NP-MRD: Showing NP-Card for (1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid (NP0159356)

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Record Information

Version

2.0

Created at

2022-09-02 17:05:47 UTC

Updated at

2022-09-02 17:05:47 UTC

NP-MRD ID

NP0159356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid

Description

Cyclopassifloic acid A, also known as cyclopassifloate a, belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. (1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid is found in Passiflora edulis. Based on a literature review very few articles have been published on Cyclopassifloic acid A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219062D          

 38 42  0  0  1  0            999 V2000
    9.4728    3.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9664    3.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2620    4.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0363    2.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6877    1.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372   -0.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    0.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  1  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
 18 34  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END

     RDKit          3D

 90 94  0  0  0  0  0  0  0  0999 V2000
    7.4603    0.2420    1.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9670   -0.9605    0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5488   -1.0396   -0.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4591   -1.0828    0.4651 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1285   -1.2140    1.8215 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0748   -2.2944   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381   -3.4173    0.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8900    0.1943   -0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3774    0.1930   -0.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8597    0.0547    1.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416    1.4306   -0.8074 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2511    1.5455   -2.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    1.7200   -0.3890 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8942    2.9844   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6323    2.8463   -0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7524    1.7550    0.0460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3189    2.4391    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    1.1452    0.2944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3879    0.7901    1.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236    0.8850    1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3787   -0.3748    1.0871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8701   -0.3742    0.7705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3664    0.9706    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6453   -0.7736    2.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0471   -1.0413    3.0634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0141   -0.8439    1.9565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0907   -1.4343   -0.2679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1108   -0.9182   -1.5743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2108   -2.6314   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7378   -2.3465   -0.1133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2342   -2.9290    1.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -0.8182   -0.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4550   -0.2074   -1.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261   -0.1707   -0.4265 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1521   -1.0740   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -0.4450    0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276    0.8426   -0.5696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0921    0.6422   -2.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4525    1.1036    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8685    0.4277    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5048    0.0107    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3527   -1.8587    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3030   -0.2026   -1.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1800   -1.9647   -1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8469   -0.8878   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9069   -1.3978    2.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709   -2.1191   -1.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9895   -2.5314   -0.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -3.2880    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.2928   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2528    1.0268    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900   -0.6861   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023   -0.8636    1.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4663    2.2540   -0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972    0.6881   -2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9928    2.5264   -2.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3849    1.5698   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705    1.8475    0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2511    3.9052   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2290    3.1062   -2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    3.8003   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966    2.6817   -1.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    3.3436    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0421    1.7716    2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641    3.0029    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8090    1.8982   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9739    1.3628    2.5161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -0.2866    1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    1.8030    1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742    0.9056    2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806   -1.1606    1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7374    1.5345   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4380    1.5880    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4085    0.8646    0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4337   -1.7390    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1459   -1.8109   -0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4910   -0.0185   -1.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4806   -3.3197   -0.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5619   -3.1903    0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2731   -2.7697   -1.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1709   -3.9025    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822    0.7920   -1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -0.8265   -2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -1.9650    0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0408   -1.5001   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9072   -1.2369   -0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -0.4622    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9357    0.7091   -2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328   -0.4059   -2.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6836    1.2878   -2.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 32  1  0
 32 33  1  6
 34 33  1  6
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  6
 32 30  1  0
 30 31  1  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 22  1  0
 22 23  1  0
 22 24  1  1
 24 26  1  0
 24 25  2  0
 37 13  1  0
 37 16  1  0
 34 18  1  0
 22 21  1  0
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  1 39  1  0
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  2 42  1  0
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  3 44  1  0
  3 45  1  0
  5 46  1  0
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 29 78  1  0
 29 79  1  0
 27 76  1  1
 28 77  1  0
 23 72  1  0
 23 73  1  0
 23 74  1  0
 26 75  1  0
M  END


  Mrv1652309022219062D          

 38 42  0  0  1  0            999 V2000
    9.4728    3.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9664    3.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2620    4.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0363    2.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6877    1.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372   -0.3651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    0.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  1  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
 18 34  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0159356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@](O)(CO)C[C@@H](O)[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)[C@@H](O)C[C@H](O)[C@@]4(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O7/c1-17(2)30(38,16-32)14-20(33)18(3)19-9-10-27(5)21-7-8-22-28(6,25(36)37)23(34)13-24(35)31(22)15-29(21,31)12-11-26(19,27)4/h17-24,32-35,38H,7-16H2,1-6H3,(H,36,37)/t18-,19+,20+,21-,22-,23-,24-,26+,27-,28-,29-,30+,31+/m0/s1

> <INCHI_KEY>
DHBRFQPOOWANLV-PDAQUDJUSA-N

> <FORMULA>
C31H52O7

> <MOLECULAR_WEIGHT>
536.75

> <EXACT_MASS>
536.371304014

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
61.85913976879872

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2S,3R,5S)-3,5,6-trihydroxy-5-(propan-2-yl)hexan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-7-carboxylic acid

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.384672488333333

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.540150118157044

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4603609233821455

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8634861717631175

> <JCHEM_POLAR_SURFACE_AREA>
138.45

> <JCHEM_REFRACTIVITY>
143.69559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2S,3R,5S)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      17.683   7.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.737   5.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.318   4.487   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.212   6.125   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.422   7.650   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.001   4.599   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.217   3.654   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.321   3.693   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.816  -0.682   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.523   1.625   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6    8                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   37                                             
CONECT   17   16                                                            
CONECT   18   16   19   34                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23   24   27                                             
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   21   33   34                                             
CONECT   33   32   34                                                       
CONECT   34   33   18   32   35                                             
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   13   16   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Cyclopassifloate a	Generator

Chemical Formula

C₃₁H₅₂O₇

Average Mass

536.7500 Da

Monoisotopic Mass

536.37130 Da

IUPAC Name

(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2S,3R,5S)-3,5,6-trihydroxy-5-(propan-2-yl)hexan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-7-carboxylic acid

Traditional Name

(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2S,3R,5S)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@](O)(CO)C[C@@H](O)[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)[C@@H](O)C[C@H](O)[C@@]4(C)C(O)=O

InChI Identifier

InChI=1S/C31H52O7/c1-17(2)30(38,16-32)14-20(33)18(3)19-9-10-27(5)21-7-8-22-28(6,25(36)37)23(34)13-24(35)31(22)15-29(21,31)12-11-26(19,27)4/h17-24,32-35,38H,7-16H2,1-6H3,(H,36,37)/t18-,19+,20+,21-,22-,23-,24-,26+,27-,28-,29-,30+,31+/m0/s1

InChI Key

DHBRFQPOOWANLV-PDAQUDJUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Passiflora edulis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
Hexahydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Bile acid, alcohol, or derivatives
Steroid acid
4-carboxy steroid
3-beta-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
15-hydroxysteroid
1-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Fatty alcohol
Beta-hydroxy acid
Hydroxy acid
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.63	ALOGPS
logP	2.38	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	143.7 m³·mol⁻¹	ChemAxon
Polarizability	61.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046689

Chemspider ID

10242767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21606648

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid (NP0159356)

MOL for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D MOL for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D SDF for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D-SDF for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

PDB for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D PDB for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

SMILES for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

INCHI for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

Structure for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D Structure for NP0159356 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-4,6-dihydroxy-7,12,16-trimethyl-15-[(2s,3r,5s)-3,5,6-trihydroxy-5-isopropylhexan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)