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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015011

Secondary Accession Numbers

HMDB15011

Metabolite Identification

Common Name

Loteprednol

Description

Loteprednol (as Loteprednol Etabonate) is a topical corticoid antiinflammatory. It is used in ophthalmic solution for the treatment of steroid responsive inflammatory conditions of the eye such as allergic conjunctivitis, uveitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, and selected infective conjunctivitides. As a nasal spray, is used for the treatment and management of seasonal allergic rhinitis.

Structure

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


  Mrv0541 04191212152D          

 30 33  0  0  1  0            999 V2000
    8.2910  -12.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5765  -12.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5765  -13.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2910  -13.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -13.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -12.5685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7199  -12.1560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7199  -13.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4344  -13.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4344  -12.5685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4344  -10.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7199  -11.3310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1488  -12.1560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1488  -11.3310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9335  -11.0761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9335  -12.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4184  -11.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8620  -13.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -11.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1488  -10.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -10.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9335  -10.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4344  -11.7435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7199  -12.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1488  -12.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6479  -10.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2190   -9.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6479   -9.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5045  -10.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7900   -9.8386    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
  3 18  2  0  0  0  0
  6 19  1  1  0  0  0
 14 20  1  1  0  0  0
 12 21  1  1  0  0  0
 15 22  1  0  0  0  0
 10 23  1  1  0  0  0
  7 24  1  6  0  0  0
 13 25  1  6  0  0  0
 15 26  1  6  0  0  0
 22 27  1  0  0  0  0
 22 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0015011
     RDKit          3D
Loteprednol
 54 57  0  0  0  0  0  0  0  0999 V2000
   -1.8353   -0.2817   -1.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    0.0854   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7877    1.3646   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    1.3141    0.8375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9415    2.5772    0.9369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507    0.2069    0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6392   -1.0404    0.0075 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4954   -2.2151    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490   -2.0666    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4546   -0.6904    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7002   -0.4674    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725    0.8932    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4693    1.1158    0.7054 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    1.9776    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518    1.7286   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249    0.4171   -0.3275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2152    0.1106   -1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -1.0043    0.5665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6070   -2.1618    0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -1.5184    0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7230   -0.0208    0.7427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3165    0.2422    2.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626    0.7968    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259    1.6298    1.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5093    0.7696   -0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118    1.6211   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8894    1.2484    0.0950 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683    0.5668   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578   -0.2987   -2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.1809   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    1.7693   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530    2.1518    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750    1.1436    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182    2.8910    1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -0.1479    1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746   -1.0241   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -2.4042    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -3.1529   -0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1848   -2.5270   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -2.7149    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094   -1.2476    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124    2.9846    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871    2.6014   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -0.9579   -2.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799    0.5661   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0275    0.6224   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104   -0.7523    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842   -2.9213    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.6594   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.7637   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -1.8820    1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.4977    2.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127    1.5215   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2977    2.6819   -0.8705 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  5 34  1  0
  6 35  1  1
  7 36  1  6
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 26 53  1  0
 26 54  1  0
M  END


  Mrv0541 04191212152D          

 30 33  0  0  1  0            999 V2000
    8.2910  -12.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5765  -12.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5765  -13.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2910  -13.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -13.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -12.5685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7199  -12.1560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7199  -13.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4344  -13.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4344  -12.5685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4344  -10.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7199  -11.3310    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1488  -12.1560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1488  -11.3310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.9335  -11.0761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9335  -12.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4184  -11.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8620  -13.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -11.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1488  -10.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0054  -10.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9335  -10.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4344  -11.7435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7199  -12.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1488  -12.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6479  -10.6636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2190   -9.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6479   -9.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5045  -10.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7900   -9.8386    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 17  1  0  0  0  0
  3 18  2  0  0  0  0
  6 19  1  1  0  0  0
 14 20  1  1  0  0  0
 12 21  1  1  0  0  0
 15 22  1  0  0  0  0
 10 23  1  1  0  0  0
  7 24  1  6  0  0  0
 13 25  1  6  0  0  0
 15 26  1  6  0  0  0
 22 27  1  0  0  0  0
 22 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015011

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H27ClO5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,18(25)27-11-22)20(15,2)10-16(24)17(14)19/h5,7,9,14-17,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17+,19-,20-,21-/m0/s1

> <INCHI_KEY>
YPZVAYHNBBHPTO-MXRBDKCISA-N

> <FORMULA>
C21H27ClO5

> <MOLECULAR_WEIGHT>
394.889

> <EXACT_MASS>
394.154701681

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.292118137845975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.5202634643333335

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.886580103724683

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.012492493247677

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8514024872015327

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
102.64849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
loteprednol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015011
     RDKit          3D
Loteprednol
 54 57  0  0  0  0  0  0  0  0999 V2000
   -1.8353   -0.2817   -1.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    0.0854   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7877    1.3646   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    1.3141    0.8375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9415    2.5772    0.9369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507    0.2069    0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6392   -1.0404    0.0075 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4954   -2.2151    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490   -2.0666    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4546   -0.6904    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7002   -0.4674    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725    0.8932    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4693    1.1158    0.7054 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    1.9776    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518    1.7286   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249    0.4171   -0.3275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2152    0.1106   -1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -1.0043    0.5665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6070   -2.1618    0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -1.5184    0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7230   -0.0208    0.7427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3165    0.2422    2.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626    0.7968    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259    1.6298    1.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5093    0.7696   -0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118    1.6211   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8894    1.2484    0.0950 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683    0.5668   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578   -0.2987   -2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.1809   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    1.7693   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530    2.1518    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750    1.1436    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182    2.8910    1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -0.1479    1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746   -1.0241   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -2.4042    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -3.1529   -0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1848   -2.5270   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -2.7149    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094   -1.2476    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124    2.9846    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871    2.6014   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -0.9579   -2.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799    0.5661   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0275    0.6224   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104   -0.7523    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842   -2.9213    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.6594   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.7637   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -1.8820    1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.4977    2.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127    1.5215   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2977    2.6819   -0.8705 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  5 34  1  0
  6 35  1  1
  7 36  1  6
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 26 53  1  0
 26 54  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      15.477 -22.691   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.143 -23.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.143 -25.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.477 -25.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.810 -25.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.810 -23.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.144 -22.691   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.144 -25.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.478 -25.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.478 -23.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.478 -20.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.144 -21.151   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.811 -22.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.811 -21.151   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.276 -20.675   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.276 -23.167   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.181 -21.921   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.809 -25.771   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.810 -21.921   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.811 -19.611   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.810 -20.381   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      22.276 -19.135   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      19.478 -21.921   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      18.144 -24.231   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      20.811 -24.231   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0      23.609 -19.905   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      20.942 -18.365   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      23.609 -18.365   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      19.608 -19.135   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0      18.275 -18.365   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5   19                                             
CONECT    7    6   10   12   24                                             
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13    7   23                                             
CONECT   11   12   14                                                       
CONECT   12    7   11   21                                                  
CONECT   13   10   14   16   25                                             
CONECT   14   11   15   13   20                                             
CONECT   15   14   17   22   26                                             
CONECT   16   13   17                                                       
CONECT   17   16   15                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   12                                                            
CONECT   22   15   27   28                                                  
CONECT   23   10                                                            
CONECT   24    7                                                            
CONECT   25   13                                                            
CONECT   26   15                                                            
CONECT   27   22   29                                                       
CONECT   28   22                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015011
HETATM    1  C1  UNL     1      -1.835  -0.282  -1.559  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.511   0.085  -0.147  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.788   1.365  -0.094  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.432   1.314   0.837  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.942   2.577   0.937  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.351   0.207   0.562  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.639  -1.040   0.008  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.495  -2.215   0.373  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.949  -2.067   0.090  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.455  -0.690   0.066  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.700  -0.467   0.394  1.00  0.00           C  
HETATM   12  C11 UNL     1       5.272   0.893   0.391  1.00  0.00           C  
HETATM   13  O2  UNL     1       6.469   1.116   0.705  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.418   1.978   0.016  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.152   1.729  -0.313  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.525   0.417  -0.327  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.215   0.111  -1.805  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.698  -1.004   0.566  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.607  -2.162   0.377  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.980  -1.518   0.646  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.723  -0.021   0.743  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.316   0.242   2.029  1.00  0.00           O  
HETATM   23  C20 UNL     1      -3.863   0.797   0.358  1.00  0.00           C  
HETATM   24  O4  UNL     1      -4.326   1.630   1.214  1.00  0.00           O  
HETATM   25  O5  UNL     1      -4.509   0.770  -0.851  1.00  0.00           O  
HETATM   26  C21 UNL     1      -5.612   1.621  -1.100  1.00  0.00           C  
HETATM   27 CL1  UNL     1      -6.889   1.248   0.095  1.00  0.00          CL  
HETATM   28  H1  UNL     1      -2.468   0.567  -1.954  1.00  0.00           H  
HETATM   29  H2  UNL     1      -0.958  -0.299  -2.204  1.00  0.00           H  
HETATM   30  H3  UNL     1      -2.467  -1.181  -1.664  1.00  0.00           H  
HETATM   31  H4  UNL     1      -0.496   1.769  -1.083  1.00  0.00           H  
HETATM   32  H5  UNL     1      -1.453   2.152   0.357  1.00  0.00           H  
HETATM   33  H6  UNL     1      -0.075   1.144   1.846  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.118   2.891   1.850  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.725  -0.148   1.577  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.575  -1.024  -1.094  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.358  -2.404   1.458  1.00  0.00           H  
HETATM   38  H11 UNL     1       1.148  -3.153  -0.138  1.00  0.00           H  
HETATM   39  H12 UNL     1       3.185  -2.527  -0.907  1.00  0.00           H  
HETATM   40  H13 UNL     1       3.508  -2.715   0.826  1.00  0.00           H  
HETATM   41  H14 UNL     1       5.409  -1.248   0.692  1.00  0.00           H  
HETATM   42  H15 UNL     1       4.812   2.985   0.004  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.587   2.601  -0.600  1.00  0.00           H  
HETATM   44  H17 UNL     1       2.350  -0.958  -2.046  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.280   0.566  -2.144  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.027   0.622  -2.403  1.00  0.00           H  
HETATM   47  H20 UNL     1      -0.710  -0.752   1.647  1.00  0.00           H  
HETATM   48  H21 UNL     1      -1.384  -2.921   1.166  1.00  0.00           H  
HETATM   49  H22 UNL     1      -1.565  -2.659  -0.586  1.00  0.00           H  
HETATM   50  H23 UNL     1      -3.698  -1.764  -0.145  1.00  0.00           H  
HETATM   51  H24 UNL     1      -3.330  -1.882   1.642  1.00  0.00           H  
HETATM   52  H25 UNL     1      -2.525  -0.498   2.670  1.00  0.00           H  
HETATM   53  H26 UNL     1      -6.013   1.522  -2.107  1.00  0.00           H  
HETATM   54  H27 UNL     1      -5.298   2.682  -0.871  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   18   21
CONECT    3    4   31   32
CONECT    4    5    6   33
CONECT    5   34
CONECT    6    7   16   35
CONECT    7    8   18   36
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   11   16
CONECT   11   12   41
CONECT   12   13   13   14
CONECT   14   15   15   42
CONECT   15   16   43
CONECT   16   17
CONECT   17   44   45   46
CONECT   18   19   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   23
CONECT   22   52
CONECT   23   24   24   25
CONECT   25   26
CONECT   26   27   53   54
END

HMDB0015011
     RDKit          3D
Loteprednol
 54 57  0  0  0  0  0  0  0  0999 V2000
   -1.8353   -0.2817   -1.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    0.0854   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7877    1.3646   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    1.3141    0.8375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9415    2.5772    0.9369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507    0.2069    0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6392   -1.0404    0.0075 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4954   -2.2151    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9490   -2.0666    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4546   -0.6904    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7002   -0.4674    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725    0.8932    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4693    1.1158    0.7054 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4181    1.9776    0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518    1.7286   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249    0.4171   -0.3275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2152    0.1106   -1.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981   -1.0043    0.5665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6070   -2.1618    0.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798   -1.5184    0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7230   -0.0208    0.7427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3165    0.2422    2.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626    0.7968    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259    1.6298    1.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5093    0.7696   -0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118    1.6211   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8894    1.2484    0.0950 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4683    0.5668   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9578   -0.2987   -2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -1.1809   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    1.7693   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530    2.1518    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750    1.1436    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182    2.8910    1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7251   -0.1479    1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746   -1.0241   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585   -2.4042    1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -3.1529   -0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1848   -2.5270   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -2.7149    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094   -1.2476    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124    2.9846    0.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871    2.6014   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -0.9579   -2.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799    0.5661   -2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0275    0.6224   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104   -0.7523    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842   -2.9213    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.6594   -0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.7637   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301   -1.8820    1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -0.4977    2.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0127    1.5215   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2977    2.6819   -0.8705 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  1
  5 34  1  0
  6 35  1  1
  7 36  1  6
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 26 53  1  0
 26 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Loteprednol etabonate	HMDB
CEHOAC	HMDB
Chloromethyl 17 ethoxycarbonyloxy 11 hydroxy 3 oxoandrosta 1,4 diene 17 carboxylate	HMDB
Etabonate, loteprednol	HMDB
Chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate	HMDB
17-Ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate, chloromethyl	HMDB
Lotemax	HMDB
Alrex	HMDB

Chemical Formula

C₂₁H₂₇ClO₅

Average Molecular Weight

394.889

Monoisotopic Molecular Weight

394.154701681

IUPAC Name

chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate

Traditional Name

loteprednol

CAS Registry Number

82034-46-6

SMILES

[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C21H27ClO5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,18(25)27-11-22)20(15,2)10-16(24)17(14)19/h5,7,9,14-17,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17+,19-,20-,21-/m0/s1

InChI Key

YPZVAYHNBBHPTO-MXRBDKCISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-1,4-steroid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organochloride
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl chloride
Alcohol
Organohalogen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:50848 )
11beta-hydroxy steroid (CHEBI:50848 )
17alpha-hydroxy steroid (CHEBI:50848 )
androstanoid (CHEBI:50848 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:50848 )
steroid acid ester (CHEBI:50848 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 - 224 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.034 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.52	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-2.9	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	3	ChemAxon
Refractivity	102.65 m³·mol⁻¹	ChemAxon
Polarizability	41.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	222.155	30932474
DeepCCS	[M+Na]+	197.253	30932474
AllCCS	[M+H]+	192.5	32859911
AllCCS	[M+H-H2O]+	190.1	32859911
AllCCS	[M+NH4]+	194.7	32859911
AllCCS	[M+Na]+	195.4	32859911
AllCCS	[M-H]-	194.2	32859911
AllCCS	[M+Na-2H]-	194.8	32859911
AllCCS	[M+HCOO]-	195.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loteprednol	[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C	4146.5	Standard polar	33892256
Loteprednol	[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C	2738.6	Standard non polar	33892256
Loteprednol	[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C	3426.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Loteprednol,1TMS,isomer #1	C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)OCCl	3334.1	Semi standard non polar	33892256
Loteprednol,1TMS,isomer #2	C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)OCCl	3222.5	Semi standard non polar	33892256
Loteprednol,2TMS,isomer #1	C[C@]12C[C@H](O[Si](C)(C)C)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)OCCl	3262.7	Semi standard non polar	33892256
Loteprednol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@]1(C(=O)OCCl)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C	3602.7	Semi standard non polar	33892256
Loteprednol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O)C(=O)OCCl)[C@@H]2CCC3=CC(=O)C=C[C@]3(C)[C@@H]12	3487.3	Semi standard non polar	33892256
Loteprednol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@@]2(C)[C@@H](CC[C@]2(O[Si](C)(C)C(C)(C)C)C(=O)OCCl)[C@@H]2CCC3=CC(=O)C=C[C@]3(C)[C@@H]12	3765.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Loteprednol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v7i-1893000000-682774df467cdebbec3b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loteprednol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-4839780000-d51f7f1f3e7bf65172bc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loteprednol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loteprednol 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 - Loteprednol 10V, Positive-QTOF	splash10-004j-0019000000-25a9a1528f2869a02f3a	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 20V, Positive-QTOF	splash10-004i-0229000000-0aac7fbe4742db297f38	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 40V, Positive-QTOF	splash10-001i-0691000000-0ee7c0d161653ecef2f7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 10V, Negative-QTOF	splash10-0006-0009000000-8a39d043964bd24e691c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 20V, Negative-QTOF	splash10-002f-1019000000-006d094367c84d7fdc6d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 40V, Negative-QTOF	splash10-0002-4091000000-cb6ff84a4e686bd3ebb2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 10V, Positive-QTOF	splash10-0002-0009000000-a0ac3be7c2d25192a078	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 20V, Positive-QTOF	splash10-08fs-1912000000-0c6368a24232c8f7e898	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 40V, Positive-QTOF	splash10-05di-3390000000-2940c512e174324e33e3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 10V, Negative-QTOF	splash10-0006-0009000000-6de0933cc349eb685660	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 20V, Negative-QTOF	splash10-001i-9037000000-68cdcec02980ed86b9a9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loteprednol 40V, Negative-QTOF	splash10-001r-1191000000-a2b788885ecb2baf3516	2021-10-11	Wishart Lab	View Spectrum

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 DB00873	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00873	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00873

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8041134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loteprednol

METLIN ID

Not Available

PubChem Compound

9865442

PDB ID

Not Available

ChEBI ID

50848

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

Pavesio CE, Decory HH: Treatment of ocular inflammatory conditions with loteprednol etabonate. Br J Ophthalmol. 2008 Apr;92(4):455-9. doi: 10.1136/bjo.2007.132621. Epub 2008 Feb 1. [PubMed:18245274 ]
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 Loteprednol (HMDB0015011)

MOL for HMDB0015011 (Loteprednol)

3D MOL for HMDB0015011 (Loteprednol)

3D SDF for HMDB0015011 (Loteprednol)

3D-SDF for HMDB0015011 (Loteprednol)

PDB for HMDB0015011 (Loteprednol)

3D PDB for HMDB0015011 (Loteprednol)

SMILES for HMDB0015011 (Loteprednol)

INCHI for HMDB0015011 (Loteprednol)

Structure for HMDB0015011 (Loteprednol)

3D Structure for HMDB0015011 (Loteprednol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra