NP-MRD: Showing NP-Card for (1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one (NP0256855)

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Record Information

Version

2.0

Created at

2022-09-07 21:49:01 UTC

Updated at

2022-09-07 21:49:02 UTC

NP-MRD ID

NP0256855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one

Description

Isobrucine 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. Isobrucine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one is found in Strychnos nux-vomica. (1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one was first documented in 1990 (PMID: 2393954). Based on a literature review a small amount of articles have been published on isobrucine (PMID: 7912074) (PMID: 10375801) (PMID: 7945866).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223492D          

 29 34  0  0  1  0            999 V2000
   -0.7382   -1.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939   -1.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302   -1.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -2.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987   -2.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7342   -1.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8711   -1.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -0.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -1.0663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085   -1.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273   -2.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287   -2.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3596   -3.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1610   -3.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211   -2.8371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3377   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8398   -1.7361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9034   -3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8531   -4.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248   -4.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -4.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -4.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -3.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -2.8106    0.0000 C   0  0  2  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  6  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
 16 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  1  0  0  0
 14 22  1  0  0  0  0
 11 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  0  0  0  0
 29 28  1  6  0  0  0
 23 29  1  0  0  0  0
 11 29  1  0  0  0  0
M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
    5.9960    1.2859    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583    1.0593   -0.6976 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9411    0.6144   -0.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973    0.3733    0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655   -0.0760    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764   -0.2519   -0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536    0.0008   -1.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583    0.4416   -1.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758    0.7077   -3.1341 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    0.5134   -4.3772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -0.7448   -0.5335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0552   -2.1677   -1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4953   -2.3111   -1.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0620   -1.0017   -1.5582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2942   -0.8987   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562    0.0383    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    0.1149    0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7447    0.9862    2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8279    1.8198    1.7137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1955    0.8691    0.6348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5326    1.2452   -0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648   -0.0461   -1.3176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2033    0.1674    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1392    0.3926    2.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1345   -0.3130    3.6949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211   -0.3634    2.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282   -0.3900    3.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -0.3816    1.4858 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239   -0.8032    0.9188 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5667    0.3768    0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4221    1.6639    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7786    2.0435    0.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    0.5062    1.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -0.1527   -2.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0748    0.9958   -5.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -0.5578   -4.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4333    1.0208   -4.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6092   -2.2183   -1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2793   -2.8693   -0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -2.9136   -2.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0191   -2.8416   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0935   -0.6743   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5864   -1.9067   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898   -0.5515    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0640    0.4024    2.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9416    1.6850    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5709    1.2356    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4561    1.8379    1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777    1.9019   -0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    1.6457   -1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5980    0.2306   -2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    1.1059    3.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338    0.3141    4.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4585   -1.3437    3.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -1.8173    1.2644 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
 16 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
  8  3  1  0
 22 11  1  0
 29 23  1  0
 28  5  1  0
 29 11  1  0
 22 14  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
 19 47  1  0
 20 48  1  1
 21 49  1  0
 21 50  1  0
 22 51  1  6
 24 52  1  0
 25 53  1  0
 25 54  1  0
 29 55  1  1
M  END


  Mrv1652309072223492D          

 29 34  0  0  1  0            999 V2000
   -0.7382   -1.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939   -1.9824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302   -1.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -2.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987   -2.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7342   -1.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0538   -1.9306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8711   -1.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -0.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -1.0663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085   -1.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3273   -2.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1287   -2.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3596   -3.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1610   -3.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211   -2.8371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3377   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8398   -1.7361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9034   -3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8531   -4.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1248   -4.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -4.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6960   -4.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923   -3.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258   -2.8106    0.0000 C   0  0  2  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  6  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
 16 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  1  0  0  0
 14 22  1  0  0  0  0
 11 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 28  1  0  0  0  0
 29 28  1  6  0  0  0
 23 29  1  0  0  0  0
 11 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@]13CCN4C\C(=C\CO)[C@H](C[C@@H]14)C1=CCC(=O)N2[C@H]31

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O4/c1-28-18-10-16-17(11-19(18)29-2)25-21(27)4-3-14-15-9-20-23(16,22(14)25)6-7-24(20)12-13(15)5-8-26/h3,5,10-11,15,20,22,26H,4,6-9,12H2,1-2H3/b13-5-/t15-,20-,22-,23+/m0/s1

> <INCHI_KEY>
XTGYWZXUYFAABL-XZZOEZDBSA-N

> <FORMULA>
C23H26N2O4

> <MOLECULAR_WEIGHT>
394.471

> <EXACT_MASS>
394.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.88642611393635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13S,14E,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,11-tetraen-9-one

> <JCHEM_LOGP>
0.3111038206666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.622147451709345

> <JCHEM_PKA_STRONGEST_BASIC>
8.569497241994311

> <JCHEM_POLAR_SURFACE_AREA>
62.24000000000001

> <JCHEM_REFRACTIVITY>
110.30049999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13S,14E,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,11-tetraen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.378  -2.403   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.549  -3.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.990  -3.631   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.819  -4.929   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.358  -4.859   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.067  -3.492   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.237  -2.194   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.699  -2.264   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.869  -0.966   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.669  -1.036   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.700  -3.604   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.359  -1.976   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.650  -1.055   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.964  -1.990   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.536  -2.416   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.944  -4.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.440  -4.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.871  -5.871   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.367  -6.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.813  -5.296   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.097  -4.399   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.168  -3.241   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.286  -6.068   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.192  -7.603   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.833  -8.340   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.498  -7.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.166  -8.313   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       4.466  -5.974   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       5.835  -5.246   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   28                                                  
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   22   29                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   16   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   14   11                                                  
CONECT   23   20   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    5   29                                                  
CONECT   29   28   23   11                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆N₂O₄

Average Mass

394.4710 Da

Monoisotopic Mass

394.18926 Da

IUPAC Name

(1R,13S,14E,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,11-tetraen-9-one

Traditional Name

(1R,13S,14E,19S,21S)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,11-tetraen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@]13CCN4C\C(=C\CO)[C@H](C[C@@H]14)C1=CCC(=O)N2[C@H]31

InChI Identifier

InChI=1S/C23H26N2O4/c1-28-18-10-16-17(11-19(18)29-2)25-21(27)4-3-14-15-9-20-23(16,22(14)25)6-7-24(20)12-13(15)5-8-26/h3,5,10-11,15,20,22,26H,4,6-9,12H2,1-2H3/b13-5-/t15-,20-,22-,23+/m0/s1

InChI Key

XTGYWZXUYFAABL-XZZOEZDBSA-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 nux-vomica	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
Indole or derivatives
Indolizidine
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Lactam
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Primary alcohol
Organic oxygen compound
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	0.31	ChemAxon
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	8.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.3 m³·mol⁻¹	ChemAxon
Polarizability	42.89 Å³	ChemAxon
Number of Rings	6	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

C00050880

Chemspider ID

20100218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56598205

PDB ID

Not Available

ChEBI ID

132660

Good Scents ID

Not Available

References

General References

Yang XW, Yan ZK: [Studies on the chemical constituents of alkaloids in seeds of Strychnos nux-vomica L]. Zhongguo Zhong Yao Za Zhi. 1993 Dec;18(12):739-40, 763-4. [PubMed:7912074 ]
Cai BC, Wang TS, Kurokawa M, Shiraki K, Hattori M: Cytotoxicities of alkaloids from processed and unprocessed seeds of Strychnos nux-vomica. Zhongguo Yao Li Xue Bao. 1998 Sep;19(5):425-8. [PubMed:10375801 ]
Wu H, Cai BC, Zheng PX, Zhao CZ, Yuan ZR: [Effect of processing on the alkaloids in Strychnos nux-vomica L]. Zhongguo Zhong Yao Za Zhi. 1994 May;19(5):277-9, 319. [PubMed:7945866 ]
Cai BC, Hattori M, Namba T: Processing of nux vomica. II. Changes in alkaloid composition of the seeds of Strychnos nux-vomica on traditional drug-processing. Chem Pharm Bull (Tokyo). 1990 May;38(5):1295-8. doi: 10.1248/cpb.38.1295. [PubMed:2393954 ]
LOTUS database [Link]

Showing NP-Card for (1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one (NP0256855)

MOL for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

3D MOL for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

3D SDF for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

3D-SDF for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

PDB for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

3D PDB for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

SMILES for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

INCHI for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

Structure for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)

3D Structure for NP0256855 ((1r,13s,14e,19s,21s)-14-(2-hydroxyethylidene)-4,5-dimethoxy-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2(7),3,5,11-tetraen-9-one)