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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:46:56 UTC

Update Date

2022-03-07 02:55:22 UTC

HMDB ID

HMDB0037531

Secondary Accession Numbers

HMDB37531

Metabolite Identification

Common Name

Dehydroxypaxilline

Description

Dehydroxypaxilline belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Dehydroxypaxilline is a metabolite of Emericella striata. Dehydroxypaxilline is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 01111302292D          

 33 38  0  0  0  0            999 V2000
   -6.9929  -12.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929  -10.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639  -10.6566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350  -12.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -11.8941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4206  -11.0691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8495  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8495  -11.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061  -12.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061  -10.6566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9917  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917  -11.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -9.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772   -9.8316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2772  -10.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627   -9.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -9.8316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1517  -10.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662  -11.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807   -9.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -8.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807   -9.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -12.7191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -10.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061  -11.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772   -9.0066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  7  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 12  1  0  0  0  0
  7 11  1  0  0  0  0
  9  8  1  0  0  0  0
  8 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 14  1  0  0  0  0
 15 16  1  0  0  0  0
 13 16  1  0  0  0  0
 15 20  1  0  0  0  0
 15 14  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 21 20  2  0  0  0  0
 20 19  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
  9 30  1  6  0  0  0
 10 31  1  1  0  0  0
 14 32  1  6  0  0  0
 19 33  1  1  0  0  0
M  END

HMDB0037531
     RDKit          3D
Dehydroxypaxilline
 64 69  0  0  0  0  0  0  0  0999 V2000
   -6.5202   -0.9700    1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195    0.0499    1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0585    1.3847    0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8002    0.2042    2.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3989   -0.3204    0.1607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4535    0.6907    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    0.3987   -0.8621 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6552    1.6368   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172    1.4175   -1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5008    0.5008   -0.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2559    1.0606    0.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -0.8279   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -1.3779   -2.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.2824   -2.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -0.9903   -1.4964 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6508   -0.9691   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856   -0.4006   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398    0.3819    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.8798    1.3933 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591    0.4182    1.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    0.5796    2.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5065   -0.0013    2.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769   -0.7921    1.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1983   -0.9832    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611   -0.3906    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.3668   -0.8807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2814    1.4868   -1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737   -0.7268   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -1.6737    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -1.5922    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985   -2.4895    1.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415   -1.6918    2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4563   -0.4371    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038   -1.4738    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7465    1.2958    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    2.1898    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7194    1.6397    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4258    0.7731    3.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8770   -0.5253   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423    0.1307   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576    2.3839   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    2.1566   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.9449   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.4162   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255    0.3786    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    1.1975    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678    2.0902    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -1.5718    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -2.4830   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -0.9776   -2.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -0.5567   -3.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -2.2692   -3.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883   -1.7535   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -0.3944   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -2.0336   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    1.5034    2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931    1.2099    3.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1197    0.1646    3.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9649   -1.2565    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5803   -1.6066   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    1.4537   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    2.4258   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    1.5306   -2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552   -2.5234    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  1  6
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30  5  1  0
 28  7  1  0
 26 10  1  0
 26 15  1  0
 25 17  1  0
 25 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  6
  7 40  1  6
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  1
 16 54  1  0
 16 55  1  0
 19 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 29 64  1  0
M  END


  Mrv0541 01111302292D          

 33 38  0  0  0  0            999 V2000
   -6.9929  -12.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9929  -10.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2784  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639  -10.6566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350  -12.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -11.8941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4206  -11.0691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8495  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8495  -11.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061  -12.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061  -10.6566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9917  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917  -11.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061   -9.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772   -9.8316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2772  -10.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627  -11.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627   -9.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -9.8316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1517  -10.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662  -11.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -9.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807   -9.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -8.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807   -9.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -12.7191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206  -10.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7061  -11.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2772   -9.0066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  7  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6 12  1  0  0  0  0
  7 11  1  0  0  0  0
  9  8  1  0  0  0  0
  8 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 14  1  0  0  0  0
 15 16  1  0  0  0  0
 13 16  1  0  0  0  0
 15 20  1  0  0  0  0
 15 14  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 21 20  2  0  0  0  0
 20 19  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
  9 30  1  6  0  0  0
 10 31  1  1  0  0  0
 14 32  1  6  0  0  0
 19 33  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0037531

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3C1CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO3/c1-25(2,30)24-21(29)14-18-19-10-9-15-13-17-16-7-5-6-8-20(16)28-23(17)27(15,4)26(19,3)12-11-22(18)31-24/h5-8,14-15,19,22,24,28,30H,9-13H2,1-4H3/t15-,19?,22-,24-,26-,27+/m0/s1

> <INCHI_KEY>
GYSZYWSJZCKCBD-WZNHOQSJSA-N

> <FORMULA>
C27H33NO3

> <MOLECULAR_WEIGHT>
419.5558

> <EXACT_MASS>
419.246043927

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
49.343420038452805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
4.626475565666666

> <ALOGPS_LOGS>
-5.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.849105645489402

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.130818406538971

> <JCHEM_PKA_STRONGEST_BASIC>
-3.17861276013896

> <JCHEM_POLAR_SURFACE_AREA>
62.32000000000001

> <JCHEM_REFRACTIVITY>
121.84239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037531
     RDKit          3D
Dehydroxypaxilline
 64 69  0  0  0  0  0  0  0  0999 V2000
   -6.5202   -0.9700    1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195    0.0499    1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0585    1.3847    0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8002    0.2042    2.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3989   -0.3204    0.1607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4535    0.6907    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    0.3987   -0.8621 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6552    1.6368   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172    1.4175   -1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5008    0.5008   -0.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2559    1.0606    0.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -0.8279   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -1.3779   -2.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.2824   -2.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -0.9903   -1.4964 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6508   -0.9691   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856   -0.4006   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398    0.3819    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.8798    1.3933 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591    0.4182    1.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    0.5796    2.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5065   -0.0013    2.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769   -0.7921    1.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1983   -0.9832    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611   -0.3906    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.3668   -0.8807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2814    1.4868   -1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737   -0.7268   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -1.6737    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -1.5922    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985   -2.4895    1.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415   -1.6918    2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4563   -0.4371    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038   -1.4738    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7465    1.2958    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    2.1898    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7194    1.6397    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4258    0.7731    3.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8770   -0.5253   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423    0.1307   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576    2.3839   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    2.1566   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.9449   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.4162   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255    0.3786    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    1.1975    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678    2.0902    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -1.5718    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -2.4830   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -0.9776   -2.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -0.5567   -3.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -2.2692   -3.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883   -1.7535   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -0.3944   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -2.0336   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    1.5034    2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931    1.2099    3.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1197    0.1646    3.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9649   -1.2565    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5803   -1.6066   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    1.4537   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    2.4258   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    1.5306   -2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552   -2.5234    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  1  6
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30  5  1  0
 28  7  1  0
 26 10  1  0
 26 15  1  0
 25 17  1  0
 25 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  6
  7 40  1  6
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  1
 16 54  1  0
 16 55  1  0
 19 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 29 64  1  0
M  END

