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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:26 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030203

Secondary Accession Numbers

HMDB30203

Metabolite Identification

Common Name

Fumitremorgin B

Description

Fumitremorgin B, also known as lanosulin, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Based on a literature review a significant number of articles have been published on Fumitremorgin B.

Structure

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


  Mrv0541 09061400402D          

 35 39  0  0  0  0            999 V2000
    3.8314   -0.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408   -0.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    0.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5377    3.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3352    2.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    2.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8893    3.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651    3.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    3.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    0.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7957    0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    2.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4682   -0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4411    0.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2700    2.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    2.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1407    2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023    2.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9179    1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078    2.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    1.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624    3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    3.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947    2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238    1.4766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0185    3.0843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724    2.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846    3.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825    0.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    4.2023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    3.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0942    2.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 11  6  1  0  0  0  0
 12 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15 10  2  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16 13  2  0  0  0  0
 17  8  1  0  0  0  0
 17 14  2  0  0  0  0
 18  9  1  0  0  0  0
 19  7  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  2  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 27 24  1  0  0  0  0
 27 26  1  0  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 11  1  0  0  0  0
 29 19  1  0  0  0  0
 29 26  1  0  0  0  0
 30 21  1  0  0  0  0
 30 25  1  0  0  0  0
 30 27  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  2  0  0  0  0
 33 26  2  0  0  0  0
 34 27  1  0  0  0  0
 35  5  1  0  0  0  0
 35 17  1  0  0  0  0
M  END

HMDB0030203
     RDKit          3D
Fumitremorgin B
 68 72  0  0  0  0  0  0  0  0999 V2000
   -5.0222    4.6793   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7895    3.2966   -0.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4969    2.7622   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266    3.5567   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1457    3.0496   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528    1.6932   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2053    0.9368   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -0.3653   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -0.3768   -0.4234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2946   -1.5331   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3242   -1.6841    1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -1.6579    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -1.8227    3.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7994   -1.4782    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    0.8647   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2569    1.4165   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -1.3953   -0.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044   -1.6434   -2.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7656   -2.1358   -3.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862   -2.2856   -4.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -2.5706   -3.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -0.7571   -0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   -1.3890    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4991   -2.6334    1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.6434    2.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -1.2003    2.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -0.0679    3.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    1.1741    2.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    0.7168    1.7732 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    1.3074    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.5535    0.7185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    0.4844   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593    0.3024   -1.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    1.2709   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    1.1907   -2.6898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    5.0090   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891    5.0077   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    5.2118    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    4.6240   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    3.6733   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567   -2.4441   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3344   -1.3535   -0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809   -1.8256    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -0.8125    4.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -2.3350    3.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000   -2.4258    4.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.8704    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5352   -2.0087    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0552   -0.3840    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    0.7625   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848   -2.2982   -0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.3801   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022   -1.3059   -4.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678   -3.0629   -4.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -2.5550   -5.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669   -3.4175   -2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -2.9880   -4.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3584   -1.7948   -2.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824   -0.6651    3.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -1.3220    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -2.1419    2.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382   -0.2624    4.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4664    0.0027    3.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.6611    3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3908    1.8523    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.8210   -2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143    2.3659   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    2.0465   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 16  3  1  0
 32 22  1  0
 15  6  1  0
 29 25  1  0
 34  7  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
M  END


  Mrv0541 09061400402D          

 35 39  0  0  0  0            999 V2000
    3.8314   -0.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2408   -0.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    0.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5377    3.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3352    2.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    2.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8893    3.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651    3.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567    3.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    0.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7957    0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8265    2.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4682   -0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4411    0.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2700    2.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6216    2.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1407    2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023    2.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9179    1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078    2.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6856    1.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624    3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047    1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    3.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3947    2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238    1.4766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0185    3.0843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724    2.0567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846    3.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825    0.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    4.2023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    3.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0942    2.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 11  6  1  0  0  0  0
 12 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15 10  2  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16 13  2  0  0  0  0
 17  8  1  0  0  0  0
 17 14  2  0  0  0  0
 18  9  1  0  0  0  0
 19  7  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  2  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 27 24  1  0  0  0  0
 27 26  1  0  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
 28 23  1  0  0  0  0
 29 11  1  0  0  0  0
 29 19  1  0  0  0  0
 29 26  1  0  0  0  0
 30 21  1  0  0  0  0
 30 25  1  0  0  0  0
 30 27  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  2  0  0  0  0
 33 26  2  0  0  0  0
 34 27  1  0  0  0  0
 35  5  1  0  0  0  0
 35 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030203

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1=C(C(C=C(C)C)N3C(=O)C4CCCN4C(=O)C3(O)C1O)N2CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3

> <INCHI_KEY>
WEIYXEFMCIRZHC-UHFFFAOYSA-N

> <FORMULA>
C27H33N3O5

> <MOLECULAR_WEIGHT>
479.568

> <EXACT_MASS>
479.242021181

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.98832965019437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.7413935126666678

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.535161709948355

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.13049435801047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7926145897706016

> <JCHEM_POLAR_SURFACE_AREA>
95.24000000000001

> <JCHEM_REFRACTIVITY>
133.33460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030203
     RDKit          3D
Fumitremorgin B
 68 72  0  0  0  0  0  0  0  0999 V2000
   -5.0222    4.6793   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7895    3.2966   -0.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4969    2.7622   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266    3.5567   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1457    3.0496   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528    1.6932   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2053    0.9368   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -0.3653   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -0.3768   -0.4234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2946   -1.5331   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3242   -1.6841    1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -1.6579    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -1.8227    3.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7994   -1.4782    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    0.8647   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2569    1.4165   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -1.3953   -0.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044   -1.6434   -2.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7656   -2.1358   -3.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862   -2.2856   -4.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -2.5706   -3.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -0.7571   -0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   -1.3890    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4991   -2.6334    1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.6434    2.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -1.2003    2.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -0.0679    3.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    1.1741    2.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    0.7168    1.7732 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    1.3074    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.5535    0.7185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    0.4844   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593    0.3024   -1.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    1.2709   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    1.1907   -2.6898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    5.0090   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891    5.0077   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    5.2118    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    4.6240   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    3.6733   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567   -2.4441   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3344   -1.3535   -0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809   -1.8256    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -0.8125    4.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -2.3350    3.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000   -2.4258    4.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.8704    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5352   -2.0087    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0552   -0.3840    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    0.7625   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848   -2.2982   -0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.3801   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022   -1.3059   -4.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678   -3.0629   -4.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -2.5550   -5.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669   -3.4175   -2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -2.9880   -4.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3584   -1.7948   -2.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824   -0.6651    3.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -1.3220    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -2.1419    2.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382   -0.2624    4.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4664    0.0027    3.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.6611    3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3908    1.8523    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.8210   -2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143    2.3659   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    2.0465   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 16  3  1  0
 32 22  1  0
 15  6  1  0
 29 25  1  0
 34  7  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
M  END

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0       7.152  -1.801   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.783  -1.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.329  -1.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.990   0.962   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.204   6.316   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.492   5.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.782   3.981   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.127   6.451   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.588   6.519   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.087   0.697   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.413   6.445   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.645   1.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.352   1.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.009   3.787   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.341  -0.821   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.557   0.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.837   5.085   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.760   5.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.263   4.234   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.471   3.854   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.580   2.880   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.241   4.967   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.013   3.444   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.036   5.926   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.942   3.275   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.398   6.321   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.603   5.362   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       6.391   2.756   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      -0.035   5.757   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       2.375   3.839   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       4.265   7.449   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.714   1.752   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.627   7.844   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.832   6.885   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.376   5.017   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5   35                                                            
CONECT    6    7   11                                                       
CONECT    7    6   19                                                       
CONECT    8    9   17                                                       
CONECT    9    8   18                                                       
CONECT   10   12   15                                                       
CONECT   11    6   29                                                       
CONECT   12   10   28                                                       
CONECT   13   16   21                                                       
CONECT   14   17   20                                                       
CONECT   15    1    2   10                                                  
CONECT   16    3    4   13                                                  
CONECT   17    8   14   35                                                  
CONECT   18    9   20   22                                                  
CONECT   19    7   25   29                                                  
CONECT   20   14   18   28                                                  
CONECT   21   13   23   30                                                  
CONECT   22   18   23   24                                                  
CONECT   23   21   22   28                                                  
CONECT   24   22   27   31                                                  
CONECT   25   19   30   32                                                  
CONECT   26   27   29   33                                                  
CONECT   27   24   26   30   34                                             
CONECT   28   12   20   23                                                  
CONECT   29   11   19   26                                                  
CONECT   30   21   25   27                                                  
CONECT   31   24                                                            
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35    5   17                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    HMDB0030203
HETATM    1  C1  UNL     1      -5.022   4.679  -0.591  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.789   3.297  -0.396  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.497   2.762  -0.564  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.427   3.557  -0.920  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.146   3.050  -1.090  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.953   1.693  -0.892  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.205   0.937  -0.996  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.180  -0.365  -0.693  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.486  -0.377  -0.423  1.00  0.00           N  
HETATM   10  C8  UNL     1      -2.295  -1.533  -0.022  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.324  -1.684   1.443  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.428  -1.658   2.174  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.351  -1.823   3.680  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.799  -1.478   1.640  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.993   0.865  -0.537  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.257   1.417  -0.377  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.933  -1.395  -0.732  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.404  -1.643  -2.109  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.766  -2.136  -3.128  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.486  -2.286  -4.440  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.638  -2.571  -3.054  1.00  0.00           C  
HETATM   22  N2  UNL     1       2.074  -0.757  -0.043  1.00  0.00           N  
HETATM   23  C20 UNL     1       2.615  -1.389   1.089  1.00  0.00           C  
HETATM   24  O2  UNL     1       2.499  -2.633   1.289  1.00  0.00           O  
HETATM   25  C21 UNL     1       3.366  -0.643   2.137  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.751  -1.200   2.377  1.00  0.00           C  
HETATM   27  C23 UNL     1       5.380  -0.068   3.186  1.00  0.00           C  
HETATM   28  C24 UNL     1       4.643   1.174   2.742  1.00  0.00           C  
HETATM   29  N3  UNL     1       3.650   0.717   1.773  1.00  0.00           N  
HETATM   30  C25 UNL     1       3.000   1.307   0.673  1.00  0.00           C  
HETATM   31  O3  UNL     1       2.751   2.553   0.719  1.00  0.00           O  
HETATM   32  C26 UNL     1       2.619   0.484  -0.510  1.00  0.00           C  
HETATM   33  O4  UNL     1       3.759   0.302  -1.296  1.00  0.00           O  
HETATM   34  C27 UNL     1       1.623   1.271  -1.315  1.00  0.00           C  
HETATM   35  O5  UNL     1       1.807   1.191  -2.690  1.00  0.00           O  
HETATM   36  H1  UNL     1      -5.972   5.009  -0.132  1.00  0.00           H  
HETATM   37  H2  UNL     1      -4.889   5.008  -1.628  1.00  0.00           H  
HETATM   38  H3  UNL     1      -4.226   5.212   0.010  1.00  0.00           H  
HETATM   39  H4  UNL     1      -2.604   4.624  -1.071  1.00  0.00           H  
HETATM   40  H5  UNL     1      -0.309   3.673  -1.369  1.00  0.00           H  
HETATM   41  H6  UNL     1      -1.957  -2.444  -0.540  1.00  0.00           H  
HETATM   42  H7  UNL     1      -3.334  -1.354  -0.415  1.00  0.00           H  
HETATM   43  H8  UNL     1      -1.381  -1.826   1.954  1.00  0.00           H  
HETATM   44  H9  UNL     1      -3.292  -0.813   4.127  1.00  0.00           H  
HETATM   45  H10 UNL     1      -2.407  -2.335   3.899  1.00  0.00           H  
HETATM   46  H11 UNL     1      -4.200  -2.426   4.039  1.00  0.00           H  
HETATM   47  H12 UNL     1      -4.964  -1.870   0.638  1.00  0.00           H  
HETATM   48  H13 UNL     1      -5.535  -2.009   2.316  1.00  0.00           H  
HETATM   49  H14 UNL     1      -5.055  -0.384   1.750  1.00  0.00           H  
HETATM   50  H15 UNL     1      -4.062   0.763  -0.101  1.00  0.00           H  
HETATM   51  H16 UNL     1       0.685  -2.298  -0.190  1.00  0.00           H  
HETATM   52  H17 UNL     1       2.480  -1.380  -2.297  1.00  0.00           H  
HETATM   53  H18 UNL     1       2.002  -1.306  -4.634  1.00  0.00           H  
HETATM   54  H19 UNL     1       2.268  -3.063  -4.307  1.00  0.00           H  
HETATM   55  H20 UNL     1       0.794  -2.555  -5.241  1.00  0.00           H  
HETATM   56  H21 UNL     1      -0.767  -3.418  -2.334  1.00  0.00           H  
HETATM   57  H22 UNL     1      -0.994  -2.988  -4.030  1.00  0.00           H  
HETATM   58  H23 UNL     1      -1.358  -1.795  -2.777  1.00  0.00           H  
HETATM   59  H24 UNL     1       2.782  -0.665   3.063  1.00  0.00           H  
HETATM   60  H25 UNL     1       5.291  -1.322   1.424  1.00  0.00           H  
HETATM   61  H26 UNL     1       4.727  -2.142   2.962  1.00  0.00           H  
HETATM   62  H27 UNL     1       5.138  -0.262   4.253  1.00  0.00           H  
HETATM   63  H28 UNL     1       6.466   0.003   3.040  1.00  0.00           H  
HETATM   64  H29 UNL     1       4.081   1.661   3.562  1.00  0.00           H  
HETATM   65  H30 UNL     1       5.391   1.852   2.269  1.00  0.00           H  
HETATM   66  H31 UNL     1       3.726   0.821  -2.135  1.00  0.00           H  
HETATM   67  H32 UNL     1       1.814   2.366  -1.069  1.00  0.00           H  
HETATM   68  H33 UNL     1       1.916   2.047  -3.139  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   39
CONECT    5    6    6   40
CONECT    6    7   15
CONECT    7    8    8   34
CONECT    8    9   17
CONECT    9   10   15
CONECT   10   11   41   42
CONECT   11   12   12   43
CONECT   12   13   14
CONECT   13   44   45   46
CONECT   14   47   48   49
CONECT   15   16   16
CONECT   16   50
CONECT   17   18   22   51
CONECT   18   19   19   52
CONECT   19   20   21
CONECT   20   53   54   55
CONECT   21   56   57   58
CONECT   22   23   32
CONECT   23   24   24   25
CONECT   25   26   29   59
CONECT   26   27   60   61
CONECT   27   28   62   63
CONECT   28   29   64   65
CONECT   29   30
CONECT   30   31   31   32
CONECT   32   33   34
CONECT   33   66
CONECT   34   35   67
CONECT   35   68
END

HMDB0030203
     RDKit          3D
Fumitremorgin B
 68 72  0  0  0  0  0  0  0  0999 V2000
   -5.0222    4.6793   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7895    3.2966   -0.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4969    2.7622   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4266    3.5567   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1457    3.0496   -1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9528    1.6932   -0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2053    0.9368   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -0.3653   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4862   -0.3768   -0.4234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2946   -1.5331   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3242   -1.6841    1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -1.6579    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -1.8227    3.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7994   -1.4782    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    0.8647   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2569    1.4165   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328   -1.3953   -0.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044   -1.6434   -2.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7656   -2.1358   -3.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862   -2.2856   -4.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -2.5706   -3.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -0.7571   -0.0427 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   -1.3890    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4991   -2.6334    1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -0.6434    2.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -1.2003    2.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3798   -0.0679    3.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    1.1741    2.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    0.7168    1.7732 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    1.3074    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.5535    0.7185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186    0.4844   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593    0.3024   -1.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6230    1.2709   -1.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    1.1907   -2.6898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    5.0090   -0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891    5.0077   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    5.2118    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    4.6240   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3088    3.6733   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9567   -2.4441   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3344   -1.3535   -0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3809   -1.8256    1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2924   -0.8125    4.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -2.3350    3.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2000   -2.4258    4.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9640   -1.8704    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5352   -2.0087    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0552   -0.3840    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617    0.7625   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848   -2.2982   -0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -1.3801   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022   -1.3059   -4.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678   -3.0629   -4.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -2.5550   -5.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669   -3.4175   -2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -2.9880   -4.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3584   -1.7948   -2.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824   -0.6651    3.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -1.3220    1.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270   -2.1419    2.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382   -0.2624    4.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4664    0.0027    3.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.6611    3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3908    1.8523    2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7263    0.8210   -2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143    2.3659   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    2.0465   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 16  3  1  0
 32 22  1  0
 15  6  1  0
 29 25  1  0
 34  7  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 33 66  1  0
 34 67  1  0
 35 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lanosulin	ChEBI

Chemical Formula

C₂₇H₃₃N₃O₅

Average Molecular Weight

479.568

Monoisotopic Molecular Weight

479.242021181

IUPAC Name

1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione

Traditional Name

1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione

CAS Registry Number

12626-17-4

SMILES

COC1=CC2=C(C=C1)C1=C(C(C=C(C)C)N3C(=O)C4CCCN4C(=O)C3(O)C1O)N2CC=C(C)C

InChI Identifier

InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3

InChI Key

WEIYXEFMCIRZHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid or derivatives
N-alkylindole
3-alkylindole
Indole
Anisole
Dioxopiperazine
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
1,4-diazinane
Piperazine
Substituted pyrrole
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary alcohol
Lactam
Carboxamide group
Alkanolamine
Azacycle
Ether
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:64531 )
indole alkaloid (CHEBI:64531 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Seizure (HMDB: HMDB0030203)

Central nervous system disorder

Psychiatric disorder

Confusion (HMDB: HMDB0030203)

Paralysis (HMDB: HMDB0030203)

Disposition

Biological location

Cellular substructure

Route of exposure

Parenteral

Dermal (HMDB: HMDB0030203)
Inhalation (HMDB: HMDB0030203)

Enteral

Ingestion (HMDB: HMDB0030203)

Source

Endogenous

Endogenous (HMDB: HMDB0030203)

Exogenous

Food

Food (HMDB: HMDB0030203)

Process

Not Available

Role

Indirect biological role

Mycotoxin (HMDB: HMDB0030203)

Biological role

mycotoxin (HMDB: HMDB0030203)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	211 - 212 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.74	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.33 m³·mol⁻¹	ChemAxon
Polarizability	52.99 Å³	ChemAxon
Number of Rings	5	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
DarkChem	[M+H]+	210.541	31661259
DarkChem	[M-H]-	210.5	31661259
DeepCCS	[M+H]+	220.069	30932474
DeepCCS	[M-H]-	217.674	30932474
DeepCCS	[M-2H]-	250.558	30932474
DeepCCS	[M+Na]+	225.982	30932474
AllCCS	[M+H]+	214.0	32859911
AllCCS	[M+H-H2O]+	212.1	32859911
AllCCS	[M+NH4]+	215.8	32859911
AllCCS	[M+Na]+	216.3	32859911
AllCCS	[M-H]-	216.1	32859911
AllCCS	[M+Na-2H]-	217.2	32859911
AllCCS	[M+HCOO]-	218.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fumitremorgin B	COC1=CC2=C(C=C1)C1=C(C(C=C(C)C)N3C(=O)C4CCCN4C(=O)C3(O)C1O)N2CC=C(C)C	5139.6	Standard polar	33892256
Fumitremorgin B	COC1=CC2=C(C=C1)C1=C(C(C=C(C)C)N3C(=O)C4CCCN4C(=O)C3(O)C1O)N2CC=C(C)C	3489.5	Standard non polar	33892256
Fumitremorgin B	COC1=CC2=C(C=C1)C1=C(C(C=C(C)C)N3C(=O)C4CCCN4C(=O)C3(O)C1O)N2CC=C(C)C	3924.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fumitremorgin B,1TMS,isomer #1	COC1=CC=C2C3=C(C(C=C(C)C)N4C(=O)C5CCCN5C(=O)C4(O[Si](C)(C)C)C3O)N(CC=C(C)C)C2=C1	3788.4	Semi standard non polar	33892256
Fumitremorgin B,1TMS,isomer #2	COC1=CC=C2C3=C(C(C=C(C)C)N4C(=O)C5CCCN5C(=O)C4(O)C3O[Si](C)(C)C)N(CC=C(C)C)C2=C1	3795.6	Semi standard non polar	33892256
Fumitremorgin B,2TMS,isomer #1	COC1=CC=C2C3=C(C(C=C(C)C)N4C(=O)C5CCCN5C(=O)C4(O[Si](C)(C)C)C3O[Si](C)(C)C)N(CC=C(C)C)C2=C1	3727.2	Semi standard non polar	33892256
Fumitremorgin B,1TBDMS,isomer #1	COC1=CC=C2C3=C(C(C=C(C)C)N4C(=O)C5CCCN5C(=O)C4(O[Si](C)(C)C(C)(C)C)C3O)N(CC=C(C)C)C2=C1	3985.5	Semi standard non polar	33892256
Fumitremorgin B,1TBDMS,isomer #2	COC1=CC=C2C3=C(C(C=C(C)C)N4C(=O)C5CCCN5C(=O)C4(O)C3O[Si](C)(C)C(C)(C)C)N(CC=C(C)C)C2=C1	3985.0	Semi standard non polar	33892256
Fumitremorgin B,2TBDMS,isomer #1	COC1=CC=C2C3=C(C(C=C(C)C)N4C(=O)C5CCCN5C(=O)C4(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)N(CC=C(C)C)C2=C1	4105.9	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 - Fumitremorgin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w31-5139500000-39a59034a27f4e4c8d48	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin B GC-MS (2 TMS) - 70eV, Positive	splash10-0apj-9014274000-4c5f595931915314386b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin B GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin B GC-MS ("Fumitremorgin B,2TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 10V, Positive-QTOF	splash10-001i-1000900000-e19d0bfd2e517960f36b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 20V, Positive-QTOF	splash10-00xu-9070600000-3254bfcb3d70c62863bf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 40V, Positive-QTOF	splash10-0gi3-9000000000-62f3e147eb01d7a8a5aa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 10V, Negative-QTOF	splash10-004i-1000900000-883706de0236f02775a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 20V, Negative-QTOF	splash10-0ufu-4009300000-35dfd4c375bfb9276168	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 40V, Negative-QTOF	splash10-0006-4092000000-31812038db5393ad0414	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 10V, Positive-QTOF	splash10-001i-0000900000-28fdcd8d6f2aef27b884	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 20V, Positive-QTOF	splash10-001i-0000900000-16bc6def02ffcbcae235	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 40V, Positive-QTOF	splash10-0296-9121700000-40edf0496ef962b765a9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 10V, Negative-QTOF	splash10-004i-0000900000-32d1eaece5685ec03760	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 20V, Negative-QTOF	splash10-004i-0004900000-f00354422eba0d8cbf29	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin B 40V, Negative-QTOF	splash10-03di-1391300000-4484b6e16e6127fff8f4	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Not Available

KNApSAcK ID

C00011297

Chemspider ID

94836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

105113

PDB ID

Not Available

ChEBI ID

64531

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Fumitremorgin B (HMDB0030203)

MOL for HMDB0030203 (Fumitremorgin B)

3D MOL for HMDB0030203 (Fumitremorgin B)

3D SDF for HMDB0030203 (Fumitremorgin B)

3D-SDF for HMDB0030203 (Fumitremorgin B)

PDB for HMDB0030203 (Fumitremorgin B)

3D PDB for HMDB0030203 (Fumitremorgin B)

SMILES for HMDB0030203 (Fumitremorgin B)

INCHI for HMDB0030203 (Fumitremorgin B)

Structure for HMDB0030203 (Fumitremorgin B)

3D Structure for HMDB0030203 (Fumitremorgin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra