NP-MRD: Showing NP-Card for 3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one (NP0233589)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 15:14:57 UTC

Updated at

2022-09-06 15:14:58 UTC

NP-MRD ID

NP0233589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one

Description

3,7,8-Trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]Docosane-18,2'-oxolane]-21-one belongs to the class of organic compounds known as furospirostanes and derivatives. These are heterocyclic steroids containing a furospirostane moiety, which a skeleton characterized by the presence of a 1,6-dioxaspiro[4.4]Nonane ring system and an androstane moiety. 3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one is found in Isis hippuris. 3,7,8-Trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]Docosane-18,2'-oxolane]-21-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251514232D          

 35 41  0  0  0  0            999 V2000
    1.3060   -0.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7740   -0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7211    0.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683   -0.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8976   -0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7382   -0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0926    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9149    0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3830   -0.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2053   -0.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6734   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4958   -0.7522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3190   -1.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7870   -2.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4966   -1.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -0.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6742   -1.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2062   -1.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8626   -1.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -2.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -1.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6927   -0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200   -1.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -2.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1833   -1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6960   -2.6301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534   -1.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -1.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -2.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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  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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 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
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
    6.7092    0.8137   -0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    0.8703    0.2147 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7180   -0.5561    0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3300   -0.3384   -0.3310 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6131    0.3449    0.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568   -0.5553    1.5195 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6453   -0.3265    2.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2503   -1.3028    1.2069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6738   -0.8295    1.1665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5061   -2.0750    1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8847   -1.9164    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2474   -0.4680    0.6491 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7175   -0.3373    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1765    1.0828    0.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8121    1.4532   -0.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9718    1.9622    0.6558 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3891    3.2800    0.4875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8736    1.7110   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819    0.2755   -0.3160 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5949   -0.2613   -1.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558    0.1790    0.1291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0687    0.0856   -1.1060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1447    1.2848   -1.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164    0.0166   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945   -1.3096   -0.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5734   -2.2898   -1.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1539   -3.2275   -1.4631 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449   -1.8922   -1.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -1.6540   -0.5382 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7377   -2.7882   -0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8353   -1.7107    0.6394 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6499    0.4271   -1.3921 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4355    1.4431   -0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2913    1.9629   -2.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354    2.5572   -0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3909    0.6199    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8340   -0.0032   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792    1.8027   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524    1.4064    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -1.2391   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -0.8394    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -0.8087    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.6890    1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324   -0.6417    3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1774   -2.2664    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8714   -0.3605    2.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5625   -2.5064    2.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0160   -2.9031    0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143   -2.3867   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6332   -2.4466    1.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0590   -0.0949    1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0621   -0.9081   -0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2310   -0.8544    1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9116    1.3094    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4980    2.3702   -0.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6564    1.8555    1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3471    3.3916    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1807    2.0527   -1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0101    2.3512   -0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -1.2636   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6959   -0.2941   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2270    0.4734   -2.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6914    1.1914    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2351   -0.8015   -1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496    1.1771   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    0.9090   -0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9501    0.0833   -1.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -3.7496   -0.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -2.6978   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2884   -2.8411    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -2.6760    1.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5947    2.1438   -2.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0499    1.2584   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250    2.9413   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4857    2.4371   -0.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8762    3.5404   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021    2.6672    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  1  0
  7  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 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 31  1  0
 31 29  1  0
 29 30  1  1
 29 28  1  0
 28 26  1  0
 26 27  2  0
  4 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33  2  1  0
 29  4  1  0
 31  6  1  0
 25  8  1  0
 25 26  1  6
 21  9  1  0
 19 12  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  3 40  1  0
  3 41  1  0
  6 42  1  1
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  1
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  1
 13 52  1  0
 13 53  1  0
 14 54  1  1
 15 55  1  0
 16 56  1  1
 17 57  1  0
 18 58  1  0
 18 59  1  0
 20 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  1
 22 64  1  6
 23 65  1  0
 24 66  1  0
 24 67  1  0
 31 71  1  1
 30 68  1  0
 30 69  1  0
 30 70  1  0
 34 72  1  0
 34 73  1  0
 34 74  1  0
 35 75  1  0
 35 76  1  0
 35 77  1  0
M  END


  Mrv1533004251514232D          

 35 41  0  0  0  0            999 V2000
    1.3060   -0.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7740   -0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7211    0.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683   -0.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3631    0.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8976   -0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7382   -0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0926    0.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9149    0.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3830   -0.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2053   -0.1384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6734   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4958   -0.7522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3190   -1.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7870   -2.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4966   -1.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0286   -0.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6742   -1.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2062   -1.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8626   -1.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277   -2.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0369   -1.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6927   -0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200   -1.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -2.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1833   -1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6960   -2.6301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534   -1.4907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -1.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540   -2.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4513   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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  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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
  4 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
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(OC3CC4C5CCC6CC(O)C(O)CC6(C)C5C(O)CC44C3C2(C)OC4=O)OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O7/c1-13-10-28(35-24(13,2)3)26(5)22-20(33-28)9-16-15-7-6-14-8-17(29)18(30)11-25(14,4)21(15)19(31)12-27(16,22)23(32)34-26/h13-22,29-31H,6-12H2,1-5H3

> <INCHI_KEY>
XRLDSQWGEQUZHL-UHFFFAOYSA-N

> <FORMULA>
C28H42O7

> <MOLECULAR_WEIGHT>
490.637

> <EXACT_MASS>
490.293053692

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.525677684088606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolane]-21-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.0545709779999974

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.793798865771635

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.852108714728804

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8498300741750615

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
126.42500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolane]-21-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.438  -0.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.846  -1.118   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.178  -0.346   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.324  -1.375   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.946   0.064   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.527  -0.046   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.011   0.473   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.009  -0.753   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.578  -0.626   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.239   0.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.775   0.887   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.648  -0.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.183  -0.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.057  -1.527   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      19.592  -1.404   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.395  -2.917   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.269  -4.185   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.860  -3.040   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.987  -1.772   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.325  -3.162   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.452  -1.894   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.810  -3.301   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.678  -4.573   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.269  -3.386   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.211  -2.168   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.760  -1.552   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.504  -2.428   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.256  -3.330   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.130  -3.868   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.675  -3.703   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.633  -4.910   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.700  -2.783   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.168  -2.624   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.834  -4.127   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.709  -3.117   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27   32                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    9   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    8   26   30                                             
CONECT   26   25    6   27                                                  
CONECT   27   26    4   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32    4   33                                                       
CONECT   33   32    2   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₇

Average Mass

490.6370 Da

Monoisotopic Mass

490.29305 Da

IUPAC Name

3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolane]-21-one

Traditional Name

3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolane]-21-one

CAS Registry Number

Not Available

SMILES

CC1CC2(OC3CC4C5CCC6CC(O)C(O)CC6(C)C5C(O)CC44C3C2(C)OC4=O)OC1(C)C

InChI Identifier

InChI=1S/C28H42O7/c1-13-10-28(35-24(13,2)3)26(5)22-20(33-28)9-16-15-7-6-14-8-17(29)18(30)11-25(14,4)21(15)19(31)12-27(16,22)23(32)34-26/h13-22,29-31H,6-12H2,1-5H3

InChI Key

XRLDSQWGEQUZHL-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

Species Name	Source	Reference
Isis hippuris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furospirostanes and derivatives. These are heterocyclic steroids containing a furospirostane moiety, which a skeleton characterized by the presence of a 1,6-dioxaspiro[4.4]Nonane ring system and an androstane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Furospirostanes and derivatives

Direct Parent

Furospirostanes and derivatives

Alternative Parents

Substituents

Furospirostane-skeleton
Triterpenoid
Spirostane skeleton
Steroid lactone
3-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
11-hydroxysteroid
Furofuran
Ketal
Gamma butyrolactone
Monosaccharide
Tetrahydrofuran
Cyclic alcohol
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.9	ALOGPS
logP	2.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	126.42 m³·mol⁻¹	ChemAxon
Polarizability	54.53 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

72831313

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one (NP0233589)

MOL for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

3D MOL for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

3D SDF for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

3D-SDF for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

PDB for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

3D PDB for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

SMILES for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

INCHI for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

Structure for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)

3D Structure for NP0233589 (3,7,8-trihydroxy-4',5,5',5',19-pentamethyl-17,20-dioxaspiro[hexacyclo[14.5.1.0¹,¹⁴.0⁴,¹³.0⁵,¹⁰.0¹⁹,²²]docosane-18,2'-oxolan]-21-one)