NP-MRD: Showing NP-Card for (1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol (NP0330475)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-12 15:52:08 UTC

Updated at

2022-09-12 15:52:08 UTC

NP-MRD ID

NP0330475

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol

Description

Cyclobullatine A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol is found in Buxus sempervirens. It was first documented in 2022 (PMID: 36130261). Based on a literature review a significant number of articles have been published on Cyclobullatine A (PMID: 36091400) (PMID: 36088383) (PMID: 36109246) (PMID: 36123682).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217522D          

 30 34  0  0  1  0            999 V2000
    0.8683   -2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -1.6009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6168   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953   -1.1154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5214    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532   -0.5346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3335    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0083    0.3804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6974    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    0.2675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365   -0.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313   -1.0634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5072   -1.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.0201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1995   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850   -1.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.4557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 30 29  1  1  0  0  0
  2 30  1  0  0  0  0
  9 30  1  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
    4.3600   -0.5039    2.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9142   -0.3976    0.9436 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8682    0.2324   -0.0095 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1637   -0.3097    0.0680 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3805   -1.6613   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1010    0.4053    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426    0.1343   -1.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    0.5690   -1.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -0.0488   -0.4973 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7356   -1.4923   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -0.3698   -0.6167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0352   -0.0987   -1.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    0.2009   -1.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230   -0.0099   -0.6353 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4523   -1.4719   -0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4422    0.8554   -0.4922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7296    0.2252   -0.7826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8459    1.2329   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1006   -0.9816   -0.1203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1790   -1.6715   -0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6401   -0.7998    1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4046    1.4712    0.8708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0676    2.8354    0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2479    0.7245    1.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173    0.5792    0.4253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7593    1.9033    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1835   -0.3822    0.6035 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4782   -0.0702    1.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7238    0.2650    1.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5869    0.3645    0.8135 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4823    0.4494    2.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2940   -1.0787    2.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -1.1655    2.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6892   -1.4364    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9081    1.3209    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4608   -2.2508   -0.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1606   -2.0788    0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7540   -1.8661   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0366    0.6457    0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4065   -0.1287    1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6969    1.3810    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4846   -0.8790   -1.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    0.8392   -2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038    1.6974   -1.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307    0.3211   -2.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -1.9346   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044   -2.1419    0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5112    0.7659   -2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1721   -0.9539   -2.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.2460   -2.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -0.4450   -2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2134   -1.7388   -1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291   -1.9832   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916   -1.8411    0.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2348    1.7242   -1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7833   -0.0853   -1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8042    1.8581   -1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8535    0.8163   -0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6679    1.9710    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8352   -2.1384   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6314   -0.9515   -1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7589   -2.4991   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -0.8440    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2521   -1.7300    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2152    0.1042    1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2801    1.3924    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    3.3812    0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8252    1.4591    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612   -0.1993    2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7415    2.5697    0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3332    1.8302   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216    2.4612   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6744   -1.3879    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1552   -0.1368    2.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472    0.4823    2.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.4489    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30  2  1  0
  2  1  1  0
  2  3  1  0
  3  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
  3  4  1  0
  4  5  1  0
  4  6  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 14 16  1  0
 14 25  1  0
 11 27  1  0
  9 30  1  0
 11  9  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 17 56  1  6
 16 55  1  6
 22 66  1  1
 23 67  1  0
 24 68  1  0
 24 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
 27 73  1  1
 28 74  1  0
 29 75  1  0
 30 76  1  6
  2 34  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 35  1  1
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  6 41  1  0
 20 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
M  END


  Mrv1652309122217522D          

 30 34  0  0  1  0            999 V2000
    0.8683   -2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -1.6009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6168   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953   -1.1154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5214    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532   -0.5346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3335    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0083    0.3804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6974    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    0.2675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365   -0.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313   -1.0634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5072   -1.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.0201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1995   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850   -1.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.4557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 30 29  1  1  0  0  0
  2 30  1  0  0  0  0
  9 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330475

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1[C@H](O)C[C@@]2(C)[C@@H]3C=C[C@H]4[C@H](C)[C@H](CC[C@@]44C[C@@]34CC[C@]12C)N(C)C)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46N2O/c1-17-19-9-10-22-25(4)15-21(30)23(18(2)28(5)6)24(25,3)13-14-27(22)16-26(19,27)12-11-20(17)29(7)8/h9-10,17-23,30H,11-16H2,1-8H3/t17-,18-,19-,20-,21+,22-,23-,24+,25-,26+,27-/m0/s1

> <INCHI_KEY>
SZDAYVWJPZICBE-KNWQDMBOSA-N

> <FORMULA>
C27H46N2O

> <MOLECULAR_WEIGHT>
414.678

> <EXACT_MASS>
414.361014109

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
51.57211564482939

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6S,7S,8S,11S,12S,14R,15S,16R)-6-(dimethylamino)-15-[(1S)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-9-en-14-ol

> <JCHEM_LOGP>
3.5466192429999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.864924853001298

> <JCHEM_PKA_STRONGEST_BASIC>
10.588857710508083

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
127.09429999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S,7S,8S,11S,12S,14R,15S,16R)-6-(dimethylamino)-15-[(1S)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-9-en-14-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.621  -4.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.144  -2.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.151  -1.811   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.365  -2.082   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.888  -3.531   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.357  -0.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.675  -0.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.191  -0.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.183  -1.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.707   0.179   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.699  -0.998   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.222   0.451   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.738   0.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.731  -0.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.403   0.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.270  -0.506   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.216   0.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.635   2.137   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      12.741   0.499   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      13.686   1.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.321  -0.927   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.698  -1.985   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.147  -2.508   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.424  -2.849   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.208  -1.904   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.839  -3.399   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.692  -2.175   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.169  -3.624   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.653  -3.895   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.660  -2.717   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   30                                             
CONECT   10    9   11                                                       
CONECT   11   10    9   12   27                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   14   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   11   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    2    9                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₆N₂O

Average Mass

414.6780 Da

Monoisotopic Mass

414.36101 Da

IUPAC Name

(1S,3R,6S,7S,8S,11S,12S,14R,15S,16R)-6-(dimethylamino)-15-[(1S)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-9-en-14-ol

Traditional Name

(1S,3R,6S,7S,8S,11S,12S,14R,15S,16R)-6-(dimethylamino)-15-[(1S)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-9-en-14-ol

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1[C@H](O)C[C@@]2(C)[C@@H]3C=C[C@H]4[C@H](C)[C@H](CC[C@@]44C[C@@]34CC[C@]12C)N(C)C)N(C)C

InChI Identifier

InChI=1S/C27H46N2O/c1-17-19-9-10-22-25(4)15-21(30)23(18(2)28(5)6)24(25,3)13-14-27(22)16-26(19,27)12-11-20(17)29(7)8/h9-10,17-23,30H,11-16H2,1-8H3/t17-,18-,19-,20-,21+,22-,23-,24+,25-,26+,27-/m0/s1

InChI Key

SZDAYVWJPZICBE-KNWQDMBOSA-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
Buxus sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
22-azasteroid
9(beta),19-cyclo-4,4-14(alpha)-trimethyl-5(alpha)-pregnane-skeleton
Steroidal alkaloid
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
Azasteroid
Steroid
Alkaloid or derivatives
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.55	ChemAxon
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	10.59	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.71 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	127.09 m³·mol⁻¹	ChemAxon
Polarizability	51.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

101603238

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yuksel S, Bonus M, Schwabe T, Pfleger C, Zimmer T, Enke U, Sass I, Gohlke H, Benndorf K, Kusch J: Uncoupling of Voltage- and Ligand-Induced Activation in HCN2 Channels by Glycine Inserts. Front Physiol. 2022 Aug 25;13:895324. doi: 10.3389/fphys.2022.895324. eCollection 2022. [PubMed:36091400 ]
Peter A, Balogh A, Csanadi Z, Danko K, Griger Z: Subclinical systolic and diastolic myocardial dysfunction in polyphasic polymyositis/dermatomyositis: a 2-year longitudinal study. Arthritis Res Ther. 2022 Sep 10;24(1):219. doi: 10.1186/s13075-022-02906-7. [PubMed:36088383 ]
Dagdigian PJ: Theoretical investigation of rotationally inelastic collisions of OH(X(2)Pi) with hydrogen atoms. J Chem Phys. 2022 Sep 14;157(10):104305. doi: 10.1063/5.0110724. [PubMed:36109246 ]
Vranic M, Perochon A, Benbow H, Doohan FM: Comprehensive analysis of pathogen-responsive wheat NAC transcription factors: new candidates for crop improvement. G3 (Bethesda). 2022 Sep 21. pii: 6709347. doi: 10.1093/g3journal/jkac247. [PubMed:36130261 ]
Regidor PA, Richter WH, Koytchev R, Kirkov V, Colli E: Evaluation of the food effect on a drospirenone only contraceptive containing 4 mg administered with and without high-fat breakfast in a randomised trial. BMC Womens Health. 2022 Sep 19;22(1):381. doi: 10.1186/s12905-022-01960-2. [PubMed:36123682 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol (NP0330475)

MOL for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

3D MOL for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

3D SDF for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

3D-SDF for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

PDB for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

3D PDB for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

SMILES for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

INCHI for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

Structure for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)

3D Structure for NP0330475 ((1s,3r,6s,7s,8s,11s,12s,14r,15s,16r)-6-(dimethylamino)-15-[(1s)-1-(dimethylamino)ethyl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-9-en-14-ol)