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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:38:28 UTC

Update Date

2021-09-26 23:16:03 UTC

HMDB ID

HMDB0258855

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Testololactone

Description

10a,12a-Dimethyl-3,4,4a,5,6,9,10,10a,10b,11,12,12a-dodecahydro-2H-naphtho[2,1-f]chromene-2,8(4bh)-dione 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. 10a,12a-Dimethyl-3,4,4a,5,6,9,10,10a,10b,11,12,12a-dodecahydro-2H-naphtho[2,1-f]chromene-2,8(4bh)-dione is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Testololactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Testololactone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258855
     RDKit          3D
Testololactone
 48 51  0  0  0  0  0  0  0  0999 V2000
    2.7808    1.6188    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.9558   -0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.8174   -1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135    1.2718   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668    0.6206    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812   -0.3785    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266   -1.7890    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -1.7560    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -0.9303    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -1.1917    1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5764   -0.4445    0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056   -0.9341    0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2593    0.8911   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372    1.3033    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    0.1352   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -0.3162   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.4306   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3504    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822   -1.0862    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403   -0.1921   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890   -0.3009   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    0.7952   -1.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475    1.2011    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    2.7180    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008    1.5605    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    2.8415   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    1.9922   -2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    2.1737   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    0.6506   -2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361    1.4743    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.1114    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1992   -2.2689   -0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280   -2.3600    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054   -1.1495    2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524   -2.7490    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8634   -1.9915    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850    1.0258   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9197    1.6233    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937    2.1635   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    1.6192    1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -0.9747   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0567   -0.9258   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    0.5413   -2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -0.8440   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -1.3535    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   -2.4066    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450   -2.0429    0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6427   -0.7159    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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  1  0
 14 15  1  0
 15 16  1  0
  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  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
M  END


  Mrv1533004171508122D          

 22 25  0  0  0  0            999 V2000
    3.8424   -3.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -3.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -3.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -2.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258855

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/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/h11,14-16H,3-10H2,1-2H3

> <INCHI_KEY>
CNIXJDVUMXTEKX-UHFFFAOYSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.414

> <EXACT_MASS>
302.188194697

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
34.13994569729059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,11-dimethyl-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-15-ene-5,14-dione

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.233503946999999

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.062020432184188

> <JCHEM_PKA_STRONGEST_BASIC>
-4.814939112720213

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
84.6977

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11-dimethyl-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-15-ene-5,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258855
     RDKit          3D
Testololactone
 48 51  0  0  0  0  0  0  0  0999 V2000
    2.7808    1.6188    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.9558   -0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.8174   -1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135    1.2718   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668    0.6206    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812   -0.3785    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266   -1.7890    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -1.7560    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -0.9303    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -1.1917    1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5764   -0.4445    0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056   -0.9341    0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2593    0.8911   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372    1.3033    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    0.1352   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -0.3162   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.4306   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3504    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822   -1.0862    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403   -0.1921   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890   -0.3009   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    0.7952   -1.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475    1.2011    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    2.7180    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008    1.5605    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    2.8415   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    1.9922   -2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    2.1737   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    0.6506   -2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361    1.4743    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.1114    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1992   -2.2689   -0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280   -2.3600    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054   -1.1495    2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524   -2.7490    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8634   -1.9915    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850    1.0258   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9197    1.6233    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937    2.1635   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    1.6192    1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -0.9747   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0567   -0.9258   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    0.5413   -2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -0.8440   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -1.3535    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   -2.4066    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450   -2.0429    0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6427   -0.7159    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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  1  0
 14 15  1  0
 15 16  1  0
  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  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.172  -6.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.750  -3.268   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.709  -5.596   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.644  -4.432   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.164  -5.305   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    5    9   16                                             
CONECT   16   15                                                            
CONECT   17    6    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0258855
HETATM    1  C1  UNL     1       2.781   1.619   0.915  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.340   0.956  -0.356  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.389   1.817  -1.095  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.014   1.272  -1.188  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.467   0.621   0.097  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.481  -0.378   0.638  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.027  -1.789   0.722  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.270  -1.756   1.586  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.263  -0.930   0.829  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.544  -1.192   1.014  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.576  -0.445   0.325  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.706  -0.934   0.166  1.00  0.00           O  
HETATM   13  C12 UNL     1      -4.259   0.891  -0.177  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.837   1.303   0.142  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.879   0.135  -0.095  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.130  -0.316  -1.521  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.793  -0.431  -0.135  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.741  -1.350   0.540  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.182  -1.086   0.268  1.00  0.00           C  
HETATM   20  C19 UNL     1       4.440  -0.192  -0.865  1.00  0.00           C  
HETATM   21  O2  UNL     1       5.489  -0.301  -1.581  1.00  0.00           O  
HETATM   22  O3  UNL     1       3.517   0.795  -1.161  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.347   1.201   1.826  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.582   2.718   0.808  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.901   1.561   1.054  1.00  0.00           H  
HETATM   26  H4  UNL     1       1.383   2.842  -0.634  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.725   1.992  -2.149  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.681   2.174  -1.323  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.135   0.651  -2.083  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.536   1.474   0.836  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.792  -0.111   1.691  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.199  -2.269  -0.262  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.728  -2.360   1.317  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.005  -1.149   2.484  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.652  -2.749   1.836  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.863  -1.991   1.703  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.485   1.026  -1.255  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.920   1.623   0.369  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.594   2.163  -0.486  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.823   1.619   1.215  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.337  -0.975  -1.915  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.057  -0.926  -1.536  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.323   0.541  -2.198  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.542  -0.844  -1.135  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.515  -1.354   1.639  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.525  -2.407   0.207  1.00  0.00           H  
HETATM   47  H25 UNL     1       4.745  -2.043   0.059  1.00  0.00           H  
HETATM   48  H26 UNL     1       4.643  -0.716   1.230  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   37   38
CONECT   14   15   39   40
CONECT   15   16
CONECT   16   41   42   43
CONECT   17   18   44
CONECT   18   19   45   46
CONECT   19   20   47   48
CONECT   20   21   21   22
END

HMDB0258855
     RDKit          3D
Testololactone
 48 51  0  0  0  0  0  0  0  0999 V2000
    2.7808    1.6188    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.9558   -0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893    1.8174   -1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0135    1.2718   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668    0.6206    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812   -0.3785    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266   -1.7890    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -1.7560    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -0.9303    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437   -1.1917    1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5764   -0.4445    0.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056   -0.9341    0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2593    0.8911   -0.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372    1.3033    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    0.1352   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -0.3162   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.4306   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7409   -1.3504    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1822   -1.0862    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4403   -0.1921   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890   -0.3009   -1.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    0.7952   -1.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475    1.2011    1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5821    2.7180    0.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008    1.5605    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829    2.8415   -0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    1.9922   -2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    2.1737   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    0.6506   -2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361    1.4743    0.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -0.1114    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1992   -2.2689   -0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280   -2.3600    1.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054   -1.1495    2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6524   -2.7490    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8634   -1.9915    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850    1.0258   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9197    1.6233    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937    2.1635   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    1.6192    1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372   -0.9747   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0567   -0.9258   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225    0.5413   -2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5415   -0.8440   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -1.3535    1.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   -2.4066    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450   -2.0429    0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6427   -0.7159    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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  1  0
 14 15  1  0
 15 16  1  0
  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  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.414

Monoisotopic Molecular Weight

302.188194697

IUPAC Name

7,11-dimethyl-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-15-ene-5,14-dione

Traditional Name

7,11-dimethyl-6-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadec-15-ene-5,14-dione

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC(=O)O2

InChI Identifier

InChI=1S/C19H26O3/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/h11,14-16H,3-10H2,1-2H3

InChI Key

CNIXJDVUMXTEKX-UHFFFAOYSA-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
Cyclohexenone
Oxane
Pyran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a small molecule (TESTOLOLACTONE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.55	ALOGPS
logP	3.23	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	19.06	ChemAxon
pKa (Strongest Basic)	-4.8	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	84.7 m³·mol⁻¹	ChemAxon
Polarizability	34.14 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
DeepCCS	[M-2H]-	205.854	30932474
DeepCCS	[M+Na]+	181.419	30932474
AllCCS	[M+H]+	176.4	32859911
AllCCS	[M+H-H2O]+	173.2	32859911
AllCCS	[M+NH4]+	179.3	32859911
AllCCS	[M+Na]+	180.2	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	181.6	32859911
AllCCS	[M+HCOO]-	181.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Testololactone	CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC(=O)O2	3583.6	Standard polar	33892256
Testololactone	CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC(=O)O2	2386.5	Standard non polar	33892256
Testololactone	CC12CCC3C(CCC4=CC(=O)CCC34C)C1CCC(=O)O2	2911.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Testololactone,1TMS,isomer #1	CC12CCC3C(CCC4=CC(O[Si](C)(C)C)=CCC43C)C1CCC(=O)O2	2777.4	Semi standard non polar	33892256
Testololactone,1TMS,isomer #1	CC12CCC3C(CCC4=CC(O[Si](C)(C)C)=CCC43C)C1CCC(=O)O2	2603.3	Standard non polar	33892256
Testololactone,1TMS,isomer #1	CC12CCC3C(CCC4=CC(O[Si](C)(C)C)=CCC43C)C1CCC(=O)O2	3222.1	Standard polar	33892256
Testololactone,1TBDMS,isomer #1	CC12CCC3C(CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC43C)C1CCC(=O)O2	3030.9	Semi standard non polar	33892256
Testololactone,1TBDMS,isomer #1	CC12CCC3C(CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC43C)C1CCC(=O)O2	2844.2	Standard non polar	33892256
Testololactone,1TBDMS,isomer #1	CC12CCC3C(CCC4=CC(O[Si](C)(C)C(C)(C)C)=CCC43C)C1CCC(=O)O2	3374.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Testololactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01w0-0790000000-a01157f0eaee60f80324	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testololactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

224000

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Testololactone (HMDB0258855)

MOL for HMDB0258855 (Testololactone)

3D MOL for HMDB0258855 (Testololactone)

3D SDF for HMDB0258855 (Testololactone)

3D-SDF for HMDB0258855 (Testololactone)

PDB for HMDB0258855 (Testololactone)

3D PDB for HMDB0258855 (Testololactone)

SMILES for HMDB0258855 (Testololactone)

INCHI for HMDB0258855 (Testololactone)

Structure for HMDB0258855 (Testololactone)

3D Structure for HMDB0258855 (Testololactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra