Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:53:33 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038568

Secondary Accession Numbers

HMDB38568

Metabolite Identification

Common Name

PC-M6

Description

PC-M6 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. PC-M6 is an extremely weak basic (essentially neutral) compound (based on its pKa). Tremorgenic mycotoxin from Penicillium crustosum, Penicillium paxilli and Acremonium lolii.

Structure

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


  Mrv0541 01291301052D          

 33 38  0  0  0  0            999 V2000
   -3.9286   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9286   -9.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -9.5464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -9.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3563   -8.3089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3582   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582   -9.5464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0726   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582  -10.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726  -10.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871  -10.3715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7871   -9.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016  -10.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160  -10.3715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2160   -9.5464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9305   -9.1340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -7.4839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -9.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -9.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871  -11.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305  -10.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450  -10.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305  -11.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450  -11.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  9  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
 10 11  1  0  0  0  0
  9 10  2  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 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  1  1  0  0  0
 12 26  1  1  0  0  0
 11 27  1  6  0  0  0
 14 28  1  1  0  0  0
 19 29  1  6  0  0  0
 23 30  1  1  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END

HMDB0038568
     RDKit          3D
PC-M6
 66 71  0  0  0  0  0  0  0  0999 V2000
    6.6918   -0.2808    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213    0.3445    1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7641    1.8333    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   -0.0848    2.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2693   -0.1394    0.5723 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2375    0.3558    1.3693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1857   -0.5485    1.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9952   -0.2693    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460    0.4010    1.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547   -0.1026    0.0695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5702    1.1032   -0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218   -1.1481   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569   -1.6146   -1.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -2.1090   -1.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -1.0554   -1.4680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6316   -1.4070   -1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759   -0.2494   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0375    0.1468    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4409    1.1660    1.0525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188    1.4480    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120    2.3913    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929    2.4430    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3321    1.5649   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4376    0.6326   -0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1395    0.5714   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.7260    0.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0334   -1.9703    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -0.6356   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084   -0.2567   -1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656    0.2576   -0.8533 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8964    1.6702   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6013   -0.3662    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -1.3111   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8807    0.3031   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231    2.1815   -0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842    2.3594    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    2.1023    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4783   -1.0071    2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842   -1.2498    0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -1.5526    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3331    0.4118    2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838   -1.2078    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0474    1.5145    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.2840    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    1.8184   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183    0.8377   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.6451   -0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2818   -2.0357    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -2.5249   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904   -0.9274   -2.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255   -3.1194   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -2.1777   -3.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0877   -0.1583   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504   -1.3940   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181   -2.3615   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.7238    1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    3.1102    1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6297    3.1786    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3476    1.6406   -0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7381   -0.0721   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -1.8053    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741   -2.8613    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -2.1671    1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.3284   -2.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.0976   -1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672    1.8821   -0.1971 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  6
 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  1
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  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  1
  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  6
 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
 30 65  1  6
 31 66  1  0
M  END


  Mrv0541 01291301052D          

 33 38  0  0  0  0            999 V2000
   -3.9286   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9286   -9.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2141   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -9.5464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -9.1339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3563   -8.3089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3582   -7.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582   -9.5464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0726   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726   -8.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582  -10.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726  -10.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871  -10.3715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7871   -9.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016   -9.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016  -10.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160  -10.3715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2160   -9.5464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9305   -9.1340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -7.4839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -9.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -9.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871  -11.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305  -10.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450  -10.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305  -11.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450  -11.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  9  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
 10 11  1  0  0  0  0
  9 10  2  0  0  0  0
 13 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 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  1  1  0  0  0
 12 26  1  1  0  0  0
 11 27  1  6  0  0  0
 14 28  1  1  0  0  0
 19 29  1  6  0  0  0
 23 30  1  1  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038568

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC3=C(NC4=C3C=CC=C4)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H]([C@H](O)C=C3C1CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H35NO3/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/h5-8,14-15,19,21-22,24,28-30H,9-13H2,1-4H3/t15-,19?,21+,22-,24-,26-,27+/m0/s1

> <INCHI_KEY>
FROHWGGMFSFTTA-QBCJVXSESA-N

> <FORMULA>
C27H35NO3

> <MOLECULAR_WEIGHT>
421.5717

> <EXACT_MASS>
421.261693991

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
49.24415615562839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7S,8R,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(22),18,20-pentaen-8-ol

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
4.011299391333333

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.445143826040887

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.597935968804737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.134997325371419

> <JCHEM_POLAR_SURFACE_AREA>
65.48

> <JCHEM_REFRACTIVITY>
122.60909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,8R,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(22),18,20-pentaen-8-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038568
     RDKit          3D
PC-M6
 66 71  0  0  0  0  0  0  0  0999 V2000
    6.6918   -0.2808    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213    0.3445    1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7641    1.8333    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   -0.0848    2.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2693   -0.1394    0.5723 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2375    0.3558    1.3693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1857   -0.5485    1.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9952   -0.2693    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460    0.4010    1.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547   -0.1026    0.0695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5702    1.1032   -0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218   -1.1481   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569   -1.6146   -1.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -2.1090   -1.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -1.0554   -1.4680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6316   -1.4070   -1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759   -0.2494   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0375    0.1468    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4409    1.1660    1.0525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188    1.4480    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120    2.3913    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929    2.4430    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3321    1.5649   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4376    0.6326   -0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1395    0.5714   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.7260    0.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0334   -1.9703    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -0.6356   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084   -0.2567   -1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656    0.2576   -0.8533 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8964    1.6702   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6013   -0.3662    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -1.3111   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8807    0.3031   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231    2.1815   -0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842    2.3594    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    2.1023    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4783   -1.0071    2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842   -1.2498    0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -1.5526    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3331    0.4118    2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838   -1.2078    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0474    1.5145    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.2840    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    1.8184   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183    0.8377   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.6451   -0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2818   -2.0357    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -2.5249   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904   -0.9274   -2.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255   -3.1194   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -2.1777   -3.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0877   -0.1583   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504   -1.3940   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181   -2.3615   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.7238    1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    3.1102    1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6297    3.1786    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3476    1.6406   -0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7381   -0.0721   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -1.8053    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741   -2.8613    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -2.1671    1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.3284   -2.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.0976   -1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672    1.8821   -0.1971 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  6
 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  1
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  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  1
  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  6
 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
 30 65  1  6
 31 66  1  0
M  END

HEADER    PROTEIN                                 29-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JAN-13         0                                  
HETATM    1  C   UNK     0      -7.333 -14.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.667 -15.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.667 -17.050   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.333 -17.820   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.000 -17.050   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.000 -15.510   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -4.666 -17.820   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.999 -14.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.332 -15.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.332 -17.050   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.665 -17.050   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.665 -15.510   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.669 -14.740   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.669 -17.820   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.002 -17.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.002 -15.510   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.669 -19.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.002 -20.130   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.336 -19.360   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.336 -17.820   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.670 -17.050   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.670 -20.130   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.003 -19.360   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.003 -17.820   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.337 -17.050   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -0.665 -13.970   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0      -1.754 -18.139   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.665 -18.590   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       3.336 -20.900   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       7.337 -20.130   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.671 -19.360   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.337 -21.670   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.671 -20.900   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    1    9    5                                                  
CONECT    7    5   10                                                       
CONECT    8    9   12                                                       
CONECT    9    6    8   10                                                  
CONECT   10    7   11    9                                                  
CONECT   11   10   12   14   27                                             
CONECT   12    8   13   11   26                                             
CONECT   13   12   16                                                       
CONECT   14   11   15   17   28                                             
CONECT   15   16   20   14                                                  
CONECT   16   15   13                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22   29                                             
CONECT   20   15   21   19                                                  
CONECT   21   20   24                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   21   25                                                  
CONECT   25   24                                                            
CONECT   26   12                                                            
CONECT   27   11                                                            
CONECT   28   14                                                            
CONECT   29   19                                                            
CONECT   30   23   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

COMPND    HMDB0038568
HETATM    1  C1  UNL     1       6.692  -0.281   0.177  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.621   0.345   1.026  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.764   1.833   0.978  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.824  -0.085   2.337  1.00  0.00           O  
HETATM    5  C4  UNL     1       4.269  -0.139   0.572  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.238   0.356   1.369  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.186  -0.549   1.230  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.995  -0.269   2.068  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.146   0.401   1.402  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.555  -0.103   0.070  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.570   1.103  -0.880  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.422  -1.148  -0.449  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.157  -1.615  -1.825  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.271  -2.109  -1.973  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.170  -1.055  -1.468  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.632  -1.407  -1.364  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.076  -0.249  -0.503  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.038   0.147   0.303  1.00  0.00           C  
HETATM   19  N1  UNL     1      -3.441   1.166   1.053  1.00  0.00           N  
HETATM   20  C17 UNL     1      -4.719   1.448   0.757  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.612   2.391   1.226  1.00  0.00           C  
HETATM   22  C19 UNL     1      -6.893   2.443   0.720  1.00  0.00           C  
HETATM   23  C20 UNL     1      -7.332   1.565  -0.264  1.00  0.00           C  
HETATM   24  C21 UNL     1      -6.438   0.633  -0.723  1.00  0.00           C  
HETATM   25  C22 UNL     1      -5.140   0.571  -0.219  1.00  0.00           C  
HETATM   26  C23 UNL     1      -1.897  -0.726   0.007  1.00  0.00           C  
HETATM   27  C24 UNL     1      -2.033  -1.970   0.842  1.00  0.00           C  
HETATM   28  C25 UNL     1       1.768  -0.636  -0.223  1.00  0.00           C  
HETATM   29  C26 UNL     1       2.608  -0.257  -1.176  1.00  0.00           C  
HETATM   30  C27 UNL     1       3.966   0.258  -0.853  1.00  0.00           C  
HETATM   31  O3  UNL     1       3.896   1.670  -0.863  1.00  0.00           O  
HETATM   32  H1  UNL     1       7.601  -0.366   0.801  1.00  0.00           H  
HETATM   33  H2  UNL     1       6.317  -1.311  -0.092  1.00  0.00           H  
HETATM   34  H3  UNL     1       6.881   0.303  -0.733  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.023   2.182  -0.038  1.00  0.00           H  
HETATM   36  H5  UNL     1       4.884   2.359   1.410  1.00  0.00           H  
HETATM   37  H6  UNL     1       6.635   2.102   1.623  1.00  0.00           H  
HETATM   38  H7  UNL     1       5.478  -1.007   2.457  1.00  0.00           H  
HETATM   39  H8  UNL     1       4.284  -1.250   0.620  1.00  0.00           H  
HETATM   40  H9  UNL     1       2.595  -1.553   1.470  1.00  0.00           H  
HETATM   41  H10 UNL     1       1.333   0.412   2.906  1.00  0.00           H  
HETATM   42  H11 UNL     1       0.684  -1.208   2.617  1.00  0.00           H  
HETATM   43  H12 UNL     1       0.047   1.514   1.421  1.00  0.00           H  
HETATM   44  H13 UNL     1      -1.035   0.284   2.091  1.00  0.00           H  
HETATM   45  H14 UNL     1       0.205   1.818  -0.525  1.00  0.00           H  
HETATM   46  H15 UNL     1      -0.318   0.838  -1.903  1.00  0.00           H  
HETATM   47  H16 UNL     1      -1.537   1.645  -0.801  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.282  -2.036   0.237  1.00  0.00           H  
HETATM   49  H18 UNL     1       0.799  -2.525  -1.990  1.00  0.00           H  
HETATM   50  H19 UNL     1       0.390  -0.927  -2.634  1.00  0.00           H  
HETATM   51  H20 UNL     1      -1.425  -3.119  -1.593  1.00  0.00           H  
HETATM   52  H21 UNL     1      -1.437  -2.178  -3.089  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.088  -0.158  -2.086  1.00  0.00           H  
HETATM   54  H23 UNL     1      -4.150  -1.394  -2.336  1.00  0.00           H  
HETATM   55  H24 UNL     1      -3.818  -2.361  -0.875  1.00  0.00           H  
HETATM   56  H25 UNL     1      -2.922   1.724   1.781  1.00  0.00           H  
HETATM   57  H26 UNL     1      -5.350   3.110   1.990  1.00  0.00           H  
HETATM   58  H27 UNL     1      -7.630   3.179   1.069  1.00  0.00           H  
HETATM   59  H28 UNL     1      -8.348   1.641  -0.634  1.00  0.00           H  
HETATM   60  H29 UNL     1      -6.738  -0.072  -1.491  1.00  0.00           H  
HETATM   61  H30 UNL     1      -1.583  -1.805   1.841  1.00  0.00           H  
HETATM   62  H31 UNL     1      -1.574  -2.861   0.421  1.00  0.00           H  
HETATM   63  H32 UNL     1      -3.115  -2.167   1.030  1.00  0.00           H  
HETATM   64  H33 UNL     1       2.289  -0.328  -2.198  1.00  0.00           H  
HETATM   65  H34 UNL     1       4.729  -0.098  -1.571  1.00  0.00           H  
HETATM   66  H35 UNL     1       3.167   1.882  -0.197  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   65
CONECT   31   66
END

