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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:56:47 UTC

Update Date

2021-09-14 15:17:02 UTC

HMDB ID

HMDB0060746

Secondary Accession Numbers

HMDB60746

Metabolite Identification

Common Name

3-keto-Digoxigenin

Description

3-keto-Digoxigenin is a metabolite of digoxin. Digoxin is a purified cardiac glycoside and extracted from the foxglove plant, Digitalis lanata. Its corresponding aglycone is digoxigenin, and its acetyl derivative is acetyldigoxin. Digoxin is widely used in the treatment of various heart conditions, namely atrial fibrillation, atrial flutter and sometimes heart failure that cannot be controlled by other medication. Digoxin preparations are commonly marketed under the trade names Lanoxin, Digitek, and Lanoxicaps. (Wikipedia )

Structure

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

  Mrv0541 07041311562D          

 28 32  0  0  0  0            999 V2000
    3.9055    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -0.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061    0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2812    0.3114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0350   -0.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274    2.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6864   -0.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  6  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 16 13  1  1  0  0  0
 17  4  1  6  0  0  0
 18 11  1  1  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20  9  1  0  0  0  0
 21  1  1  1  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22  2  1  1  0  0  0
 22 16  1  0  0  0  0
 22 19  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  1  0  0  0  0
 24 15  2  0  0  0  0
 19 25  1  1  0  0  0
 26 20  2  0  0  0  0
 23 27  1  1  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
M  END

HMDB0060746
     RDKit          3D
3-keto-Digoxigenin
 60 64  0  0  0  0  0  0  0  0999 V2000
   -3.0700   -1.1849   -1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190   -0.2368   -0.2706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4743   -0.5614    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    0.4455    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    1.1653    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2478    1.5253    0.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.4564   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261    1.1507   -0.8160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2224    2.2407   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.8389    0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.7008   -0.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1986   -0.5013    0.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5610   -1.6122   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.8431   -0.2129 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3770   -2.9702   -0.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.6579   -0.4486 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9672   -0.5974   -1.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521   -0.9621    0.3836 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2216   -0.3346    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    0.5521   -0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.8925   -0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    1.7133   -1.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5032    0.1411    0.2757 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4969   -0.6440    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -0.6724    1.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332    0.2853    1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956    0.5231    0.1939 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7035    1.7495   -0.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -2.2286   -1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1534   -0.9060   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -0.9799   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -0.7109    1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9898   -1.5621    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514   -0.0758    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    1.1400    2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6745    1.0171   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384    2.5728   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413    1.1497   -1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9354    3.0671   -0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    2.7317    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    1.4782    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    2.7147    0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.9835   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -0.8592    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -2.5622   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309   -1.3438   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016   -2.0325    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -3.7077   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.0490   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.2782   -2.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987    0.3892   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1356   -2.0808    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9036    1.0009   -1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854   -1.7372    0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3531   -0.3915    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882   -1.5817    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039   -0.2969    2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -0.0302    2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.2368    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682    2.3304    0.6917 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  8  2  1  0
 27 11  1  0
 12  2  1  0
 27 16  1  0
 24 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  0
 13 46  1  0
 14 47  1  1
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 20 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 28 60  1  0
M  END

  Mrv0541 07041311562D          

 28 32  0  0  0  0            999 V2000
    3.9055    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478   -0.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061    0.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661    2.1537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8100    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    0.9689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8418    1.8632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3737    1.2325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2812    0.3114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0350   -0.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7494    0.9421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0297    1.7180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6221    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -0.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274    2.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6864   -0.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  6  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 16 13  1  1  0  0  0
 17  4  1  6  0  0  0
 18 11  1  1  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20  9  1  0  0  0  0
 21  1  1  1  0  0  0
 21  7  1  0  0  0  0
 21 14  1  0  0  0  0
 21 18  1  0  0  0  0
 22  2  1  1  0  0  0
 22 16  1  0  0  0  0
 22 19  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
 23 22  1  0  0  0  0
 24 15  2  0  0  0  0
 19 25  1  1  0  0  0
 26 20  2  0  0  0  0
 23 27  1  1  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060746

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3CC(=O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14,16-19,25,27H,3-8,10-12H2,1-2H3/t14-,16-,17-,18+,19-,21+,22+,23+/m1/s1

> <INCHI_KEY>
POWMMMXVDBMFMP-QPMAGJLNSA-N

> <FORMULA>
C23H32O5

> <MOLECULAR_WEIGHT>
388.4972

> <EXACT_MASS>
388.224974134

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
42.50964521596758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.044044321666668

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.971827339212389

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.151116397737988

> <JCHEM_PKA_STRONGEST_BASIC>
-2.976075200901148

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
104.12799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,2S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060746
     RDKit          3D
3-keto-Digoxigenin
 60 64  0  0  0  0  0  0  0  0999 V2000
   -3.0700   -1.1849   -1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190   -0.2368   -0.2706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4743   -0.5614    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    0.4455    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    1.1653    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2478    1.5253    0.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.4564   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261    1.1507   -0.8160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2224    2.2407   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.8389    0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.7008   -0.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1986   -0.5013    0.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5610   -1.6122   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.8431   -0.2129 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3770   -2.9702   -0.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.6579   -0.4486 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9672   -0.5974   -1.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521   -0.9621    0.3836 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2216   -0.3346    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    0.5521   -0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.8925   -0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    1.7133   -1.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5032    0.1411    0.2757 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4969   -0.6440    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -0.6724    1.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332    0.2853    1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956    0.5231    0.1939 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7035    1.7495   -0.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -2.2286   -1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1534   -0.9060   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -0.9799   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -0.7109    1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9898   -1.5621    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514   -0.0758    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    1.1400    2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6745    1.0171   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384    2.5728   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413    1.1497   -1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9354    3.0671   -0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    2.7317    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    1.4782    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    2.7147    0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.9835   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -0.8592    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -2.5622   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309   -1.3438   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016   -2.0325    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -3.7077   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.0490   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.2782   -2.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987    0.3892   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1356   -2.0808    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9036    1.0009   -1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854   -1.7372    0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3531   -0.3915    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882   -1.5817    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039   -0.2969    2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -0.0302    2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.2368    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682    2.3304    0.6917 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  8  2  1  0
 27 11  1  0
 12  2  1  0
 27 16  1  0
 24 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  0
 13 46  1  0
 14 47  1  1
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 20 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 28 60  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       7.290   1.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.594   0.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.344   5.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.828   4.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.322   1.665   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.298   3.288   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.806   1.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.573   4.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.209  -0.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.853   4.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.774   0.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.758   0.643   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.781   0.593   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.337   4.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.845   3.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.726   1.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.305   3.478   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.298   2.301   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.258   0.581   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.065  -1.751   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.813   2.572   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.266   1.759   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.789   3.207   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.361   3.385   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.735  -0.867   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.115  -3.290   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.158   4.702   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.281  -0.806   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4   14                                                       
CONECT    4    3   17                                                       
CONECT    5    7   15                                                       
CONECT    6    8   16                                                       
CONECT    7    5   21                                                       
CONECT    8    6   23                                                       
CONECT    9   13   20                                                       
CONECT   10   14   15                                                       
CONECT   11   18   19                                                       
CONECT   12   13   28                                                       
CONECT   13    9   12   16                                                  
CONECT   14    3   10   21                                                  
CONECT   15    5   10   24                                                  
CONECT   16    6   13   22                                                  
CONECT   17    4   18   23                                                  
CONECT   18   11   17   21                                                  
CONECT   19   11   22   25                                                  
CONECT   20    9   26   28                                                  
CONECT   21    1    7   14   18                                             
CONECT   22    2   16   19   23                                             
CONECT   23    8   17   22   27                                             
CONECT   24   15                                                            
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   23                                                            
CONECT   28   12   20                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0060746
HETATM    1  C1  UNL     1      -3.070  -1.185  -1.395  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.619  -0.237  -0.271  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.474  -0.561   0.917  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.506   0.446   1.263  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.095   1.165   0.134  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.248   1.525   0.163  1.00  0.00           O  
HETATM    7  C6  UNL     1      -4.276   1.456  -1.053  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.826   1.151  -0.816  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.222   2.241  -0.012  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.909   1.839   0.652  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.352   0.701  -0.139  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.199  -0.501   0.066  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.561  -1.612  -0.769  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.797  -1.843  -0.213  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.377  -2.970  -0.814  1.00  0.00           O  
HETATM   16  C14 UNL     1       1.763  -0.658  -0.449  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.967  -0.597  -1.912  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.952  -0.962   0.384  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.222  -0.335   0.082  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.558   0.552  -0.814  1.00  0.00           C  
HETATM   21  C19 UNL     1       5.971   0.893  -0.745  1.00  0.00           C  
HETATM   22  O3  UNL     1       6.579   1.713  -1.479  1.00  0.00           O  
HETATM   23  O4  UNL     1       6.503   0.141   0.276  1.00  0.00           O  
HETATM   24  C20 UNL     1       5.497  -0.644   0.843  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.473  -0.672   1.808  1.00  0.00           C  
HETATM   26  C22 UNL     1       1.333   0.285   1.667  1.00  0.00           C  
HETATM   27  C23 UNL     1       1.096   0.523   0.194  1.00  0.00           C  
HETATM   28  O5  UNL     1       1.703   1.749  -0.109  1.00  0.00           O  
HETATM   29  H1  UNL     1      -3.088  -2.229  -1.070  1.00  0.00           H  
HETATM   30  H2  UNL     1      -4.153  -0.906  -1.559  1.00  0.00           H  
HETATM   31  H3  UNL     1      -2.567  -0.980  -2.337  1.00  0.00           H  
HETATM   32  H4  UNL     1      -2.832  -0.711   1.836  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.990  -1.562   0.807  1.00  0.00           H  
HETATM   34  H6  UNL     1      -5.351  -0.076   1.805  1.00  0.00           H  
HETATM   35  H7  UNL     1      -4.095   1.140   2.054  1.00  0.00           H  
HETATM   36  H8  UNL     1      -4.675   1.017  -1.993  1.00  0.00           H  
HETATM   37  H9  UNL     1      -4.338   2.573  -1.217  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.341   1.150  -1.839  1.00  0.00           H  
HETATM   39  H11 UNL     1      -1.935   3.067  -0.728  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.914   2.732   0.706  1.00  0.00           H  
HETATM   41  H13 UNL     1      -1.189   1.478   1.674  1.00  0.00           H  
HETATM   42  H14 UNL     1      -0.251   2.715   0.728  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.408   0.984  -1.216  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.085  -0.859   1.132  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.125  -2.562  -0.644  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.631  -1.344  -1.820  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.702  -2.032   0.870  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.487  -3.708  -0.157  1.00  0.00           H  
HETATM   49  H21 UNL     1       2.969  -1.049  -2.183  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.267  -1.278  -2.496  1.00  0.00           H  
HETATM   51  H23 UNL     1       1.799   0.389  -2.388  1.00  0.00           H  
HETATM   52  H24 UNL     1       3.136  -2.081   0.382  1.00  0.00           H  
HETATM   53  H25 UNL     1       3.904   1.001  -1.524  1.00  0.00           H  
HETATM   54  H26 UNL     1       5.685  -1.737   0.694  1.00  0.00           H  
HETATM   55  H27 UNL     1       5.353  -0.391   1.910  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.088  -1.582   2.310  1.00  0.00           H  
HETATM   57  H29 UNL     1       3.304  -0.297   2.438  1.00  0.00           H  
HETATM   58  H30 UNL     1       0.423  -0.030   2.213  1.00  0.00           H  
HETATM   59  H31 UNL     1       1.651   1.237   2.185  1.00  0.00           H  
HETATM   60  H32 UNL     1       1.768   2.330   0.692  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   12
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6    6    7
CONECT    7    8   36   37
CONECT    8    9   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   27   43
CONECT   12   13   44
CONECT   13   14   45   46
CONECT   14   15   16   47
CONECT   15   48
CONECT   16   17   18   27
CONECT   17   49   50   51
CONECT   18   19   25   52
CONECT   19   20   20   24
CONECT   20   21   53
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   54   55
CONECT   25   26   56   57
CONECT   26   27   58   59
CONECT   27   28
CONECT   28   60
END

HMDB0060746
     RDKit          3D
3-keto-Digoxigenin
 60 64  0  0  0  0  0  0  0  0999 V2000
   -3.0700   -1.1849   -1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6190   -0.2368   -0.2706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4743   -0.5614    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065    0.4455    1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0949    1.1653    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2478    1.5253    0.1630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.4564   -1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261    1.1507   -0.8160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2224    2.2407   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.8389    0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.7008   -0.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1986   -0.5013    0.0658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5610   -1.6122   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970   -1.8431   -0.2129 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3770   -2.9702   -0.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.6579   -0.4486 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9672   -0.5974   -1.9120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9521   -0.9621    0.3836 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2216   -0.3346    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5579    0.5521   -0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.8925   -0.7453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    1.7133   -1.4790 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5032    0.1411    0.2757 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4969   -0.6440    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -0.6724    1.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332    0.2853    1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956    0.5231    0.1939 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7035    1.7495   -0.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -2.2286   -1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1534   -0.9060   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -0.9799   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -0.7109    1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9898   -1.5621    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514   -0.0758    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    1.1400    2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6745    1.0171   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3384    2.5728   -1.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413    1.1497   -1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9354    3.0671   -0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142    2.7317    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    1.4782    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509    2.7147    0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078    0.9835   -1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -0.8592    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -2.5622   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6309   -1.3438   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7016   -2.0325    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -3.7077   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9691   -1.0490   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.2782   -2.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987    0.3892   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1356   -2.0808    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9036    1.0009   -1.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6854   -1.7372    0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3531   -0.3915    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0882   -1.5817    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039   -0.2969    2.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -0.0302    2.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510    1.2368    2.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682    2.3304    0.6917 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  8  2  1  0
 27 11  1  0
 12  2  1  0
 27 16  1  0
 24 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  1
 13 45  1  0
 13 46  1  0
 14 47  1  1
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  1
 20 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 28 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Oxazepam	HMDB
(RS)-Oxazepam	HMDB
Serax	HMDB
Tazepam	HMDB
ZAXOPAM	HMDB
WY-3498oxozepam	HMDB
Oxazipam	HMDB
Oxozepam	HMDB
Adumbran	HMDB
Nortemazepam	HMDB
3-Hydroxynordiazepam	HMDB

Chemical Formula

C₂₃H₃₂O₅

Average Molecular Weight

388.4972

Monoisotopic Molecular Weight

388.224974134

IUPAC Name

4-[(1S,2S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

Traditional Name

4-[(1S,2S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3CC(=O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C23H32O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14,16-19,25,27H,3-8,10-12H2,1-2H3/t14-,16-,17-,18+,19-,21+,22+,23+/m1/s1

InChI Key

POWMMMXVDBMFMP-QPMAGJLNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
3-oxosteroid
12-hydroxysteroid
3-oxo-5-beta-steroid
14-hydroxysteroid
Oxosteroid
Hydroxysteroid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060746)

Organ

Kidney (HMDB: HMDB0060746)
Liver (HMDB: HMDB0060746)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060746)

Cellular substructure

Cytoplasm (HMDB: HMDB0060746)
Membrane (HMDB: HMDB0060746)

Source

Endogenous

Endogenous (HMDB: HMDB0060746)

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
Water Solubility	0.036 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2.04	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	104.13 m³·mol⁻¹	ChemAxon
Polarizability	42.51 Å³	ChemAxon
Number of Rings	5	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]+	192.179	31661259
DarkChem	[M-H]-	187.516	31661259
DeepCCS	[M-2H]-	222.551	30932474
DeepCCS	[M+Na]+	197.166	30932474
AllCCS	[M+H]+	196.4	32859911
AllCCS	[M+H-H2O]+	193.9	32859911
AllCCS	[M+NH4]+	198.6	32859911
AllCCS	[M+Na]+	199.2	32859911
AllCCS	[M-H]-	198.1	32859911
AllCCS	[M+Na-2H]-	198.8	32859911
AllCCS	[M+HCOO]-	199.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-keto-Digoxigenin	C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3CC(=O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC1	3649.4	Standard polar	33892256
3-keto-Digoxigenin	C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3CC(=O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC1	3362.1	Standard non polar	33892256
3-keto-Digoxigenin	C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3CC(=O)CC[C@]3(C)[C@H]1C[C@H]2O)C1=CC(=O)OC1	3996.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-keto-Digoxigenin,1TMS,isomer #1	C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C	3513.4	Semi standard non polar	33892256
3-keto-Digoxigenin,1TMS,isomer #2	C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O	3522.7	Semi standard non polar	33892256
3-keto-Digoxigenin,1TMS,isomer #3	C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O	3552.3	Semi standard non polar	33892256
3-keto-Digoxigenin,1TMS,isomer #4	C[C@]12[C@H](O)C[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1	3537.2	Semi standard non polar	33892256
3-keto-Digoxigenin,2TMS,isomer #1	C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C	3451.2	Semi standard non polar	33892256
3-keto-Digoxigenin,2TMS,isomer #2	C[C@]12[C@H](O)C[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C1=CC(=O)OC1	3486.9	Semi standard non polar	33892256
3-keto-Digoxigenin,2TMS,isomer #3	C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C	3502.4	Semi standard non polar	33892256
3-keto-Digoxigenin,2TMS,isomer #4	C[C@]12[C@H](O[Si](C)(C)C)C[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1	3496.9	Semi standard non polar	33892256
3-keto-Digoxigenin,2TMS,isomer #5	C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O	3525.9	Semi standard non polar	33892256
3-keto-Digoxigenin,3TMS,isomer #1	C[C@]12[C@H](O[Si](C)(C)C)C[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C1=CC(=O)OC1	3434.7	Semi standard non polar	33892256
3-keto-Digoxigenin,3TMS,isomer #1	C[C@]12[C@H](O[Si](C)(C)C)C[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C1=CC(=O)OC1	3306.5	Standard non polar	33892256
3-keto-Digoxigenin,3TMS,isomer #1	C[C@]12[C@H](O[Si](C)(C)C)C[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@]1(O[Si](C)(C)C)CC[C@@H]2C1=CC(=O)OC1	3832.9	Standard polar	33892256
3-keto-Digoxigenin,3TMS,isomer #2	C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C	3450.6	Semi standard non polar	33892256
3-keto-Digoxigenin,3TMS,isomer #2	C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C	3274.2	Standard non polar	33892256
3-keto-Digoxigenin,3TMS,isomer #2	C[C@]12CC=C(O[Si](C)(C)C)C[C@H]1CC[C@@H]1[C@@H]2C[C@@H](O[Si](C)(C)C)[C@]2(C)[C@@H](C3=CC(=O)OC3)CC[C@]12O[Si](C)(C)C	3833.8	Standard polar	33892256
3-keto-Digoxigenin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@]12CC[C@H](C3=CC(=O)OC3)[C@@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@@H]2CC(=O)CC[C@]12C	3759.2	Semi standard non polar	33892256
3-keto-Digoxigenin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H](CC[C@@H]3CC(=O)CC[C@]23C)[C@@]2(O)CC[C@H](C3=CC(=O)OC3)[C@@]12C	3765.3	Semi standard non polar	33892256
3-keto-Digoxigenin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O)[C@@H]3CC[C@@H]2C1	3791.5	Semi standard non polar	33892256
3-keto-Digoxigenin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O)[C@@]2(C)CC1	3758.4	Semi standard non polar	33892256
3-keto-Digoxigenin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H](CC[C@@H]3CC(=O)CC[C@]23C)[C@@]2(O[Si](C)(C)C(C)(C)C)CC[C@H](C3=CC(=O)OC3)[C@@]12C	3925.8	Semi standard non polar	33892256
3-keto-Digoxigenin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@@H]2C1	3939.1	Semi standard non polar	33892256
3-keto-Digoxigenin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C[C@@H](O)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC1	3904.9	Semi standard non polar	33892256
3-keto-Digoxigenin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O)[C@@H]3CC[C@@H]2C1	3973.8	Semi standard non polar	33892256
3-keto-Digoxigenin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O)[C@@]2(C)CC1	3925.6	Semi standard non polar	33892256
3-keto-Digoxigenin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@@H]2C1	4097.3	Semi standard non polar	33892256
3-keto-Digoxigenin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@@H]2C1	3825.6	Standard non polar	33892256
3-keto-Digoxigenin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]4(O[Si](C)(C)C(C)(C)C)[C@@H]3CC[C@@H]2C1	4085.6	Standard polar	33892256
3-keto-Digoxigenin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC1	4060.5	Semi standard non polar	33892256
3-keto-Digoxigenin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC1	3896.9	Standard non polar	33892256
3-keto-Digoxigenin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@@H]3[C@H](C[C@@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC1	4080.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-keto-Digoxigenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abi-0649000000-77a021ecbdec98b29024	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-keto-Digoxigenin GC-MS (2 TMS) - 70eV, Positive	splash10-0gb9-1420690000-ae15153e498756a96de1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-keto-Digoxigenin 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 - 3-keto-Digoxigenin 10V, Positive-QTOF	splash10-0fmi-0009000000-1a6236ba0e88d01a692c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 20V, Positive-QTOF	splash10-0it9-0109000000-c3c1dbc0a0728bfb970b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 40V, Positive-QTOF	splash10-0j6r-5529000000-d9c5e9ed9ecd89058230	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 10V, Negative-QTOF	splash10-000i-0009000000-4aae9e0a9cf012f740c9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 20V, Negative-QTOF	splash10-014u-0009000000-1ee75f703b4aaf96fe3b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 40V, Negative-QTOF	splash10-002f-2009000000-1717a042b4520e68fc51	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 10V, Positive-QTOF	splash10-0079-0009000000-cb65b0a3c0c8a29cceaa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 20V, Positive-QTOF	splash10-0fki-0039000000-55ffb170383bbb7b7698	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 40V, Positive-QTOF	splash10-00os-4942000000-965dd7b07d0ef3756dbd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 10V, Negative-QTOF	splash10-000i-0009000000-e537f902942ad9865de2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 20V, Negative-QTOF	splash10-000f-0009000000-174768f6594ec59bcab5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-keto-Digoxigenin 40V, Negative-QTOF	splash10-0079-3339000000-f0fbebbe3a129e882817	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

10189794

KEGG Compound ID

C07359

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxazepam

METLIN ID

Not Available

PubChem Compound

12113849

PDB ID

Not Available

ChEBI ID

175109

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3-keto-Digoxigenin (HMDB0060746)

MOL for HMDB0060746 (3-keto-Digoxigenin)

3D MOL for HMDB0060746 (3-keto-Digoxigenin)

3D SDF for HMDB0060746 (3-keto-Digoxigenin)

3D-SDF for HMDB0060746 (3-keto-Digoxigenin)

PDB for HMDB0060746 (3-keto-Digoxigenin)

3D PDB for HMDB0060746 (3-keto-Digoxigenin)

SMILES for HMDB0060746 (3-keto-Digoxigenin)

INCHI for HMDB0060746 (3-keto-Digoxigenin)

Structure for HMDB0060746 (3-keto-Digoxigenin)

3D Structure for HMDB0060746 (3-keto-Digoxigenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra