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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014398

Secondary Accession Numbers

HMDB14398

Metabolite Identification

Common Name

Medrysone

Description

Medrysone is only found in individuals that have used or taken this drug. It is a corticosteroid used in ophthalmology. [Wikipedia ]There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Initially, the drug binds to the glucocorticoid receptor in the cytosol. This migrates to the nucleus and binds to genetic elements which cause activation and repression of the involved genes in the inflammatory pathway.

Structure

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

253
  Mrv0541 02231214332D          

 28 31  0  0  1  0            999 V2000
    3.9559    1.2662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5852    2.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.0287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0993    0.8537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.3838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703    0.0287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9196   -0.3894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849    1.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.8537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799    1.1052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799   -0.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3614    0.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -1.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9130   -1.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550    0.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1363    1.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9435    2.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.6276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -0.7093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.3587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  1  0  0  0
  2 20  2  0  0  0  0
  3 24  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 26  1  6  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 17  1  1  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 27  1  1  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 28  1  6  0  0  0
  8 16  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 14  1  0  0  0  0
 11 20  1  1  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  1  6  0  0  0
 16 22  2  0  0  0  0
 18 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 24  1  0  0  0  0
 22 24  1  0  0  0  0
M  END

HMDB0014398
     RDKit          3D
Medrysone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.9405    0.5209   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742    0.3287   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    0.1350   -1.8960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    0.3758    0.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5225   -0.6792    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.0943    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823   -0.1446    0.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1188   -0.5146    0.5756 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8754   -0.4424    1.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755   -0.8992    1.7032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0714   -0.6102    2.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9013   -0.2202    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201   -0.1287    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699    0.5036   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1846    0.2971   -0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    1.4498   -1.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    1.6597   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716    0.3443   -0.5989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3648   -0.5917   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    0.5814   -0.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0885    0.8352   -1.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0755   -0.1916   -2.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231    1.1502   -1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0209   -0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2997   -1.2404   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5400   -0.4178   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4800    1.3400   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9376    0.8742    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345    1.3501    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355   -0.2957    2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0319   -1.5593    0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -2.1633    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981   -0.9143    2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    0.8454    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522   -1.5066    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    0.6297    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.0502    2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -2.0091    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756   -0.7018    3.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    0.4544    2.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072   -1.3146    3.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -0.5380    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309    1.1585   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858    2.4286   -1.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    2.3535   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    2.1264   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.9580   -1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -1.4594   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -0.1104   -2.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714    1.5118    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    1.7338   -2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0686    0.0957   -3.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    2.0689   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    1.2197   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -1.1461   -2.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.7057   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.0445   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24  4  1  0
 24  7  1  0
 20  8  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  1
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  6
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 21 51  1  6
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END

253
  Mrv0541 02231214332D          

 28 31  0  0  1  0            999 V2000
    3.9559    1.2662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5852    2.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.0287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0993    0.8537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.3838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703    0.0287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9196   -0.3894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849    1.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.8537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799    1.1052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799   -0.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3614    0.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -1.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9130   -1.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    1.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550    0.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1363    1.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9435    2.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.6276    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -0.7093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420    0.3587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  1  0  0  0
  2 20  2  0  0  0  0
  3 24  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 26  1  6  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 17  1  1  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 27  1  1  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 28  1  6  0  0  0
  8 16  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 14  1  0  0  0  0
 11 20  1  1  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  1  6  0  0  0
 16 22  2  0  0  0  0
 18 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 24  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014398

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1

> <INCHI_KEY>
GZENKSODFLBBHQ-ILSZZQPISA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.4877

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.916409731169125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,8S,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
3.1268587000000005

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.73356965070513

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.136773343262778

> <JCHEM_PKA_STRONGEST_BASIC>
-0.259491695774292

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
98.84639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
medrysone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014398
     RDKit          3D
Medrysone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.9405    0.5209   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742    0.3287   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    0.1350   -1.8960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    0.3758    0.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5225   -0.6792    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.0943    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823   -0.1446    0.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1188   -0.5146    0.5756 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8754   -0.4424    1.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755   -0.8992    1.7032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0714   -0.6102    2.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9013   -0.2202    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201   -0.1287    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699    0.5036   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1846    0.2971   -0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    1.4498   -1.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    1.6597   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716    0.3443   -0.5989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3648   -0.5917   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    0.5814   -0.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0885    0.8352   -1.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0755   -0.1916   -2.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231    1.1502   -1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0209   -0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2997   -1.2404   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5400   -0.4178   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4800    1.3400   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9376    0.8742    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345    1.3501    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355   -0.2957    2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0319   -1.5593    0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -2.1633    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981   -0.9143    2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    0.8454    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522   -1.5066    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    0.6297    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.0502    2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -2.0091    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756   -0.7018    3.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    0.4544    2.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072   -1.3146    3.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -0.5380    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309    1.1585   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858    2.4286   -1.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    2.3535   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    2.1264   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.9580   -1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -1.4594   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -0.1104   -2.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714    1.5118    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    1.7338   -2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0686    0.0957   -3.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    2.0689   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    1.2197   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -1.1461   -2.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.7057   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.0445   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24  4  1  0
 24  7  1  0
 20  8  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  1
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  6
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 21 51  1  6
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 253                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.384   2.364   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.292   4.673   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080  -3.107   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.385   0.054   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.385   1.594   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.052  -0.716   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.718   0.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.317  -0.727   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.052   2.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.718   1.594   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.842   2.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.842  -0.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.076  -2.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.741   0.824   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.693  -3.133   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.304  -2.331   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.385   3.134   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.889   0.142   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.328   0.813   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.321   3.527   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.429  -0.671   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.864  -3.177   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.699  -4.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.417  -2.342   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.828   3.844   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      11.516  -1.172   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      11.123  -1.324   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       9.785   0.670   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   20                                                            
CONECT    3   24                                                            
CONECT    4    5    6   12   26                                             
CONECT    5    4    9   11   17                                             
CONECT    6    4    7   13   27                                             
CONECT    7    6    8   10   28                                             
CONECT    8    7   16   18   19                                             
CONECT    9    5   10                                                       
CONECT   10    1    7    9                                                  
CONECT   11    5   14   20                                                  
CONECT   12    4   14                                                       
CONECT   13    6   15                                                       
CONECT   14   11   12                                                       
CONECT   15   13   16   23                                                  
CONECT   16    8   15   22                                                  
CONECT   17    5                                                            
CONECT   18    8   21                                                       
CONECT   19    8                                                            
CONECT   20    2   11   25                                                  
CONECT   21   18   24                                                       
CONECT   22   16   24                                                       
CONECT   23   15                                                            
CONECT   24    3   21   22                                                  
CONECT   25   20                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014398
HETATM    1  C1  UNL     1      -5.940   0.521  -0.176  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.574   0.329  -0.689  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.448   0.135  -1.896  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.438   0.376   0.247  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.523  -0.679   1.331  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.091  -1.094   1.645  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.282  -0.145   0.846  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.119  -0.515   0.576  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.875  -0.442   1.910  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.276  -0.899   1.703  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.071  -0.610   2.962  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.901  -0.220   0.541  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.220  -0.129   0.556  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.970   0.504  -0.503  1.00  0.00           C  
HETATM   15  O2  UNL     1       6.185   0.297  -0.706  1.00  0.00           O  
HETATM   16  C14 UNL     1       4.268   1.450  -1.403  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.829   1.660  -0.974  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.172   0.344  -0.599  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.365  -0.592  -1.777  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.727   0.581  -0.288  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.088   0.835  -1.526  1.00  0.00           C  
HETATM   22  O3  UNL     1      -0.076  -0.192  -2.434  1.00  0.00           O  
HETATM   23  C20 UNL     1      -1.523   1.150  -1.191  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.123   0.021  -0.408  1.00  0.00           C  
HETATM   25  C22 UNL     1      -2.300  -1.240  -1.173  1.00  0.00           C  
HETATM   26  H1  UNL     1      -6.540  -0.418  -0.183  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.480   1.340  -0.734  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.938   0.874   0.888  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.335   1.350   0.760  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.036  -0.296   2.238  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.032  -1.559   0.906  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.914  -2.163   1.432  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.898  -0.914   2.724  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.299   0.845   1.356  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.252  -1.507   0.119  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.820   0.630   2.222  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.320  -1.050   2.623  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.258  -2.009   1.571  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.376  -0.702   3.836  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.387   0.454   2.929  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.907  -1.315   3.090  1.00  0.00           H  
HETATM   42  H17 UNL     1       4.799  -0.538   1.388  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.331   1.159  -2.472  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.786   2.429  -1.310  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.846   2.353  -0.110  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.317   2.126  -1.838  1.00  0.00           H  
HETATM   47  H22 UNL     1       3.411  -0.958  -1.723  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.697  -1.459  -1.596  1.00  0.00           H  
HETATM   49  H24 UNL     1       2.239  -0.110  -2.746  1.00  0.00           H  
HETATM   50  H25 UNL     1       0.671   1.512   0.328  1.00  0.00           H  
HETATM   51  H26 UNL     1       0.329   1.734  -2.024  1.00  0.00           H  
HETATM   52  H27 UNL     1      -0.069   0.096  -3.372  1.00  0.00           H  
HETATM   53  H28 UNL     1      -1.603   2.069  -0.594  1.00  0.00           H  
HETATM   54  H29 UNL     1      -2.073   1.220  -2.161  1.00  0.00           H  
HETATM   55  H30 UNL     1      -2.202  -1.146  -2.266  1.00  0.00           H  
HETATM   56  H31 UNL     1      -3.315  -1.706  -1.005  1.00  0.00           H  
HETATM   57  H32 UNL     1      -1.583  -2.045  -0.846  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    4
CONECT    4    5   24   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   24   34
CONECT    8    9   20   35
CONECT    9   10   36   37
CONECT   10   11   12   38
CONECT   11   39   40   41
CONECT   12   13   13   18
CONECT   13   14   42
CONECT   14   15   15   16
CONECT   16   17   43   44
CONECT   17   18   45   46
CONECT   18   19   20
CONECT   19   47   48   49
CONECT   20   21   50
CONECT   21   22   23   51
CONECT   22   52
CONECT   23   24   53   54
CONECT   24   25
CONECT   25   55   56   57
END

HMDB0014398
     RDKit          3D
Medrysone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.9405    0.5209   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742    0.3287   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4481    0.1350   -1.8960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380    0.3758    0.2469 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5225   -0.6792    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0905   -1.0943    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823   -0.1446    0.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1188   -0.5146    0.5756 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8754   -0.4424    1.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755   -0.8992    1.7032 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0714   -0.6102    2.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9013   -0.2202    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201   -0.1287    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9699    0.5036   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1846    0.2971   -0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    1.4498   -1.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    1.6597   -0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716    0.3443   -0.5989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3648   -0.5917   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    0.5814   -0.2883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0885    0.8352   -1.5257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0755   -0.1916   -2.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231    1.1502   -1.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    0.0209   -0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2997   -1.2404   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5400   -0.4178   -0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4800    1.3400   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9376    0.8742    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345    1.3501    0.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0355   -0.2957    2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0319   -1.5593    0.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -2.1633    1.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981   -0.9143    2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987    0.8454    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522   -1.5066    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    0.6297    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.0502    2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -2.0091    1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756   -0.7018    3.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871    0.4544    2.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072   -1.3146    3.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -0.5380    1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309    1.1585   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858    2.4286   -1.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8455    2.3535   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    2.1264   -1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.9580   -1.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -1.4594   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390   -0.1104   -2.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714    1.5118    0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    1.7338   -2.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0686    0.0957   -3.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031    2.0689   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    1.2197   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024   -1.1461   -2.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.7057   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.0445   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24  4  1  0
 24  7  1  0
 20  8  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  1
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  6
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 21 51  1  6
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11beta-Hydroxy-6alpha-methylpregn-4-ene-3,20-dione	Kegg
HMS	Kegg
11b-Hydroxy-6a-methylpregn-4-ene-3,20-dione	Generator
11Β-hydroxy-6α-methylpregn-4-ene-3,20-dione	Generator
Hydroxymesterone	HMDB
11-Hydroxy-6-methylprogesterone	HMDB
HMS Liquifilm	HMDB
HMS Suspension	HMDB

Chemical Formula

C₂₂H₃₂O₃

Average Molecular Weight

344.4877

Monoisotopic Molecular Weight

344.23514489

IUPAC Name

(1S,2R,8S,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

medrysone

CAS Registry Number

2668-66-8

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1

InChI Key

GZENKSODFLBBHQ-ILSZZQPISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

corticosteroid hormone (CHEBI:34829 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014398)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.034 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	183.16	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001163

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	3.06	ALOGPS
logP	3.13	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	19.14	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.85 m³·mol⁻¹	ChemAxon
Polarizability	39.92 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]+	183.387	31661259
DarkChem	[M-H]-	180.116	31661259
DeepCCS	[M-2H]-	223.827	30932474
DeepCCS	[M+Na]+	198.17	30932474
AllCCS	[M+H]+	186.1	32859911
AllCCS	[M+H-H2O]+	183.4	32859911
AllCCS	[M+NH4]+	188.5	32859911
AllCCS	[M+Na]+	189.2	32859911
AllCCS	[M-H]-	191.9	32859911
AllCCS	[M+Na-2H]-	192.4	32859911
AllCCS	[M+HCOO]-	193.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.64 minutes	32390414
Predicted by Siyang on May 30, 2022	14.8854 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2748.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	284.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	610.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	668.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1173.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	499.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1507.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	242.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	355.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Medrysone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C	3845.3	Standard polar	33892256
Medrysone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C	2929.5	Standard non polar	33892256
Medrysone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)CC[C@]12C	3263.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Medrysone,1TMS,isomer #1	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2931.9	Semi standard non polar	33892256
Medrysone,1TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3058.8	Semi standard non polar	33892256
Medrysone,1TMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2939.6	Semi standard non polar	33892256
Medrysone,1TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3017.5	Semi standard non polar	33892256
Medrysone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2926.2	Semi standard non polar	33892256
Medrysone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2906.9	Standard non polar	33892256
Medrysone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3261.6	Standard polar	33892256
Medrysone,2TMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2819.4	Semi standard non polar	33892256
Medrysone,2TMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2887.8	Standard non polar	33892256
Medrysone,2TMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3273.5	Standard polar	33892256
Medrysone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2869.8	Semi standard non polar	33892256
Medrysone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2875.2	Standard non polar	33892256
Medrysone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3349.6	Standard polar	33892256
Medrysone,2TMS,isomer #4	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2939.9	Semi standard non polar	33892256
Medrysone,2TMS,isomer #4	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2962.2	Standard non polar	33892256
Medrysone,2TMS,isomer #4	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3279.7	Standard polar	33892256
Medrysone,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2883.8	Semi standard non polar	33892256
Medrysone,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2938.6	Standard non polar	33892256
Medrysone,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3359.9	Standard polar	33892256
Medrysone,3TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2805.0	Semi standard non polar	33892256
Medrysone,3TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2938.0	Standard non polar	33892256
Medrysone,3TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3239.4	Standard polar	33892256
Medrysone,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2814.0	Semi standard non polar	33892256
Medrysone,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2910.5	Standard non polar	33892256
Medrysone,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3312.0	Standard polar	33892256
Medrysone,1TBDMS,isomer #1	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3174.7	Semi standard non polar	33892256
Medrysone,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3284.1	Semi standard non polar	33892256
Medrysone,1TBDMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3180.6	Semi standard non polar	33892256
Medrysone,1TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3238.6	Semi standard non polar	33892256
Medrysone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3354.2	Semi standard non polar	33892256
Medrysone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3399.9	Standard non polar	33892256
Medrysone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3504.0	Standard polar	33892256
Medrysone,2TBDMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3252.0	Semi standard non polar	33892256
Medrysone,2TBDMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3350.0	Standard non polar	33892256
Medrysone,2TBDMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3502.0	Standard polar	33892256
Medrysone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3304.8	Semi standard non polar	33892256
Medrysone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3363.1	Standard non polar	33892256
Medrysone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3563.6	Standard polar	33892256
Medrysone,2TBDMS,isomer #4	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3412.0	Semi standard non polar	33892256
Medrysone,2TBDMS,isomer #4	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3396.4	Standard non polar	33892256
Medrysone,2TBDMS,isomer #4	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3517.1	Standard polar	33892256
Medrysone,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3344.8	Semi standard non polar	33892256
Medrysone,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3369.5	Standard non polar	33892256
Medrysone,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3573.8	Standard polar	33892256
Medrysone,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3435.9	Semi standard non polar	33892256
Medrysone,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3561.6	Standard non polar	33892256
Medrysone,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3521.8	Standard polar	33892256
Medrysone,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3427.5	Semi standard non polar	33892256
Medrysone,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3529.6	Standard non polar	33892256
Medrysone,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]12C	3560.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00253	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00253	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00253

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

216968

KEGG Compound ID

C14643

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Medrysone

METLIN ID

Not Available

PubChem Compound

247839

PDB ID

Not Available

ChEBI ID

775124

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 Medrysone (HMDB0014398)

MOL for HMDB0014398 (Medrysone)

3D MOL for HMDB0014398 (Medrysone)

3D SDF for HMDB0014398 (Medrysone)

3D-SDF for HMDB0014398 (Medrysone)

PDB for HMDB0014398 (Medrysone)

3D PDB for HMDB0014398 (Medrysone)

SMILES for HMDB0014398 (Medrysone)

INCHI for HMDB0014398 (Medrysone)

Structure for HMDB0014398 (Medrysone)

3D Structure for HMDB0014398 (Medrysone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized