NP-MRD: Showing NP-Card for (1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate (NP0272549)

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Record Information

Version

2.0

Created at

2022-09-08 19:12:37 UTC

Updated at

2022-09-08 19:12:37 UTC

NP-MRD ID

NP0272549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate

Description

Brucine N-oxide belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. (1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate is found in Strychnos lucida, Strychnos nux-vomica and Strychnos wallichiana. (1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate was first documented in 2016 (PMID: 27125604). Based on a literature review a small amount of articles have been published on Brucine N-oxide (PMID: 32343845) (PMID: 30282042) (PMID: 26625339) (PMID: 26578094).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221122D          

 30 36  0  0  1  0            999 V2000
    5.7807    1.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0582    0.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3520    1.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6296    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234    1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9396    2.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    2.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    2.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907    2.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969    2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    2.5408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5443    3.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998    4.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707    3.7278    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.9874    4.5322    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.2147    3.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508    2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9886    1.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    0.8108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.9064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9132    0.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7471    0.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016   -0.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    1.0382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6964    1.7184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8623    1.6318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4800    2.3506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0637    2.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059    3.0615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  6  1  1  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  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 26 25  1  1  0  0  0
 11 26  1  0  0  0  0
 27 26  1  6  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  6  0  0  0
 11 30  1  0  0  0  0
 14 30  1  0  0  0  0
M  CHG  2  14   1  15  -1
M  END

     RDKit          3D

 56 62  0  0  0  0  0  0  0  0999 V2000
    5.3950    2.2229    1.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1286    0.9799    0.8709 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305    0.5407    0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203    1.2916    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    0.8805    0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464   -0.3607    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590   -1.1191   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450   -0.6891    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -1.4760   -0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307   -2.7345   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2005   -0.6040   -0.1289 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5146   -1.8333    0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -2.9554   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4550   -2.2446   -1.3069 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.3470   -2.9364   -2.4707 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.8358   -1.9683   -0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0815   -0.5707   -0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8598   -0.3842    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2955    0.9225    1.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1487    1.5906    1.4847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5234    2.2959    0.4375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5890    3.3161    1.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2230    2.7596    1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5595    3.4958    2.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831    1.5012    0.8617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    0.5670    0.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7316    1.3993   -0.4435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4778    0.5520   -1.4096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3851   -0.0598   -2.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448   -1.0483   -1.4531 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4541    2.4836    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7345    3.0206    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516    2.1835    2.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554    2.2666    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589   -2.1084   -0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961   -3.2525   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -3.3591   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1011   -2.6009   -1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -2.1490    1.3519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -1.6885    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370   -3.4244   -0.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -3.7042    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873   -2.2969   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -2.6265   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2186   -1.2916    0.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9841    0.7399    1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8257    1.4965    0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3312    2.7729   -0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679    3.7417    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962    4.1407    0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4095    0.3111    1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606    2.0604   -1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2043    1.1286   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -0.5729   -3.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6878    0.7638   -2.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590   -1.3665   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  3  1  0
 26 11  1  0
 25  5  1  0
 30 11  1  0
 30 14  1  0
 28 17  1  0
 27 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 26 51  1  1
 27 52  1  6
 28 53  1  6
 29 54  1  0
 29 55  1  0
 30 56  1  6
M  CHG  2  14   1  15  -1
M  END


  Mrv1652309082221122D          

 30 36  0  0  1  0            999 V2000
    5.7807    1.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0582    0.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3520    1.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6296    0.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234    1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9396    2.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    2.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    2.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907    2.5423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969    2.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    2.5408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5443    3.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998    4.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707    3.7278    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.9874    4.5322    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.2147    3.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508    2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9886    1.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4113    0.8108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    0.9064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9132    0.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7471    0.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016   -0.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    1.0382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6964    1.7184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8623    1.6318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4800    2.3506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0637    2.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059    3.0615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  6  1  1  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  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 26 25  1  1  0  0  0
 11 26  1  0  0  0  0
 27 26  1  6  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  6  0  0  0
 11 30  1  0  0  0  0
 14 30  1  0  0  0  0
M  CHG  2  14   1  15  -1
M  END
> <DATABASE_ID>
NP0272549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@@]13CC[N+]4([O-])CC5=CCO[C@H]6CC(=O)N2[C@H]1[C@H]6[C@H]5C[C@@H]34

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O5/c1-28-16-8-14-15(9-17(16)29-2)24-20(26)10-18-21-13-7-19-23(14,22(21)24)4-5-25(19,27)11-12(13)3-6-30-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+,25?/m0/s1

> <INCHI_KEY>
HHHQMKWPZAYIAE-AWRJASDASA-N

> <FORMULA>
C23H26N2O5

> <MOLECULAR_WEIGHT>
410.47

> <EXACT_MASS>
410.184171945

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.97376521769603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,11S,18S,20R,21R,22S)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate

> <JCHEM_LOGP>
-0.5131963790000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.236602715064972

> <JCHEM_PKA_STRONGEST_BASIC>
3.399770869503294

> <JCHEM_POLAR_SURFACE_AREA>
71.05999999999999

> <JCHEM_REFRACTIVITY>
109.47899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11S,18S,20R,21R,22S)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.791   2.410   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.442   1.666   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.124   2.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.775   1.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.457   2.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.487   4.055   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.836   4.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.154   4.002   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.503   4.746   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.821   3.950   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.023   4.743   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.749   6.298   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.733   7.588   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.185   6.959   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0       1.843   8.460   0.000  0.00  0.00           O-1
HETATM   16  C   UNK     0       0.401   6.848   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.281   5.279   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.555   4.230   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.845   2.661   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.768   1.513   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.807   1.692   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.705   0.402   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.261   0.508   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.110  -0.778   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       3.991   1.938   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.167   3.208   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.610   3.046   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.896   4.388   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.986   5.243   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.998   5.715   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   26   30                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    5   26                                                  
CONECT   26   25   11   27                                                  
CONECT   27   26   21   28                                                  
CONECT   28   27   17   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   11   14                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆N₂O₅

Average Mass

410.4700 Da

Monoisotopic Mass

410.18417 Da

IUPAC Name

(1S,11S,18S,20R,21R,22S)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate

Traditional Name

(1S,11S,18S,20R,21R,22S)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@@]13CC[N+]4([O-])CC5=CCO[C@H]6CC(=O)N2[C@H]1[C@H]6[C@H]5C[C@@H]34

InChI Identifier

InChI=1S/C23H26N2O5/c1-28-16-8-14-15(9-17(16)29-2)24-20(26)10-18-21-13-7-19-23(14,22(21)24)4-5-25(19,27)11-12(13)3-6-30-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+,25?/m0/s1

InChI Key

HHHQMKWPZAYIAE-AWRJASDASA-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
Strychnos lucida	LOTUS Database	35616633
Strychnos nux-vomica	LOTUS Database	35616633
Strychnos wallichiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Quinolidine
Indole or derivatives
Indolizidine
Anisole
Phenol ether
Alkyl aryl ether
Delta-lactam
Piperidinone
Piperidine
Benzenoid
N-alkylpyrrolidine
Trialkyl amine oxide
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
N-oxide
Trisubstituted n-oxide
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic zwitterion
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.51	ChemAxon
pKa (Strongest Acidic)	17.24	ChemAxon
pKa (Strongest Basic)	3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.48 m³·mol⁻¹	ChemAxon
Polarizability	42.97 Å³	ChemAxon
Number of Rings	7	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

C00025156

Chemspider ID

9297581

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11122452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wei S, Li YL, Gong Q, Liang H, Liu Q, Bernardi RE, Zhang HT, Chen F, Lawrence AJ, Liang JH: Brucine N-Oxide Reduces Ethanol Intake and Preference in Alcohol-Preferring Male Fawn-Hooded Rats. Alcohol Clin Exp Res. 2020 Jun;44(6):1321-1328. doi: 10.1111/acer.14344. Epub 2020 May 17. [PubMed:32343845 ]
Yuan C, Luo Z, Zhou Y, Lei S, Xu C, Peng C, Li S, Li X, Zhu X, Gao T: Removal of hERG potassium channel affinity through introduction of an oxygen atom: Molecular insights from structure-activity relationships of strychnine and its analogs. Toxicol Appl Pharmacol. 2018 Dec 1;360:109-119. doi: 10.1016/j.taap.2018.09.042. Epub 2018 Sep 30. [PubMed:30282042 ]
Guo J, Meng H, Li HH, Wang QF: Determination of strychnine, brucine, strychnine N-oxide, and brucine N-oxide in plasma samples after the oral administration of processed semen strychni extract by high-performance liquid chromatography with ultrasound-assisted mixed cloud point extraction. J Sep Sci. 2016 Jul;39(13):2553-61. doi: 10.1002/jssc.201501379. Epub 2016 May 27. [PubMed:27125604 ]
Lin A, Su X, She D, Qiu K, He Q, Liu Y: LC-MS/MS determination and comparative pharmacokinetics of strychnine, brucine and their metabolites in rat plasma after intragastric administration of each monomer and the total alkaloids from Semen Strychni. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jan 1;1008:65-73. doi: 10.1016/j.jchromb.2015.11.012. Epub 2015 Nov 14. [PubMed:26625339 ]
Gu W, Wang D, Pan Z, Liu X, Cai B, Chen J: Ultra-performance liquid chromatography-tandem mass spectrometric assay for the simultaneous determination of brucine, strychnine and brucine N-oxide in rat plasma: application to a pharmacokinetic study. Biomed Chromatogr. 2016 Jul;30(7):1097-1103. doi: 10.1002/bmc.3656. Epub 2016 Jan 4. [PubMed:26578094 ]
LOTUS database [Link]

Showing NP-Card for (1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate (NP0272549)

MOL for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

3D MOL for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

3D SDF for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

3D-SDF for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

PDB for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

3D PDB for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

SMILES for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

INCHI for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

Structure for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)

3D Structure for NP0272549 ((1s,11s,18s,20r,21r,22s)-4,5-dimethoxy-9-oxo-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-17-ium-17-olate)