NP-MRD: Showing NP-Card for (1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid (NP0227528)

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Record Information

Version

2.0

Created at

2022-09-06 06:52:21 UTC

Updated at

2022-09-06 06:52:21 UTC

NP-MRD ID

NP0227528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid

Description

Musambin 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)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid is found in Markhamia lutea. Based on a literature review very few articles have been published on Musambin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208522D          

 36 40  0  0  1  0            999 V2000
    3.4412    5.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    4.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2457    3.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693    4.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802    3.7324    0.0000 C   0  0  0  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
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    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
    5.0757    5.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8929    5.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  1  0  0  0
 14 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  9 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  1  0  0  0
  4 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 84 88  0  0  0  0  0  0  0  0999 V2000
    7.9687    0.1552   -1.5215 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7994   -0.1907   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9372   -0.2134    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4495   -0.5704    0.2477 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3993   -0.4937   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0627   -0.8009   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9901   -0.7356   -1.1705 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4110   -1.8267   -2.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6157   -1.0305   -0.7959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3330   -2.3328   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -2.1180    0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542   -0.8642    0.1534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0098   -1.2448   -1.1972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4201   -0.1502    1.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5094   -1.0995    1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8319   -0.4608    1.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2212    0.3455    0.4586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6463    0.7643    0.5518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0368    1.0438    2.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5097   -0.3624    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2925   -0.2250   -0.9305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5273   -1.6122    0.6609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174    1.9731   -0.2381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2283    2.4666    0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758    3.0403   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7054    2.3841   -0.8263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0845    1.6868   -1.9501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461    1.4463    0.3000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5102    2.0896    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333    1.1179    0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9218    1.7301   -0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997    1.1579   -0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983   -0.0387   -0.0393 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4314    0.4673    1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4504   -1.8306    0.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1346   -1.7711    2.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9407    0.4249   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1615    0.1874   -2.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8734   -0.3227    0.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8925    0.7071    1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8634   -1.1016    1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    0.1730    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    0.5649   -1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5945   -1.1689   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0307   -0.1354    0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1632   -1.8696    0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0556    0.2108   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0553   -1.3840   -2.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842   -2.6746   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -2.2114   -2.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.1054   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0653   -3.1228   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684   -2.7374    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5933   -2.9626    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966   -2.0206    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6195   -2.2221   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8607   -0.5048   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295   -1.4052   -1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053    0.1018    1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684   -1.9147    0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2374   -1.6548    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    0.1494    2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5567   -1.2854    1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349   -0.3447   -0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0584    0.1331    2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0711    1.4688    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4597   -2.4169    0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096    1.6742   -1.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9400    1.8432   -0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3133    3.8334   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7823    3.4956    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0007    3.1968   -0.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6839    0.8071   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2152    3.1742    1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676    1.8072    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062    2.8284   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812    1.7735   -1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5891    0.8865   -1.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157    1.9231   -0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3211   -2.6525    2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 35  1  0
 35 36  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 28  1  0
 28 29  1  1
 30 29  1  1
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  1
 28 26  1  0
 26 27  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 23 18  1  0
 18 19  1  0
 18 20  1  6
 20 22  1  0
 20 21  2  0
 33  9  1  0
 33 12  1  0
 30 14  1  0
 18 17  1  0
 30 28  1  0
  8 48  1  0
  8 49  1  0
  8 50  1  0
  7 47  1  6
  6 45  1  0
  6 46  1  0
  5 43  1  0
  5 44  1  0
  4 42  1  1
 36 84  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  1 37  1  0
  1 38  1  0
  9 51  1  6
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 13 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  1
 15 60  1  0
 15 61  1  0
 16 62  1  0
 16 63  1  0
 17 64  1  6
 29 75  1  0
 29 76  1  0
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 31 78  1  0
 32 79  1  0
 32 80  1  0
 34 81  1  0
 34 82  1  0
 34 83  1  0
 26 73  1  6
 27 74  1  0
 25 71  1  0
 25 72  1  0
 23 69  1  6
 24 70  1  0
 19 65  1  0
 19 66  1  0
 19 67  1  0
 22 68  1  0
M  END


  Mrv1652309062208522D          

 36 40  0  0  1  0            999 V2000
    3.4412    5.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    4.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2457    3.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693    4.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802    3.7324    0.0000 C   0  0  0  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
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    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
    5.0757    5.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8929    5.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  1  0  0  0
 14 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  9 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  1  0  0  0
  4 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(OO)C(C)=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/C30H48O6/c1-17(2)20(36-35)8-7-18(3)19-11-12-27(5)21-9-10-22-28(6,25(33)34)23(31)15-24(32)30(22)16-29(21,30)14-13-26(19,27)4/h18-24,31-32,35H,1,7-16H2,2-6H3,(H,33,34)/t18-,19-,20?,21+,22+,23+,24+,26-,27+,28+,29+,30-/m1/s1

> <INCHI_KEY>
DBWPILOLPUDSNJ-PEQOZSMCSA-N

> <FORMULA>
C30H48O6

> <MOLECULAR_WEIGHT>
504.708

> <EXACT_MASS>
504.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
58.47277152948391

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-15-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-7-carboxylic acid

> <JCHEM_LOGP>
4.712207886000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.710272455078682

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.460360899437

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9785931003917394

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
137.0155

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       6.424  10.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.004   8.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.059   7.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.529   8.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.110   6.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.816  -0.682   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.523   1.625   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.475   9.609   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      11.000   9.399   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   33                                             
CONECT   13   12                                                            
CONECT   14   12   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   17   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   14   28   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    9   12   34                                             
CONECT   34   33                                                            
CONECT   35    4   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₆

Average Mass

504.7080 Da

Monoisotopic Mass

504.34509 Da

IUPAC Name

(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-15-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[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)-15-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(OO)C(C)=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/C30H48O6/c1-17(2)20(36-35)8-7-18(3)19-11-12-27(5)21-9-10-22-28(6,25(33)34)23(31)15-24(32)30(22)16-29(21,30)14-13-26(19,27)4/h18-24,31-32,35H,1,7-16H2,2-6H3,(H,33,34)/t18-,19-,20?,21+,22+,23+,24+,26-,27+,28+,29+,30-/m1/s1

InChI Key

DBWPILOLPUDSNJ-PEQOZSMCSA-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
Markhamia lutea	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
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Tetrahydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
4-carboxy steroid
Steroid acid
1-hydroxysteroid
3-beta-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Hydroxysteroid
15-hydroxysteroid
3-hydroxysteroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.71	ChemAxon
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.02 m³·mol⁻¹	ChemAxon
Polarizability	58.47 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44472194

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)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid (NP0227528)

MOL for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D MOL for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D SDF for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D-SDF for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

PDB for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D PDB for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

SMILES for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

INCHI for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

Structure for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)

3D Structure for NP0227528 ((1s,3s,4s,6s,7s,8r,11s,12s,15r,16r)-15-[(2r)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-7-carboxylic acid)