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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:28:35 UTC

Update Date

2021-09-24 01:28:35 UTC

HMDB ID

HMDB0303382

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Demissidine

Description

3-epidemissidine belongs to solanidines and derivatives class of compounds. Those are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system. 3-epidemissidine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-epidemissidine can be found in alcoholic beverages, potato, and root vegetables, which makes 3-epidemissidine a potential biomarker for the consumption of these food products.

Structure

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


  Mrv1652312191900402D          

 33 36  0  0  1  0            999 V2000
   -0.0626   -5.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518   -6.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518   -7.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -5.8105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3663   -4.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808   -6.2230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0808   -7.0480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952   -5.8105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7952   -4.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5097   -6.2230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5097   -7.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3104   -4.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5299   -5.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3369   -5.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

HMDB0303382
     RDKit          3D
Demissidine
 81 84  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652312191900402D          

 33 36  0  0  1  0            999 V2000
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 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0303382

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C1CCC2C3COC(=O)C4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O5/c1-15(2)16(3)24(30)25(31)17(4)20-7-8-21-19-14-33-26(32)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-25,29-31H,7-14H2,1-6H3/t16-,17-,18+,19?,20?,21?,22?,23?,24+,25+,27+,28+/m0/s1

> <INCHI_KEY>
LLFIMDUWAVPJEJ-IPLAFFEMSA-N

> <FORMULA>
C28H48O5

> <MOLECULAR_WEIGHT>
464.687

> <EXACT_MASS>
464.350174646

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.51334835082804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^{2,7}.0^{12,16}]octadecan-8-one

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
4.204970492

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.859298646706513

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.644245350899563

> <JCHEM_PKA_STRONGEST_BASIC>
-2.698325938373002

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
129.0451

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^{2,7}.0^{12,16}]octadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303382
     RDKit          3D
Demissidine
 81 84  0  0  0  0  0  0  0  0999 V2000
   -6.4980   -2.2925    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9670   -0.8611    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1708   -0.1056    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -1.0253   -0.0829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8142   -1.9166    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4558    0.0786   -0.9063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6605    0.5035   -1.6362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130    1.3114   -0.5370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6005    2.1351   -1.7120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    1.3884    0.2259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6481    0.7982    1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009    1.0830   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.9923   -1.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    2.3609   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.1258   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106    1.0697   -0.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    2.3005   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    2.3032   -0.6529 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879    1.2238   -0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342    1.3144   -1.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1491    0.0536    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4163   -0.7503    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016   -1.8465   -0.6168 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6394   -1.9511   -1.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -1.7248   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9660   -1.6019   -1.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420   -0.7877    0.2394 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9328   -1.8162    1.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468   -0.0275    0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261   -1.0172    0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -0.4275    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.9522    0.2112 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0636    2.0242    1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5615   -2.8538    0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8000   -2.8479    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5181   -2.2617    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6653   -0.5400    1.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5232   -0.6039   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9725   -0.2409    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0018    0.9747    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -1.7527   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345   -1.8168    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473   -2.9988    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224   -1.6856    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636   -0.3817   -1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3817    1.1304   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5603    1.9354    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8612    3.0387   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471    2.5374    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    0.6029    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3428    1.5703    2.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128   -0.1339    1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959    0.0481   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041    2.9791   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147    1.5739   -2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375    2.5161   -2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180    3.2783   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.2739   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.7281   -1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279    2.2350    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    3.2487   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0701    0.4179    1.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330   -0.0460    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -1.1160    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2552   -2.8368   -0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6643   -1.4728   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.9442   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3507   -2.6884   -2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -1.2389   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -2.6600   -0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844   -1.4153    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9563   -2.0303    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -2.7833    1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604    0.3818    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882   -1.9219    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4518   -1.4201   -0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.1702    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463   -0.3684    1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    2.8222    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366    1.5073    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    2.5629    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32 12  1  0
 32 15  1  0
 29 16  1  0
 27 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  6
  5 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  6
  7 46  1  0
  8 47  1  1
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  0
 26 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END

HEADER    PROTEIN                                 19-DEC-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-DEC-19         0                                  
HETATM    1  C   UNK     0      -0.117 -10.846   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.217 -11.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.217 -13.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.550 -10.846   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.550  -9.306   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.884 -11.616   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.884 -13.156   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.218 -10.846   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.218  -9.306   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.551 -11.616   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.551 -13.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.885 -10.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.046  -9.315   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.552  -8.995   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.322 -10.328   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.829 -10.648   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.677  -9.363   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.211  -9.225   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.275 -10.338   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.740  -9.862   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      15.069 -11.864   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.414 -12.614   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.437 -14.154   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      17.782 -14.904   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.115 -14.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.770 -14.194   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.747 -12.654   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.487 -13.541   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.305 -12.113   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.274 -13.257   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.768 -12.937   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.292 -11.473   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.148 -12.503   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   16   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   12   15   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0303382
HETATM    1  C1  UNL     1      -6.498  -2.293   1.196  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.967  -0.861   0.932  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.171  -0.106   0.415  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.892  -1.025  -0.083  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.814  -1.917   0.471  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.456   0.079  -0.906  1.00  0.00           C  
HETATM    7  O1  UNL     1      -5.661   0.504  -1.636  1.00  0.00           O  
HETATM    8  C7  UNL     1      -3.813   1.311  -0.537  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.601   2.135  -1.712  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.543   1.388   0.226  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.648   0.798   1.579  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.301   1.083  -0.536  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.003   1.992  -1.670  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.491   2.361  -1.552  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.987   1.126  -0.906  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.411   1.070  -0.561  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.088   2.300  -0.092  1.00  0.00           C  
HETATM   18  O3  UNL     1       4.425   2.303  -0.653  1.00  0.00           O  
HETATM   19  C16 UNL     1       5.288   1.224  -0.419  1.00  0.00           C  
HETATM   20  O4  UNL     1       6.334   1.314  -1.105  1.00  0.00           O  
HETATM   21  C17 UNL     1       5.149   0.054   0.475  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.416  -0.750   0.408  1.00  0.00           C  
HETATM   23  C19 UNL     1       6.402  -1.846  -0.617  1.00  0.00           C  
HETATM   24  O5  UNL     1       7.639  -1.951  -1.266  1.00  0.00           O  
HETATM   25  C20 UNL     1       5.331  -1.725  -1.648  1.00  0.00           C  
HETATM   26  C21 UNL     1       3.966  -1.602  -1.021  1.00  0.00           C  
HETATM   27  C22 UNL     1       3.942  -0.788   0.239  1.00  0.00           C  
HETATM   28  C23 UNL     1       3.933  -1.816   1.392  1.00  0.00           C  
HETATM   29  C24 UNL     1       2.647  -0.028   0.437  1.00  0.00           C  
HETATM   30  C25 UNL     1       1.526  -1.017   0.317  1.00  0.00           C  
HETATM   31  C26 UNL     1       0.217  -0.427   0.772  1.00  0.00           C  
HETATM   32  C27 UNL     1      -0.020   0.952   0.211  1.00  0.00           C  
HETATM   33  C28 UNL     1       0.064   2.024   1.241  1.00  0.00           C  
HETATM   34  H1  UNL     1      -6.561  -2.854   0.235  1.00  0.00           H  
HETATM   35  H2  UNL     1      -5.800  -2.848   1.837  1.00  0.00           H  
HETATM   36  H3  UNL     1      -7.518  -2.262   1.604  1.00  0.00           H  
HETATM   37  H4  UNL     1      -5.665  -0.540   1.939  1.00  0.00           H  
HETATM   38  H5  UNL     1      -7.523  -0.604  -0.487  1.00  0.00           H  
HETATM   39  H6  UNL     1      -7.973  -0.241   1.190  1.00  0.00           H  
HETATM   40  H7  UNL     1      -7.002   0.975   0.333  1.00  0.00           H  
HETATM   41  H8  UNL     1      -5.416  -1.753  -0.855  1.00  0.00           H  
HETATM   42  H9  UNL     1      -3.835  -1.817   1.590  1.00  0.00           H  
HETATM   43  H10 UNL     1      -4.047  -2.999   0.288  1.00  0.00           H  
HETATM   44  H11 UNL     1      -2.822  -1.686   0.061  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.864  -0.382  -1.765  1.00  0.00           H  
HETATM   46  H13 UNL     1      -5.382   1.130  -2.325  1.00  0.00           H  
HETATM   47  H14 UNL     1      -4.560   1.935   0.048  1.00  0.00           H  
HETATM   48  H15 UNL     1      -3.861   3.039  -1.425  1.00  0.00           H  
HETATM   49  H16 UNL     1      -2.447   2.537   0.422  1.00  0.00           H  
HETATM   50  H17 UNL     1      -3.704   0.603   1.900  1.00  0.00           H  
HETATM   51  H18 UNL     1      -2.343   1.570   2.390  1.00  0.00           H  
HETATM   52  H19 UNL     1      -2.113  -0.134   1.774  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.496   0.048  -0.999  1.00  0.00           H  
HETATM   54  H21 UNL     1      -1.504   2.979  -1.656  1.00  0.00           H  
HETATM   55  H22 UNL     1      -1.115   1.574  -2.681  1.00  0.00           H  
HETATM   56  H23 UNL     1       0.938   2.516  -2.554  1.00  0.00           H  
HETATM   57  H24 UNL     1       0.618   3.278  -0.977  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.758   0.274  -1.616  1.00  0.00           H  
HETATM   59  H26 UNL     1       2.943   0.728  -1.504  1.00  0.00           H  
HETATM   60  H27 UNL     1       3.328   2.235   1.016  1.00  0.00           H  
HETATM   61  H28 UNL     1       2.649   3.249  -0.384  1.00  0.00           H  
HETATM   62  H29 UNL     1       5.070   0.418   1.542  1.00  0.00           H  
HETATM   63  H30 UNL     1       7.233  -0.046   0.110  1.00  0.00           H  
HETATM   64  H31 UNL     1       6.741  -1.116   1.414  1.00  0.00           H  
HETATM   65  H32 UNL     1       6.255  -2.837  -0.107  1.00  0.00           H  
HETATM   66  H33 UNL     1       7.664  -1.473  -2.118  1.00  0.00           H  
HETATM   67  H34 UNL     1       5.509  -0.944  -2.415  1.00  0.00           H  
HETATM   68  H35 UNL     1       5.351  -2.688  -2.235  1.00  0.00           H  
HETATM   69  H36 UNL     1       3.275  -1.239  -1.815  1.00  0.00           H  
HETATM   70  H37 UNL     1       3.607  -2.660  -0.838  1.00  0.00           H  
HETATM   71  H38 UNL     1       3.384  -1.415   2.269  1.00  0.00           H  
HETATM   72  H39 UNL     1       4.956  -2.030   1.744  1.00  0.00           H  
HETATM   73  H40 UNL     1       3.529  -2.783   1.030  1.00  0.00           H  
HETATM   74  H41 UNL     1       2.660   0.382   1.462  1.00  0.00           H  
HETATM   75  H42 UNL     1       1.688  -1.922   0.961  1.00  0.00           H  
HETATM   76  H43 UNL     1       1.452  -1.420  -0.719  1.00  0.00           H  
HETATM   77  H44 UNL     1      -0.549  -1.170   0.469  1.00  0.00           H  
HETATM   78  H45 UNL     1       0.246  -0.368   1.873  1.00  0.00           H  
HETATM   79  H46 UNL     1      -0.696   2.822   1.181  1.00  0.00           H  
HETATM   80  H47 UNL     1       0.037   1.507   2.245  1.00  0.00           H  
HETATM   81  H48 UNL     1       1.034   2.563   1.251  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4   37
CONECT    3   38   39   40
CONECT    4    5    6   41
CONECT    5   42   43   44
CONECT    6    7    8   45
CONECT    7   46
CONECT    8    9   10   47
CONECT    9   48
CONECT   10   11   12   49
CONECT   11   50   51   52
CONECT   12   13   32   53
CONECT   13   14   54   55
CONECT   14   15   56   57
CONECT   15   16   32   58
CONECT   16   17   29   59
CONECT   17   18   60   61
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   27   62
CONECT   22   23   63   64
CONECT   23   24   25   65
CONECT   24   66
CONECT   25   26   67   68
CONECT   26   27   69   70
CONECT   27   28   29
CONECT   28   71   72   73
CONECT   29   30   74
CONECT   30   31   75   76
CONECT   31   32   77   78
CONECT   32   33
CONECT   33   79   80   81
END

HMDB0303382
     RDKit          3D
Demissidine
 81 84  0  0  0  0  0  0  0  0999 V2000
   -6.4980   -2.2925    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9670   -0.8611    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1708   -0.1056    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919   -1.0253   -0.0829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8142   -1.9166    0.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4558    0.0786   -0.9063 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6605    0.5035   -1.6362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130    1.3114   -0.5370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6005    2.1351   -1.7120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    1.3884    0.2259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6481    0.7982    1.5793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009    1.0830   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.9923   -1.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909    2.3609   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    1.1258   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106    1.0697   -0.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    2.3005   -0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    2.3032   -0.6529 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879    1.2238   -0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342    1.3144   -1.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1491    0.0536    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4163   -0.7503    0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016   -1.8465   -0.6168 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6394   -1.9511   -1.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3310   -1.7248   -1.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9660   -1.6019   -1.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420   -0.7877    0.2394 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9328   -1.8162    1.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468   -0.0275    0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261   -1.0172    0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -0.4275    0.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    0.9522    0.2112 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0636    2.0242    1.2407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5615   -2.8538    0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8000   -2.8479    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5181   -2.2617    1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6653   -0.5400    1.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5232   -0.6039   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9725   -0.2409    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0018    0.9747    0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4158   -1.7527   -0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345   -1.8168    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0473   -2.9988    0.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8224   -1.6856    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636   -0.3817   -1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3817    1.1304   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5603    1.9354    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8612    3.0387   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471    2.5374    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035    0.6029    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3428    1.5703    2.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128   -0.1339    1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4959    0.0481   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041    2.9791   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147    1.5739   -2.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375    2.5161   -2.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6180    3.2783   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580    0.2739   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9429    0.7281   -1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279    2.2350    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    3.2487   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0701    0.4179    1.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2330   -0.0460    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -1.1160    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2552   -2.8368   -0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6643   -1.4728   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.9442   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3507   -2.6884   -2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -1.2389   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -2.6600   -0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844   -1.4153    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9563   -2.0303    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -2.7833    1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6604    0.3818    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882   -1.9219    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4518   -1.4201   -0.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -1.1702    0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463   -0.3684    1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    2.8222    1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0366    1.5073    2.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    2.5629    1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  1
 32 12  1  0
 32 15  1  0
 29 16  1  0
 27 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  6
  5 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  6
  7 46  1  0
  8 47  1  1
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  0
 26 70  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
 29 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(22R,23R,24S)-3alpha,22,23-Trihydroxy-7-oxa-5alpha-ergostane-6-one	Kegg
(22R,23R,24S)-3a,22,23-Trihydroxy-7-oxa-5a-ergostane-6-one	Generator
(22R,23R,24S)-3Α,22,23-trihydroxy-7-oxa-5α-ergostane-6-one	Generator

Chemical Formula

C₂₈H₄₈O₅

Average Molecular Weight

464.687

Monoisotopic Molecular Weight

464.350174646

IUPAC Name

(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^{2,7}.0^{12,16}]octadecan-8-one

Traditional Name

(2R,5R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^{2,7}.0^{12,16}]octadecan-8-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C1CCC2C3COC(=O)C4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C28H48O5/c1-15(2)16(3)24(30)25(31)17(4)20-7-8-21-19-14-33-26(32)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-25,29-31H,7-14H2,1-6H3/t16-,17-,18+,19?,20?,21?,22?,23?,24+,25+,27+,28+/m0/s1

InChI Key

LLFIMDUWAVPJEJ-IPLAFFEMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Brassinolides and derivatives

Alternative Parents

Substituents

Brassinolide-skeleton
Caprolactone
Oxepane
Cyclic alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

brassinosteroid (CHEBI:81307 )

Ontology

Not Available

Potato (FooDB: FOOD00175)

Not Available

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0303382)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.44	ALOGPS
logP	4.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.05 m³·mol⁻¹	ChemAxon
Polarizability	54.51 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	214.428	32859911
AllCCS	[M+H-H2O]+	212.672	32859911
AllCCS	[M+Na]+	216.489	32859911
AllCCS	[M+NH4]+	216.032	32859911
AllCCS	[M-H]-	211.284	32859911
AllCCS	[M+Na-2H]-	213.78	32859911
AllCCS	[M+HCOO]-	216.675	32859911
DeepCCS	[M-2H]-	244.249	30932474
DeepCCS	[M+Na]+	218.994	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demissidine 10V, Positive-QTOF	splash10-014i-0019800000-7cd97ecaccaca3c7c30c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demissidine 20V, Positive-QTOF	splash10-014i-2419100000-c44f5daa433ee7d8a3ad	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demissidine 40V, Positive-QTOF	splash10-05u6-9622000000-03d8c0b056e01876dad3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demissidine 10V, Negative-QTOF	splash10-03di-0000900000-5b7b5d9dd09b2c049e78	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demissidine 20V, Negative-QTOF	splash10-03di-0102900000-9e1f8b3f4af282b275d9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demissidine 40V, Negative-QTOF	splash10-02w9-2009500000-c1d901bd4a929c867c0a	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030628

KNApSAcK ID

Not Available

Chemspider ID

30791587

KEGG Compound ID

C17735

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173985

PDB ID

Not Available

ChEBI ID

81307

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Demissidine (HMDB0303382)

MOL for HMDB0303382 (Demissidine)

3D MOL for HMDB0303382 (Demissidine)

3D SDF for HMDB0303382 (Demissidine)

3D-SDF for HMDB0303382 (Demissidine)

PDB for HMDB0303382 (Demissidine)

3D PDB for HMDB0303382 (Demissidine)

SMILES for HMDB0303382 (Demissidine)

INCHI for HMDB0303382 (Demissidine)

Structure for HMDB0303382 (Demissidine)

3D Structure for HMDB0303382 (Demissidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra