NP-MRD: Showing NP-Card for mulinolic acid (NP0029760)

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Record Information

Version

2.0

Created at

2021-06-19 21:17:59 UTC

Updated at

2021-06-29 23:57:20 UTC

NP-MRD ID

NP0029760

Secondary Accession Numbers

None

Natural Product Identification

Common Name

mulinolic acid

Provided By

JEOL Database JEOL Logo

Description

Mulinolic acid is also known as mulinolate. mulinolic acid is found in Azorella acaulis, Azorella atacamensis, Azorella compacta , Azorella madreporica, Azorella prolifera, Laretia acaulis, Laretia acaulis (Cav.) Gill et Hook and Mulinum spinosum (Cav.) Pers . mulinolic acid was first documented in 2005 (PMID: 16177976). Based on a literature review a small amount of articles have been published on mulinolic acid (PMID: 26425819) (PMID: 25008488) (PMID: 24660449) (PMID: 23837591).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123183D          

 55 57  0  0  0  0            999 V2000
   -2.7970    2.9469    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    2.7498    1.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6820    4.1121    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593    1.6192    0.2971 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0585    2.0245   -1.0131 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1347    0.9514   -1.2665 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9463   -0.0597   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1071   -0.9864    0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8056   -1.5669   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866   -2.6322   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -3.5691   -1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5078   -4.7694   -2.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400   -2.8930   -1.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -4.0922   -0.1130 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6306   -3.0616    0.9168 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6495   -1.9870    1.3903 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8898   -2.6869    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -1.1816    2.5518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1309   -0.1976    2.1012 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4110    0.7850    1.0492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4803    1.6981    1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981    2.1142    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    2.0841    2.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799    2.0226    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    3.2466   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    3.7201    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    2.4295    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    4.0514    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    4.5772    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    4.7979    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431    0.9013    0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    2.9987   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    2.0760   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334    1.4004   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967    0.4840   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.7085   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -0.3604    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900   -1.0041   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -2.8350   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -4.4438   -3.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -5.4315   -2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954   -5.3560   -2.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.2576   -2.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -4.6175    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -4.8524   -0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -2.5923    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156   -3.6359    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4597   -3.2476    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -3.3865    2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -1.9561    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -1.8748    3.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9813   -0.7588    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.3306    2.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    2.6699    3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0  0  0  0
 18 16  1  0  0  0  0
 15 14  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
 14 11  1  0  0  0  0
  6  5  1  0  0  0  0
  7 36  1  6  0  0  0
  5  4  1  0  0  0  0
  4  2  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20  7  1  0  0  0  0
 16 17  1  1  0  0  0
  8 37  1  1  0  0  0
 16  8  1  0  0  0  0
 11 12  1  0  0  0  0
  7  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
  2  3  1  0  0  0  0
 20 19  1  0  0  0  0
 21 23  1  0  0  0  0
 16 15  1  0  0  0  0
 21 22  2  0  0  0  0
 19 18  1  0  0  0  0
 11 13  1  6  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  4 31  1  6  0  0  0
  9 38  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 10 39  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
  2 27  1  1  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 12 40  1  0  0  0  0
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  1 24  1  0  0  0  0
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  1 26  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
 23 55  1  0  0  0  0
 13 43  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -2.7970    2.9469    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    2.7498    1.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6820    4.1121    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593    1.6192    0.2971 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0585    2.0245   -1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1347    0.9514   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -0.0597   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1071   -0.9864    0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8056   -1.5669   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866   -2.6322   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -3.5691   -1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5078   -4.7694   -2.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400   -2.8930   -1.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -4.0922   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6306   -3.0616    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6495   -1.9870    1.3903 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8898   -2.6869    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -1.1816    2.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -0.1976    2.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110    0.7850    1.0492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4803    1.6981    1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981    2.1142    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    2.0841    2.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7654    3.2466   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5033    2.4295    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    4.0514    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    4.5772    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8801   -0.3604    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900   -1.0041   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -2.8350   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6343   -5.4315   -2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4048   -2.2576   -2.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3065   -4.8524   -0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -2.5923    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156   -3.6359    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0
 18 16  1  0
 15 14  1  0
  7  6  1  0
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  6  5  1  0
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  4 20  1  0
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 16 17  1  1
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  5 32  1  0
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  4 31  1  6
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 13 43  1  0
M  END


  Mrv1652306192123183D          

 55 57  0  0  0  0            999 V2000
   -2.7970    2.9469    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    2.7498    1.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6820    4.1121    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593    1.6192    0.2971 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0585    2.0245   -1.0131 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1347    0.9514   -1.2665 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9463   -0.0597   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1071   -0.9864    0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8056   -1.5669   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866   -2.6322   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -3.5691   -1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5078   -4.7694   -2.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400   -2.8930   -1.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -4.0922   -0.1130 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6306   -3.0616    0.9168 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6495   -1.9870    1.3903 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8898   -2.6869    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -1.1816    2.5518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1309   -0.1976    2.1012 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4110    0.7850    1.0492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4803    1.6981    1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981    2.1142    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    2.0841    2.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799    2.0226    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    3.2466   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    3.7201    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    2.4295    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    4.0514    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    4.5772    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    4.7979    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431    0.9013    0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    2.9987   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    2.0760   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334    1.4004   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967    0.4840   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.7085   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -0.3604    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900   -1.0041   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -2.8350   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -4.4438   -3.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -5.4315   -2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954   -5.3560   -2.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.2576   -2.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -4.6175    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -4.8524   -0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -2.5923    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156   -3.6359    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4597   -3.2476    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -3.3865    2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -1.9561    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -1.8748    3.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355   -0.6197    3.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.7588    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.3306    2.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    2.6699    3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0  0  0  0
 18 16  1  0  0  0  0
 15 14  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
 14 11  1  0  0  0  0
  6  5  1  0  0  0  0
  7 36  1  6  0  0  0
  5  4  1  0  0  0  0
  4  2  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20  7  1  0  0  0  0
 16 17  1  1  0  0  0
  8 37  1  1  0  0  0
 16  8  1  0  0  0  0
 11 12  1  0  0  0  0
  7  8  1  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
  2  3  1  0  0  0  0
 20 19  1  0  0  0  0
 21 23  1  0  0  0  0
 16 15  1  0  0  0  0
 21 22  2  0  0  0  0
 19 18  1  0  0  0  0
 11 13  1  6  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  4 31  1  6  0  0  0
  9 38  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 10 39  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
  2 27  1  1  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
 23 55  1  0  0  0  0
 13 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029760

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])=C([H])[C@@]3([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-13(2)14-5-6-16-15-7-8-19(4,23)11-9-18(15,3)10-12-20(14,16)17(21)22/h7-8,13-16,23H,5-6,9-12H2,1-4H3,(H,21,22)/t14-,15+,16+,18-,19+,20+/m1/s1

> <INCHI_KEY>
LRZJASNGRXSNCR-MXFTUIMMSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.02114811158242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,5aS,8R,10aS,10bS)-8-hydroxy-5a,8-dimethyl-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
4.1645488713333325

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.38157168656997

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.798091868914158

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3197009034209826

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
92.2359

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,5aS,8R,10aS,10bS)-8-hydroxy-3-isopropyl-5a,8-dimethyl-1H,2H,3H,4H,5H,6H,7H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -2.7970    2.9469    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    2.7498    1.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6820    4.1121    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593    1.6192    0.2971 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0585    2.0245   -1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1347    0.9514   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -0.0597   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1071   -0.9864    0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8056   -1.5669   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866   -2.6322   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -3.5691   -1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5078   -4.7694   -2.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400   -2.8930   -1.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -4.0922   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6306   -3.0616    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6495   -1.9870    1.3903 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8898   -2.6869    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -1.1816    2.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -0.1976    2.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110    0.7850    1.0492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4803    1.6981    1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981    2.1142    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    2.0841    2.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799    2.0226    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    3.2466   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    3.7201    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    2.4295    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    4.0514    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    4.5772    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    4.7979    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431    0.9013    0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    2.9987   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    2.0760   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334    1.4004   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967    0.4840   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.7085   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -0.3604    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900   -1.0041   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -2.8350   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -4.4438   -3.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -5.4315   -2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954   -5.3560   -2.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.2576   -2.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -4.6175    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -4.8524   -0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -2.5923    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156   -3.6359    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4597   -3.2476    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -3.3865    2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -1.9561    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -1.8748    3.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355   -0.6197    3.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.7588    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.3306    2.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    2.6699    3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
 18 16  1  0
 15 14  1  0
  7  6  1  0
 10 11  1  0
 14 11  1  0
  6  5  1  0
  7 36  1  6
  5  4  1  0
  4  2  1  0
  4 20  1  0
 20 21  1  1
 20  7  1  0
 16 17  1  1
  8 37  1  1
 16  8  1  0
 11 12  1  0
  7  8  1  0
  2  1  1  0
  8  9  1  0
  2  3  1  0
 20 19  1  0
 21 23  1  0
 16 15  1  0
 21 22  2  0
 19 18  1  0
 11 13  1  6
 19 53  1  0
 19 54  1  0
 18 51  1  0
 18 52  1  0
  6 34  1  0
  6 35  1  0
  5 32  1  0
  5 33  1  0
  4 31  1  6
  9 38  1  0
 15 46  1  0
 15 47  1  0
 10 39  1  0
 14 44  1  0
 14 45  1  0
  2 27  1  1
 17 48  1  0
 17 49  1  0
 17 50  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 23 55  1  0
 13 43  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.797   2.947   0.502  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.383   2.750   1.070  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.682   4.112   1.074  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.659   1.619   0.297  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.059   2.025  -1.013  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.135   0.951  -1.266  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.946  -0.060  -0.134  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.107  -0.986   0.270  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.806  -1.567  -0.934  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.487  -2.632  -1.683  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.319  -3.569  -1.538  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.508  -4.769  -2.480  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.140  -2.893  -1.977  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.100  -4.092  -0.113  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.631  -3.062   0.917  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.650  -1.987   1.390  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.890  -2.687   1.997  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.967  -1.182   2.552  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.131  -0.198   2.101  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.411   0.785   1.049  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.480   1.698   1.671  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.498   2.114   1.142  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.195   2.084   2.931  0.00  0.00           O+0
HETATM   24  H   UNK     0      -3.380   2.023   0.576  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.765   3.247  -0.551  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.337   3.720   1.060  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.503   2.430   2.113  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.356   4.051   1.404  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.697   4.577   0.083  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.197   4.798   1.757  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.443   0.901   0.006  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.551   2.999  -0.943  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.653   2.076  -1.845  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.133   1.400  -1.259  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.997   0.484  -2.248  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.128  -0.709  -0.480  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.880  -0.360   0.738  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.690  -1.004  -1.240  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.148  -2.835  -2.526  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.603  -4.444  -3.523  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.634  -5.431  -2.450  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.395  -5.356  -2.219  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.405  -2.258  -2.663  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.993  -4.617   0.246  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.307  -4.852  -0.151  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.289  -2.592   0.551  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.316  -3.636   1.800  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.460  -3.248   1.250  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.599  -3.386   2.789  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.576  -1.956   2.441  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.536  -1.875   3.286  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.736  -0.620   3.099  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.981  -0.759   1.696  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.520   0.331   2.979  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.943   2.670   3.172  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    4    1    3   27                                             
CONECT    3    2   28   29   30                                             
CONECT    4    5    2   20   31                                             
CONECT    5    6    4   32   33                                             
CONECT    6    7    5   34   35                                             
CONECT    7    6   36   20    8                                             
CONECT    8   37   16    7    9                                             
CONECT    9   10    8   38                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   14   12   13                                             
CONECT   12   11   40   41   42                                             
CONECT   13   11   43                                                       
CONECT   14   15   11   44   45                                             
CONECT   15   14   16   46   47                                             
CONECT   16   18   17    8   15                                             
CONECT   17   16   48   49   50                                             
CONECT   18   16   19   51   52                                             
CONECT   19   20   18   53   54                                             
CONECT   20    4   21    7   19                                             
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   55                                                       
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   23                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -2.7970    2.9469    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    2.7498    1.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6820    4.1121    1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593    1.6192    0.2971 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0585    2.0245   -1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1347    0.9514   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463   -0.0597   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1071   -0.9864    0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8056   -1.5669   -0.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4866   -2.6322   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -3.5691   -1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5078   -4.7694   -2.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1400   -2.8930   -1.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -4.0922   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6306   -3.0616    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6495   -1.9870    1.3903 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8898   -2.6869    1.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -1.1816    2.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1309   -0.1976    2.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110    0.7850    1.0492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4803    1.6981    1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4981    2.1142    1.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    2.0841    2.9312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3799    2.0226    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    3.2466   -0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3370    3.7201    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5033    2.4295    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    4.0514    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966    4.5772    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    4.7979    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431    0.9013    0.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    2.9987   -0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527    2.0760   -1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334    1.4004   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9967    0.4840   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -0.7085   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -0.3604    0.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900   -1.0041   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1483   -2.8350   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6028   -4.4438   -3.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -5.4315   -2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954   -5.3560   -2.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.2576   -2.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -4.6175    0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -4.8524   -0.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2885   -2.5923    0.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156   -3.6359    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4597   -3.2476    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5985   -3.3865    2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -1.9561    2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355   -1.8748    3.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7355   -0.6197    3.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -0.7588    1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.3306    2.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    2.6699    3.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
 18 16  1  0
 15 14  1  0
  7  6  1  0
 10 11  1  0
 14 11  1  0
  6  5  1  0
  7 36  1  6
  5  4  1  0
  4  2  1  0
  4 20  1  0
 20 21  1  1
 20  7  1  0
 16 17  1  1
  8 37  1  1
 16  8  1  0
 11 12  1  0
  7  8  1  0
  2  1  1  0
  8  9  1  0
  2  3  1  0
 20 19  1  0
 21 23  1  0
 16 15  1  0
 21 22  2  0
 19 18  1  0
 11 13  1  6
 19 53  1  0
 19 54  1  0
 18 51  1  0
 18 52  1  0
  6 34  1  0
  6 35  1  0
  5 32  1  0
  5 33  1  0
  4 31  1  6
  9 38  1  0
 15 46  1  0
 15 47  1  0
 10 39  1  0
 14 44  1  0
 14 45  1  0
  2 27  1  1
 17 48  1  0
 17 49  1  0
 17 50  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
 23 55  1  0
 13 43  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Mulinolate	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Mass

320.4730 Da

Monoisotopic Mass

320.23514 Da

IUPAC Name

(3R,3aS,5aS,8R,10aS,10bS)-8-hydroxy-5a,8-dimethyl-3-(propan-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H,8H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

Traditional Name

(3R,3aS,5aS,8R,10aS,10bS)-8-hydroxy-3-isopropyl-5a,8-dimethyl-1H,2H,3H,4H,5H,6H,7H,10aH,10bH-cyclohepta[e]indene-3a-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])=C([H])[C@@]3([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H32O3/c1-13(2)14-5-6-16-15-7-8-19(4,23)11-9-18(15,3)10-12-20(14,16)17(21)22/h7-8,13-16,23H,5-6,9-12H2,1-4H3,(H,21,22)/t14-,15+,16+,18-,19+,20+/m1/s1

InChI Key

LRZJASNGRXSNCR-MXFTUIMMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Azorella acaulis	LOTUS Database	35616633
Azorella atacamensis	LOTUS Database	35616633
Azorella compacta	Plant	KNApSAcK
Azorella madreporica	LOTUS Database	35616633
Azorella prolifera	LOTUS Database	35616633
Azorella ruizii	JEOL database	Loyolaa, L. A., et al, Phytochemistry 53, 961 (2000)
Laretia acaulis (Cav.) Gill et Hook	Plant	KNApSAcK
Mulinum spinosum (Cav.) Pers	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as valparane and mulinane diterpenoids. These are diterpenoids with a structure based on either the valparane or mulinane skeleton. Valparane and mulinane are tricyclic compounds containing a tetradecahydrocyclohepta[e]indene skeleton. Valparane carries a 1-methylethyl at the 3-position, as well as three methyl groups at the 5a-, 8-, and 10b-position of the ring system. Mulinane carries a 1-methylethyl at the 3-position, as well as three methyl groups at the 3a-, 5a-, and 8-position of the ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Valparane and mulinane diterpenoids

Alternative Parents

Substituents

Valparane or mulinane diterpenoid
Tertiary alcohol
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	3.85	ALOGPS
logP	4.16	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.8	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.24 m³·mol⁻¹	ChemAxon
Polarizability	37.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

8194510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10018937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Borquez J, Bartolucci NL, Echiburu-Chau C, Winterhalter P, Vallejos J, Jerz G, Simirgiotis MJ: Isolation of cytotoxic diterpenoids from the Chilean medicinal plant Azorella compacta Phil from the Atacama Desert by high-speed counter-current chromatography. J Sci Food Agric. 2016 Jun;96(8):2832-8. doi: 10.1002/jsfa.7451. Epub 2015 Oct 1. [PubMed:26425819 ]
Areche C, Sepulveda B, San Martin A, Garcia-Beltran O, Simirgiotis M, Canete A: An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers. Org Biomol Chem. 2014 Sep 7;12(33):6406-13. doi: 10.1039/c4ob00966e. [PubMed:25008488 ]
Astudillo L, Gutierrez M, Quesada L, San-Martin A, Espinoza L, Penailillo P: New diterpenes from Azorella spinosa. Nat Prod Commun. 2014 Jan;9(1):9-12. [PubMed:24660449 ]
Areche C, Rojas-Alvarez F, Campos-Briones C, Lima C, Perez EG, Sepulveda B: Further mulinane diterpenoids from Azorella compacta. J Pharm Pharmacol. 2013 Aug;65(8):1231-8. doi: 10.1111/jphp.12083. Epub 2013 May 21. [PubMed:23837591 ]
Fuentes NL, Sagua H, Morales G, Borquez J, San Martin A, Soto J, Loyola LA: Experimental antihyperglycemic effect of diterpenoids of llareta Azorella compacta (Umbelliferae) Phil in rats. Phytother Res. 2005 Aug;19(8):713-6. doi: 10.1002/ptr.1740. [PubMed:16177976 ]
Loyolaa, L. A., et al. (2000). Loyolaa, L. A., et al, Phytochemistry 53, 961 (2000). Phytochem..

Showing NP-Card for mulinolic acid (NP0029760)

MOL for NP0029760 (mulinolic acid)

3D MOL for NP0029760 (mulinolic acid)

3D SDF for NP0029760 (mulinolic acid)

3D-SDF for NP0029760 (mulinolic acid)

PDB for NP0029760 (mulinolic acid)

3D PDB for NP0029760 (mulinolic acid)

SMILES for NP0029760 (mulinolic acid)

INCHI for NP0029760 (mulinolic acid)

Structure for NP0029760 (mulinolic acid)

3D Structure for NP0029760 (mulinolic acid)