NP-MRD: Showing NP-Card for A80915C (NP0006977)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 03:53:46 UTC

Updated at

2021-07-15 16:56:19 UTC

NP-MRD ID

NP0006977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

A80915C

Provided By

NPAtlas

Description

(3R,4aR,10aS)-3,4a-dichloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6,8-dihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. A80915C is found in Streptomyces sp. CNQ-525. A80915C was first documented in 2007 (PMID: 17392281). Based on a literature review very few articles have been published on (3R,4aR,10aS)-3,4a-dichloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6,8-dihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118363D          

 68 71  0  0  0  0            999 V2000
    6.2004    2.2728    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    2.0334    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.7875    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494    3.7753    2.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4765    2.6070    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.6225    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.8697   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792    1.0493   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4903    0.3482   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1198   -1.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -0.8573   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -0.3338   -1.5745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9871   -1.7503   -1.9465 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0007   -2.6931   -0.7856 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4180   -3.7564   -0.9429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9621   -1.9971    0.5429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3703   -2.0478    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -2.9129    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.7635    0.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    0.0727   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0800    0.1649   -1.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2582    0.5817   -0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4977    0.5889   -1.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0258    0.7276   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    1.7877   -0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -0.6597   -1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4518   -1.9055   -2.2041 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5685   -1.2670    0.1147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1973   -1.4466    0.7846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6810   -0.0347    0.9705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8198    0.1312    2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    0.6926    1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705    1.4416   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    2.4550    0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639    3.3595    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8551    1.8252    0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4684    1.8787    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    4.3261    2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    3.2061    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5123   -0.3668   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.2856   -2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0734   -1.8114   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -2.0112   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1131   -3.3600   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.3444    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.8618    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.0924    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.9202    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -2.5532    2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -3.1033    1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    0.7524   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2858   -0.8748   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1548    1.6848   -0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4387   -0.1359   -3.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    1.7063   -2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.7683   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830    1.4360   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    2.2398   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335    2.5753   -0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2331   -0.4575   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.6037    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0394   -2.2566   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -1.9197    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -1.9339    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637    0.4959    3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.8046    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.9461    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631    1.4613    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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  1  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  1  0  0  0
 20 33  1  0  0  0  0
 33 34  2  0  0  0  0
  8  2  1  0  0  0  0
 20 12  1  0  0  0  0
 30 22  1  0  0  0  0
 33  6  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  9 40  1  0  0  0  0
 12 41  1  6  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 44  1  6  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 22 53  1  1  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
 25 57  1  0  0  0  0
 25 58  1  0  0  0  0
 25 59  1  0  0  0  0
 26 60  1  6  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
 29 63  1  0  0  0  0
 29 64  1  0  0  0  0
 31 65  1  0  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 32 68  1  0  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    6.2004    2.2728    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    2.0334    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.7875    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494    3.7753    2.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4765    2.6070    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.6225    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.8697   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792    1.0493   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4903    0.3482   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1198   -1.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -0.8573   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -0.3338   -1.5745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9871   -1.7503   -1.9465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -2.6931   -0.7856 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4180   -3.7564   -0.9429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9621   -1.9971    0.5429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3703   -2.0478    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -2.9129    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.7635    0.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    0.0727   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0800    0.1649   -1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2582    0.5817   -0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4977    0.5889   -1.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0258    0.7276   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    1.7877   -0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -0.6597   -1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4518   -1.9055   -2.2041 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5685   -1.2670    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1973   -1.4466    0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -0.0347    0.9705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8198    0.1312    2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    0.6926    1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705    1.4416   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    2.4550    0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639    3.3595    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8551    1.8252    0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4684    1.8787    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    4.3261    2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    3.2061    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5123   -0.3668   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.2856   -2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0734   -1.8114   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -2.0112   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1131   -3.3600   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.3444    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.8618    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.0924    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.9202    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -2.5532    2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -3.1033    1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    0.7524   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2858   -0.8748   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1548    1.6848   -0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4387   -0.1359   -3.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    1.7063   -2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.7683   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830    1.4360   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    2.2398   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335    2.5753   -0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2331   -0.4575   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.6037    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0394   -2.2566   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -1.9197    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -1.9339    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637    0.4959    3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.8046    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.9461    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631    1.4613    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  1
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  1
 20 33  1  0
 33 34  2  0
  8  2  1  0
 20 12  1  0
 30 22  1  0
 33  6  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
  9 40  1  0
 12 41  1  6
 13 42  1  0
 13 43  1  0
 14 44  1  6
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  1
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 28 61  1  0
 28 62  1  0
 29 63  1  0
 29 64  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
M  END


  Mrv1652306242118363D          

 68 71  0  0  0  0            999 V2000
    6.2004    2.2728    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    2.0334    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.7875    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494    3.7753    2.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4765    2.6070    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.6225    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.8697   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792    1.0493   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4903    0.3482   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1198   -1.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -0.8573   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -0.3338   -1.5745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9871   -1.7503   -1.9465 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0007   -2.6931   -0.7856 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4180   -3.7564   -0.9429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9621   -1.9971    0.5429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3703   -2.0478    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -2.9129    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.7635    0.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    0.0727   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0800    0.1649   -1.0356 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2582    0.5817   -0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4977    0.5889   -1.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0258    0.7276   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    1.7877   -0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -0.6597   -1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4518   -1.9055   -2.2041 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5685   -1.2670    0.1147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1973   -1.4466    0.7846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6810   -0.0347    0.9705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8198    0.1312    2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    0.6926    1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705    1.4416   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    2.4550    0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639    3.3595    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8551    1.8252    0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4684    1.8787    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    4.3261    2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    3.2061    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5123   -0.3668   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.2856   -2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0734   -1.8114   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -2.0112   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1131   -3.3600   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.3444    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.8618    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.0924    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.9202    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -2.5532    2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -3.1033    1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    0.7524   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2858   -0.8748   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1548    1.6848   -0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4387   -0.1359   -3.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    1.7063   -2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.7683   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830    1.4360   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    2.2398   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335    2.5753   -0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2331   -0.4575   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.6037    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0394   -2.2566   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -1.9197    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -1.9339    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637    0.4959    3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.8046    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.9461    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631    1.4613    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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  1  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  1  0  0  0
 20 33  1  0  0  0  0
 33 34  2  0  0  0  0
  8  2  1  0  0  0  0
 20 12  1  0  0  0  0
 30 22  1  0  0  0  0
 33  6  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  9 40  1  0  0  0  0
 12 41  1  6  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 44  1  6  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 22 53  1  1  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
 25 57  1  0  0  0  0
 25 58  1  0  0  0  0
 25 59  1  0  0  0  0
 26 60  1  6  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
 29 63  1  0  0  0  0
 29 64  1  0  0  0  0
 31 65  1  0  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 32 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(O[H])=C2C(=C1[H])C(=O)[C@@]1(OC(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(Cl)C([H])([H])[C@]1([H])C2=O)C([H])([H])[C@]1([H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(Cl)C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H34Cl2O6/c1-12-15(29)9-13-19(20(12)30)21(31)14-10-18(28)24(4,5)34-26(14,22(13)32)11-16-23(2,3)17(27)7-8-25(16,6)33/h9,14,16-18,29-30,33H,7-8,10-11H2,1-6H3/t14-,16+,17+,18-,25+,26-/m1/s1

> <INCHI_KEY>
XGGIVXWAYKZBIV-JBPAMENMSA-N

> <FORMULA>
C26H33Cl3O6

> <MOLECULAR_WEIGHT>
547.89

> <EXACT_MASS>
546.1342719

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.63177694787248

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4aR,10aS)-3,4a-dichloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6,8-dihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
5.885757844333335