HMDB0038568
     RDKit          3D
PC-M6
 66 71  0  0  0  0  0  0  0  0999 V2000
    6.6918   -0.2808    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213    0.3445    1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7641    1.8333    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8236   -0.0848    2.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2693   -0.1394    0.5723 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2375    0.3558    1.3693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1857   -0.5485    1.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9952   -0.2693    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1460    0.4010    1.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547   -0.1026    0.0695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5702    1.1032   -0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218   -1.1481   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1569   -1.6146   -1.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707   -2.1090   -1.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696   -1.0554   -1.4680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6316   -1.4070   -1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759   -0.2494   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0375    0.1468    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4409    1.1660    1.0525 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7188    1.4480    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120    2.3913    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929    2.4430    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3321    1.5649   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4376    0.6326   -0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1395    0.5714   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -0.7260    0.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0334   -1.9703    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -0.6356   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084   -0.2567   -1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9656    0.2576   -0.8533 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8964    1.6702   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6013   -0.3662    0.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -1.3111   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8807    0.3031   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231    2.1815   -0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8842    2.3594    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6349    2.1023    1.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4783   -1.0071    2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2842   -1.2498    0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -1.5526    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3331    0.4118    2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838   -1.2078    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0474    1.5145    1.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346    0.2840    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    1.8184   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183    0.8377   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.6451   -0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2818   -2.0357    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -2.5249   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904   -0.9274   -2.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4255   -3.1194   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -2.1777   -3.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0877   -0.1583   -2.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1504   -1.3940   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8181   -2.3615   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.7238    1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    3.1102    1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6297    3.1786    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3476    1.6406   -0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7381   -0.0721   -1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -1.8053    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5741   -2.8613    0.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -2.1671    1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.3284   -2.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.0976   -1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672    1.8821   -0.1971 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  6
 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  1
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  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  1
  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  6
 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
 30 65  1  6
 31 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-Hydroxy-13-deoxypaxilline	HMDB
3-Hydroxy-4-deoxypaxilline	HMDB

Chemical Formula

C₂₇H₃₅NO₃

Average Molecular Weight

421.5717

Monoisotopic Molecular Weight

421.261693991

IUPAC Name

(1S,2S,5S,7S,8R,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(22),18,20-pentaen-8-ol

Traditional Name

(1S,2S,5S,7S,8R,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(22),18,20-pentaen-8-ol

CAS Registry Number

133613-76-0

SMILES

[H][C@]12CC3=C(NC4=C3C=CC=C4)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H]([C@H](O)C=C3C1CC2)C(C)(C)O

InChI Identifier

InChI=1S/C27H35NO3/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/h5-8,14-15,19,21-22,24,28-30H,9-13H2,1-4H3/t15-,19?,21+,22-,24-,26-,27+/m0/s1

InChI Key

FROHWGGMFSFTTA-QBCJVXSESA-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: HMDB0038568)

Cellular substructure

Extracellular (HMDB: HMDB0038568)
Membrane (HMDB: HMDB0038568)

Source

Endogenous

Endogenous (HMDB: HMDB0038568)

Exogenous

Food

Food (HMDB: HMDB0038568)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0038568)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038568)

Nutrient

Nutrient (HMDB: HMDB0038568)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038568)

Emulsifier (HMDB: HMDB0038568)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	260 - 263 °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	0.0014 g/L	ALOGPS
logP	4.94	ALOGPS
logP	4.01	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	65.48 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.61 m³·mol⁻¹	ChemAxon
Polarizability	49.24 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]+	193.873	31661259
DarkChem	[M-H]-	189.84	31661259
DeepCCS	[M-2H]-	247.124	30932474
DeepCCS	[M+Na]+	221.412	30932474
AllCCS	[M+H]+	207.0	32859911
AllCCS	[M+H-H2O]+	204.7	32859911
AllCCS	[M+NH4]+	209.1	32859911
AllCCS	[M+Na]+	209.7	32859911
AllCCS	[M-H]-	211.8	32859911
AllCCS	[M+Na-2H]-	212.8	32859911
AllCCS	[M+HCOO]-	214.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PC-M6	[H][C@]12CC3=C(NC4=C3C=CC=C4)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H]([C@H](O)C=C3C1CC2)C(C)(C)O	4444.6	Standard polar	33892256
PC-M6	[H][C@]12CC3=C(NC4=C3C=CC=C4)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H]([C@H](O)C=C3C1CC2)C(C)(C)O	3357.5	Standard non polar	33892256
PC-M6	[H][C@]12CC3=C(NC4=C3C=CC=C4)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H]([C@H](O)C=C3C1CC2)C(C)(C)O	3636.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
PC-M6,1TMS,isomer #1	CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=C[C@H]1O[Si](C)(C)C	3732.1	Semi standard non polar	33892256
PC-M6,1TMS,isomer #2	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=C[C@H]1O	3719.3	Semi standard non polar	33892256
PC-M6,1TMS,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=C[C@H]1O	3729.5	Semi standard non polar	33892256
PC-M6,2TMS,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=C[C@H]1O[Si](C)(C)C	3714.2	Semi standard non polar	33892256
PC-M6,2TMS,isomer #2	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=C[C@H]1O[Si](C)(C)C	3705.6	Semi standard non polar	33892256
PC-M6,2TMS,isomer #3	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=C[C@H]1O	3679.5	Semi standard non polar	33892256
PC-M6,3TMS,isomer #1	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=C[C@H]1O[Si](C)(C)C	3711.6	Semi standard non polar	33892256
PC-M6,3TMS,isomer #1	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=C[C@H]1O[Si](C)(C)C	3562.9	Standard non polar	33892256
PC-M6,1TBDMS,isomer #1	CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)C(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=C[C@H]1O[Si](C)(C)C(C)(C)C	3967.1	Semi standard non polar	33892256
PC-M6,1TBDMS,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([NH]C6=CC=CC=C56)[C@@]43C)C2=C[C@H]1O	3962.0	Semi standard non polar	33892256
PC-M6,1TBDMS,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=C[C@H]1O	3918.6	Semi standard non polar	33892256
PC-M6,2TBDMS,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=C[C@H]1O[Si](C)(C)C(C)(C)C	4148.7	Semi standard non polar	33892256
PC-M6,2TBDMS,isomer #2	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=C[C@H]1O[Si](C)(C)C(C)(C)C	4098.6	Semi standard non polar	33892256
PC-M6,2TBDMS,isomer #3	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=C[C@H]1O	4090.3	Semi standard non polar	33892256
PC-M6,3TBDMS,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(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=C[C@H]1O[Si](C)(C)C(C)(C)C	4282.6	Semi standard non polar	33892256
PC-M6,3TBDMS,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(N([Si](C)(C)C(C)(C)C)C6=CC=CC=C56)[C@@]43C)C2=C[C@H]1O[Si](C)(C)C(C)(C)C	4242.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PC-M6 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6009200000-048e42b42dcdb8fe767c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PC-M6 GC-MS (2 TMS) - 70eV, Positive	splash10-0uel-8415590000-dbd09d8548baa6501002	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PC-M6 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PC-M6 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 - PC-M6 10V, Positive-QTOF	splash10-0fk9-0102900000-46d722db84936d0fc209	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 20V, Positive-QTOF	splash10-0uk9-1366900000-88160431177db06301a7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 40V, Positive-QTOF	splash10-0w29-2296000000-adec62c3fc78dc702810	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 10V, Negative-QTOF	splash10-00di-1001900000-6bb89388b1765346b20c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 20V, Negative-QTOF	splash10-0fk9-4104900000-4d89d185894609a494e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 40V, Negative-QTOF	splash10-0uxr-1119000000-4625000343860c82f3cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 10V, Negative-QTOF	splash10-00di-0000900000-3db7eda26ebe3f32b2d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 20V, Negative-QTOF	splash10-00di-3005900000-1f2d1cbb397367092a1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 40V, Negative-QTOF	splash10-0gb9-4009400000-0f784bc651d9d23c69cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 10V, Positive-QTOF	splash10-00di-0000900000-0f865bca37dcececbd15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 20V, Positive-QTOF	splash10-0fk9-5738900000-71062b785395536e66c4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PC-M6 40V, Positive-QTOF	splash10-053r-9533000000-73085cd1eeeb3b6b7829	2021-09-24	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

FDB017955

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

101590875

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 PC-M6 (HMDB0038568)

MOL for HMDB0038568 (PC-M6)

3D MOL for HMDB0038568 (PC-M6)

3D SDF for HMDB0038568 (PC-M6)

3D-SDF for HMDB0038568 (PC-M6)

PDB for HMDB0038568 (PC-M6)

3D PDB for HMDB0038568 (PC-M6)

SMILES for HMDB0038568 (PC-M6)

INCHI for HMDB0038568 (PC-M6)

Structure for HMDB0038568 (PC-M6)

3D Structure for HMDB0038568 (PC-M6)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra