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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:29:44 UTC

Update Date

2021-09-26 23:12:51 UTC

HMDB ID

HMDB0256876

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Protoveratrine

Description

16,17-bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2-hydroxy-2-methylbutanoate belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 16,17-bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2-hydroxy-2-methylbutanoate is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Protoveratrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Protoveratrine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004171501172D          

 56 62  0  0  0  0            999 V2000
    1.9295    6.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071    5.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606    4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381    3.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    3.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    3.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692    2.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    2.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4397    3.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9243    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018    0.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034   -0.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275   -0.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050   -1.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740    0.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    0.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    1.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147    2.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634    2.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003    1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881    0.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7014    0.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790    0.0895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481    1.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565    0.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161   -0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614   -0.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696    1.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333    1.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    2.5007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9491    2.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608    1.3713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    2.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470    2.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105    3.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2081    3.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9902    3.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447    4.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905    1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    1.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797    2.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -1.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8210   -0.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4310    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 41 46  1  0  0  0  0
 26 46  1  0  0  0  0
 46 47  1  0  0  0  0
  8 47  1  0  0  0  0
 24 47  1  0  0  0  0
 47 48  1  0  0  0  0
 30 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END

HMDB0256876
     RDKit          3D
Protoveratrine
119125  0  0  0  0  0  0  0  0999 V2000
   -0.7336    6.8606   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    5.3459   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320    4.9617   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    5.3309    1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    3.5034   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    3.1189   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    2.5487    0.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    1.1537    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    0.7804    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    1.1352    2.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780   -0.6272    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -1.5121    1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981   -2.9642    1.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4059   -3.2277    0.9856 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615   -4.6310    0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129   -4.7556   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3074   -6.1455   -0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7619   -3.6907   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7648   -3.2059    1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4835   -2.5587    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529   -1.1091    1.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4836   -0.2671    1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116   -1.0081   -0.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330   -1.1454    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922   -1.9821   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885   -0.9374   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -0.4461    0.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7506   -0.1423   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    1.0898    0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -1.2215   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0066   -0.5897    0.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -0.7036    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448   -1.3752    2.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0160   -0.0632    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9876    0.8921    2.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4189    0.6443    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0502   -1.1070    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7817   -1.9665    2.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -2.2433   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232   -2.5566   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5195   -1.3407   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8688   -1.5693   -3.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527   -0.1165   -1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    1.1702   -2.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    2.1969   -1.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    3.1382   -2.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9208    4.1820   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959    3.0540   -3.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    1.2017   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3616    1.1993   -3.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    2.2308   -3.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675    2.0943   -5.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    3.3014   -3.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    0.1556   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8879    0.3265    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512    0.6316    1.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0600    7.3322   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647    7.0758    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870    7.3342   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    4.8495    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4560    5.2122   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448    5.5530   -0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640    4.8572    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    4.8026    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6976    6.4210    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369    0.9420   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992    1.4520    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7608    2.1233    2.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -0.7549    3.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1430   -1.3196    2.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3798   -3.5445    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978   -3.2776    2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -5.0579    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065   -5.1111    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023   -4.6052   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4927   -6.8347   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5922   -6.4723    0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333   -6.1470   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6507   -2.8328   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7571   -4.1962   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350   -4.1642    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6785   -2.6607    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -2.7212    2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4030    0.7291    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4491   -0.1344    2.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4898   -0.6392    1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9927   -0.2922   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385   -1.2517   -0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4897   -2.7701   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3496   -2.4543    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375    1.2531   -0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -1.7567    0.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7068    0.3982    3.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276    1.6788    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9951    1.3448    2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3700    1.6035    0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0473   -0.6361    1.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1443   -1.7835    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6435   -1.3864    3.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6876   -2.6105    3.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
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 56119  1  0
M  END


  Mrv1533004171501172D          

 56 62  0  0  0  0            999 V2000
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    1.8606    4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381    3.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    3.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    3.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692    2.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9987   -0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  5  7  1  0  0  0  0
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  8  9  1  0  0  0  0
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 32 33  1  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
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 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
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 43 45  1  0  0  0  0
 41 46  1  0  0  0  0
 26 46  1  0  0  0  0
 46 47  1  0  0  0  0
  8 47  1  0  0  0  0
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 47 48  1  0  0  0  0
 30 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
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 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256876

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(OC(C)=O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C41H63NO14/c1-10-20(4)34(46)55-33-28(45)27-23(18-42-17-19(3)12-13-25(42)38(27,9)49)24-16-39-32(40(24,33)50)30(53-22(6)44)29(52-21(5)43)31-36(39,7)15-14-26(41(31,51)56-39)54-35(47)37(8,48)11-2/h19-20,23-33,45,48-51H,10-18H2,1-9H3

> <INCHI_KEY>
HYTGGNIMZXFORS-UHFFFAOYSA-N

> <FORMULA>
C41H63NO14

> <MOLECULAR_WEIGHT>
793.948

> <EXACT_MASS>
793.424855713

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
85.63216180733242

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16,17-bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.8391392623333331

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.464831908501829

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.794131014507197

> <JCHEM_PKA_STRONGEST_BASIC>
7.97110647071212

> <JCHEM_POLAR_SURFACE_AREA>
218.81999999999996

> <JCHEM_REFRACTIVITY>
194.82090000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256876
     RDKit          3D
Protoveratrine
119125  0  0  0  0  0  0  0  0999 V2000
   -0.7336    6.8606   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    5.3459   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320    4.9617   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    5.3309    1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    3.5034   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    3.1189   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    2.5487    0.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7360    0.7804    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    1.1352    2.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780   -0.6272    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -1.5121    1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981   -2.9642    1.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7129   -4.7556   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3074   -6.1455   -0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8688   -1.5693   -3.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527   -0.1165   -1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    1.1702   -2.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    2.1969   -1.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    3.1382   -2.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9208    4.1820   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959    3.0540   -3.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    1.2017   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3616    1.1993   -3.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    2.2308   -3.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675    2.0943   -5.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    3.3014   -3.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    0.1556   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8879    0.3265    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2023   -4.6052   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4927   -6.8347   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5922   -6.4723    0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333   -6.1470   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6507   -2.8328   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7571   -4.1962   -0.2618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350   -4.1642    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6785   -2.6607    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588   -2.7212    2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4030    0.7291    1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1385   -1.2517   -0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4897   -2.7701   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3496   -2.4543    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1375    1.2531   -0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4769   -1.7567    0.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7068    0.3982    3.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276    1.6788    2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9951    1.3448    2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3700    1.6035    0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0473   -0.6361    1.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1443   -1.7835    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6435   -1.3864    3.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6876   -2.6105    3.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9569   -2.6915    2.8588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866   -3.2013   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3743   -1.9628   -2.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -3.0387   -0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3364   -3.2766   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -2.5654   -3.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345   -1.5011   -3.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2560   -0.8410   -3.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3396   -0.2629   -2.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9732    4.2974   -1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4326    5.1584   -1.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584    3.9232   -0.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010    2.2139   -1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118    2.0171   -5.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1637    1.1059   -5.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3419    2.9278   -5.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1807   -0.3820   -1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431    0.1542    1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       3.602  11.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.307  10.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.473   8.707   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.935   8.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.178   7.337   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.716   7.263   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.344   6.042   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.049   4.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.587   4.599   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.421   5.894   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.292   3.230   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.459   1.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.163   0.565   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.702   0.491   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       8.406  -0.878   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.945  -0.952   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.649  -2.322   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.778   0.342   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.073   1.712   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.535   1.786   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.830   3.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.174   3.907   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.958   4.690   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.920   2.009   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.778   0.928   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.309   1.574   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.521   0.167   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.343   1.140   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.396   2.679   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.719   0.297   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.897  -1.043   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.362  -0.852   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.022   0.767   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.235  -0.123   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.063   2.191   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.996   3.725   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.213   4.668   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.638   4.086   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.847   2.560   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.856   5.029   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.461   4.169   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       0.766   5.679   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.389   6.698   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -1.848   6.207   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.084   8.207   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.662   3.168   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.216   3.378   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.389   4.677   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -4.216   0.656   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -5.276  -0.461   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -4.838  -1.938   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -6.774  -0.102   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -6.415   1.395   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -7.133  -1.600   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -8.271   0.257   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -9.331  -0.861   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   47                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   11   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   12   25   47                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33   46                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30   35                                             
CONECT   29   28                                                            
CONECT   30   28   31   49                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   28   36                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   26   47                                                  
CONECT   47   46    8   24   48                                             
CONECT   48   47                                                            
CONECT   49   30   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   56                                                       
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

COMPND    HMDB0256876
HETATM    1  C1  UNL     1      -0.734   6.861  -0.069  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.803   5.346  -0.324  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.232   4.962  -0.182  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.664   5.331   1.249  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.504   3.503  -0.272  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.384   3.119  -1.076  1.00  0.00           O  
HETATM    7  O2  UNL     1      -1.876   2.549   0.451  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.076   1.154   0.445  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.736   0.780   1.787  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.800   1.135   2.780  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.078  -0.627   1.978  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.875  -1.512   1.699  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.198  -2.964   1.728  1.00  0.00           C  
HETATM   14  N1  UNL     1      -3.406  -3.228   0.986  1.00  0.00           N  
HETATM   15  C11 UNL     1      -3.661  -4.631   0.800  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.713  -4.756  -0.292  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.307  -6.146  -0.326  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.762  -3.691  -0.124  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.765  -3.206   1.332  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.483  -2.559   1.721  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.353  -1.109   1.363  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.484  -0.267   1.910  1.00  0.00           C  
HETATM   23  O4  UNL     1      -4.412  -1.008  -0.018  1.00  0.00           O  
HETATM   24  C19 UNL     1      -1.333  -1.145   0.394  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.192  -1.982  -0.106  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.689  -0.937  -0.744  1.00  0.00           C  
HETATM   27  O5  UNL     1       1.541  -0.446   0.210  1.00  0.00           O  
HETATM   28  C22 UNL     1       2.751  -0.142  -0.345  1.00  0.00           C  
HETATM   29  O6  UNL     1       3.200   1.090   0.114  1.00  0.00           O  
HETATM   30  C23 UNL     1       3.753  -1.222  -0.038  1.00  0.00           C  
HETATM   31  O7  UNL     1       5.007  -0.590   0.111  1.00  0.00           O  
HETATM   32  C24 UNL     1       5.689  -0.704   1.312  1.00  0.00           C  
HETATM   33  O8  UNL     1       5.145  -1.375   2.221  1.00  0.00           O  
HETATM   34  C25 UNL     1       7.016  -0.063   1.537  1.00  0.00           C  
HETATM   35  C26 UNL     1       6.988   0.892   2.707  1.00  0.00           C  
HETATM   36  O9  UNL     1       7.419   0.644   0.390  1.00  0.00           O  
HETATM   37  C27 UNL     1       8.050  -1.107   1.793  1.00  0.00           C  
HETATM   38  C28 UNL     1       7.782  -1.967   2.991  1.00  0.00           C  
HETATM   39  C29 UNL     1       3.761  -2.243  -1.152  1.00  0.00           C  
HETATM   40  C30 UNL     1       2.323  -2.557  -1.501  1.00  0.00           C  
HETATM   41  C31 UNL     1       1.520  -1.341  -1.885  1.00  0.00           C  
HETATM   42  C32 UNL     1       0.869  -1.569  -3.191  1.00  0.00           C  
HETATM   43  C33 UNL     1       2.453  -0.117  -1.860  1.00  0.00           C  
HETATM   44  C34 UNL     1       1.736   1.170  -2.141  1.00  0.00           C  
HETATM   45  O10 UNL     1       2.460   2.197  -1.527  1.00  0.00           O  
HETATM   46  C35 UNL     1       3.191   3.138  -2.193  1.00  0.00           C  
HETATM   47  C36 UNL     1       3.921   4.182  -1.457  1.00  0.00           C  
HETATM   48  O11 UNL     1       3.196   3.054  -3.432  1.00  0.00           O  
HETATM   49  C37 UNL     1       0.270   1.202  -1.909  1.00  0.00           C  
HETATM   50  O12 UNL     1      -0.362   1.199  -3.195  1.00  0.00           O  
HETATM   51  C38 UNL     1      -1.036   2.231  -3.767  1.00  0.00           C  
HETATM   52  C39 UNL     1      -1.668   2.094  -5.134  1.00  0.00           C  
HETATM   53  O13 UNL     1      -1.125   3.301  -3.137  1.00  0.00           O  
HETATM   54  C40 UNL     1      -0.325   0.156  -1.125  1.00  0.00           C  
HETATM   55  C41 UNL     1      -0.888   0.327   0.245  1.00  0.00           C  
HETATM   56  O14 UNL     1       0.151   0.632   1.124  1.00  0.00           O  
HETATM   57  H1  UNL     1       0.060   7.332  -0.664  1.00  0.00           H  
HETATM   58  H2  UNL     1      -0.565   7.076   0.998  1.00  0.00           H  
HETATM   59  H3  UNL     1      -1.687   7.334  -0.368  1.00  0.00           H  
HETATM   60  H4  UNL     1      -0.157   4.850   0.419  1.00  0.00           H  
HETATM   61  H5  UNL     1      -0.456   5.212  -1.366  1.00  0.00           H  
HETATM   62  H6  UNL     1      -2.845   5.553  -0.858  1.00  0.00           H  
HETATM   63  H7  UNL     1      -3.664   4.857   1.379  1.00  0.00           H  
HETATM   64  H8  UNL     1      -1.983   4.803   1.935  1.00  0.00           H  
HETATM   65  H9  UNL     1      -2.698   6.421   1.386  1.00  0.00           H  
HETATM   66  H10 UNL     1      -2.837   0.942  -0.312  1.00  0.00           H  
HETATM   67  H11 UNL     1      -3.599   1.452   1.981  1.00  0.00           H  
HETATM   68  H12 UNL     1      -1.761   2.123   2.796  1.00  0.00           H  
HETATM   69  H13 UNL     1      -3.243  -0.755   3.095  1.00  0.00           H  
HETATM   70  H14 UNL     1      -1.143  -1.320   2.522  1.00  0.00           H  
HETATM   71  H15 UNL     1      -1.380  -3.544   1.303  1.00  0.00           H  
HETATM   72  H16 UNL     1      -2.398  -3.278   2.793  1.00  0.00           H  
HETATM   73  H17 UNL     1      -4.010  -5.058   1.764  1.00  0.00           H  
HETATM   74  H18 UNL     1      -2.706  -5.111   0.519  1.00  0.00           H  
HETATM   75  H19 UNL     1      -4.202  -4.605  -1.264  1.00  0.00           H  
HETATM   76  H20 UNL     1      -4.493  -6.835  -0.681  1.00  0.00           H  
HETATM   77  H21 UNL     1      -5.592  -6.472   0.695  1.00  0.00           H  
HETATM   78  H22 UNL     1      -6.133  -6.147  -1.038  1.00  0.00           H  
HETATM   79  H23 UNL     1      -5.651  -2.833  -0.786  1.00  0.00           H  
HETATM   80  H24 UNL     1      -6.757  -4.196  -0.262  1.00  0.00           H  
HETATM   81  H25 UNL     1      -5.835  -4.164   1.932  1.00  0.00           H  
HETATM   82  H26 UNL     1      -6.679  -2.661   1.556  1.00  0.00           H  
HETATM   83  H27 UNL     1      -4.259  -2.721   2.801  1.00  0.00           H  
HETATM   84  H28 UNL     1      -5.403   0.729   1.381  1.00  0.00           H  
HETATM   85  H29 UNL     1      -5.449  -0.134   2.997  1.00  0.00           H  
HETATM   86  H30 UNL     1      -6.490  -0.639   1.608  1.00  0.00           H  
HETATM   87  H31 UNL     1      -4.993  -0.292  -0.325  1.00  0.00           H  
HETATM   88  H32 UNL     1      -2.139  -1.252  -0.389  1.00  0.00           H  
HETATM   89  H33 UNL     1      -0.490  -2.770  -0.810  1.00  0.00           H  
HETATM   90  H34 UNL     1       0.350  -2.454   0.742  1.00  0.00           H  
HETATM   91  H35 UNL     1       4.138   1.253  -0.077  1.00  0.00           H  
HETATM   92  H36 UNL     1       3.477  -1.757   0.898  1.00  0.00           H  
HETATM   93  H37 UNL     1       6.707   0.398   3.637  1.00  0.00           H  
HETATM   94  H38 UNL     1       6.228   1.679   2.516  1.00  0.00           H  
HETATM   95  H39 UNL     1       7.995   1.345   2.790  1.00  0.00           H  
HETATM   96  H40 UNL     1       7.370   1.604   0.547  1.00  0.00           H  
HETATM   97  H41 UNL     1       9.047  -0.636   1.939  1.00  0.00           H  
HETATM   98  H42 UNL     1       8.144  -1.783   0.918  1.00  0.00           H  
HETATM   99  H43 UNL     1       7.643  -1.386   3.929  1.00  0.00           H  
HETATM  100  H44 UNL     1       8.688  -2.611   3.195  1.00  0.00           H  
HETATM  101  H45 UNL     1       6.957  -2.691   2.859  1.00  0.00           H  
HETATM  102  H46 UNL     1       4.187  -3.201  -0.749  1.00  0.00           H  
HETATM  103  H47 UNL     1       4.374  -1.963  -2.010  1.00  0.00           H  
HETATM  104  H48 UNL     1       1.878  -3.039  -0.587  1.00  0.00           H  
HETATM  105  H49 UNL     1       2.336  -3.277  -2.322  1.00  0.00           H  
HETATM  106  H50 UNL     1       1.181  -2.565  -3.588  1.00  0.00           H  
HETATM  107  H51 UNL     1      -0.235  -1.501  -3.208  1.00  0.00           H  
HETATM  108  H52 UNL     1       1.256  -0.841  -3.932  1.00  0.00           H  
HETATM  109  H53 UNL     1       3.340  -0.263  -2.458  1.00  0.00           H  
HETATM  110  H54 UNL     1       1.922   1.339  -3.255  1.00  0.00           H  
HETATM  111  H55 UNL     1       4.973   4.297  -1.807  1.00  0.00           H  
HETATM  112  H56 UNL     1       3.433   5.158  -1.661  1.00  0.00           H  
HETATM  113  H57 UNL     1       3.958   3.923  -0.400  1.00  0.00           H  
HETATM  114  H58 UNL     1       0.001   2.214  -1.469  1.00  0.00           H  
HETATM  115  H59 UNL     1      -0.812   2.017  -5.845  1.00  0.00           H  
HETATM  116  H60 UNL     1      -2.164   1.106  -5.132  1.00  0.00           H  
HETATM  117  H61 UNL     1      -2.342   2.928  -5.337  1.00  0.00           H  
HETATM  118  H62 UNL     1      -1.181  -0.382  -1.692  1.00  0.00           H  
HETATM  119  H63 UNL     1       0.143   0.154   1.965  1.00  0.00           H  
CONECT    1    2   57   58   59
CONECT    2    3   60   61
CONECT    3    4    5   62
CONECT    4   63   64   65
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   55   66
CONECT    9   10   11   67
CONECT   10   68
CONECT   11   12   21   69
CONECT   12   13   24   70
CONECT   13   14   71   72
CONECT   14   15   20
CONECT   15   16   73   74
CONECT   16   17   18   75
CONECT   17   76   77   78
CONECT   18   19   79   80
CONECT   19   20   81   82
CONECT   20   21   83
CONECT   21   22   23
CONECT   22   84   85   86
CONECT   23   87
CONECT   24   25   55   88
CONECT   25   26   89   90
CONECT   26   27   41   54
CONECT   27   28
CONECT   28   29   30   43
CONECT   29   91
CONECT   30   31   39   92
CONECT   31   32
CONECT   32   33   33   34
CONECT   34   35   36   37
CONECT   35   93   94   95
CONECT   36   96
CONECT   37   38   97   98
CONECT   38   99  100  101
CONECT   39   40  102  103
CONECT   40   41  104  105
CONECT   41   42   43
CONECT   42  106  107  108
CONECT   43   44  109
CONECT   44   45   49  110
CONECT   45   46
CONECT   46   47   48   48
CONECT   47  111  112  113
CONECT   49   50   54  114
CONECT   50   51
CONECT   51   52   53   53
CONECT   52  115  116  117
CONECT   54   55  118
CONECT   55   56
CONECT   56  119
END

HMDB0256876
     RDKit          3D
Protoveratrine
119125  0  0  0  0  0  0  0  0999 V2000
   -0.7336    6.8606   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8035    5.3459   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320    4.9617   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    5.3309    1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    3.5034   -0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    3.1189   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8757    2.5487    0.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758    1.1537    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    0.7804    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    1.1352    2.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780   -0.6272    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -1.5121    1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981   -2.9642    1.7281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4059   -3.2277    0.9856 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615   -4.6310    0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7129   -4.7556   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3074   -6.1455   -0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7619   -3.6907   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7648   -3.2059    1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4835   -2.5587    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529   -1.1091    1.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4836   -0.2671    1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116   -1.0081   -0.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330   -1.1454    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922   -1.9821   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885   -0.9374   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -0.4461    0.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7506   -0.1423   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1997    1.0898    0.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7526   -1.2215   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0066   -0.5897    0.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889   -0.7036    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448   -1.3752    2.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0160   -0.0632    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9876    0.8921    2.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4189    0.6443    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0502   -1.1070    1.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7817   -1.9665    2.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7610   -2.2433   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232   -2.5566   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5195   -1.3407   -1.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8688   -1.5693   -3.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527   -0.1165   -1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356    1.1702   -2.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    2.1969   -1.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    3.1382   -2.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9208    4.1820   -1.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1959    3.0540   -3.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    1.2017   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3616    1.1993   -3.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    2.2308   -3.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6675    2.0943   -5.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    3.3014   -3.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    0.1556   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8879    0.3265    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512    0.6316    1.1243 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0600    7.3322   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647    7.0758    0.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6870    7.3342   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    4.8495    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4560    5.2122   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448    5.5530   -0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640    4.8572    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    4.8026    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6976    6.4210    1.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369    0.9420   -0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5992    1.4520    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7608    2.1233    2.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -0.7549    3.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1430   -1.3196    2.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3798   -3.5445    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978   -3.2776    2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -5.0579    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7065   -5.1111    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023   -4.6052   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4927   -6.8347   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16,17-Bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0,.0,.0,.0,.0,]hexacosan-22-yl 2-hydroxy-2-methylbutanoic acid	Generator
Cryptenamine	MeSH
Neoprotoveratrin	MeSH
Protalba	MeSH
Protoveratrine a	MeSH
Protoveratrines	MeSH
Protoverin	MeSH
Tensatrin	MeSH
Veralba	MeSH
Veratetrin	MeSH

Chemical Formula

C₄₁H₆₃NO₁₄

Average Molecular Weight

793.948

Monoisotopic Molecular Weight

793.424855713

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(OC(C)=O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)CC

InChI Identifier

InChI=1S/C41H63NO14/c1-10-20(4)34(46)55-33-28(45)27-23(18-42-17-19(3)12-13-25(42)38(27,9)49)24-16-39-32(40(24,33)50)30(53-22(6)44)29(52-21(5)43)31-36(39,7)15-14-26(41(31,51)56-39)54-35(47)37(8,48)11-2/h19-20,23-33,45,48-51H,10-18H2,1-9H3

InChI Key

HYTGGNIMZXFORS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetophenone
Xylenol
Benzoyl
O-cresol
P-cresol
Resorcinol
Aryl alkyl ketone
Xylene
M-xylene
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.13	ALOGPS
logP	1.84	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.79	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	218.82 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	194.82 m³·mol⁻¹	ChemAxon
Polarizability	85.63 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	310.65	30932474
DeepCCS	[M+Na]+	284.636	30932474
AllCCS	[M+H]+	262.2	32859911
AllCCS	[M+H-H2O]+	262.0	32859911
AllCCS	[M+NH4]+	262.4	32859911
AllCCS	[M+Na]+	262.4	32859911
AllCCS	[M-H]-	261.7	32859911
AllCCS	[M+Na-2H]-	266.8	32859911
AllCCS	[M+HCOO]-	272.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protoveratrine	CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(OC(C)=O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)CC	4227.9	Standard polar	33892256
Protoveratrine	CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(OC(C)=O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)CC	4326.3	Standard non polar	33892256
Protoveratrine	CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(OC(C)=O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)CC	4717.0	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 - Protoveratrine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoveratrine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoveratrine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoveratrine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protoveratrine GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4974

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Protoveratrine (HMDB0256876)

MOL for HMDB0256876 (Protoveratrine)

3D MOL for HMDB0256876 (Protoveratrine)

3D SDF for HMDB0256876 (Protoveratrine)

3D-SDF for HMDB0256876 (Protoveratrine)

PDB for HMDB0256876 (Protoveratrine)

3D PDB for HMDB0256876 (Protoveratrine)

SMILES for HMDB0256876 (Protoveratrine)

INCHI for HMDB0256876 (Protoveratrine)

Structure for HMDB0256876 (Protoveratrine)

3D Structure for HMDB0256876 (Protoveratrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra