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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:41:55 UTC

Update Date

2022-11-23 22:13:43 UTC

HMDB ID

HMDB0253310

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hypocrellin A

Description

Hypocrellin A belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. Based on a literature review a significant number of articles have been published on Hypocrellin A. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hypocrellin a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hypocrellin A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1533004171517362D          

 40 45  0  0  0  0            999 V2000
    2.1620    2.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567    1.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    0.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5856    1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2974    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145    1.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039   -0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210   -0.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986   -1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896   -1.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4254   -1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357   -1.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5737   -2.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046   -3.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -3.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764   -3.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815   -3.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9752   -3.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -4.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4854   -4.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -2.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301   -2.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642   -3.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -4.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -2.8828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4236   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118   -1.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053   -1.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278    1.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461   -0.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -0.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -1.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525   -1.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1407   -1.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
  7 37  2  0  0  0  0
 37 38  1  0  0  0  0
 13 38  2  0  0  0  0
 38 39  1  0  0  0  0
 22 39  2  0  0  0  0
 39 40  1  0  0  0  0
 28 40  2  0  0  0  0
 35 40  1  0  0  0  0
M  END

HMDB0253310
     RDKit          3D
hypocrellin a
 66 71  0  0  0  0  0  0  0  0999 V2000
   -3.0045    4.3347   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    3.7913    1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    3.0517    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    3.6797    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    5.0229    0.8119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    2.8585    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    3.5392    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    4.7916    0.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    2.8552    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344    1.4547   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7543    0.9097   -0.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375    1.7356   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.7859   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.5986   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272   -1.3128   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -0.8399   -0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8093   -1.6985   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821   -2.7072   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -3.3607   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2151   -4.6081   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -2.6433   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -3.3913    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426   -4.7401   -0.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730   -2.7103    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -3.5241    0.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -4.0103    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -1.3353    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -0.5744    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011    0.8329    0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    1.6890    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    1.3217    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417    0.3218    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8237   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    0.3200    0.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.0539    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3394   -1.7526   -0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8080   -1.8672   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -2.2210   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.4752    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0517   -1.2511    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800    5.4116   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8474    3.7989   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    4.2786    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7302    5.7889    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    3.3791   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8126    2.5029   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467    2.2473    0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8111    1.1557   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6003   -2.1993   -1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0017   -2.3977    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6881   -1.0776   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898   -3.2595   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -5.4780   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -5.1254    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785   -3.4999    2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9544   -3.8244    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010    0.9150    2.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368    2.2012    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    1.4768   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747    0.0248   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.4627   -1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598    0.1837    1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -1.5840    1.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2833   -1.8893   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764   -2.8427   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -1.0438   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 29 39  1  0
 28 40  1  0
 30  3  1  0
 39  6  2  0
 39 13  1  0
 40 14  1  0
 40 21  2  0
 35 27  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  9 45  1  0
 12 46  1  0
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 12 48  1  0
 17 49  1  0
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 18 52  1  0
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 31 57  1  0
 31 58  1  0
 33 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 37 64  1  0
 37 65  1  0
 37 66  1  0
M  END

  Mrv1533004171517362D          

 40 45  0  0  0  0            999 V2000
    2.1620    2.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567    1.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    0.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5856    1.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2974    0.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145    1.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2921   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039   -0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210   -0.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986   -1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896   -1.7113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4254   -1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5737   -2.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1046   -3.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -3.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764   -3.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2349   -4.2128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1301   -2.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1642   -3.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1407   -1.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
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  8 10  2  0  0  0  0
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 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
  7 37  2  0  0  0  0
 37 38  1  0  0  0  0
 13 38  2  0  0  0  0
 38 39  1  0  0  0  0
 22 39  2  0  0  0  0
 39 40  1  0  0  0  0
 28 40  2  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253310

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)C2=C3C1=C1C(OC)=CC(=O)C4=C1C1=C(C(C(C)=O)C(C)(O)CC(C(OC)=C2O)=C31)C(OC)=C4O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,34-36H,9H2,1-6H3

> <INCHI_KEY>
VANSZAOQCMTTPB-UHFFFAOYSA-N

> <FORMULA>
C30H26O10

> <MOLECULAR_WEIGHT>
546.528

> <EXACT_MASS>
546.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.130806520961535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.5457756676666676

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.741481393330778

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.138765067581505

> <JCHEM_PKA_STRONGEST_BASIC>
3.6528176008479503

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
147.4815

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253310
     RDKit          3D
hypocrellin a
 66 71  0  0  0  0  0  0  0  0999 V2000
   -3.0045    4.3347   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    3.7913    1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    3.0517    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    3.6797    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    5.0229    0.8119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    2.8585    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    3.5392    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    4.7916    0.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    2.8552    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344    1.4547   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7543    0.9097   -0.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375    1.7356   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.7859   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.5986   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272   -1.3128   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -0.8399   -0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8093   -1.6985   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821   -2.7072   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -3.3607   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2151   -4.6081   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -2.6433   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -3.3913    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426   -4.7401   -0.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730   -2.7103    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -3.5241    0.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -4.0103    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -1.3353    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -0.5744    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011    0.8329    0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    1.6890    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    1.3217    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417    0.3218    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8237   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    0.3200    0.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.0539    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3394   -1.7526   -0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8080   -1.8672   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -2.2210   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.4752    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0517   -1.2511    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800    5.4116   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8474    3.7989   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    4.2786    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7302    5.7889    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    3.3791   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8126    2.5029   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467    2.2473    0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8111    1.1557   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6003   -2.1993   -1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0017   -2.3977    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6881   -1.0776   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898   -3.2595   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -5.4780   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -5.1254    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785   -3.4999    2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9544   -3.8244    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010    0.9150    2.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368    2.2012    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    1.4768   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747    0.0248   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.4627   -1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598    0.1837    1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -1.5840    1.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2833   -1.8893   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764   -2.8427   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -1.0438   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 29 39  1  0
 28 40  1  0
 30  3  1  0
 39  6  2  0
 39 13  1  0
 40 14  1  0
 40 21  2  0
 35 27  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  9 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 31 57  1  0
 31 58  1  0
 33 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 37 64  1  0
 37 65  1  0
 37 66  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.036   3.841   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.026   2.301   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.355   1.523   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.693   2.284   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.022   1.505   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.360   2.267   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.012  -0.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.341  -0.813   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.679  -0.052   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.331  -2.353   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.621  -3.194   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.994  -2.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.093  -2.908   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.538  -4.382   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.662  -5.649   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.092  -6.221   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.423  -7.170   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.126  -5.754   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.554  -7.184   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.172  -7.864   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.506  -8.394   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.085  -4.618   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.976  -5.399   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.040  -6.937   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.739  -7.762   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.647  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.309  -5.381   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.657  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.329  -2.301   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.010  -3.063   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.339  -0.761   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.677  -0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.687   1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.359   2.319   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.006  -0.779   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.345  -0.017   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.673  -0.796   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.663  -2.336   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.325  -3.097   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.996  -2.319   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   38                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   39                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   40                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   40                                                  
CONECT   36   35    3   37                                                  
CONECT   37   36    7   38                                                  
CONECT   38   37   13   39                                                  
CONECT   39   38   22   40                                                  
CONECT   40   39   28   35                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

