NP-MRD: Showing NP-Card for harunmadagascarin D (NP0032874)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 23:34:20 UTC

Updated at

2021-06-30 00:02:19 UTC

NP-MRD ID

NP0032874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

harunmadagascarin D

Provided By

JEOL Database JEOL Logo

Description

(6S,8S,10S)-1,8,12-Trihydroxy-6,7,8,9-tetrahydro-4,6-bis(3-methyl-2-butenyl)-3,9,9-trimethyl-6,10-methanocycloocta[b]naphthalene-11,13(10H)-dione belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). harunmadagascarin D is found in Harungana madagascariensis and Harungana madagascariensis Lam.ex.Poir. . harunmadagascarin D was first documented in 2007 (Kouam, S. F., et al.). Based on a literature review very few articles have been published on (6S,8S,10S)-1,8,12-Trihydroxy-6,7,8,9-tetrahydro-4,6-bis(3-methyl-2-butenyl)-3,9,9-trimethyl-6,10-methanocycloocta[b]naphthalene-11,13(10H)-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101343D          

 71 74  0  0  0  0            999 V2000
    0.3377    1.3417    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    2.1897    2.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    1.5660    3.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    3.4158    2.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    4.1690    2.0518 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1817    4.8896    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    6.2708    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    7.0775    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    6.9240   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    6.2252   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    6.9753   -2.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    4.8432   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    4.1003   -2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    4.7877   -4.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    2.7249   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    2.0544   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    2.7853   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    4.1680   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    0.5616   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8925    0.1816   -0.5910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1718    0.9906   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.5854    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    1.5370    1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    2.3703    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -0.3043   -1.5450 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4056   -0.2360   -2.7275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906    1.0076   -2.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.3937   -4.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7252   -0.0282   -5.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.8850   -4.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.4710   -4.2329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    1.9676   -4.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1119    2.5676   -5.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.1301   -3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.5112   -3.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337    0.9700    4.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.4815    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.8881    3.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    0.6151    2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230    1.3759    4.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508    2.2062    2.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    3.9444    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854    4.8817    2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895    3.5302    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    6.6191    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002    7.1600    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    8.0948    1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    7.9851   -0.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    6.3578   -3.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    4.1409   -4.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.2469    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850    0.2377    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815   -0.8724   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    1.0745   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    2.5408    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488    0.8854    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116    1.1594    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    1.9277    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    3.4059    0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634    2.3941   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.0038   -0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -1.3543   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.0184   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    0.9104   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647   -0.1693   -6.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    1.0112   -5.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.6618   -5.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -2.0367   -5.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -2.2608   -3.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.5175   -4.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067    0.2261   -5.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 34  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  0  0  0  0
 12 10  1  0  0  0  0
 10  9  2  0  0  0  0
  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
  4  2  2  3  0  0  0
 13 14  1  0  0  0  0
 12 18  2  0  0  0  0
  7  8  1  0  0  0  0
  5  4  1  0  0  0  0
 32 33  2  0  0  0  0
 18 17  1  0  0  0  0
 19 20  1  1  0  0  0
 17 16  2  0  0  0  0
 20 21  1  0  0  0  0
  9  7  1  0  0  0  0
 21 22  2  3  0  0  0
 15 13  2  0  0  0  0
 22 23  1  0  0  0  0
 13 12  1  0  0  0  0
 22 24  1  0  0  0  0
  6  5  1  0  0  0  0
 15 16  1  0  0  0  0
 31 28  1  0  0  0  0
  2  1  1  0  0  0  0
 19 25  1  0  0  0  0
  7  6  2  0  0  0  0
 28 26  1  0  0  0  0
 25 26  1  0  0  0  0
  6 18  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  6  0  0  0
 15 32  1  0  0  0  0
 28 30  1  0  0  0  0
 16 19  1  0  0  0  0
 34 35  2  0  0  0  0
  5 43  1  0  0  0  0
  5 44  1  0  0  0  0
  4 42  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  9 48  1  0  0  0  0
 17 51  1  0  0  0  0
 31 71  1  6  0  0  0
 11 49  1  0  0  0  0
 14 50  1  0  0  0  0
  8 45  1  0  0  0  0
  8 46  1  0  0  0  0
  8 47  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 21 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
 23 57  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  1  0  0  0
 27 64  1  0  0  0  0
 29 65  1  0  0  0  0
 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
 30 70  1  0  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
    0.3377    1.3417    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    2.1897    2.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    1.5660    3.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    3.4158    2.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    4.1690    2.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1817    4.8896    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    6.2708    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    7.0775    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    6.9240   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    6.2252   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    6.9753   -2.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    4.8432   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    4.1003   -2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    4.7877   -4.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    2.7249   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    2.0544   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    2.7853   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    4.1680   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    0.5616   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8925    0.1816   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9906   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.5854    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    1.5370    1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    2.3703    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -0.3043   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -0.2360   -2.7275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906    1.0076   -2.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.3937   -4.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7252   -0.0282   -5.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.8850   -4.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.4710   -4.2329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    1.9676   -4.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1119    2.5676   -5.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.1301   -3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.5112   -3.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337    0.9700    4.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.4815    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.8881    3.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    0.6151    2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230    1.3759    4.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508    2.2062    2.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    3.9444    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854    4.8817    2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895    3.5302    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    6.6191    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002    7.1600    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    8.0948    1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    7.9851   -0.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    6.3578   -3.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    4.1409   -4.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.2469    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850    0.2377    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815   -0.8724   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    1.0745   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    2.5408    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488    0.8854    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116    1.1594    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    1.9277    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    3.4059    0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634    2.3941   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.0038   -0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -1.3543   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.0184   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    0.9104   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647   -0.1693   -6.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    1.0112   -5.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.6618   -5.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -2.0367   -5.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -2.2608   -3.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.5175   -4.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067    0.2261   -5.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 34  1  0
 31 32  1  0
 31 34  1  0
 12 10  1  0
 10  9  2  0
  2  3  1  0
 10 11  1  0
  4  2  2  3
 13 14  1  0
 12 18  2  0
  7  8  1  0
  5  4  1  0
 32 33  2  0
 18 17  1  0
 19 20  1  1
 17 16  2  0
 20 21  1  0
  9  7  1  0
 21 22  2  3
 15 13  2  0
 22 23  1  0
 13 12  1  0
 22 24  1  0
  6  5  1  0
 15 16  1  0
 31 28  1  0
  2  1  1  0
 19 25  1  0
  7  6  2  0
 28 26  1  0
 25 26  1  0
  6 18  1  0
 26 27  1  0
 28 29  1  6
 15 32  1  0
 28 30  1  0
 16 19  1  0
 34 35  2  0
  5 43  1  0
  5 44  1  0
  4 42  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  9 48  1  0
 17 51  1  0
 31 71  1  6
 11 49  1  0
 14 50  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  1
 27 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
M  END


  Mrv1652306202101343D          

 71 74  0  0  0  0            999 V2000
    0.3377    1.3417    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    2.1897    2.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    1.5660    3.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    3.4158    2.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    4.1690    2.0518 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1817    4.8896    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    6.2708    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    7.0775    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    6.9240   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    6.2252   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    6.9753   -2.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    4.8432   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    4.1003   -2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    4.7877   -4.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    2.7249   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    2.0544   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    2.7853   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    4.1680   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    0.5616   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8925    0.1816   -0.5910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1718    0.9906   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.5854    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    1.5370    1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    2.3703    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -0.3043   -1.5450 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4056   -0.2360   -2.7275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906    1.0076   -2.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.3937   -4.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7252   -0.0282   -5.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.8850   -4.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.4710   -4.2329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    1.9676   -4.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1119    2.5676   -5.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.1301   -3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.5112   -3.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337    0.9700    4.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.4815    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.8881    3.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    0.6151    2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230    1.3759    4.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508    2.2062    2.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    3.9444    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854    4.8817    2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895    3.5302    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    6.6191    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002    7.1600    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    8.0948    1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    7.9851   -0.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    6.3578   -3.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    4.1409   -4.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.2469    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850    0.2377    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815   -0.8724   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    1.0745   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    2.5408    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488    0.8854    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116    1.1594    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    1.9277    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    3.4059    0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634    2.3941   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.0038   -0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -1.3543   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.0184   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    0.9104   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647   -0.1693   -6.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    1.0112   -5.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.6618   -5.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -2.0367   -5.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -2.2608   -3.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.5175   -4.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067    0.2261   -5.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 34  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  0  0  0  0
 12 10  1  0  0  0  0
 10  9  2  0  0  0  0
  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
  4  2  2  3  0  0  0
 13 14  1  0  0  0  0
 12 18  2  0  0  0  0
  7  8  1  0  0  0  0
  5  4  1  0  0  0  0
 32 33  2  0  0  0  0
 18 17  1  0  0  0  0
 19 20  1  1  0  0  0
 17 16  2  0  0  0  0
 20 21  1  0  0  0  0
  9  7  1  0  0  0  0
 21 22  2  3  0  0  0
 15 13  2  0  0  0  0
 22 23  1  0  0  0  0
 13 12  1  0  0  0  0
 22 24  1  0  0  0  0
  6  5  1  0  0  0  0
 15 16  1  0  0  0  0
 31 28  1  0  0  0  0
  2  1  1  0  0  0  0
 19 25  1  0  0  0  0
  7  6  2  0  0  0  0
 28 26  1  0  0  0  0
 25 26  1  0  0  0  0
  6 18  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  6  0  0  0
 15 32  1  0  0  0  0
 28 30  1  0  0  0  0
 16 19  1  0  0  0  0
 34 35  2  0  0  0  0
  5 43  1  0  0  0  0
  5 44  1  0  0  0  0
  4 42  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  9 48  1  0  0  0  0
 17 51  1  0  0  0  0
 31 71  1  6  0  0  0
 11 49  1  0  0  0  0
 14 50  1  0  0  0  0
  8 45  1  0  0  0  0
  8 46  1  0  0  0  0
  8 47  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 21 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
 23 57  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  1  0  0  0
 27 64  1  0  0  0  0
 29 65  1  0  0  0  0
 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
 30 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C(C2=C1C(O[H])=C1C(=O)[C@]3([H])C(=O)[C@@](C1=C2[H])(C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C3(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O5/c1-15(2)8-9-18-17(5)12-21(31)23-19(18)13-20-24(26(23)33)27(34)25-28(35)30(20,11-10-16(3)4)14-22(32)29(25,6)7/h8,10,12-13,22,25,31-33H,9,11,14H2,1-7H3/t22-,25+,30-/m0/s1

> <INCHI_KEY>
NRVDUEFDDRPHGV-KIYFCNKGSA-N

> <FORMULA>
C30H36O5

> <MOLECULAR_WEIGHT>
476.613

> <EXACT_MASS>
476.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.354245692706826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,13S,15S)-8,10,15-trihydroxy-6,14,14-trimethyl-1,5-bis(3-methylbut-2-en-1-yl)tetracyclo[11.3.1.0^{2,11}.0^{4,9}]heptadeca-2,4(9),5,7,10-pentaene-12,17-dione

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
7.082406189333335

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.041470679518996

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.780227759517252

> <JCHEM_PKA_STRONGEST_BASIC>
-2.959728556613319

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
140.9055

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,15S)-8,10,15-trihydroxy-6,14,14-trimethyl-1,5-bis(3-methylbut-2-en-1-yl)tetracyclo[11.3.1.0^{2,11}.0^{4,9}]heptadeca-2,4(9),5,7,10-pentaene-12,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
    0.3377    1.3417    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    2.1897    2.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    1.5660    3.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    3.4158    2.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    4.1690    2.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1817    4.8896    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    6.2708    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    7.0775    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    6.9240   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    6.2252   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    6.9753   -2.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    4.8432   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    4.1003   -2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    4.7877   -4.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    2.7249   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    2.0544   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    2.7853   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    4.1680   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    0.5616   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8925    0.1816   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9906   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.5854    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    1.5370    1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    2.3703    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -0.3043   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -0.2360   -2.7275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906    1.0076   -2.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.3937   -4.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7252   -0.0282   -5.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.8850   -4.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.4710   -4.2329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    1.9676   -4.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1119    2.5676   -5.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.1301   -3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.5112   -3.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337    0.9700    4.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.4815    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.8881    3.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    0.6151    2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230    1.3759    4.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508    2.2062    2.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    3.9444    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854    4.8817    2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895    3.5302    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    6.6191    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002    7.1600    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    8.0948    1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    7.9851   -0.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    6.3578   -3.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    4.1409   -4.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.2469    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850    0.2377    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815   -0.8724   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    1.0745   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    2.5408    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488    0.8854    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116    1.1594    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    1.9277    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    3.4059    0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634    2.3941   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.0038   -0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -1.3543   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.0184   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    0.9104   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647   -0.1693   -6.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    1.0112   -5.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.6618   -5.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -2.0367   -5.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -2.2608   -3.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.5175   -4.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067    0.2261   -5.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 34  1  0
 31 32  1  0
 31 34  1  0
 12 10  1  0
 10  9  2  0
  2  3  1  0
 10 11  1  0
  4  2  2  3
 13 14  1  0
 12 18  2  0
  7  8  1  0
  5  4  1  0
 32 33  2  0
 18 17  1  0
 19 20  1  1
 17 16  2  0
 20 21  1  0
  9  7  1  0
 21 22  2  3
 15 13  2  0
 22 23  1  0
 13 12  1  0
 22 24  1  0
  6  5  1  0
 15 16  1  0
 31 28  1  0
  2  1  1  0
 19 25  1  0
  7  6  2  0
 28 26  1  0
 25 26  1  0
  6 18  1  0
 26 27  1  0
 28 29  1  6
 15 32  1  0
 28 30  1  0
 16 19  1  0
 34 35  2  0
  5 43  1  0
  5 44  1  0
  4 42  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  9 48  1  0
 17 51  1  0
 31 71  1  6
 11 49  1  0
 14 50  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  1
 27 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.338   1.342   3.388  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.484   2.190   2.916  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.841   1.566   3.111  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.365   3.416   2.369  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.098   4.169   2.052  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.182   4.890   0.706  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.502   6.271   0.682  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.729   7.077   1.933  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.607   6.924  -0.545  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.432   6.225  -1.732  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.581   6.975  -2.873  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.131   4.843  -1.764  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.011   4.100  -2.969  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.176   4.788  -4.157  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.309   2.725  -2.971  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.520   2.054  -1.758  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.333   2.785  -0.568  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.010   4.168  -0.525  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.876   0.562  -1.719  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.893   0.182  -0.591  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.172   0.991  -0.579  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.777   1.585   0.468  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.310   1.537   1.895  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.049   2.370   0.267  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.410  -0.304  -1.545  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.406  -0.236  -2.728  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.091   1.008  -2.640  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.737  -0.394  -4.127  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.725  -0.028  -5.256  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.366  -1.885  -4.334  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.553   0.471  -4.233  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.320   1.968  -4.258  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.112   2.568  -5.314  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.441   0.130  -3.070  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.477  -0.511  -3.224  0.00  0.00           O+0
HETATM   36  H   UNK     0       0.534   0.970   4.400  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.206   0.482   2.724  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.607   1.888   3.434  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.901   0.615   2.571  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.023   1.376   4.174  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.651   2.206   2.745  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.279   3.944   2.092  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.085   4.882   2.862  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.790   3.530   2.055  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.508   6.619   2.552  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.200   7.160   2.505  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.064   8.095   1.702  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.841   7.985  -0.594  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.456   6.358  -3.624  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.115   4.141  -4.899  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.430   2.247   0.372  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.385   0.238   0.377  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.182  -0.872  -0.705  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.660   1.075  -1.551  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.041   2.541   2.238  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.449   0.885   2.048  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.112   1.159   2.540  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.864   1.928   0.849  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.909   3.406   0.594  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.363   2.394  -0.781  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.929  -0.004  -0.624  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.117  -1.354  -1.413  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.161  -1.018  -2.580  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.963   0.910  -3.064  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.265  -0.169  -6.240  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.063   1.011  -5.199  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.619  -0.662  -5.213  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.124  -2.037  -5.303  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.312  -2.261  -3.561  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.261  -2.518  -4.314  0.00  0.00           H+0
HETATM   71  H   UNK     0      -1.107   0.226  -5.150  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3    4    1                                                  
CONECT    3    2   39   40   41                                             
CONECT    4    2    5   42                                                  
CONECT    5    4    6   43   44                                             
CONECT    6    5    7   18                                                  
CONECT    7    8    9    6                                                  
CONECT    8    7   45   46   47                                             
CONECT    9   10    7   48                                                  
CONECT   10   12    9   11                                                  
CONECT   11   10   49                                                       
CONECT   12   10   18   13                                                  
CONECT   13   14   15   12                                                  
CONECT   14   13   50                                                       
CONECT   15   13   16   32                                                  
CONECT   16   17   15   19                                                  
CONECT   17   18   16   51                                                  
CONECT   18   12   17    6                                                  
CONECT   19   34   20   25   16                                             
CONECT   20   19   21   52   53                                             
CONECT   21   20   22   54                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   55   56   57                                             
CONECT   24   22   58   59   60                                             
CONECT   25   19   26   61   62                                             
CONECT   26   28   25   27   63                                             
CONECT   27   26   64                                                       
CONECT   28   31   26   29   30                                             
CONECT   29   28   65   66   67                                             
CONECT   30   28   68   69   70                                             
CONECT   31   32   34   28   71                                             
CONECT   32   31   33   15                                                  
CONECT   33   32                                                            
CONECT   34   19   31   35                                                  
CONECT   35   34                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44    5                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49   11                                                            
CONECT   50   14                                                            
CONECT   51   17                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   25                                                            
CONECT   63   26                                                            
CONECT   64   27                                                            
CONECT   65   29                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
CONECT   68   30                                                            
CONECT   69   30                                                            
CONECT   70   30                                                            
CONECT   71   31                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  148    0
END

RDKit          3D

71 74  0  0  0  0  0  0  0  0999 V2000
    0.3377    1.3417    3.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    2.1897    2.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    1.5660    3.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    3.4158    2.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    4.1690    2.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1817    4.8896    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023    6.2708    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    7.0775    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    6.9240   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4318    6.2252   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    6.9753   -2.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    4.8432   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107    4.1003   -2.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    4.7877   -4.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    2.7249   -2.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    2.0544   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3325    2.7853   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102    4.1680   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    0.5616   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8925    0.1816   -0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    0.9906   -0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    1.5854    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    1.5370    1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    2.3703    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -0.3043   -1.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056   -0.2360   -2.7275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0906    1.0076   -2.6405 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7368   -0.3937   -4.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7252   -0.0282   -5.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657   -1.8850   -4.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533    0.4710   -4.2329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    1.9676   -4.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1119    2.5676   -5.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406    0.1301   -3.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -0.5112   -3.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337    0.9700    4.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.4815    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.8881    3.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008    0.6151    2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0230    1.3759    4.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508    2.2062    2.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    3.9444    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854    4.8817    2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7895    3.5302    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076    6.6191    2.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002    7.1600    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    8.0948    1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    7.9851   -0.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    6.3578   -3.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145    4.1409   -4.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.2469    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3850    0.2377    0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1815   -0.8724   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    1.0745   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    2.5408    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4488    0.8854    2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1116    1.1594    2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    1.9277    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9088    3.4059    0.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634    2.3941   -0.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.0038   -0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -1.3543   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1609   -1.0184   -2.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9630    0.9104   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647   -0.1693   -6.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    1.0112   -5.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -0.6618   -5.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -2.0367   -5.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -2.2608   -3.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609   -2.5175   -4.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1067    0.2261   -5.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 34  1  0
 31 32  1  0
 31 34  1  0
 12 10  1  0
 10  9  2  0
  2  3  1  0
 10 11  1  0
  4  2  2  3
 13 14  1  0
 12 18  2  0
  7  8  1  0
  5  4  1  0
 32 33  2  0
 18 17  1  0
 19 20  1  1
 17 16  2  0
 20 21  1  0
  9  7  1  0
 21 22  2  3
 15 13  2  0
 22 23  1  0
 13 12  1  0
 22 24  1  0
  6  5  1  0
 15 16  1  0
 31 28  1  0
  2  1  1  0
 19 25  1  0
  7  6  2  0
 28 26  1  0
 25 26  1  0
  6 18  1  0
 26 27  1  0
 28 29  1  6
 15 32  1  0
 28 30  1  0
 16 19  1  0
 34 35  2  0
  5 43  1  0
  5 44  1  0
  4 42  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  3 41  1  0
  9 48  1  0
 17 51  1  0
 31 71  1  6
 11 49  1  0
 14 50  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  1
 27 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₅

Average Mass

476.6130 Da

Monoisotopic Mass

476.25627 Da

IUPAC Name

(1S,13S,15S)-8,10,15-trihydroxy-6,14,14-trimethyl-1,5-bis(3-methylbut-2-en-1-yl)tetracyclo[11.3.1.0^{2,11}.0^{4,9}]heptadeca-2,4(9),5,7,10-pentaene-12,17-dione

Traditional Name

(1S,13S,15S)-8,10,15-trihydroxy-6,14,14-trimethyl-1,5-bis(3-methylbut-2-en-1-yl)tetracyclo[11.3.1.0^{2,11}.0^{4,9}]heptadeca-2,4(9),5,7,10-pentaene-12,17-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C(C2=C1C(O[H])=C1C(=O)[C@]3([H])C(=O)[C@@](C1=C2[H])(C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C3(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C30H36O5/c1-15(2)8-9-18-17(5)12-21(31)23-19(18)13-20-24(26(23)33)27(34)25-28(35)30(20,11-10-16(3)4)14-22(32)29(25,6)7/h8,10,12-13,22,25,31-33H,9,11,14H2,1-7H3/t22-,25+,30-/m0/s1

InChI Key

NRVDUEFDDRPHGV-KIYFCNKGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Harungana madagascariensis	JEOL database	Kouam, S. F., et al, J. Nat. Prod. 70, 600 (2007)
Harungana madagascariensis Lam.ex.Poir.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
1-naphthol
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
1,3-diketone
1,3-dicarbonyl compound
Vinylogous acid
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.82	ALOGPS
logP	7.08	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.91 m³·mol⁻¹	ChemAxon
Polarizability	53.35 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

17342823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16215169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kouam, S. F., et al. (2007). Kouam, S. F., et al, J. Nat. Prod. 70, 600 (2007) . J. Nat. Prod..

Showing NP-Card for harunmadagascarin D (NP0032874)

MOL for NP0032874 (harunmadagascarin D)

3D MOL for NP0032874 (harunmadagascarin D)

3D SDF for NP0032874 (harunmadagascarin D)

3D-SDF for NP0032874 (harunmadagascarin D)

PDB for NP0032874 (harunmadagascarin D)

3D PDB for NP0032874 (harunmadagascarin D)

SMILES for NP0032874 (harunmadagascarin D)

INCHI for NP0032874 (harunmadagascarin D)

Structure for NP0032874 (harunmadagascarin D)

3D Structure for NP0032874 (harunmadagascarin D)