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.190208044044265

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6473900727163775

> <JCHEM_PKA_STRONGEST_BASIC>
-2.902398407254182

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
135.735

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aR,10aS)-3,4a-dichloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6,8-dihydroxy-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    6.2004    2.2728    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    2.0334    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.7875    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494    3.7753    2.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4765    2.6070    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.6225    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.8697   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792    1.0493   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4903    0.3482   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1198   -1.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -0.8573   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -0.3338   -1.5745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9871   -1.7503   -1.9465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -2.6931   -0.7856 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4180   -3.7564   -0.9429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9621   -1.9971    0.5429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3703   -2.0478    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -2.9129    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.7635    0.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    0.0727   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0800    0.1649   -1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2582    0.5817   -0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4977    0.5889   -1.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0258    0.7276   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    1.7877   -0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -0.6597   -1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4518   -1.9055   -2.2041 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5685   -1.2670    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1973   -1.4466    0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -0.0347    0.9705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8198    0.1312    2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    0.6926    1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705    1.4416   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    2.4550    0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639    3.3595    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8551    1.8252    0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4684    1.8787    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    4.3261    2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    3.2061    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5123   -0.3668   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.2856   -2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0734   -1.8114   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -2.0112   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1131   -3.3600   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.3444    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.8618    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.0924    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.9202    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -2.5532    2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -3.1033    1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    0.7524   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2858   -0.8748   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1548    1.6848   -0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4387   -0.1359   -3.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    1.7063   -2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.7683   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830    1.4360   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    2.2398   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335    2.5753   -0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2331   -0.4575   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.6037    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0394   -2.2566   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -1.9197    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -1.9339    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637    0.4959    3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.8046    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.9461    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631    1.4613    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  1
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  1
 20 33  1  0
 33 34  2  0
  8  2  1  0
 20 12  1  0
 30 22  1  0
 33  6  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
  9 40  1  0
 12 41  1  6
 13 42  1  0
 13 43  1  0
 14 44  1  6
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  1
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 28 61  1  0
 28 62  1  0
 29 63  1  0
 29 64  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.200   2.273   1.287  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.790   2.033   0.927  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.809   2.788   1.530  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.149   3.775   2.479  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.477   2.607   1.232  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.159   1.623   0.287  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.158   0.870  -0.312  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.479   1.049  -0.016  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.490   0.348  -0.567  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.663  -0.120  -1.258  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.508  -0.857  -1.861  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.239  -0.334  -1.575  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.987  -1.750  -1.946  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.001  -2.693  -0.786  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       2.418  -3.756  -0.943  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       0.962  -1.997   0.543  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.370  -2.048   1.123  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.152  -2.913   1.483  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.488  -0.764   0.588  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.293   0.073  -0.438  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.080   0.165  -1.036  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.258   0.582  -0.319  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.498   0.589  -1.256  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.026   0.728  -2.697  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.367   1.788  -0.961  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.294  -0.660  -1.213  0.00  0.00           C+0
HETATM   27 Cl   UNK     0      -3.452  -1.906  -2.204  0.00  0.00          Cl+0
HETATM   28  C   UNK     0      -4.569  -1.267   0.115  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.197  -1.447   0.785  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.681  -0.035   0.971  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.820   0.131   2.141  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.893   0.693   1.304  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.771   1.442  -0.042  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.028   2.455   0.022  0.00  0.00           O+0
HETATM   35  H   UNK     0       6.464   3.360   1.289  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.855   1.825   0.492  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.468   1.879   2.292  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.449   4.326   2.921  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.694   3.206   1.710  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.512  -0.367  -1.228  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.978   0.286  -2.488  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.073  -1.811  -2.564  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.813  -2.011  -2.684  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.113  -3.360  -0.892  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.142  -2.344   0.416  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.401  -2.862   1.914  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.566  -1.092   1.670  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.639  -3.920   1.530  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.176  -2.553   2.529  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.850  -3.103   1.081  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.922   0.752  -1.999  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.286  -0.875  -1.462  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.155   1.685  -0.063  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.439  -0.136  -3.034  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.509   1.706  -2.853  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.932   0.768  -3.336  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.283   1.436  -0.412  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.696   2.240  -1.917  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.833   2.575  -0.397  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.233  -0.458  -1.792  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.177  -0.604   0.731  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.039  -2.257  -0.067  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.270  -1.920   1.750  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.544  -1.934   0.032  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.464   0.496   3.019  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.394  -0.805   2.561  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.109   0.946   2.004  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.663   1.461   1.862  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   38                                                       
CONECT    5    3    6   39                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   40                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20   41                                             
CONECT   13   12   14   42   43                                             
CONECT   14   13   15   16   44                                             
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16   45   46   47                                             
CONECT   18   16   48   49   50                                             
CONECT   19   16   20                                                       
CONECT   20   19   21   33   12                                             
CONECT   21   20   22   51   52                                             
CONECT   22   21   23   30   53                                             
CONECT   23   22   24   25   26                                             
CONECT   24   23   54   55   56                                             
CONECT   25   23   57   58   59                                             
CONECT   26   23   27   28   60                                             
CONECT   27   26                                                            
CONECT   28   26   29   61   62                                             
CONECT   29   28   30   63   64                                             
CONECT   30   29   31   32   22                                             
CONECT   31   30   65   66   67                                             
CONECT   32   30   68                                                       
CONECT   33   20   34    6                                                  
CONECT   34   33                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    9                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
CONECT   65   31                                                            
CONECT   66   31                                                            
CONECT   67   31                                                            
CONECT   68   32                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

RDKit          3D

68 71  0  0  0  0  0  0  0  0999 V2000
    6.2004    2.2728    1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    2.0334    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.7875    1.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1494    3.7753    2.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4765    2.6070    1.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1587    1.6225    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.8697   -0.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792    1.0493   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4903    0.3482   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1198   -1.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -0.8573   -1.8612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -0.3338   -1.5745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9871   -1.7503   -1.9465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007   -2.6931   -0.7856 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4180   -3.7564   -0.9429 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9621   -1.9971    0.5429 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3703   -2.0478    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515   -2.9129    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -0.7635    0.5880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2928    0.0727   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0800    0.1649   -1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2582    0.5817   -0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4977    0.5889   -1.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0258    0.7276   -2.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3667    1.7877   -0.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2936   -0.6597   -1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4518   -1.9055   -2.2041 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5685   -1.2670    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1973   -1.4466    0.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -0.0347    0.9705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8198    0.1312    2.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    0.6926    1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7705    1.4416   -0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    2.4550    0.0219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4639    3.3595    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8551    1.8252    0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4684    1.8787    2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    4.3261    2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    3.2061    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5123   -0.3668   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    0.2856   -2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0734   -1.8114   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8126   -2.0112   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1131   -3.3600   -0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.3444    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -2.8618    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5660   -1.0924    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.9202    1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -2.5532    2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -3.1033    1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    0.7524   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2858   -0.8748   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1548    1.6848   -0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4387   -0.1359   -3.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    1.7063   -2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    0.7683   -3.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2830    1.4360   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    2.2398   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8335    2.5753   -0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2331   -0.4575   -1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -0.6037    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0394   -2.2566   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -1.9197    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438   -1.9339    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637    0.4959    3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.8046    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.9461    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631    1.4613    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  1
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  1
 20 33  1  0
 33 34  2  0
  8  2  1  0
 20 12  1  0
 30 22  1  0
 33  6  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
  9 40  1  0
 12 41  1  6
 13 42  1  0
 13 43  1  0
 14 44  1  6
 17 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  1
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 28 61  1  0
 28 62  1  0
 29 63  1  0
 29 64  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₃₃Cl₃O₆

Average Mass

547.8900 Da

Monoisotopic Mass

546.13427 Da

IUPAC Name

(3R,4aR,10aS)-3,4a-dichloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6,8-dihydroxy-2,2,7-trimethyl-2H,3H,4H,4aH,5H,10H,10aH-naphtho[2,3-b]pyran-5,10-dione

Traditional Name

(3R,4aR,10aS)-3,4a-dichloro-10a-{[(3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl}-6,8-dihydroxy-2,2,7-trimethyl-3H,4H-naphtho[2,3-b]pyran-5,10-dione

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=C2C(=O)[C@]3(CC4[C@@](C)(O)CC[C@H](Cl)C4(C)C)OC(C)(C)[C@H](Cl)C[C@]3(Cl)C(=O)C2=C1O

InChI Identifier

InChI=1S/C26H33Cl3O6/c1-12-14(30)9-13-18(19(12)31)21(33)25(29)11-17(28)23(4,5)35-26(25,20(13)32)10-15-22(2,3)16(27)7-8-24(15,6)34/h9,15-17,30-31,34H,7-8,10-11H2,1-6H3/t15?,16-,17+,24-,25-,26-/m0/s1

InChI Key

XGGIVXWAYKZBIV-JBPAMENMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces sp. CNQ-525	NPAtlas	17392281

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexyl halide
Pyranone
Cyclohexanol
Benzenoid
Pyran
Oxane
Alpha-haloketone
Alpha-chloroketone
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.52	ALOGPS
logP	5.89	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	135.74 m³·mol⁻¹	ChemAxon
Polarizability	54.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA024669

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

102085481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Winter JM, Moffitt MC, Zazopoulos E, McAlpine JB, Dorrestein PC, Moore BS: Molecular basis for chloronium-mediated meroterpene cyclization: cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster. J Biol Chem. 2007 Jun 1;282(22):16362-8. doi: 10.1074/jbc.M611046200. Epub 2007 Mar 28. [PubMed:17392281 ]

Showing NP-Card for A80915C (NP0006977)

MOL for NP0006977 (A80915C)

3D MOL for NP0006977 (A80915C)

3D SDF for NP0006977 (A80915C)

3D-SDF for NP0006977 (A80915C)

PDB for NP0006977 (A80915C)

3D PDB for NP0006977 (A80915C)

SMILES for NP0006977 (A80915C)

INCHI for NP0006977 (A80915C)

Structure for NP0006977 (A80915C)

3D Structure for NP0006977 (A80915C)