COMPND    HMDB0253310
HETATM    1  C1  UNL     1      -3.004   4.335  -0.023  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.222   3.791   1.051  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.071   3.052   0.782  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.136   3.680   0.666  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.218   5.023   0.812  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.235   2.858   0.397  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.430   3.539   0.303  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.550   4.792   0.433  1.00  0.00           O  
HETATM    9  C6  UNL     1       3.563   2.855   0.056  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.534   1.455  -0.105  1.00  0.00           C  
HETATM   11  O4  UNL     1       4.754   0.910  -0.347  1.00  0.00           O  
HETATM   12  C8  UNL     1       5.938   1.736  -0.423  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.351   0.786  -0.011  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.294  -0.599  -0.125  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.427  -1.313  -0.361  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.688  -0.840  -0.524  1.00  0.00           O  
HETATM   17  C12 UNL     1       5.809  -1.699  -0.772  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.382  -2.707  -0.464  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.206  -3.361  -0.331  1.00  0.00           C  
HETATM   20  O6  UNL     1       2.215  -4.608  -0.431  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.063  -2.643  -0.095  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.102  -3.391   0.000  1.00  0.00           C  
HETATM   23  O7  UNL     1      -0.143  -4.740  -0.096  1.00  0.00           O  
HETATM   24  C17 UNL     1      -1.273  -2.710   0.205  1.00  0.00           C  
HETATM   25  O8  UNL     1      -2.433  -3.524   0.302  1.00  0.00           O  
HETATM   26  C18 UNL     1      -2.847  -4.010   1.541  1.00  0.00           C  
HETATM   27  C19 UNL     1      -1.318  -1.335   0.314  1.00  0.00           C  
HETATM   28  C20 UNL     1      -0.168  -0.574   0.233  1.00  0.00           C  
HETATM   29  C21 UNL     1      -0.101   0.833   0.360  1.00  0.00           C  
HETATM   30  C22 UNL     1      -1.175   1.689   0.637  1.00  0.00           C  
HETATM   31  C23 UNL     1      -2.572   1.322   0.996  1.00  0.00           C  
HETATM   32  C24 UNL     1      -3.242   0.322   0.194  1.00  0.00           C  
HETATM   33  C25 UNL     1      -3.290   0.824  -1.241  1.00  0.00           C  
HETATM   34  O9  UNL     1      -4.604   0.320   0.602  1.00  0.00           O  
HETATM   35  C26 UNL     1      -2.768  -1.054   0.326  1.00  0.00           C  
HETATM   36  C27 UNL     1      -3.339  -1.753  -0.919  1.00  0.00           C  
HETATM   37  C28 UNL     1      -4.808  -1.867  -1.089  1.00  0.00           C  
HETATM   38  O10 UNL     1      -2.628  -2.221  -1.778  1.00  0.00           O  
HETATM   39  C29 UNL     1       1.144   1.475   0.245  1.00  0.00           C  
HETATM   40  C30 UNL     1       1.052  -1.251   0.018  1.00  0.00           C  
HETATM   41  H1  UNL     1      -2.780   5.412  -0.164  1.00  0.00           H  
HETATM   42  H2  UNL     1      -2.847   3.799  -0.963  1.00  0.00           H  
HETATM   43  H3  UNL     1      -4.073   4.279   0.268  1.00  0.00           H  
HETATM   44  H4  UNL     1       0.730   5.789   0.821  1.00  0.00           H  
HETATM   45  H5  UNL     1       4.522   3.379  -0.021  1.00  0.00           H  
HETATM   46  H6  UNL     1       5.813   2.503  -1.234  1.00  0.00           H  
HETATM   47  H7  UNL     1       6.047   2.247   0.565  1.00  0.00           H  
HETATM   48  H8  UNL     1       6.811   1.156  -0.696  1.00  0.00           H  
HETATM   49  H9  UNL     1       5.600  -2.199  -1.763  1.00  0.00           H  
HETATM   50  H10 UNL     1       6.002  -2.398   0.041  1.00  0.00           H  
HETATM   51  H11 UNL     1       6.688  -1.078  -0.936  1.00  0.00           H  
HETATM   52  H12 UNL     1       4.290  -3.260  -0.649  1.00  0.00           H  
HETATM   53  H13 UNL     1       0.402  -5.478  -0.221  1.00  0.00           H  
HETATM   54  H14 UNL     1      -2.751  -5.125   1.624  1.00  0.00           H  
HETATM   55  H15 UNL     1      -2.378  -3.500   2.414  1.00  0.00           H  
HETATM   56  H16 UNL     1      -3.954  -3.824   1.658  1.00  0.00           H  
HETATM   57  H17 UNL     1      -2.501   0.915   2.061  1.00  0.00           H  
HETATM   58  H18 UNL     1      -3.237   2.201   1.125  1.00  0.00           H  
HETATM   59  H19 UNL     1      -2.403   1.477  -1.377  1.00  0.00           H  
HETATM   60  H20 UNL     1      -3.175   0.025  -1.990  1.00  0.00           H  
HETATM   61  H21 UNL     1      -4.176   1.463  -1.421  1.00  0.00           H  
HETATM   62  H22 UNL     1      -4.660   0.184   1.585  1.00  0.00           H  
HETATM   63  H23 UNL     1      -3.210  -1.584   1.176  1.00  0.00           H  
HETATM   64  H24 UNL     1      -5.283  -1.889  -0.067  1.00  0.00           H  
HETATM   65  H25 UNL     1      -5.076  -2.843  -1.556  1.00  0.00           H  
HETATM   66  H26 UNL     1      -5.282  -1.044  -1.619  1.00  0.00           H  
CONECT    1    2   41   42   43
CONECT    2    3
CONECT    3    4    4   30
CONECT    4    5    6
CONECT    5   44
CONECT    6    7   39   39
CONECT    7    8    8    9
CONECT    9   10   10   45
CONECT   10   11   13
CONECT   11   12
CONECT   12   46   47   48
CONECT   13   14   14   39
CONECT   14   15   40
CONECT   15   16   18   18
CONECT   16   17
CONECT   17   49   50   51
CONECT   18   19   52
CONECT   19   20   20   21
CONECT   21   22   40   40
CONECT   22   23   24   24
CONECT   23   53
CONECT   24   25   27
CONECT   25   26
CONECT   26   54   55   56
CONECT   27   28   28   35
CONECT   28   29   40
CONECT   29   30   30   39
CONECT   30   31
CONECT   31   32   57   58
CONECT   32   33   34   35
CONECT   33   59   60   61
CONECT   34   62
CONECT   35   36   63
CONECT   36   37   38   38
CONECT   37   64   65   66
END

HMDB0253310
     RDKit          3D
hypocrellin a
 66 71  0  0  0  0  0  0  0  0999 V2000
   -3.0045    4.3347   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    3.7913    1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0712    3.0517    0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    3.6797    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    5.0229    0.8119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    2.8585    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    3.5392    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    4.7916    0.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5633    2.8552    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344    1.4547   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7543    0.9097   -0.3473 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375    1.7356   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.7859   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.5986   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272   -1.3128   -0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -0.8399   -0.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8093   -1.6985   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821   -2.7072   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2057   -3.3607   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2151   -4.6081   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -2.6433   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015   -3.3913    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426   -4.7401   -0.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730   -2.7103    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -3.5241    0.3022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -4.0103    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -1.3353    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -0.5744    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011    0.8329    0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747    1.6890    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5721    1.3217    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417    0.3218    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8237   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044    0.3200    0.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.0539    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3394   -1.7526   -0.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8080   -1.8672   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -2.2210   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.4752    0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0517   -1.2511    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7800    5.4116   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8474    3.7989   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    4.2786    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7302    5.7889    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    3.3791   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8126    2.5029   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0467    2.2473    0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8111    1.1557   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6003   -2.1993   -1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0017   -2.3977    0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6881   -1.0776   -0.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2898   -3.2595   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -5.4780   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -5.1254    1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3785   -3.4999    2.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9544   -3.8244    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010    0.9150    2.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2368    2.2012    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    1.4768   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747    0.0248   -1.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.4627   -1.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598    0.1837    1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098   -1.5840    1.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2833   -1.8893   -0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764   -2.8427   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -1.0438   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 29 39  1  0
 28 40  1  0
 30  3  1  0
 39  6  2  0
 39 13  1  0
 40 14  1  0
 40 21  2  0
 35 27  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
  9 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 31 57  1  0
 31 58  1  0
 33 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 37 64  1  0
 37 65  1  0
 37 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hypocrellin	HMDB
1-Acetyl-2,3-dihydro-2,6,11-trihydroxy-4,8,9,13-tetramethoxy-2-methyl-1H-cyclohepta(ghi)perylene-5,12-dione	MeSH

Chemical Formula

C₃₀H₂₆O₁₀

Average Molecular Weight

546.528

Monoisotopic Molecular Weight

546.152597037

IUPAC Name

12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

Traditional Name

12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C3C1=C1C(OC)=CC(=O)C4=C1C1=C(C(C(C)=O)C(C)(O)CC(C(OC)=C2O)=C31)C(OC)=C4O

InChI Identifier

InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,34-36H,9H2,1-6H3

InChI Key

VANSZAOQCMTTPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Phenanthrol
Anthracene
Phenanthrene
1-naphthol
2-naphthol
Anisole
Alkyl aryl ether
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Ketone
Polyol
Ether
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.17	ALOGPS
logP	2.55	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	3.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	147.48 m³·mol⁻¹	ChemAxon
Polarizability	55.13 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	253.887	30932474
DeepCCS	[M+Na]+	228.597	30932474
AllCCS	[M+H]+	220.9	32859911
AllCCS	[M+H-H2O]+	219.3	32859911
AllCCS	[M+NH4]+	222.4	32859911
AllCCS	[M+Na]+	222.9	32859911
AllCCS	[M-H]-	230.6	32859911
AllCCS	[M+Na-2H]-	231.5	32859911
AllCCS	[M+HCOO]-	232.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
hypocrellin a	COC1=CC(=O)C2=C3C1=C1C(OC)=CC(=O)C4=C1C1=C(C(C(C)=O)C(C)(O)CC(C(OC)=C2O)=C31)C(OC)=C4O	6514.8	Standard polar	33892256
hypocrellin a	COC1=CC(=O)C2=C3C1=C1C(OC)=CC(=O)C4=C1C1=C(C(C(C)=O)C(C)(O)CC(C(OC)=C2O)=C31)C(OC)=C4O	4288.2	Standard non polar	33892256
hypocrellin a	COC1=CC(=O)C2=C3C1=C1C(OC)=CC(=O)C4=C1C1=C(C(C(C)=O)C(C)(O)CC(C(OC)=C2O)=C31)C(OC)=C4O	4934.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
hypocrellin a,4TMS,isomer #1	COC1=C(O[Si](C)(C)C)C2=C3C(=C4C(OC)=CC(=O)C5=C4C4=C(C(=C(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC1=C43)C(OC)=C5O[Si](C)(C)C)C(OC)=CC2=O	4202.1	Semi standard non polar	33892256
hypocrellin a,4TMS,isomer #1	COC1=C(O[Si](C)(C)C)C2=C3C(=C4C(OC)=CC(=O)C5=C4C4=C(C(=C(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC1=C43)C(OC)=C5O[Si](C)(C)C)C(OC)=CC2=O	4212.6	Standard non polar	33892256
hypocrellin a,4TMS,isomer #1	COC1=C(O[Si](C)(C)C)C2=C3C(=C4C(OC)=CC(=O)C5=C4C4=C(C(=C(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC1=C43)C(OC)=C5O[Si](C)(C)C)C(OC)=CC2=O	4809.7	Standard polar	33892256
hypocrellin a,4TMS,isomer #2	C=C(O[Si](C)(C)C)C1C2=C(OC)C(O[Si](C)(C)C)=C3C(=O)C=C(OC)C4=C3C2=C2C(=C(OC)C(O[Si](C)(C)C)=C3C(=O)C=C(OC)C4=C32)CC1(C)O[Si](C)(C)C	4235.7	Semi standard non polar	33892256
hypocrellin a,4TMS,isomer #2	C=C(O[Si](C)(C)C)C1C2=C(OC)C(O[Si](C)(C)C)=C3C(=O)C=C(OC)C4=C3C2=C2C(=C(OC)C(O[Si](C)(C)C)=C3C(=O)C=C(OC)C4=C32)CC1(C)O[Si](C)(C)C	4126.0	Standard non polar	33892256
hypocrellin a,4TMS,isomer #2	C=C(O[Si](C)(C)C)C1C2=C(OC)C(O[Si](C)(C)C)=C3C(=O)C=C(OC)C4=C3C2=C2C(=C(OC)C(O[Si](C)(C)C)=C3C(=O)C=C(OC)C4=C32)CC1(C)O[Si](C)(C)C	4897.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hypocrellin A GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-04	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 - Hypocrellin A 10V, Positive-QTOF	splash10-004j-0000090000-1391ac38ed94793de5b8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypocrellin A 20V, Positive-QTOF	splash10-004r-0000490000-90d062720861fdb70911	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypocrellin A 40V, Positive-QTOF	splash10-01wr-0000920000-723eb2234323025cf85c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypocrellin A 10V, Negative-QTOF	splash10-0002-0000090000-2d36ed6c12bf2b7d0ef2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypocrellin A 20V, Negative-QTOF	splash10-0002-0000090000-7a3410b819ce9f90c135	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hypocrellin A 40V, Negative-QTOF	splash10-0002-0000950000-a3c33c580b4db8cc4942	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3536

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3664

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Hypocrellin A (HMDB0253310)

MOL for HMDB0253310 (Hypocrellin A)

3D MOL for HMDB0253310 (Hypocrellin A)

3D SDF for HMDB0253310 (Hypocrellin A)

3D-SDF for HMDB0253310 (Hypocrellin A)

PDB for HMDB0253310 (Hypocrellin A)

3D PDB for HMDB0253310 (Hypocrellin A)

SMILES for HMDB0253310 (Hypocrellin A)

INCHI for HMDB0253310 (Hypocrellin A)

Structure for HMDB0253310 (Hypocrellin A)

3D Structure for HMDB0253310 (Hypocrellin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra