NP-MRD: Showing NP-Card for (1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate (NP0291308)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-09 22:21:05 UTC

Updated at

2022-09-09 22:21:05 UTC

NP-MRD ID

NP0291308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate

Description

(1R,2R,7S,9R,10R,14S,15S)-14-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-9-yl acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate is found in Khaya senegalensis. Based on a literature review very few articles have been published on (1R,2R,7S,9R,10R,14S,15S)-14-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-9-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200212D          

 39 43  0  0  1  0            999 V2000
    2.0296   -4.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -5.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0735    1.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017    1.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292    2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8908    0.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1126    2.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5814   -1.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4023   -3.0335    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  6  0  0  0
 22 38  1  0  0  0  0
  5 38  1  0  0  0  0
 17 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END

     RDKit          3D

 87 91  0  0  0  0  0  0  0  0999 V2000
   -1.7659    2.5133    3.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406    2.7111    2.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    3.7322    1.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4025    1.7096    1.2511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5287    1.7864   -0.1700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9713    1.6951   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5336    0.3439   -0.7496 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0175    0.3781   -0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7790   -0.5041   -1.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5705    1.7933   -0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4426   -0.0361    0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6759   -0.1180    1.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4532   -0.3266    1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2584   -0.6300    1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901   -0.7116    0.0142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2707   -2.1069   -0.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171   -0.5902   -0.0786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5738   -1.7716   -0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.7270   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.4288    0.1477 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4182   -0.4713    1.6179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238    0.6598   -0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466    1.6226   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291    1.2849   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8787   -0.2175   -0.3286 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9958   -0.7134    0.4741 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3137   -0.3396   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563   -1.1014    0.6314 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5840   -1.2027   -0.0436 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3119   -2.1800    0.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4244    0.0156   -0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8075   -0.4181   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9735    1.1486   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6739    0.4607    1.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -2.3477    0.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2621   -2.1738    0.5713 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8180   -2.8947   -0.5382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    0.6234   -0.7906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0756    0.6749   -2.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9592    3.1108    3.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682    2.7528    3.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070    1.4272    3.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021    2.7596   -0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452    2.4047   -1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5423    2.1587    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4472    0.0189   -1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4445    0.1036   -2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0728   -1.0063   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4563   -1.2109   -1.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5557    2.3783    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6733    1.6668   -0.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1600    2.2960   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138   -0.2884    2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099   -0.8492    2.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3839   -2.1216   -0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8997   -2.8430    0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9780   -2.3535   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9596   -0.4171    0.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7715   -1.9561   -1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -2.7417   -0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412   -1.8988   -1.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2660   -2.5216    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3913   -0.5559    2.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0912   -1.4147    2.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376    0.4383    2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832    2.5890   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905    1.7624    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105    1.5983   -1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705   -0.5775   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617   -0.2113    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3668   -0.8934   -1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4480    0.7223   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -0.6823    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4305   -1.6312   -1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6694   -2.8637    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -0.8550   -1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2381   -1.2145    0.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4585    0.4468   -0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4841    1.9718   -0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3457    0.7971   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8573    1.6224   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770    1.0749    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409   -2.6387    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513   -2.7164   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2683   -0.2885   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7456    1.5081   -2.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0861    1.0000   -2.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 38  1  0
 38 39  1  6
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 35  1  0
 35 36  1  0
 36 37  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 38  5  1  0
 36 26  1  0
 15  7  1  0
 38 17  1  0
 22 20  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  5 43  1  6
  6 44  1  0
  6 45  1  0
  7 46  1  6
  9 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  0
 10 51  1  0
 10 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  1
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 25 69  1  6
 24 67  1  0
 24 68  1  0
 23 66  1  0
 39 85  1  0
 39 86  1  0
 39 87  1  0
 26 70  1  1
 27 71  1  0
 27 72  1  0
 28 73  1  1
 36 83  1  1
 37 84  1  0
 29 74  1  6
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 34 82  1  0
M  END


  Mrv1652309102200212D          

 39 43  0  0  1  0            999 V2000
    2.0296   -4.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -5.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0735    1.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5017    1.6120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292    2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8908    0.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1126    2.3395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5814   -1.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4023   -3.0335    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  6  0  0  0
 22 38  1  0  0  0  0
  5 38  1  0  0  0  0
 17 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0291308

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC=C3[C@]12C)[C@@H]1C[C@@H](O[C@@H]1O)[C@H](O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O7/c1-17(33)38-25-16-23-28(2,3)24(34)12-14-31(23,7)22-11-13-30(6)19(9-10-21(30)32(22,25)8)18-15-20(39-27(18)36)26(35)29(4,5)37/h10,12,14,18-20,22-23,25-27,35-37H,9,11,13,15-16H2,1-8H3/t18-,19-,20+,22+,23+,25+,26-,27-,30-,31+,32-/m0/s1

> <INCHI_KEY>
JZTBUDLVYHKZEX-IICAVNBUSA-N

> <FORMULA>
C32H48O7

> <MOLECULAR_WEIGHT>
544.729

> <EXACT_MASS>
544.340003886

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
60.472215122323135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7S,9R,10R,14S,15S)-14-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate

> <JCHEM_LOGP>
3.631057477666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.111220877418184

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.111150483503742

> <JCHEM_PKA_STRONGEST_BASIC>
-3.125617421231034

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
148.88510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7S,9R,10R,14S,15S)-14-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.789  -8.830   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.305  -8.559   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.297  -9.737   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.828  -7.111   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.341  -6.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.779   2.283   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.471   3.096   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.137   3.009   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.495   3.735   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.863   1.651   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.410   4.367   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.285  -2.925   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.351  -5.663   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   38                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   25                                             
CONECT   21   20                                                            
CONECT   22   20   23   38                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   28   36                                                       
CONECT   36   35   26   37                                                  
CONECT   37   36                                                            
CONECT   38   22    5   17   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,7S,9R,10R,14S,15S)-14-[(2S,3S,5R)-5-[(1S)-1,2-Dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,11-dien-9-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₈O₇

Average Mass

544.7290 Da

Monoisotopic Mass

544.34000 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC=C3[C@]12C)[C@@H]1C[C@@H](O[C@@H]1O)[C@H](O)C(C)(C)O

InChI Identifier

InChI=1S/C32H48O7/c1-17(33)38-25-16-23-28(2,3)24(34)12-14-31(23,7)22-11-13-30(6)19(9-10-21(30)32(22,25)8)18-15-20(39-27(18)36)26(35)29(4,5)37/h10,12,14,18-20,22-23,25-27,35-37H,9,11,13,15-16H2,1-8H3/t18-,19-,20+,22+,23+,25+,26-,27-,30-,31+,32-/m0/s1

InChI Key

JZTBUDLVYHKZEX-IICAVNBUSA-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
Khaya senegalensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
3-oxo-delta-1-steroid
3-oxosteroid
Oxosteroid
3-oxo-5-beta-steroid
Steroid
Delta-1-steroid
Cyclohexenone
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
1,2-diol
Cyclic ketone
Ketone
Hemiacetal
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
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

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

163194155

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate (NP0291308)

MOL for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D MOL for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D SDF for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D-SDF for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

PDB for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D PDB for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

SMILES for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

INCHI for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

Structure for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D Structure for NP0291308 ((1s,3br,4r,5as,9ar,9br,11as)-1-[(2s,3s,5r)-5-[(1s)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)