NP-MRD: Showing NP-Card for Brucine (NP0050841)

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Record Information

Version

2.0

Created at

2022-04-27 22:14:46 UTC

Updated at

2022-04-27 22:14:46 UTC

NP-MRD ID

NP0050841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brucine

Description

BRUCINE, also known as bruzin, 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. Brucine is found in Brucea javanica, Festuca pratensis, Strychnos aculeata, Strychnos axillaris, Strychnos ignatii , Strychnos ligustrina , Strychnos lucida, Strychnos nux-vomica, Strychnos nux-vomica , Strychnos panamensis and Strychnos wallichiana. Brucine was first documented in 2022 (PMID: 35620295). Based on a literature review a small amount of articles have been published on BRUCINE (PMID: 35931305) (PMID: 35794473) (PMID: 35644218) (PMID: 35600819).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304051723482D          

 29 35  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  0  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
 25 24  1  1  0  0  0
 11 25  1  0  0  0  0
 26 25  1  6  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 28  1  6  0  0  0
 11 29  1  0  0  0  0
 14 29  1  0  0  0  0
M  END

     RDKit          3D

 55 61  0  0  0  0  0  0  0  0999 V2000
   -5.2201    2.7413    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0773    1.3529    0.4422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177    0.7501    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166    1.5553    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4142    1.0459    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.3193    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059   -1.1196    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6794   -0.6195    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7995   -1.4300    0.3748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7568   -2.8274    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1733   -0.6680   -0.1186 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3194   -1.3713   -1.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8594   -2.7385   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373   -2.6856    0.1210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -2.3855    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1379   -0.9445    0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8722   -0.3842   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3023    1.0510   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    1.8301   -0.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425    2.0972    0.4148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7734    3.3272    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    2.9991    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    3.9301   -0.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1579    1.6802   -0.0213 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    0.6359   -0.1722 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8311    0.9518    0.9198 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5659   -0.2412    1.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4812   -1.1605    1.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752   -1.6717    0.8251 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8006    3.2254   -0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3003    2.9779    0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7208    3.2265    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8049    2.6403    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -2.2031    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4150   -3.2353    1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254   -3.1203   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7418   -3.2684    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456   -1.4589   -1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.8376   -2.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679   -3.5253   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5987   -3.0827   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808   -2.7177   -0.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425   -2.9606    0.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857   -1.0713   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9341    1.2955    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542    1.2071   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979    2.3512    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528    3.9934   -0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160    3.8867    1.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    0.7917   -1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2624    1.3439    1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2919    0.0351    2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8348   -0.6214    2.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -2.0373    2.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2058   -2.2159    1.2728 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  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  8  3  1  0
 25 11  1  0
 24  5  1  0
 29 11  1  0
 29 14  1  0
 27 16  1  0
 26 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  1
 21 48  1  0
 21 49  1  0
 25 50  1  6
 26 51  1  1
 27 52  1  1
 28 53  1  0
 28 54  1  0
 29 55  1  1
M  END


  Mrv1652304051723482D          

 29 35  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  0  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
 25 24  1  1  0  0  0
 11 25  1  0  0  0  0
 26 25  1  6  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 28  1  6  0  0  0
 11 29  1  0  0  0  0
 14 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@@]13CCN4CC5=CCO[C@H]6CC(=O)N2[C@H]1[C@H]6[C@H]5C[C@@H]34

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1

> <INCHI_KEY>
RRKTZKIUPZVBMF-IBTVXLQLSA-N

> <FORMULA>
C23H26N2O4

> <MOLECULAR_WEIGHT>
394.471

> <EXACT_MASS>
394.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.195273802491144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-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-9-one

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
0.611178804333333

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.238964946382097

> <JCHEM_PKA_STRONGEST_BASIC>
8.847883000497335

> <JCHEM_POLAR_SURFACE_AREA>
51.24

> <JCHEM_REFRACTIVITY>
107.4341

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-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-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-APR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-APR-17         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+0
HETATM   15  C   UNK     0       0.401   6.848   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.281   5.279   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.555   4.230   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.845   2.661   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.768   1.513   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.807   1.692   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.705   0.402   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.261   0.508   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.110  -0.778   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       3.991   1.938   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.167   3.208   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.610   3.046   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.896   4.388   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.986   5.243   0.000  0.00  0.00           C+0
HETATM   29  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   24                                                  
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   25   29                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   25                                                  
CONECT   25   24   11   26                                                  
CONECT   26   25   20   27                                                  
CONECT   27   26   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   11   14                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   70    0
END

View in JSmol

Synonyms

Value	Source
Bruzin	MeSH
Dimethoxystrychnine	MeSH
10,11-Dimethoxystrychnine	MeSH

Chemical Formula

C₂₃H₂₆N₂O₄

Average Mass

394.4710 Da

Monoisotopic Mass

394.18926 Da

IUPAC Name

(1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-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-9-one

Traditional Name

(1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-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-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@@]13CCN4CC5=CCO[C@H]6CC(=O)N2[C@H]1[C@H]6[C@H]5C[C@@H]34

InChI Identifier

InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1

InChI Key

RRKTZKIUPZVBMF-IBTVXLQLSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Brucea javanica	LOTUS Database	35616633
Lolium pratense	LOTUS Database	35616633
Strychnos aculeata	Plant	KNApSAcK
Strychnos axillaris	LOTUS Database	35616633
Strychnos ignatii	Plant	KNApSAcK
Strychnos ligustrina	Plant	KNApSAcK
Strychnos lucida	Plant	KNApSAcK
Strychnos nux-vomica	LOTUS Database	35616633
Strychnos nux-vomica L.	Plant	KNApSAcK
Strychnos panamensis	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
Alkyl aryl ether
Delta-lactam
Piperidinone
Aralkylamine
Piperidine
Benzenoid
N-alkylpyrrolidine
Tertiary carboxylic acid amide
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Lactam
Carboxamide group
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Dialkyl ether
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monoterpenoid indole alkaloid (CHEBI:3193 )
Indole alkaloids (C09084 )

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	1.85	ALOGPS
logP	0.61	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	17.24	ChemAxon
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.24 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.43 m³·mol⁻¹	ChemAxon
Polarizability	42.2 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00001695

Chemspider ID

390579

KEGG Compound ID

C09084

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1225961

References

General References

Jiang W, Tang M, Yang L, Zhao X, Gao J, Jiao Y, Li T, Tie C, Gao T, Han Y, Jiang JD: Analgesic Alkaloids Derived From Traditional Chinese Medicine in Pain Management. Front Pharmacol. 2022 May 10;13:851508. doi: 10.3389/fphar.2022.851508. eCollection 2022. [PubMed:35620295 ]
Guo Y, Meng Z, Gu Y, Li W, Sun S, Wang Q, Kuang H: HPLC-MS/MS analysis of primary alkaloids in rat plasma after oral administration of "Nux vomica - Glycyrrhiza glabra decoction": A pharmacokinetic study. J Ethnopharmacol. 2022 Nov 15;298:115588. doi: 10.1016/j.jep.2022.115588. Epub 2022 Aug 2. [PubMed:35931305 ]
Hong B, Grzech D, Caputi L, Sonawane P, Lopez CER, Kamileen MO, Hernandez Lozada NJ, Grabe V, O'Connor SE: Biosynthesis of strychnine. Nature. 2022 Jul;607(7919):617-622. doi: 10.1038/s41586-022-04950-4. Epub 2022 Jul 6. [PubMed:35794473 ]
Duan X, Sun H, Zhang T, Qin J, Cui R, Sun H: Brucine restores sodium nitroprusside-induced chondrocyte dysfunction by suppressing the GSK-3beta/beta-catenin pathway. Chem Biol Interact. 2022 May 26:109980. doi: 10.1016/j.cbi.2022.109980. [PubMed:35644218 ]
Chen S, Ali I, Li X, Long D, Zhang Y, Long R, Huang X: Shifts in Fecal Metabolite Profiles Associated With Ramadan Fasting Among Chinese and Pakistani Individuals. Front Nutr. 2022 May 3;9:845086. doi: 10.3389/fnut.2022.845086. eCollection 2022. [PubMed:35600819 ]

Showing NP-Card for Brucine (NP0050841)

MOL for NP0050841 (Brucine)

3D MOL for NP0050841 (Brucine)

3D SDF for NP0050841 (Brucine)

3D-SDF for NP0050841 (Brucine)

PDB for NP0050841 (Brucine)

3D PDB for NP0050841 (Brucine)

SMILES for NP0050841 (Brucine)

INCHI for NP0050841 (Brucine)

Structure for NP0050841 (Brucine)

3D Structure for NP0050841 (Brucine)