HEADER    PROTEIN                                 11-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JAN-13         0                                  
HETATM    1  C   UNK     0     -13.053 -22.973   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.387 -22.203   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.387 -20.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.053 -19.892   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.720 -20.662   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.720 -22.203   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0     -10.386 -19.892   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -7.719 -22.972   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.385 -22.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.385 -20.662   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.052 -20.662   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.052 -22.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.051 -22.972   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.051 -19.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.718 -20.662   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.718 -22.202   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.051 -18.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.718 -17.582   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.384 -18.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.384 -19.892   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.050 -20.662   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.050 -17.582   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.283 -18.352   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.283 -19.892   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.617 -20.662   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.617 -17.582   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.951 -18.352   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.617 -16.042   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.951 -16.812   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -6.385 -23.742   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      -6.385 -19.122   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.051 -21.432   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      -2.384 -16.812   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    7    6                                                  
CONECT    6    1    5   12                                                  
CONECT    7    5   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13   10   30                                             
CONECT   10   11    9   14   31                                             
CONECT   11    7   10   12                                                  
CONECT   12    6    8   11                                                  
CONECT   13    9   16                                                       
CONECT   14   10   15   17   32                                             
CONECT   15   16   20   14                                                  
CONECT   16   15   13                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22   33                                             
CONECT   20   15   21   19                                                  
CONECT   21   20   24                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   21   25                                                  
CONECT   25   24                                                            
CONECT   26   23   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   14                                                            
CONECT   33   19                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

COMPND    HMDB0037531
HETATM    1  C1  UNL     1      -6.520  -0.970   1.337  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.419   0.050   1.204  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.059   1.385   0.882  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.800   0.204   2.450  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.399  -0.320   0.161  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.454   0.691   0.085  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.448   0.399  -0.862  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.655   1.637  -1.105  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.217   1.418  -1.491  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.501   0.501  -0.485  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.256   1.061   0.877  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.220  -0.828  -0.654  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.114  -1.378  -2.054  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.310  -1.282  -2.623  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.178  -0.990  -1.496  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.651  -0.969  -1.643  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.986  -0.401  -0.282  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.940   0.382   0.161  1.00  0.00           C  
HETATM   19  N1  UNL     1       3.253   0.880   1.393  1.00  0.00           N  
HETATM   20  C17 UNL     1       4.459   0.418   1.703  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.275   0.580   2.796  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.507  -0.001   2.907  1.00  0.00           C  
HETATM   23  C20 UNL     1       6.977  -0.792   1.890  1.00  0.00           C  
HETATM   24  C21 UNL     1       6.198  -0.983   0.779  1.00  0.00           C  
HETATM   25  C22 UNL     1       4.961  -0.391   0.683  1.00  0.00           C  
HETATM   26  C23 UNL     1       1.917   0.367  -0.881  1.00  0.00           C  
HETATM   27  C24 UNL     1       2.281   1.487  -1.843  1.00  0.00           C  
HETATM   28  C25 UNL     1      -1.674  -0.727  -0.373  1.00  0.00           C  
HETATM   29  C26 UNL     1      -2.303  -1.674   0.324  1.00  0.00           C  
HETATM   30  C27 UNL     1      -3.716  -1.592   0.591  1.00  0.00           C  
HETATM   31  O3  UNL     1      -4.399  -2.489   1.144  1.00  0.00           O  
HETATM   32  H1  UNL     1      -6.341  -1.692   2.160  1.00  0.00           H  
HETATM   33  H2  UNL     1      -7.456  -0.437   1.595  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.704  -1.474   0.369  1.00  0.00           H  
HETATM   35  H4  UNL     1      -6.747   1.296   0.004  1.00  0.00           H  
HETATM   36  H5  UNL     1      -5.325   2.190   0.733  1.00  0.00           H  
HETATM   37  H6  UNL     1      -6.719   1.640   1.751  1.00  0.00           H  
HETATM   38  H7  UNL     1      -5.426   0.773   3.003  1.00  0.00           H  
HETATM   39  H8  UNL     1      -4.877  -0.525  -0.803  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.042   0.131  -1.790  1.00  0.00           H  
HETATM   41  H10 UNL     1      -1.758   2.384  -0.275  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.125   2.157  -1.982  1.00  0.00           H  
HETATM   43  H12 UNL     1      -0.244   0.945  -2.505  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.246   2.416  -1.536  1.00  0.00           H  
HETATM   45  H14 UNL     1       0.626   0.379   1.641  1.00  0.00           H  
HETATM   46  H15 UNL     1      -0.829   1.197   1.099  1.00  0.00           H  
HETATM   47  H16 UNL     1       0.668   2.090   0.898  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.159  -1.572   0.113  1.00  0.00           H  
HETATM   49  H18 UNL     1      -0.333  -2.483  -1.962  1.00  0.00           H  
HETATM   50  H19 UNL     1      -0.870  -0.978  -2.721  1.00  0.00           H  
HETATM   51  H20 UNL     1       1.368  -0.557  -3.452  1.00  0.00           H  
HETATM   52  H21 UNL     1       1.613  -2.269  -3.077  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.988  -1.753  -0.687  1.00  0.00           H  
HETATM   54  H23 UNL     1       4.090  -0.394  -2.438  1.00  0.00           H  
HETATM   55  H24 UNL     1       4.020  -2.034  -1.697  1.00  0.00           H  
HETATM   56  H25 UNL     1       2.690   1.503   2.005  1.00  0.00           H  
HETATM   57  H26 UNL     1       4.893   1.210   3.600  1.00  0.00           H  
HETATM   58  H27 UNL     1       7.120   0.165   3.812  1.00  0.00           H  
HETATM   59  H28 UNL     1       7.965  -1.256   1.983  1.00  0.00           H  
HETATM   60  H29 UNL     1       6.580  -1.607  -0.013  1.00  0.00           H  
HETATM   61  H30 UNL     1       3.348   1.454  -2.145  1.00  0.00           H  
HETATM   62  H31 UNL     1       2.241   2.426  -1.212  1.00  0.00           H  
HETATM   63  H32 UNL     1       1.685   1.531  -2.744  1.00  0.00           H  
HETATM   64  H33 UNL     1      -1.755  -2.523   0.702  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4    5
CONECT    3   35   36   37
CONECT    4   38
CONECT    5    6   30   39
CONECT    6    7
CONECT    7    8   28   40
CONECT    8    9   41   42
CONECT    9   10   43   44
CONECT   10   11   12   26
CONECT   11   45   46   47
CONECT   12   13   28   48
CONECT   13   14   49   50
CONECT   14   15   51   52
CONECT   15   16   26   53
CONECT   16   17   54   55
CONECT   17   18   18   25
CONECT   18   19   26
CONECT   19   20   56
CONECT   20   21   21   25
CONECT   21   22   57
CONECT   22   23   23   58
CONECT   23   24   59
CONECT   24   25   25   60
CONECT   26   27
CONECT   27   61   62   63
CONECT   28   29   29
CONECT   29   30   64
CONECT   30   31   31
END

HMDB0037531
     RDKit          3D
Dehydroxypaxilline
 64 69  0  0  0  0  0  0  0  0999 V2000
   -6.5202   -0.9700    1.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195    0.0499    1.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0585    1.3847    0.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8002    0.2042    2.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3989   -0.3204    0.1607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4535    0.6907    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482    0.3987   -0.8621 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6552    1.6368   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2172    1.4175   -1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5008    0.5008   -0.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2559    1.0606    0.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -0.8279   -0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -1.3779   -2.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.2824   -2.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1779   -0.9903   -1.4964 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6508   -0.9691   -1.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9856   -0.4006   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398    0.3819    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530    0.8798    1.3933 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591    0.4182    1.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2749    0.5796    2.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5065   -0.0013    2.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769   -0.7921    1.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1983   -0.9832    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611   -0.3906    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167    0.3668   -0.8807 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2814    1.4868   -1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737   -0.7268   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3033   -1.6737    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7158   -1.5922    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3985   -2.4895    1.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3415   -1.6918    2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4563   -0.4371    1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038   -1.4738    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7465    1.2958    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249    2.1898    0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7194    1.6397    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4258    0.7731    3.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8770   -0.5253   -0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423    0.1307   -1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576    2.3839   -0.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248    2.1566   -1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    0.9449   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.4162   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255    0.3786    1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    1.1975    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6678    2.0902    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -1.5718    0.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -2.4830   -1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8705   -0.9776   -2.7214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -0.5567   -3.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -2.2692   -3.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9883   -1.7535   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0896   -0.3944   -2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -2.0336   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6899    1.5034    2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931    1.2099    3.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1197    0.1646    3.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9649   -1.2565    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5803   -1.6066   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    1.4537   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    2.4258   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    1.5306   -2.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552   -2.5234    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  1  6
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30  5  1  0
 28  7  1  0
 26 10  1  0
 26 15  1  0
 25 17  1  0
 25 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  6
  7 40  1  6
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  1
 16 54  1  0
 16 55  1  0
 19 56  1  0
 21 57  1  0
 22 58  1  0
 23 59  1  0
 24 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 29 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃NO₃

Average Molecular Weight

419.5558

Monoisotopic Molecular Weight

419.246043927

IUPAC Name

(1S,2S,5S,7R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

Traditional Name

(1S,2S,5S,7R,14S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-9,16(24),17,19,21-pentaen-8-one

CAS Registry Number

112900-05-7

SMILES

[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3C1CC2)C(C)(C)O

InChI Identifier

InChI=1S/C27H33NO3/c1-25(2,30)24-21(29)14-18-19-10-9-15-13-17-16-7-5-6-8-20(16)28-23(17)27(15,4)26(19,3)12-11-22(18)31-24/h5-8,14-15,19,22,24,28,30H,9-13H2,1-4H3/t15-,19?,22-,24-,26-,27+/m0/s1

InChI Key

GYSZYWSJZCKCBD-WZNHOQSJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037531)

Cellular substructure

Extracellular (HMDB: HMDB0037531)
Membrane (HMDB: HMDB0037531)

Source

Endogenous

Endogenous (HMDB: HMDB0037531)

Exogenous

Food

Food (HMDB: HMDB0037531)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037531)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037531)

Nutrient

Nutrient (HMDB: HMDB0037531)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037531)

Emulsifier (HMDB: HMDB0037531)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	232 - 234 °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	0.00043 g/L	ALOGPS
logP	5.62	ALOGPS
logP	4.63	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	121.84 m³·mol⁻¹	ChemAxon
Polarizability	49.34 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.143	31661259
DarkChem	[M-H]-	192.675	31661259
DeepCCS	[M-2H]-	245.671	30932474
DeepCCS	[M+Na]+	220.065	30932474
AllCCS	[M+H]+	205.4	32859911
AllCCS	[M+H-H2O]+	203.1	32859911
AllCCS	[M+NH4]+	207.5	32859911
AllCCS	[M+Na]+	208.1	32859911
AllCCS	[M-H]-	211.8	32859911
AllCCS	[M+Na-2H]-	212.7	32859911
AllCCS	[M+HCOO]-	213.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydroxypaxilline	[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3C1CC2)C(C)(C)O	4743.4	Standard polar	33892256
Dehydroxypaxilline	[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3C1CC2)C(C)(C)O	3481.7	Standard non polar	33892256
Dehydroxypaxilline	[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3C1CC2)C(C)(C)O	3702.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydroxypaxilline,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O	3847.7	Semi standard non polar	33892256
Dehydroxypaxilline,1TMS,isomer #2	CC(C)(O)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3777.2	Semi standard non polar	33892256
Dehydroxypaxilline,1TMS,isomer #3	CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O	3857.4	Semi standard non polar	33892256
Dehydroxypaxilline,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3790.7	Semi standard non polar	33892256
Dehydroxypaxilline,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3480.5	Standard non polar	33892256
Dehydroxypaxilline,2TMS,isomer #2	CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O	3833.0	Semi standard non polar	33892256
Dehydroxypaxilline,2TMS,isomer #2	CC(C)(O[Si](C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O	3582.3	Standard non polar	33892256
Dehydroxypaxilline,2TMS,isomer #3	CC(C)(O)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3757.2	Semi standard non polar	33892256
Dehydroxypaxilline,2TMS,isomer #3	CC(C)(O)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3447.3	Standard non polar	33892256
Dehydroxypaxilline,3TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3745.6	Semi standard non polar	33892256
Dehydroxypaxilline,3TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3543.2	Standard non polar	33892256
Dehydroxypaxilline,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O	4087.3	Semi standard non polar	33892256
Dehydroxypaxilline,1TBDMS,isomer #2	CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3996.7	Semi standard non polar	33892256
Dehydroxypaxilline,1TBDMS,isomer #3	CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O	4037.6	Semi standard non polar	33892256
Dehydroxypaxilline,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	4205.0	Semi standard non polar	33892256
Dehydroxypaxilline,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3954.8	Standard non polar	33892256
Dehydroxypaxilline,2TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O	4239.1	Semi standard non polar	33892256
Dehydroxypaxilline,2TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=CC1=O	4057.5	Standard non polar	33892256
Dehydroxypaxilline,2TBDMS,isomer #3	CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	4125.6	Semi standard non polar	33892256
Dehydroxypaxilline,2TBDMS,isomer #3	CC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	3904.4	Standard non polar	33892256
Dehydroxypaxilline,3TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	4300.8	Semi standard non polar	33892256
Dehydroxypaxilline,3TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2C3CC[C@H]4CC5=C(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@]4(C)[C@@]3(C)CC[C@@H]2O1	4178.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxypaxilline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pc3-5129200000-d29db0e35400a0871afc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxypaxilline GC-MS (1 TMS) - 70eV, Positive	splash10-01si-9825800000-7a7362e189a7dec37e17	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxypaxilline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydroxypaxilline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 10V, Positive-QTOF	splash10-0fk9-0002900000-2d0393b16bc3e23eb2cf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 20V, Positive-QTOF	splash10-0uk9-1368900000-e92682013b84e802b1ff	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 40V, Positive-QTOF	splash10-0w2i-3395000000-5c44d12ace84d8478729	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 10V, Negative-QTOF	splash10-014i-1001900000-f61f0322fd73488e6375	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 20V, Negative-QTOF	splash10-014i-4003900000-5b97630ad2a711169d0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 40V, Negative-QTOF	splash10-0gb9-2219000000-2cfaaf325067c091ae92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 10V, Negative-QTOF	splash10-014i-0000900000-dd10e18085c0555c8467	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 20V, Negative-QTOF	splash10-014i-2005900000-1ea9815e78d93e980c9b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 40V, Negative-QTOF	splash10-0aou-8009300000-fdffa04bac8090c994db	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 10V, Positive-QTOF	splash10-00di-0000900000-4f0e914c3fd3b2b3b9e3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 20V, Positive-QTOF	splash10-0fl0-2668900000-8974a57bc522f8419dfd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydroxypaxilline 40V, Positive-QTOF	splash10-0uei-5494100000-610e89182f28c38fbd4a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB016612

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

71019045

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

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

Showing metabocard for Dehydroxypaxilline (HMDB0037531)

MOL for HMDB0037531 (Dehydroxypaxilline)

3D MOL for HMDB0037531 (Dehydroxypaxilline)

3D SDF for HMDB0037531 (Dehydroxypaxilline)

3D-SDF for HMDB0037531 (Dehydroxypaxilline)

PDB for HMDB0037531 (Dehydroxypaxilline)

3D PDB for HMDB0037531 (Dehydroxypaxilline)

SMILES for HMDB0037531 (Dehydroxypaxilline)

INCHI for HMDB0037531 (Dehydroxypaxilline)

Structure for HMDB0037531 (Dehydroxypaxilline)

3D Structure for HMDB0037531 (Dehydroxypaxilline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra