NP-MRD: Showing NP-Card for (5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione (NP0324940)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 05:19:19 UTC

Updated at

2022-09-12 05:19:20 UTC

NP-MRD ID

NP0324940

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione

Description

(5AR,6S,12R,12aR,13aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1H,2H,3H,5H,5aH,6H,11H,12H,12aH,13H,13aH-indolizino[7,6-b]carbazole-5,13-dione belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. (5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione is found in Aspergillus caespitosus. Based on a literature review very few articles have been published on (5aR,6S,12R,12aR,13aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1H,2H,3H,5H,5aH,6H,11H,12H,12aH,13H,13aH-indolizino[7,6-b]carbazole-5,13-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207192D          

 35 39  0  0  1  0            999 V2000
    7.2522    2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8086    1.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9844    1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6038    2.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    2.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3360    1.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223    1.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001    0.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1383    0.2391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741   -0.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0468   -0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827   -1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459   -2.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553   -1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167    0.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6324    0.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5101   -0.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1556   -1.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0334   -1.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9233   -0.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9869    0.8192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2192    0.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -0.2988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5737    1.0309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2400    0.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422    2.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6960    1.8468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4637    2.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    2.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091    1.6351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2314    2.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    1.9371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9991    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
  3 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
    5.3920    4.6526    0.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080    3.4274    0.2521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    2.9144    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8627    3.6040    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    3.0817    1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    1.8874    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0567    1.1501    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040    0.0092    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4464    0.0557   -0.2780 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0350   -0.9724   -1.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -2.0369   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9756   -2.3669   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -3.4846    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8577   -1.6960   -1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800    1.1624    0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227    1.7125   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9774   -0.8743    0.1902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8693   -2.0353   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6637   -3.2334   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521   -4.4142   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5398   -3.4234    1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428    0.0198   -0.1294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3806   -0.6913   -0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4832   -1.8774   -0.6713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    0.1322   -0.6146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0566    0.2386   -2.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439    1.5251   -2.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3334    2.3733   -0.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4019    1.5158   -0.2524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3980    1.8983    0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653    3.0464    1.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4290    0.8558    1.1009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1372    0.0687    2.0437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2081    1.4271    1.7411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0399    0.9736    3.0593 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017    4.8938    0.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101    5.4819    0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4658    4.5420    1.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1376    4.5516    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9396    3.6451    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8343   -0.4525   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -1.3170   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842   -2.5753    0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9952   -4.2511   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7306   -3.9181    0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2718   -3.0248    0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -1.5745   -2.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7599   -2.3653   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2645   -0.7391   -1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0443    1.2162   -0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1441   -1.2198    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590   -1.9598   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -4.8446   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -5.2162   -0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2490   -4.1308   -2.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1576   -2.7109    1.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242   -4.4598    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -3.1892    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.6885   -0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4229   -0.2503    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475    0.3559   -2.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6661   -0.6384   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9387    1.3474   -1.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7435    2.0549   -3.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1412    2.6162   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374    3.2999   -1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072    0.7250    2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    2.5239    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859    0.2688    3.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 15  1  0
 15 16  2  0
 15  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  9  8  1  0
  8  7  2  0
  7 34  1  0
 34 35  1  0
 34 32  1  0
 32 33  1  1
 32 22  1  0
 22 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 16  3  1  0
 17  8  1  0
 29 25  1  0
  7  6  1  0
 30 32  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
 16 50  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 34 68  1  1
 35 69  1  0
 33 67  1  0
 22 59  1  6
 17 51  1  1
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 25 60  1  1
 26 61  1  0
 26 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  0
 28 66  1  0
M  END


  Mrv1652309122207192D          

 35 39  0  0  1  0            999 V2000
    7.2522    2.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8086    1.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9844    1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6038    2.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    2.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3360    1.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223    1.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4001    0.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1383    0.2391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741   -0.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0468   -0.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1827   -1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459   -2.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553   -1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167    0.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6324    0.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5101   -0.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1556   -1.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0334   -1.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9233   -0.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9869    0.8192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2192    0.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0970   -0.2988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5737    1.0309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2400    0.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0422    2.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6960    1.8468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4637    2.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    2.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091    1.6351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2314    2.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    1.9371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9991    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
  3 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0324940

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)N(CC=C(C)C)C1=C2[C@H](O)[C@]2(O)[C@@H]([C@H]1C=C(C)C)C(=O)[C@@H]1CCCN1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34N2O5/c1-15(2)10-12-29-21-14-17(35-5)8-9-18(21)22-24(29)19(13-16(3)4)23-25(31)20-7-6-11-30(20)27(33)28(23,34)26(22)32/h8-10,13-14,19-20,23,26,32,34H,6-7,11-12H2,1-5H3/t19-,20+,23+,26+,28-/m1/s1

> <INCHI_KEY>
KGGKDBGWQMLMND-KCZDIRIGSA-N

> <FORMULA>
C28H34N2O5

> <MOLECULAR_WEIGHT>
478.589

> <EXACT_MASS>
478.246772203

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.64033015475904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,6S,12R,12aR,13aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1H,2H,3H,5H,5aH,6H,11H,12H,12aH,13H,13aH-indolizino[7,6-b]carbazole-5,13-dione

> <JCHEM_LOGP>
2.919341913666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.738494299909448

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.362866475199148

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6241535243596097

> <JCHEM_POLAR_SURFACE_AREA>
92.0

> <JCHEM_REFRACTIVITY>
135.1897

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,6S,12R,12aR,13aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1H,2H,3H,6H,12H,12aH,13aH-indolizino[7,6-b]carbazole-5,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      13.537   4.006   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.709   2.707   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.171   2.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.460   4.141   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.922   4.209   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.094   2.911   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.575   2.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.347   1.134   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.725   0.446   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.978  -1.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.421  -1.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.674  -3.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.486  -4.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.117  -3.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.805   1.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.343   1.477   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.914   0.570   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.686  -0.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.890  -1.912   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.662  -3.435   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.324  -1.348   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.709   1.529   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.276   0.965   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.048  -0.558   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.071   1.924   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.448   1.671   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.159   3.037   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.079   4.135   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       1.299   3.447   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       2.732   4.011   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.960   5.534   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.937   3.052   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.165   4.575   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.370   3.616   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.598   5.139   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9    6   16                                                  
CONECT   16   15    3                                                       
CONECT   17    8   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   32                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   22   33   34                                             
CONECT   33   32                                                            
CONECT   34   32    7   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄N₂O₅

Average Mass

478.5890 Da

Monoisotopic Mass

478.24677 Da

IUPAC Name

(5aR,6S,12R,12aR,13aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1H,2H,3H,5H,5aH,6H,11H,12H,12aH,13H,13aH-indolizino[7,6-b]carbazole-5,13-dione

Traditional Name

(5aR,6S,12R,12aR,13aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1H,2H,3H,6H,12H,12aH,13aH-indolizino[7,6-b]carbazole-5,13-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)N(CC=C(C)C)C1=C2[C@H](O)[C@]2(O)[C@@H]([C@H]1C=C(C)C)C(=O)[C@@H]1CCCN1C2=O

InChI Identifier

InChI=1S/C28H34N2O5/c1-15(2)10-12-29-21-14-17(35-5)8-9-18(21)22-24(29)19(13-16(3)4)23-25(31)20-7-6-11-30(20)27(33)28(23,34)26(22)32/h8-10,13-14,19-20,23,26,32,34H,6-7,11-12H2,1-5H3/t19-,20+,23+,26+,28-/m1/s1

InChI Key

KGGKDBGWQMLMND-KCZDIRIGSA-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
Aspergillus caespitosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Isoquinolone
Aromatic monoterpenoid
N-alkylindole
Monoterpenoid
3-alkylindole
Indolizidine
Indole
Anisole
Piperidinedione
Alkyl aryl ether
Delta-lactam
Piperidinone
Benzenoid
Piperidine
Substituted pyrrole
Heteroaromatic compound
Tertiary alcohol
Tertiary carboxylic acid amide
Pyrrole
Pyrrolidine
Ketone
1,2-diol
Carboxamide group
Lactam
Secondary alcohol
Azacycle
Carboxylic acid derivative
Ether
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
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	2.92	ChemAxon
pKa (Strongest Acidic)	11.36	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.19 m³·mol⁻¹	ChemAxon
Polarizability	53.64 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162975835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione (NP0324940)

MOL for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

3D MOL for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

3D SDF for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

3D-SDF for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

PDB for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

3D PDB for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

SMILES for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

INCHI for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

Structure for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)

3D Structure for NP0324940 ((5ar,6s,12r,12ar,13as)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1h,2h,3h,6h,12h,12ah,13ah-indolizino[7,6-b]carbazole-5,13-dione)