NP-MRD: Showing NP-Card for 3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate (NP0311867)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 08:09:47 UTC

Updated at

2022-09-11 08:09:48 UTC

NP-MRD ID

NP0311867

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate

Description

3,4,6,7,9,14-Hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadecan-16-yl 3-hydroxy-2-methylbutanoate belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton. 3,4,6,7,9,14-Hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadecan-16-yl 3-hydroxy-2-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520232D          

 34 37  0  0  0  0            999 V2000
    1.2769    3.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901    3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301    3.2800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1334    2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688    2.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0869    1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3171    1.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    0.5624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -0.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    0.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481    0.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    1.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    1.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2546    0.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913    0.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -0.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338   -0.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926   -1.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0528   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -2.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5010   -0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185   -1.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -2.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468   -0.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -1.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -0.6858    0.0000 O   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  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  9 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 76 79  0  0  0  0  0  0  0  0999 V2000
    5.5934    3.2901    1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5419    2.3705    1.7821 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4782    3.1516    2.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0491    1.4796    0.6803 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1572    0.6434    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9005    0.6352    1.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4071    0.6601    2.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601   -0.2304    0.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -1.0984    0.4247 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6061   -2.5292    0.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5155   -3.4190    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7284   -2.5885    0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261   -1.7231   -0.5554 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2311   -0.7589   -0.6482 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0494    0.6800   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923    1.3558   -0.3400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9305    1.7845   -1.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.7638    0.7165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2064    0.6820    1.8656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247   -0.5018    0.4289 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2288   -0.2458    0.4074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9483   -1.3416    0.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3305    0.8066    1.5211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5282    1.4866    1.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1417    1.6946    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8115    2.4992    2.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333    2.6435    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654   -1.3541   -0.6771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6928   -1.0149   -2.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9323   -2.6033   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1481   -1.1513   -1.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652   -2.4631   -1.4111 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2480   -2.3796   -1.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2483   -3.5536   -2.0872 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4286    2.7359    0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102    3.9061    2.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1302    3.9551    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9973    1.7710    2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7324    3.1595    1.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6619    2.1327   -0.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009    1.2792   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7287    0.0862    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6793   -0.0927   -0.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -0.9584    1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599   -2.8777    0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7627   -4.0108    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2891   -4.1738   -0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5867   -3.3176    0.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -2.0156    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7179   -2.5302   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2766    1.0550   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    1.1847   -0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285    2.3784    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2564    1.9769   -2.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.2627    2.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212   -1.1340    1.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5826    0.2181   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3475   -1.8715    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2086    0.3686    2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1855    0.8583    0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    1.8718    3.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    3.0056    2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770    3.3096    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9038    3.4474   -0.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4752    3.2171    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175    2.1827   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5283   -0.3285   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0051   -1.9216   -2.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7621   -0.6909   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6179   -3.1961   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.3494   -1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5734   -1.2302   -2.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -3.3046   -2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -1.5438   -2.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8470   -2.3293   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380   -4.1563   -2.4420 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  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 31  1  6
 31 32  1  0
 32 33  1  0
 32 34  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 20 28  1  0
 28 29  1  0
 28 30  1  1
 14  9  1  0
 25 18  1  0
 32 10  1  0
 28 13  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  4 40  1  6
  5 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  1
 10 45  1  1
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  6
 31 71  1  0
 31 72  1  0
 33 73  1  0
 33 74  1  0
 33 75  1  0
 34 76  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  1
 17 54  1  0
 19 55  1  0
 20 56  1  1
 21 57  1  6
 22 58  1  0
 23 59  1  1
 24 60  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
M  END


  Mrv1533004161520232D          

 34 37  0  0  0  0            999 V2000
    1.2769    3.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7901    3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301    3.2800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1334    2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688    2.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0869    1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3171    1.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    0.5624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0043   -0.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3483    0.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481    0.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    1.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    1.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2546    0.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913    0.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -0.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6338   -0.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2926   -1.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0528   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -2.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5010   -0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8185   -1.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223   -2.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005   -1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468   -0.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4294   -1.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -0.6858    0.0000 O   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  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  9 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(C)C(=O)OC1C2CCC3C1(CC2(C)O)CC(O)C1(O)C(C(O)C(O)C1(C)C)C3(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O9/c1-11(12(2)26)20(30)34-19-13-7-8-14-23(6,32)17-16(28)18(29)21(3,4)25(17,33)15(27)9-24(14,19)10-22(13,5)31/h11-19,26-29,31-33H,7-10H2,1-6H3

> <INCHI_KEY>
YKGHWWGUARTVTE-UHFFFAOYSA-N

> <FORMULA>
C25H42O9

> <MOLECULAR_WEIGHT>
486.602

> <EXACT_MASS>
486.282882932

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
51.3667475788413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
-1.2077898716666642

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.534614330276959

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.852541818624399

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867801043926335

> <JCHEM_POLAR_SURFACE_AREA>
167.91

> <JCHEM_REFRACTIVITY>
120.4997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.383   7.201   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.475   5.957   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.056   6.123   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.116   4.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.488   5.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.029   2.877   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.592   3.431   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.315   1.050   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.875  -0.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.650   0.176   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.396   1.623   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.992   1.679   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.765   0.263   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.266   0.640   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.754   2.229   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.385   1.889   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.491  -0.285   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.942   0.232   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.944   1.497   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.882  -0.987   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.516  -0.745   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.013  -2.258   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.432  -3.111   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.339  -4.091   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.535  -1.824   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.128  -3.435   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.371  -2.854   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.082  -4.505   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.844  -2.549   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.005  -1.200   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.681  -2.225   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.274  -1.414   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.802  -2.669   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.377  -1.280   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   17   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    9   13   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   10   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3,4,6,7,9,14-Hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0,.0,]hexadecan-16-yl 3-hydroxy-2-methylbutanoic acid	Generator
3,4,6,7,9,14-Hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₂₅H₄₂O₉

Average Mass

486.6020 Da

Monoisotopic Mass

486.28288 Da

IUPAC Name

3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate

Traditional Name

3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(O)C(C)C(=O)OC1C2CCC3C1(CC2(C)O)CC(O)C1(O)C(C(O)C(O)C1(C)C)C3(C)O

InChI Identifier

InChI=1S/C25H42O9/c1-11(12(2)26)20(30)34-19-13-7-8-14-23(6,32)17-16(28)18(29)21(3,4)25(17,33)15(27)9-24(14,19)10-22(13,5)31/h11-19,26-29,31-33H,7-10H2,1-6H3

InChI Key

YKGHWWGUARTVTE-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Leucothol and grayanotoxane diterpenoids

Alternative Parents

Substituents

Grayanotoxane diterpenoid
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	0.43	ALOGPS
logP	-1.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	167.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.5 m³·mol⁻¹	ChemAxon
Polarizability	51.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

73002622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate (NP0311867)

MOL for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

3D MOL for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

3D SDF for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

3D-SDF for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

PDB for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

3D PDB for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

SMILES for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

INCHI for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

Structure for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)

3D Structure for NP0311867 (3,4,6,7,9,14-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl 3-hydroxy-2-methylbutanoate)