NP-MRD: Showing NP-Card for (1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one (NP0307525)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 00:42:18 UTC

Updated at

2022-09-11 00:42:18 UTC

NP-MRD ID

NP0307525

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one

Description

(1R,3R,3'R,3'aS,4aS,6'S,6aS,6bS,7'aR,9R,11aS,11bS)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-icosahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-11-one belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides. (1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one is found in Veratrum album. Based on a literature review very few articles have been published on (1R,3R,3'R,3'aS,4aS,6'S,6aS,6bS,7'aR,9R,11aS,11bS)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-1,2,3,3'a,4,4',4a,5,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-icosahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-11-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112202422D          

 33 38  0  0  1  0            999 V2000
    3.0068    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147    0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100    0.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051    0.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.5133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3425    0.1660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0414   -0.6021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5560   -1.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3718   -1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6729   -0.3556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1875   -1.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4886   -0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7898    0.5358    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6055    0.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2752    1.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594    1.0573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9448    1.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1583    0.2892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6437    0.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -0.5530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6304   -1.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350   -0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.1146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9823   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937   -0.1750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4953   -0.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0839    0.2047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8823   -0.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337    1.2078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    0.6203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3370    0.6577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5562    1.4530    0.0000 C   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
  4  5  2  0  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  6 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
  7 20  1  0  0  0  0
 20  3  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
    1.3709    0.3861    2.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585   -0.2381    1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663   -0.2638    0.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795    0.1925    1.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.5744    2.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.1129   -0.0025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086   -1.1194   -0.7371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2763   -1.0857   -2.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4090   -0.1348   -2.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776   -0.0598   -1.1405 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4390   -0.9363   -1.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9780    1.3530   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1263    1.5056   -0.2389 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2601    2.8875    0.0298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8479    0.8353    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3559    0.6803    1.2643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2123    0.0112    2.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981   -0.1695    0.2332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9188   -1.6289    0.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -0.9054   -0.6410 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4380   -2.2432   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -2.2112   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -0.8347    0.4203 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3193   -1.0331    1.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4666   -0.5879    0.7046 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4818   -0.0154    1.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825    0.8926    0.8364 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1705    2.3414    1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3307    0.5499   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0336    0.6926   -1.2132 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0397    0.5776   -0.1979 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7163    0.0392   -0.6959 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0023   -0.7130   -1.9715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    0.6361    2.7218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432   -0.2684    3.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211    1.3538    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1587    0.9897   -0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -2.0497   -0.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5580   -2.0957   -2.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4566   -0.7472   -2.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9903   -0.4670   -3.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233    0.8848   -2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0346   -0.5833   -1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1402    2.0172   -0.8175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2546    1.6414   -2.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0498    1.1679   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4009    3.3577   -0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2109    1.4440    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3881   -0.1225    1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9189    1.6794    1.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0309   -0.4364    2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -1.9560    1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9224   -1.7024    1.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961   -2.2953   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916   -0.2678   -1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3566   -2.7225   -1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787   -2.8885    0.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527   -2.8903    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5864   -2.5716   -0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9445   -1.3754    0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9952    0.6053    2.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -0.8433    2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4313    0.6432    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4269    2.5273    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1084    2.8522    1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8987    2.8980    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7517   -0.4786   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0234    1.2287   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297    1.5233   -1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9148    1.5105    0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0758    0.9318   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662   -1.3018   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8737   -1.3528   -1.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2050    0.0723   -2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 23 24  1  1
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  1
 18  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 23 32  1  0
  2 23  1  0
 25 31  1  0
  3 20  1  0
  6  7  1  0
 18 10  1  0
 33 72  1  0
 33 73  1  0
 33 74  1  0
 32 71  1  6
 31 70  1  1
 30 69  1  0
 29 67  1  0
 29 68  1  0
 27 63  1  1
 28 64  1  0
 28 65  1  0
 28 66  1  0
 26 61  1  0
 26 62  1  0
 25 60  1  6
 22 58  1  0
 22 59  1  0
 21 56  1  0
 21 57  1  0
 20 55  1  6
  7 38  1  1
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  6
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  1
 17 51  1  0
 19 52  1  0
 19 53  1  0
 19 54  1  0
  6 37  1  6
  1 34  1  0
  1 35  1  0
  1 36  1  0
M  END


  Mrv1652309112202422D          

 33 38  0  0  1  0            999 V2000
    3.0068    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2147    0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100    0.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051    0.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.5133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3425    0.1660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0414   -0.6021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5560   -1.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3718   -1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6729   -0.3556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1875   -1.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4886   -0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7898    0.5358    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6055    0.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2752    1.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4594    1.0573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9448    1.7022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1583    0.2892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6437    0.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -0.5530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6304   -1.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350   -0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6272   -0.1146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9823   -0.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2937   -0.1750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4953   -0.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0839    0.2047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8823   -0.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1353    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9337    1.2078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    0.6203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3370    0.6577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5562    1.4530    0.0000 C   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
  4  5  2  0  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  6 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
  7 20  1  0  0  0  0
 20  3  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0307525

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2NC[C@@H](C)C[C@H]2O[C@]11CC[C@H]2[C@@H]3CC[C@]4(O)C[C@H](O)C[C@@H](O)[C@]4(C)[C@H]3C(=O)C2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO5/c1-13-9-19-23(28-12-13)15(3)27(33-19)8-6-17-18-5-7-26(32)11-16(29)10-20(30)25(26,4)22(18)24(31)21(17)14(27)2/h13,15-20,22-23,28-30,32H,5-12H2,1-4H3/t13-,15+,16+,17-,18-,19+,20+,22+,23-,25+,26-,27-/m0/s1

> <INCHI_KEY>
WQAJKOXBERTWBK-URHSYSSLSA-N

> <FORMULA>
C27H41NO5

> <MOLECULAR_WEIGHT>
459.627

> <EXACT_MASS>
459.298473424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.78643858259085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'S,3R,3'R,3aS,5'R,6S,7'S,7aR,10'S,11'S)-3',5',7'-trihydroxy-2',3,6,15'-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadecan]-15'-en-17'-one

> <JCHEM_LOGP>
1.2550310683333308

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.66738203716439

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.976359383451548

> <JCHEM_PKA_STRONGEST_BASIC>
9.933978679362196

> <JCHEM_POLAR_SURFACE_AREA>
99.02000000000001

> <JCHEM_REFRACTIVITY>
124.99459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,3R,3'R,3aS,5'R,6S,7'S,7aR,10'S,11'S)-3',5',7'-trihydroxy-2',3,6,15'-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadecan]-15'-en-17'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.613   2.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.001   0.867   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.485   0.458   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.783   1.288   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.874   2.825   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.973   0.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.411  -1.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.371  -2.328   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.894  -2.097   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.456  -0.664   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.417  -1.867   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.979  -0.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.541   1.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.064   1.230   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.580   2.204   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.058   1.974   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.097   3.177   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.495   0.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.535   1.744   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.873  -1.032   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.777  -2.113   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.292  -1.704   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.904  -0.214   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.700  -1.175   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.415  -0.327   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.925  -0.715   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.157   0.382   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.647  -0.006   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.253   1.867   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.743   2.255   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       2.824   1.158   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.362   1.228   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.772   2.712   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    6   10   19                                             
CONECT   19   18                                                            
CONECT   20    7    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   24   32                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   23   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₅

Average Mass

459.6270 Da

Monoisotopic Mass

459.29847 Da

IUPAC Name

(1'S,2R,2'S,3R,3'R,3aS,5'R,6S,7'S,7aR,10'S,11'S)-3',5',7'-trihydroxy-2',3,6,15'-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadecan]-15'-en-17'-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2NC[C@@H](C)C[C@H]2O[C@]11CC[C@H]2[C@@H]3CC[C@]4(O)C[C@H](O)C[C@@H](O)[C@]4(C)[C@H]3C(=O)C2=C1C

InChI Identifier

InChI=1S/C27H41NO5/c1-13-9-19-23(28-12-13)15(3)27(33-19)8-6-17-18-5-7-26(32)11-16(29)10-20(30)25(26,4)22(18)24(31)21(17)14(27)2/h13,15-20,22-23,28-30,32H,5-12H2,1-4H3/t13-,15+,16+,17-,18-,19+,20+,22+,23-,25+,26-,27-/m0/s1

InChI Key

WQAJKOXBERTWBK-URHSYSSLSA-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
Veratrum album	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Jerveratrum-type alkaloids

Alternative Parents

Substituents

Jerveratrum-type alkaloid
Azasteroid
Alkaloid or derivatives
Piperidine
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Ketone
Secondary alcohol
Dialkyl ether
Secondary aliphatic amine
Ether
Polyol
Oxacycle
Secondary amine
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
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	1.26	ChemAxon
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	9.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	124.99 m³·mol⁻¹	ChemAxon
Polarizability	52.79 Å³	ChemAxon
Number of Rings	6	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

162922408

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one (NP0307525)

MOL for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

3D MOL for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

3D SDF for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

3D-SDF for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

PDB for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

3D PDB for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

SMILES for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

INCHI for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

Structure for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)

3D Structure for NP0307525 ((1r,3r,3'r,3'as,4as,6's,6as,6bs,7'ar,9r,11as,11bs)-1,3,4a-trihydroxy-3',6',10,11b-tetramethyl-2,3,3'a,4,4',5,5',6,6',6a,6b,7,7',7'a,8,11a-hexadecahydro-1h,3'h-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridin]-11-one)