NP-MRD: Showing NP-Card for (6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0287471)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 16:34:12 UTC

Updated at

2022-09-09 16:34:12 UTC

NP-MRD ID

NP0287471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione

Description

Cohaerin C belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione is found in Annulohypoxylon cohaerens. (6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione was first documented in 2013 (PMID: 23969107). Based on a literature review very few articles have been published on Cohaerin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218342D          

 35 38  0  0  1  0            999 V2000
    5.6542    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411    4.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6555    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6555    2.6705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3700    3.9080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4562    4.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8431    5.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2632    4.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6757    4.1855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1606    4.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4827    4.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0347    4.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376    3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1856    2.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4405    1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8885    1.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1434    0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9504    0.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5024    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2053   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6533   -1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9083   -1.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8463   -0.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5914   -0.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7844   -0.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0815    1.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8266    2.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3786    2.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237    3.5724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  2  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 20 34  1  0  0  0  0
 35 34  1  1  0  0  0
 11 35  1  0  0  0  0
 15 35  1  0  0  0  0
M  END

     RDKit          3D

 69 72  0  0  0  0  0  0  0  0999 V2000
    8.2353   -0.3699   -2.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2033   -1.0831   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8760   -1.6651   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8029   -0.6138   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578   -1.2312   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091   -0.0983    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781   -0.6820    0.4118 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2865   -1.3460    1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835    0.2873    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180    0.1587   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9952    1.3901    1.4802 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6816    2.6115    0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5699    2.7180    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0828    3.6703    1.6337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    3.4391    1.5604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0796    4.2480    2.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7043    3.7767    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680    4.6794   -0.4236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8117    3.0224   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    1.8457   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3064    1.0935   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -0.0646   -0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8342   -0.8346   -0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2296   -1.9882   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5393   -2.5575    0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3497   -2.7237   -0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4575   -1.8456   -1.3195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1549   -2.6134   -2.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0229   -0.5508   -1.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5416   -0.3516   -1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9412    0.2199   -2.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0200   -0.5456    0.9692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    0.1144    1.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4969    1.2989    1.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3743    1.9534    1.7819 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1435   -1.1334   -2.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2520    0.0678   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5094    0.4442   -2.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6408   -0.4487   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9217   -1.9495   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9677   -2.1799    0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6246   -2.4354   -1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0950    0.0794    0.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325    0.0057   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658   -1.8803   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4988   -1.8125    0.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.3894   -0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    0.5128    0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335   -1.4990   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984   -1.3486    2.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9572   -0.7179    2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -2.3699    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160    1.1415    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082    5.2697    2.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4868    4.3420    3.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0445    3.8008    2.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958    3.4587   -1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7967    1.5467   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0240   -3.5282    1.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6727   -1.9049    1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4996   -2.8139    0.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9869   -3.4270   -1.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7943   -3.3764   -0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2225   -1.6404   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5867   -3.3035   -2.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4756    0.3088   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4031   -0.4781   -2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -0.3208    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5591    1.8383    2.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 35  1  0
 35 34  1  0
 34 33  2  0
 33 32  1  0
 32 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  1  1
 15 14  1  0
 14 12  1  0
 12 13  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  2  0
 12 11  1  0
 30 23  1  0
 15 35  1  0
 20 34  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  6
  8 50  1  0
  8 51  1  0
  8 52  1  0
 11 53  1  1
 35 69  1  1
 33 68  1  0
 21 58  1  0
 19 57  1  0
 16 54  1  0
 16 55  1  0
 16 56  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  1
 28 65  1  0
 29 66  1  0
 29 67  1  0
M  END


  Mrv1652309092218342D          

 35 38  0  0  1  0            999 V2000
    5.6542    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411    3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411    4.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6555    3.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6555    2.6705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3700    3.9080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4562    4.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8431    5.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2632    4.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6757    4.1855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1606    4.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4827    4.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0347    4.6271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7376    3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1856    2.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4405    1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8885    1.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1434    0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9504    0.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5024    0.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2053   -0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6533   -1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9083   -1.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8463   -0.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5914   -0.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7844   -0.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0815    1.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8266    2.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3786    2.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1237    3.5724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  2  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 20 34  1  0  0  0  0
 35 34  1  1  0  0  0
 11 35  1  0  0  0  0
 15 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287471

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(C)C(=O)[C@@H]1[C@@H]2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C1=C(C)CC(O)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O7/c1-5-6-7-8-9-15(2)26(32)24-25-19-14-34-21(23-16(3)10-18(29)13-20(23)30)11-17(19)12-22(31)28(25,4)35-27(24)33/h11-12,14-15,18,24-25,29H,5-10,13H2,1-4H3/t15?,18?,24-,25-,28-/m0/s1

> <INCHI_KEY>
GKKNMNFXYPXAOJ-GNEHSSTKSA-N

> <FORMULA>
C28H34O7

> <MOLECULAR_WEIGHT>
482.573

> <EXACT_MASS>
482.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.76472379823646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR,9S,9aR)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_LOGP>
3.8232098406666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.994286564125058

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.406600102759091

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7963155586442623

> <JCHEM_POLAR_SURFACE_AREA>
106.97000000000001

> <JCHEM_REFRACTIVITY>
132.61889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6aR,9S,9aR)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.555   7.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.888   6.525   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.222   7.295   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.556   6.525   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.889   7.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.223   6.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.557   7.295   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.557   8.835   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.890   6.525   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      19.890   4.985   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      21.224   7.295   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.385   8.827   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      20.241   9.857   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      22.891   9.147   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.661   7.813   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.567   9.059   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.168   7.493   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.198   8.637   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      25.644   6.028   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.613   4.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.089   3.419   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.059   2.275   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.534   0.810   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.041   0.490   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.071   1.634   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.517  -0.975   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.486  -2.119   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      25.962  -3.584   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      23.980  -1.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.504  -0.334   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      21.998  -0.014   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      22.552   2.595   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      22.076   4.060   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.107   5.204   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.631   6.669   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   35                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   35                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30                                                            
CONECT   32   22   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   20   35                                                  
CONECT   35   34   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₇

Average Mass

482.5730 Da

Monoisotopic Mass

482.23045 Da

IUPAC Name

(6aR,9S,9aR)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aR,9S,9aR)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9H,9aH-furo[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)C(=O)[C@@H]1[C@@H]2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C1=C(C)CC(O)CC1=O

InChI Identifier

InChI=1S/C28H34O7/c1-5-6-7-8-9-15(2)26(32)24-25-19-14-34-21(23-16(3)10-18(29)13-20(23)30)11-17(19)12-22(31)28(25,4)35-27(24)33/h11-12,14-15,18,24-25,29H,5-10,13H2,1-4H3/t15?,18?,24-,25-,28-/m0/s1

InChI Key

GKKNMNFXYPXAOJ-GNEHSSTKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annulohypoxylon cohaerens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
1,3-dicarbonyl compound
Pyran
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.82	ChemAxon
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.62 m³·mol⁻¹	ChemAxon
Polarizability	52.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053152

Chemspider ID

78437274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Surup F, Mohr KI, Jansen R, Stadler M: Cohaerins G-K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C-K. Phytochemistry. 2013 Nov;95:252-8. doi: 10.1016/j.phytochem.2013.07.027. Epub 2013 Aug 19. [PubMed:23969107 ]
LOTUS database [Link]

Showing NP-Card for (6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0287471)

MOL for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D MOL for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D SDF for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D-SDF for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

PDB for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D PDB for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

SMILES for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

INCHI for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

Structure for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D Structure for NP0287471 ((6ar,9s,9ar)-3-(4-hydroxy-2-methyl-6-oxocyclohex-1-en-1-yl)-6a-methyl-9-(2-methyloctanoyl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione)