   0.696  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   17   22
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   15   30
CONECT    6    7   17   31
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   10   15
CONECT   10   11   36
CONECT   11   12   12   13
CONECT   13   14   14   37
CONECT   14   15   38
CONECT   15   16
CONECT   16   39   40   41
CONECT   17   18   42
CONECT   18   19   43   44
CONECT   19   20   45   46
CONECT   20   21   21   22
END

HMDB0015031
     RDKit          3D
Testolactone
 46 49  0  0  0  0  0  0  0  0999 V2000
    2.3807   -0.8736   -1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2001   -0.9480    0.0892 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2721   -2.0877    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0512   -1.8774   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6611   -0.6146    0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2147    0.5865    0.2149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3487    1.7450    0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8102    1.9492    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052    0.7349    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8036    0.6085    1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5577   -0.5988    0.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7130   -0.7051    1.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910   -1.6313   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7926   -1.4666   -0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856   -0.2846   -0.3238 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7596    0.4263   -1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390    0.3132    0.6980 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4550    1.5316    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144    1.2445    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123   -0.0536    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4222   -0.1069    1.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713   -1.1582    0.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -0.0173   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -0.8622   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.8314   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1065   -1.9979    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -3.0810    0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -2.7179    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0046   -1.9047   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753   -0.7734    1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    0.7927   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1916    2.6907    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.6211    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    2.6808    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270    2.4420    1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2012    1.3924    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5938   -2.5278   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -2.2332   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7636    0.4367   -2.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -0.1404   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    1.4845   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822    0.1713    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2162    2.3283    1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9220   -0.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951    1.3047   -0.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4640    2.0864    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 17  2  1  0
 22  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  6 31  1  6
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4AS,4BR,10ar,10BS,12as)-10a,12a-dimethyl-3,4,4a,5,6,10a,10b,11,12,12a-decahydro-2H-naphtho[2,1-F]chromene-2,8(4BH)-dione	ChEBI
1,2-Didehydrotestololactone	ChEBI
1-Dehydrotestololactone	ChEBI
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid delta-lactone	ChEBI
D-homo-17a-Oxaandrosta-1,4-diene-3,17-dione	ChEBI
delta(1)-Testololactone	ChEBI
Teslac	ChEBI
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oate delta-lactone	Generator
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oate Δ-lactone	Generator
13-Hydroxy-3-oxo-13,17-secoandrosta-1,4-dien-17-oic acid Δ-lactone	Generator
Δ(1)-testololactone	Generator
1-Dehydrotestolactone	MeSH, HMDB
1 Dehydrotestolactone	MeSH, HMDB
delta(1)-Testolactone	MeSH, HMDB
1,2-Dehydrotestololactone	HMDB
Testolactone	HMDB
delta1-Dehydrotestololactone	HMDB
delta1-Testolactone	HMDB
delta1-Testololactone	HMDB
Δ1-Dehydrotestololactone	HMDB
Δ1-Testolactone	HMDB
Δ1-Testololactone	HMDB

Chemical Formula

C₁₉H₂₄O₃

Average Molecular Weight

300.3921

Monoisotopic Molecular Weight

300.172544634

IUPAC Name

(1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione

Traditional Name

(1R,2S,7S,10S,11R)-7,11-dimethyl-6-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-12,15-diene-5,14-dione

CAS Registry Number

968-93-4

SMILES

[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]

InChI Identifier

InChI=1S/C19H24O3/c1-18-9-7-13(20)11-12(18)3-4-14-15(18)8-10-19(2)16(14)5-6-17(21)22-19/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15+,16+,18+,19+/m1/s1

InChI Key

BPEWUONYVDABNZ-DZBHQSCQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Pyran
Oxane
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3-oxo-Delta(1),Delta(4)-steroid (CHEBI:9460 )
seco-androstane (CHEBI:9460 )
Androstane and derivatives (C02197 )
C19 steroids (androgens) and derivatives (LMST02020084 )

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

Membrane (HMDB: HMDB0015031)
Extracellular (HMDB: HMDB0015031)

Source

Exogenous

Exogenous (HMDB: HMDB0015031)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.023 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	2.33	ALOGPS
logP	3.23	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	18.84	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.79 m³·mol⁻¹	ChemAxon
Polarizability	33.42 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]+	172.521	31661259
DarkChem	[M-H]-	164.553	31661259
DeepCCS	[M-2H]-	206.899	30932474
DeepCCS	[M+Na]+	181.807	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.5	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.7	32859911
AllCCS	[M-H]-	180.8	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Testolactone	[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]	3642.7	Standard polar	33892256
Testolactone	[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]	2431.0	Standard non polar	33892256
Testolactone	[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@]1(C)OC(=O)CC[C@@]21[H]	2940.0	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 - Testolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-0690000000-49e361148d5394e26c86	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testolactone 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 - Testolactone 10V, Positive-QTOF	splash10-0udi-0096000000-cdcc5f9f8e7f59492fe0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 20V, Positive-QTOF	splash10-0pb9-0291000000-34b2744abd958e22e648	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 40V, Positive-QTOF	splash10-0fdo-4590000000-e7db8fb6ab17e0d60421	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 10V, Negative-QTOF	splash10-052b-0090000000-8efa821a1c48e1557a70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 20V, Negative-QTOF	splash10-052b-0090000000-0995c390179d691601d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 40V, Negative-QTOF	splash10-0006-7090000000-a32554f7118b988d790a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 10V, Positive-QTOF	splash10-0udi-0029000000-4635acc995962c6e08b0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 20V, Positive-QTOF	splash10-0znc-0892000000-2b63265434d11c289904	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 40V, Positive-QTOF	splash10-0ab9-2900000000-5c09785873ed37a7d2c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 10V, Negative-QTOF	splash10-0002-0090000000-dd82c6133109d0e6e28e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 20V, Negative-QTOF	splash10-0002-0090000000-46bc79dbf2f9c8a57658	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testolactone 40V, Negative-QTOF	splash10-001j-0390000000-357d4c19f4162151e216	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00894	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00894	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00894

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13172

KEGG Compound ID

C02197

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Testolactone

METLIN ID

Not Available

PubChem Compound

13769

PDB ID

Not Available

ChEBI ID

9460

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

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. [PubMed:11792932 ]
Herzog AG, Klein P, Jacobs AR: Testosterone versus testosterone and testolactone in treating reproductive and sexual dysfunction in men with epilepsy and hypogonadism. Neurology. 1998 Mar;50(3):782-4. [PubMed:9521275 ]
Dunkel L: Use of aromatase inhibitors to increase final height. Mol Cell Endocrinol. 2006 Jul 25;254-255:207-16. [PubMed:16766117 ]
Cepa MM, Tavares da Silva EJ, Correia-da-Silva G, Roleira FM, Teixeira NA: Structure-activity relationships of new A,D-ring modified steroids as aromatase inhibitors: design, synthesis, and biological activity evaluation. J Med Chem. 2005 Oct 6;48(20):6379-85. [PubMed:16190763 ]

Showing metabocard for Testolactone (HMDB0015031)

MOL for HMDB0015031 (Testolactone)

3D MOL for HMDB0015031 (Testolactone)

3D SDF for HMDB0015031 (Testolactone)

3D-SDF for HMDB0015031 (Testolactone)

PDB for HMDB0015031 (Testolactone)

3D PDB for HMDB0015031 (Testolactone)

SMILES for HMDB0015031 (Testolactone)

INCHI for HMDB0015031 (Testolactone)

Structure for HMDB0015031 (Testolactone)

3D Structure for HMDB0015031 (Testolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References