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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:59:09 UTC

Update Date

2022-03-07 02:54:01 UTC

HMDB ID

HMDB0034191

Secondary Accession Numbers

HMDB34191

Metabolite Identification

Common Name

Withaperuvin B

Description

Withaperuvin B belongs to the class of organic compounds known as withanolides and derivatives. These are C28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22, and 26 to form a lactone ring. Withaperuvin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Withaperuvin is found in fruits. Withaperuvin is a constituent of Physalis peruviana (Cape gooseberry).

Structure

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

  Mrv1652303062020442D          

 39 43  0  0  0  0            999 V2000
 9997.8821 9999.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8821 9996.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9996.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9998.1353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3069 9999.3700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1697 9996.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1697 9999.7853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1689 9998.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4544 9998.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4544 9997.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1689 9997.3048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8834 9997.7172    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8834 9998.5423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5942 9998.9559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5942 9997.3059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3087 9997.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9998.5434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.306910000.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5924 9999.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019310000.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.906710001.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.319410001.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.875710002.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.875710001.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161210001.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.446710001.4455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.446710002.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.161210002.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.445510000.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.731910001.8567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10003.592610002.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161210003.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.592610001.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.731910001.0317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.733210000.2020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4476 9999.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4476 9998.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0187 9998.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0187 9999.7895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
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 18 19  1  0  0  0  0
 15  3  1  6  0  0  0
 19 14  1  0  0  0  0
 14  4  1  6  0  0  0
 17  5  1  1  0  0  0
 11  6  1  1  0  0  0
  8  7  2  0  0  0  0
 14 13  1  0  0  0  0
 13  1  1  1  0  0  0
 12 15  1  0  0  0  0
 12  2  1  1  0  0  0
 28 32  2  0  0  0  0
 23 31  1  0  0  0  0
 24 33  1  0  0  0  0
 26 30  1  1  0  0  0
 34 26  1  0  0  0  0
 28 27  1  0  0  0  0
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 28 23  1  0  0  0  0
 26 25  1  0  0  0  0
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 34 22  1  6  0  0  0
 34 21  1  1  0  0  0
 35 36  1  0  0  0  0
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 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 17 38  1  0  0  0  0
 39 20  1  1  0  0  0
 18 39  1  0  0  0  0
 35 29  1  1  0  0  0
 35 34  1  0  0  0  0
M  END

HMDB0034191
     RDKit          3D
Withaperuvin B
 74 78  0  0  0  0  0  0  0  0999 V2000
    6.4738    1.0412   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5551   -0.1283   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -0.5777    1.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3838    0.0512    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -1.6705    1.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -2.0989    2.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306   -2.2266    0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908   -1.6871   -0.6769 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2623   -1.2077   -1.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4439   -2.4459   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271   -0.6683   -2.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.1444   -0.1252 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805    0.8540   -0.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.5419    1.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -0.2452    1.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    0.3492    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.8442    0.5340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5509    0.8303    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8890    1.4485    1.4733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7168    1.5241    2.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.6590    0.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7475    1.4010    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0959   -0.6070    1.0497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9706   -0.2673    2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8504   -1.4399    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5731   -1.3658   -1.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -0.4788   -1.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -0.5488   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7239    1.7958   -1.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957   -0.0905   -0.4288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5578   -0.5748   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799    0.2045   -1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    0.5562   -0.4802 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7857    2.0779   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -0.7410   -1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635    1.8886    0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3386    1.3017   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5052    0.6441   -0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7403    0.6711    2.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161    0.7000    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8755   -0.7408    2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -2.6081   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990   -2.5812   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176   -2.5370   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0670   -3.3833   -1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298   -1.3758   -2.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523    1.4320   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -0.0060    2.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941   -1.6250    1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.5266    2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    1.8492    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007   -0.1915    2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.4883    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    2.4854    1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493    2.4481    2.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058    2.3392    0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026   -1.2388    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8992   -0.8610    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6276   -2.1048    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -2.0013   -1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7182    2.0041   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    2.6392   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219    1.7010   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -0.9789    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441   -0.5782   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -1.6413   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -0.2891   -2.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634    1.1636   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644    2.6334   -0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374    2.4161    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5392   -1.2818   -1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  1
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 21 22  1  6
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 36  2  1  0
 34 12  1  0
 34 16  1  0
 31 17  1  0
 29 21  1  0
  1 37  1  0
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  4 40  1  0
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 11 47  1  0
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 32 67  1  0
 33 68  1  0
 33 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  1  0
M  END

  Mrv1652303062020442D          

 39 43  0  0  0  0            999 V2000
 9997.8821 9999.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8821 9996.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9996.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9998.1353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3069 9999.3700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1697 9996.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1697 9999.7853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1689 9998.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4544 9998.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4544 9997.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1689 9997.3048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8834 9997.7172    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8834 9998.5423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5942 9998.9559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5942 9997.3059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3087 9997.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9998.5434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.306910000.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5924 9999.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019310000.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10002.875710002.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10002.161210001.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.446710001.4455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.446710002.2706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10001.445510000.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10003.592610002.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.161210003.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.592610001.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.731910001.0317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.733210000.2020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4476 9999.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10000.0187 9998.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0187 9999.7895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
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 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 15  3  1  6  0  0  0
 19 14  1  0  0  0  0
 14  4  1  6  0  0  0
 17  5  1  1  0  0  0
 11  6  1  1  0  0  0
  8  7  2  0  0  0  0
 14 13  1  0  0  0  0
 13  1  1  1  0  0  0
 12 15  1  0  0  0  0
 12  2  1  1  0  0  0
 28 32  2  0  0  0  0
 23 31  1  0  0  0  0
 24 33  1  0  0  0  0
 26 30  1  1  0  0  0
 34 26  1  0  0  0  0
 28 27  1  0  0  0  0
 27 26  1  0  0  0  0
 28 23  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  2  0  0  0  0
 34 22  1  6  0  0  0
 34 21  1  1  0  0  0
 35 36  1  0  0  0  0
 35 39  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 17 38  1  0  0  0  0
 39 20  1  1  0  0  0
 18 39  1  0  0  0  0
 35 29  1  1  0  0  0
 35 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034191

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC(C)=C(C)C(=O)O1)[C@](C)(O)[C@]1(O)CC=C2[C@]3([H])C[C@H](O)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O8/c1-14-12-22(36-23(32)15(14)2)26(5,33)27(34)11-9-17-16-13-21(31)28(35)20(30)7-6-19(29)25(28,4)18(16)8-10-24(17,27)3/h6-7,9,16,18,20-22,30-31,33-35H,8,10-13H2,1-5H3/t16-,18-,20-,21-,22+,24-,25-,26-,27-,28+/m0/s1

> <INCHI_KEY>
IHIHXNCZVACPKN-WOONZQPCSA-N

> <FORMULA>
C28H38O8

> <MOLECULAR_WEIGHT>
502.604

> <EXACT_MASS>
502.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.64380305436242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1S)-1-hydroxy-1-[(1S,2R,6S,7S,8S,10R,14S,15S)-6,7,8,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-14-yl]ethyl]-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.2886776073333326

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.830783469211053

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.167455738409158

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2981285761591277

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
132.52829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1S)-1-hydroxy-1-[(1S,2R,6S,7S,8S,10R,14S,15S)-6,7,8,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-14-yl]ethyl]-3,4-dimethyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034191
     RDKit          3D
Withaperuvin B
 74 78  0  0  0  0  0  0  0  0999 V2000
    6.4738    1.0412   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5551   -0.1283   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -0.5777    1.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3838    0.0512    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -1.6705    1.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -2.0989    2.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306   -2.2266    0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908   -1.6871   -0.6769 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2623   -1.2077   -1.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4439   -2.4459   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271   -0.6683   -2.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.1444   -0.1252 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805    0.8540   -0.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.5419    1.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -0.2452    1.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    0.3492    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.8442    0.5340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5509    0.8303    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8890    1.4485    1.4733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7168    1.5241    2.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.6590    0.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7475    1.4010    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0959   -0.6070    1.0497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9706   -0.2673    2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8504   -1.4399    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5731   -1.3658   -1.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -0.4788   -1.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -0.5488   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974    0.4685   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7239    1.7958   -1.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957   -0.0905   -0.4288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5578   -0.5748   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799    0.2045   -1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    0.5562   -0.4802 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7857    2.0779   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -0.7410   -1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635    1.8886    0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3386    1.3017   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5052    0.6441   -0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7403    0.6711    2.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161    0.7000    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8755   -0.7408    2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -2.6081   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990   -2.5812   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176   -2.5370   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0670   -3.3833   -1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298   -1.3758   -2.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523    1.4320   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -0.0060    2.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941   -1.6250    1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.5266    2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    1.8492    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007   -0.1915    2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.4883    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    2.4854    1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493    2.4481    2.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058    2.3392    0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026   -1.2388    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8992   -0.8610    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6276   -2.1048    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -2.0013   -1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7182    2.0041   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    2.6392   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219    1.7010   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -0.9789    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441   -0.5782   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -1.6413   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -0.2891   -2.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634    1.1636   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644    2.6334   -0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374    2.4161    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    2.3532   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4005    0.0432   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392   -1.2818   -1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
  8 36  1  0
 36  2  1  0
 34 12  1  0
 34 16  1  0
 31 17  1  0
 29 21  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  8 43  1  6
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 17 52  1  6
 18 53  1  0
 18 54  1  0
 19 55  1  6
 20 56  1  0
 22 57  1  0
 23 58  1  1
 24 59  1  0
 25 60  1  0
 26 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  1
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8662.7138665.491   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8662.7138660.859   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8664.0438660.083   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8664.0438663.186   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8665.3738665.491   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0    8661.3838660.083   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.3838666.266   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8661.3828664.716   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8660.0488663.946   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.0488662.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.3828661.636   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.7168662.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7168663.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0438664.718   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.0438661.638   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3768662.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3768663.948   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.3738667.042   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.0398666.272   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.7038667.819   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8666.4938668.593   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8667.2638669.932   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8672.0358670.905   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.0358669.365   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8670.7018668.595   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.3678669.365   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8669.3678670.905   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0    8670.7018671.675   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    8669.3658667.826   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0    8668.0338670.133   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0    8673.3738671.673   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8670.7018673.213   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8673.3738668.593   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8668.0338668.593   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8668.0358667.044   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8669.3698666.274   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8669.3698664.734   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8666.7028664.734   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8666.7028666.274   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   12                                                            
CONECT    3   15                                                            
CONECT    4   14                                                            
CONECT    5   17                                                            
CONECT    6   11                                                            
CONECT    7    8                                                            
CONECT    8    9   13    7                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11   13   15    2                                             
CONECT   13    8   12   14    1                                             
CONECT   14   17   19    4   13                                             
CONECT   15   16    3   12                                                  
CONECT   16   15   17                                                       
CONECT   17   14   16    5   38                                             
CONECT   18   19   39                                                       
CONECT   19   18   14                                                       
CONECT   20   39                                                            
CONECT   21   34                                                            
CONECT   22   34                                                            
CONECT   23   31   28   24                                                  
CONECT   24   33   25   23                                                  
CONECT   25   26   24                                                       
CONECT   26   30   34   27   25                                             
CONECT   27   28   26                                                       
CONECT   28   32   27   23                                                  
CONECT   29   35                                                            
CONECT   30   26                                                            
CONECT   31   23                                                            
CONECT   32   28                                                            
CONECT   33   24                                                            
CONECT   34   26   22   21   35                                             
CONECT   35   36   39   29   34                                             
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   17                                                  
CONECT   39   35   38   20   18                                             
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

COMPND    HMDB0034191
HETATM    1  C1  UNL     1       6.474   1.041  -0.313  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.555  -0.128  -0.013  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.527  -0.578   1.223  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.384   0.051   2.297  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.640  -1.671   1.567  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.621  -2.099   2.757  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.831  -2.227   0.590  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.691  -1.687  -0.677  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.262  -1.208  -1.011  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.444  -2.446  -1.136  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.427  -0.668  -2.314  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.756  -0.144  -0.125  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.780   0.854  -0.124  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.667  -0.542   1.331  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.236  -0.245   1.695  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.376   0.349   0.702  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.753   0.844   0.534  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.551   0.830   1.819  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.889   1.448   1.473  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.717   1.524   2.590  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.637   0.659   0.425  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.748   1.401   0.060  1.00  0.00           O  
HETATM   23  C17 UNL     1      -5.096  -0.607   1.050  1.00  0.00           C  
HETATM   24  O7  UNL     1      -5.971  -0.267   2.086  1.00  0.00           O  
HETATM   25  C18 UNL     1      -5.850  -1.440   0.092  1.00  0.00           C  
HETATM   26  C19 UNL     1      -5.573  -1.366  -1.184  1.00  0.00           C  
HETATM   27  C20 UNL     1      -4.534  -0.479  -1.696  1.00  0.00           C  
HETATM   28  O8  UNL     1      -4.283  -0.549  -2.921  1.00  0.00           O  
HETATM   29  C21 UNL     1      -3.797   0.469  -0.835  1.00  0.00           C  
HETATM   30  C22 UNL     1      -3.724   1.796  -1.538  1.00  0.00           C  
HETATM   31  C23 UNL     1      -2.496  -0.091  -0.429  1.00  0.00           C  
HETATM   32  C24 UNL     1      -1.558  -0.575  -1.445  1.00  0.00           C  
HETATM   33  C25 UNL     1      -0.280   0.204  -1.660  1.00  0.00           C  
HETATM   34  C26 UNL     1       0.508   0.556  -0.480  1.00  0.00           C  
HETATM   35  C27 UNL     1       0.786   2.078  -0.538  1.00  0.00           C  
HETATM   36  C28 UNL     1       4.758  -0.741  -1.078  1.00  0.00           C  
HETATM   37  H1  UNL     1       6.263   1.889   0.363  1.00  0.00           H  
HETATM   38  H2  UNL     1       6.339   1.302  -1.381  1.00  0.00           H  
HETATM   39  H3  UNL     1       7.505   0.644  -0.217  1.00  0.00           H  
HETATM   40  H4  UNL     1       5.740   0.671   2.948  1.00  0.00           H  
HETATM   41  H5  UNL     1       7.116   0.700   1.785  1.00  0.00           H  
HETATM   42  H6  UNL     1       6.876  -0.741   2.905  1.00  0.00           H  
HETATM   43  H7  UNL     1       3.862  -2.608  -1.365  1.00  0.00           H  
HETATM   44  H8  UNL     1       0.699  -2.581  -0.327  1.00  0.00           H  
HETATM   45  H9  UNL     1       0.918  -2.537  -2.113  1.00  0.00           H  
HETATM   46  H10 UNL     1       2.067  -3.383  -1.090  1.00  0.00           H  
HETATM   47  H11 UNL     1       2.730  -1.376  -2.938  1.00  0.00           H  
HETATM   48  H12 UNL     1       2.752   1.432  -0.891  1.00  0.00           H  
HETATM   49  H13 UNL     1       2.356  -0.006   2.000  1.00  0.00           H  
HETATM   50  H14 UNL     1       1.794  -1.625   1.514  1.00  0.00           H  
HETATM   51  H15 UNL     1      -0.146  -0.527   2.679  1.00  0.00           H  
HETATM   52  H16 UNL     1      -1.851   1.849   0.131  1.00  0.00           H  
HETATM   53  H17 UNL     1      -2.701  -0.192   2.154  1.00  0.00           H  
HETATM   54  H18 UNL     1      -2.063   1.488   2.560  1.00  0.00           H  
HETATM   55  H19 UNL     1      -3.783   2.485   1.094  1.00  0.00           H  
HETATM   56  H20 UNL     1      -4.949   2.448   2.844  1.00  0.00           H  
HETATM   57  H21 UNL     1      -5.706   2.339   0.395  1.00  0.00           H  
HETATM   58  H22 UNL     1      -4.303  -1.239   1.499  1.00  0.00           H  
HETATM   59  H23 UNL     1      -5.899  -0.861   2.854  1.00  0.00           H  
HETATM   60  H24 UNL     1      -6.628  -2.105   0.461  1.00  0.00           H  
HETATM   61  H25 UNL     1      -6.157  -2.001  -1.860  1.00  0.00           H  
HETATM   62  H26 UNL     1      -4.718   2.004  -1.985  1.00  0.00           H  
HETATM   63  H27 UNL     1      -3.452   2.639  -0.910  1.00  0.00           H  
HETATM   64  H28 UNL     1      -3.022   1.701  -2.418  1.00  0.00           H  
HETATM   65  H29 UNL     1      -2.742  -0.979   0.236  1.00  0.00           H  
HETATM   66  H30 UNL     1      -2.044  -0.578  -2.472  1.00  0.00           H  
HETATM   67  H31 UNL     1      -1.270  -1.641  -1.308  1.00  0.00           H  
HETATM   68  H32 UNL     1       0.227  -0.289  -2.506  1.00  0.00           H  
HETATM   69  H33 UNL     1      -0.663   1.164  -2.153  1.00  0.00           H  
HETATM   70  H34 UNL     1      -0.164   2.633  -0.430  1.00  0.00           H  
HETATM   71  H35 UNL     1       1.437   2.416   0.262  1.00  0.00           H  
HETATM   72  H36 UNL     1       1.126   2.353  -1.577  1.00  0.00           H  
HETATM   73  H37 UNL     1       4.400   0.043  -1.792  1.00  0.00           H  
HETATM   74  H38 UNL     1       5.539  -1.282  -1.724  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3    3   36
CONECT    3    4    5
CONECT    4   40   41   42
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   36   43
CONECT    9   10   11   12
CONECT   10   44   45   46
CONECT   11   47
CONECT   12   13   14   34
CONECT   13   48
CONECT   14   15   49   50
CONECT   15   16   16   51
CONECT   16   17   34
CONECT   17   18   31   52
CONECT   18   19   53   54
CONECT   19   20   21   55
CONECT   20   56
CONECT   21   22   23   29
CONECT   22   57
CONECT   23   24   25   58
CONECT   24   59
CONECT   25   26   26   60
CONECT   26   27   61
CONECT   27   28   28   29
CONECT   29   30   31
CONECT   30   62   63   64
CONECT   31   32   65
CONECT   32   33   66   67
CONECT   33   34   68   69
CONECT   34   35
CONECT   35   70   71   72
CONECT   36   73   74
END

HMDB0034191
     RDKit          3D
Withaperuvin B
 74 78  0  0  0  0  0  0  0  0999 V2000
    6.4738    1.0412   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5551   -0.1283   -0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5268   -0.5777    1.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3838    0.0512    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -1.6705    1.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211   -2.0989    2.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8306   -2.2266    0.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908   -1.6871   -0.6769 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2623   -1.2077   -1.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4439   -2.4459   -1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271   -0.6683   -2.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.1444   -0.1252 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805    0.8540   -0.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -0.5419    1.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -0.2452    1.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    0.3492    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.8442    0.5340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5509    0.8303    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8890    1.4485    1.4733 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7168    1.5241    2.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.6590    0.4248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7475    1.4010    0.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0959   -0.6070    1.0497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9706   -0.2673    2.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8504   -1.4399    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5731   -1.3658   -1.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -0.4788   -1.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832   -0.5488   -2.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974    0.4685   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7239    1.7958   -1.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4957   -0.0905   -0.4288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5578   -0.5748   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799    0.2045   -1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    0.5562   -0.4802 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7857    2.0779   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7578   -0.7410   -1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2635    1.8886    0.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3386    1.3017   -1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5052    0.6441   -0.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7403    0.6711    2.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161    0.7000    1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8755   -0.7408    2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8617   -2.6081   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990   -2.5812   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176   -2.5370   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0670   -3.3833   -1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298   -1.3758   -2.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523    1.4320   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -0.0060    2.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941   -1.6250    1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.5266    2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    1.8492    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7007   -0.1915    2.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    1.4883    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    2.4854    1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493    2.4481    2.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058    2.3392    0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026   -1.2388    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8992   -0.8610    2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6276   -2.1048    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -2.0013   -1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7182    2.0041   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    2.6392   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219    1.7010   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -0.9789    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0441   -0.5782   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704   -1.6413   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -0.2891   -2.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634    1.1636   -2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644    2.6334   -0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4374    2.4161    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    2.3532   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4005    0.0432   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5392   -1.2818   -1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  6
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
  8 36  1  0
 36  2  1  0
 34 12  1  0
 34 16  1  0
 31 17  1  0
 29 21  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  8 43  1  6
 10 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 17 52  1  6
 18 53  1  0
 18 54  1  0
 19 55  1  6
 20 56  1  0
 22 57  1  0
 23 58  1  1
 24 59  1  0
 25 60  1  0
 26 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  1
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Withaperuvin B	HMDB

Chemical Formula

C₂₈H₃₈O₈

Average Molecular Weight

502.604

Monoisotopic Molecular Weight

502.256668184

IUPAC Name

(6R)-6-[(1S)-1-hydroxy-1-[(1S,2R,6S,7S,8S,10R,14S,15S)-6,7,8,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-14-yl]ethyl]-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

(6R)-6-[(1S)-1-hydroxy-1-[(1S,2R,6S,7S,8S,10R,14S,15S)-6,7,8,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-14-yl]ethyl]-3,4-dimethyl-5,6-dihydropyran-2-one

CAS Registry Number

81644-35-1

SMILES

[H][C@@]1(CC(C)=C(C)C(=O)O1)[C@](C)(O)[C@]1(O)CC=C2[C@]3([H])C[C@H](O)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C

InChI Identifier

InChI=1S/C28H38O8/c1-14-12-22(36-23(32)15(14)2)26(5,33)27(34)11-9-17-16-13-21(31)28(35)20(30)7-6-19(29)25(28,4)18(16)8-10-24(17,27)3/h6-7,9,16,18,20-22,30-31,33-35H,8,10-13H2,1-5H3/t16-,18-,20-,21-,22+,24-,25-,26-,27-,28+/m0/s1

InChI Key

IHIHXNCZVACPKN-WOONZQPCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
20-hydroxysteroid
17-hydroxysteroid
Oxosteroid
1-oxosteroid
Hydroxysteroid
5-hydroxysteroid
6-hydroxysteroid
4-hydroxysteroid
Cyclohexenone
Dihydropyranone
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0034191)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0034191)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034191)

Source

Exogenous

Food

Food (HMDB: HMDB0034191)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0034191)

Endogenous

Plant

Plant (HMDB: HMDB0034191)

Animal

Animal (HMDB: HMDB0034191)

Endogenous (HMDB: HMDB0034191)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034191)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034191)

Lipid metabolism pathway (HMDB: HMDB0034191)

Cellular process

Cell signaling (HMDB: HMDB0034191)

Biochemical process

Lipid transport (HMDB: HMDB0034191)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034191)

Molecular messenger

Signaling molecule (HMDB: HMDB0034191)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034191)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	269 - 270 °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	1.04 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.29	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.53 m³·mol⁻¹	ChemAxon
Polarizability	53.64 Å³	ChemAxon
Number of Rings	5	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]-	237.283	30932474
DeepCCS	[M+Na]+	211.125	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Withaperuvin B	[H][C@@]1(CC(C)=C(C)C(=O)O1)[C@](C)(O)[C@]1(O)CC=C2[C@]3([H])C[C@H](O)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C	4311.7	Standard polar	33892256
Withaperuvin B	[H][C@@]1(CC(C)=C(C)C(=O)O1)[C@](C)(O)[C@]1(O)CC=C2[C@]3([H])C[C@H](O)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C	3842.9	Standard non polar	33892256
Withaperuvin B	[H][C@@]1(CC(C)=C(C)C(=O)O1)[C@](C)(O)[C@]1(O)CC=C2[C@]3([H])C[C@H](O)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C	4312.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Withaperuvin B,1TMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4138.8	Semi standard non polar	33892256
Withaperuvin B,1TMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4152.8	Semi standard non polar	33892256
Withaperuvin B,1TMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4124.9	Semi standard non polar	33892256
Withaperuvin B,1TMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4080.6	Semi standard non polar	33892256
Withaperuvin B,1TMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4102.5	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4091.5	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #10	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4017.1	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4035.1	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4010.1	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4033.0	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4061.0	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #6	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4040.0	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #7	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4061.2	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #8	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4013.1	Semi standard non polar	33892256
Withaperuvin B,2TMS,isomer #9	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4039.6	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3974.7	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #10	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3957.0	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3974.5	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3998.0	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3942.5	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3971.6	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #6	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3974.3	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #7	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3969.4	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #8	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3984.8	Semi standard non polar	33892256
Withaperuvin B,3TMS,isomer #9	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3993.1	Semi standard non polar	33892256
Withaperuvin B,4TMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3898.4	Semi standard non polar	33892256
Withaperuvin B,4TMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3916.0	Semi standard non polar	33892256
Withaperuvin B,4TMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3940.1	Semi standard non polar	33892256
Withaperuvin B,4TMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3905.9	Semi standard non polar	33892256
Withaperuvin B,4TMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3918.0	Semi standard non polar	33892256
Withaperuvin B,5TMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	3864.2	Semi standard non polar	33892256
Withaperuvin B,1TBDMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4370.7	Semi standard non polar	33892256
Withaperuvin B,1TBDMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4378.1	Semi standard non polar	33892256
Withaperuvin B,1TBDMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4334.1	Semi standard non polar	33892256
Withaperuvin B,1TBDMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4299.9	Semi standard non polar	33892256
Withaperuvin B,1TBDMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4322.1	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4552.9	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #10	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4448.6	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4487.5	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4458.9	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4495.8	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4503.2	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #6	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4470.7	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #7	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4512.1	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #8	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4436.3	Semi standard non polar	33892256
Withaperuvin B,2TBDMS,isomer #9	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4460.6	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #1	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4640.3	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #10	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4580.5	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #2	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4630.6	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #3	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4675.3	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #4	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4598.3	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #5	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4623.7	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #6	CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4631.2	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #7	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4593.7	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #8	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4612.4	Semi standard non polar	33892256
Withaperuvin B,3TBDMS,isomer #9	CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C1	4630.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_3_9) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_3_10) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_4_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_4_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_4_5) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_5_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TBDMS_2_10) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TBDMS_3_9) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS (TBDMS_3_10) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Withaperuvin B GC-MS ("Withaperuvin B,2TMS,#10" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin B 10V, Negative-QTOF	splash10-0udi-0004290000-92a4ab8f1780bf9e3dca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin B 20V, Negative-QTOF	splash10-0a4i-0009010000-a3f01b1039da5edee313	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin B 40V, Negative-QTOF	splash10-0006-9304000000-8006b14fecfba613952f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin B 10V, Positive-QTOF	splash10-0uxr-0302970000-5e409be2293b3a6ad67d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin B 20V, Positive-QTOF	splash10-066r-7109600000-ac60e6a9db6af43a4382	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Withaperuvin B 40V, Positive-QTOF	splash10-014i-2942000000-8c96536688011cd1d69a	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012487

KNApSAcK ID

C00058211

Chemspider ID

113385425

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156908039

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Withaperuvin B (HMDB0034191)

MOL for HMDB0034191 (Withaperuvin B)

3D MOL for HMDB0034191 (Withaperuvin B)

3D SDF for HMDB0034191 (Withaperuvin B)

3D-SDF for HMDB0034191 (Withaperuvin B)

PDB for HMDB0034191 (Withaperuvin B)

3D PDB for HMDB0034191 (Withaperuvin B)

SMILES for HMDB0034191 (Withaperuvin B)

INCHI for HMDB0034191 (Withaperuvin B)

Structure for HMDB0034191 (Withaperuvin B)

3D Structure for HMDB0034191 (Withaperuvin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra