NP-MRD: Showing NP-Card for isopseudostrychnine (NP0041374)

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Record Information

Version

2.0

Created at

2021-06-20 23:18:10 UTC

Updated at

2021-06-30 00:15:51 UTC

NP-MRD ID

NP0041374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isopseudostrychnine

Provided By

JEOL Database JEOL Logo

Description

(1S,13S,14E,19R,21S)-19-hydroxy-14-(2-hydroxyethylidene)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]Henicosa-2,4,6,11-tetraen-9-one 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. isopseudostrychnine is found in Strychnos nux-vomica. isopseudostrychnine was first documented in 2012 (Zhao, N., et al.). Based on a literature review very few articles have been published on (1S,13S,14E,19R,21S)-19-hydroxy-14-(2-hydroxyethylidene)-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]Henicosa-2,4,6,11-tetraen-9-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101183D          

 48 53  0  0  0  0            999 V2000
    5.0773   -2.1286   -1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -2.4829   -1.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.9245   -2.2483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2809   -4.3508   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -3.4800   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.8267   -0.4117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1716   -2.6812    0.5726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5710   -1.4353   -0.2184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0039   -0.4549    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -1.6313   -1.1073 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4126   -1.1125   -2.4420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2377   -0.1794   -2.2211 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5622   -0.9083   -1.1312 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6270   -0.0002   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652    1.1878    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.8958    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784    1.4188    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400    0.2282   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -0.4637   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -1.6832   -1.5456 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.0611   -1.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2523   -2.9902   -1.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1780   -4.0492   -1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3936   -5.1121   -2.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -6.3118   -2.2733 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0826   -6.2136   -3.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -4.0288   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2507   -4.7340    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7246   -2.4809    1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9326   -0.3172    0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2695   -0.5839   -2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5987    0.7963   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -0.0070   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    1.5693    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4843    2.8232    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.9761    0.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0390   -0.1321   -0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765   -2.1025   -2.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1435   -7.2172   -2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -6.4292   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -5.3753   -3.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
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  5  4  2  0  0  0  0
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 15 38  1  0  0  0  0
  7 31  1  0  0  0  0
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  3 27  1  0  0  0  0
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 24 45  1  0  0  0  0
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 25 47  1  0  0  0  0
 26 48  1  0  0  0  0
  9 33  1  0  0  0  0
M  END

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
    5.0773   -2.1286   -1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -2.4829   -1.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.9245   -2.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -4.3508   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0400    0.2282   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -0.4637   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -1.6832   -1.5456 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.0611   -1.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2523   -2.9902   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0826   -6.2136   -3.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
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  5  4  2  0
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  9 33  1  0
M  END


  Mrv1652306212101183D          

 48 53  0  0  0  0            999 V2000
    5.0773   -2.1286   -1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -2.4829   -1.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.9245   -2.2483 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2809   -4.3508   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -3.4800   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.8267   -0.4117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1716   -2.6812    0.5726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5710   -1.4353   -0.2184 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7273   -1.6313   -1.1073 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4126   -1.1125   -2.4420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2377   -0.1794   -2.2211 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5622   -0.9083   -1.1312 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6270   -0.0002   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652    1.1878    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.8958    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784    1.4188    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400    0.2282   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4250   -2.0611   -1.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2523   -2.9902   -1.1280 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0826   -6.2136   -3.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -4.0288   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9326   -0.3172    0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4768    1.5693    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4843    2.8232    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2765   -2.1025   -2.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1435   -7.2172   -2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -6.4292   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -5.3753   -3.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  2  0  0  0  0
 20  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
 13 14  1  0  0  0  0
  2  1  2  0  0  0  0
 13 21  1  0  0  0  0
 13 12  1  6  0  0  0
 16 17  2  0  0  0  0
 12 11  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 10  1  0  0  0  0
 22 10  1  0  0  0  0
 14 19  1  0  0  0  0
 22 23  1  0  0  0  0
 13  8  1  0  0  0  0
 23 24  2  0  0  0  0
  5  6  1  0  0  0  0
 24 25  1  0  0  0  0
  6  7  1  0  0  0  0
 25 26  1  0  0  0  0
  7  8  1  0  0  0  0
  6 30  1  1  0  0  0
  5 21  1  0  0  0  0
  8  9  1  1  0  0  0
 23  6  1  0  0  0  0
 21 42  1  6  0  0  0
  8 10  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 15 38  1  0  0  0  0
  7 31  1  0  0  0  0
  7 32  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
 24 45  1  0  0  0  0
 25 46  1  0  0  0  0
 25 47  1  0  0  0  0
 26 48  1  0  0  0  0
  9 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(\[H])=C1\C([H])([H])N2C([H])([H])C([H])([H])[C@]34C5=C([H])C([H])=C([H])C([H])=C5N5C(=O)C([H])([H])C([H])=C([C@@]35[H])[C@@]1([H])C([H])([H])[C@]24O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O3/c24-10-7-13-12-22-9-8-20-16-3-1-2-4-17(16)23-18(25)6-5-14(19(20)23)15(13)11-21(20,22)26/h1-5,7,15,19,24,26H,6,8-12H2/b13-7-/t15-,19-,20-,21+/m0/s1

> <INCHI_KEY>
FHSINSSEIZLFHR-AKQJGEJZSA-N

> <FORMULA>
C21H22N2O3

> <MOLECULAR_WEIGHT>
350.418

> <EXACT_MASS>
350.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.92467963620373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,14E,19R,21S)-19-hydroxy-14-(2-hydroxyethylidene)-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

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
0.20806084433333336

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.622616640880125

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.625812961316807

> <JCHEM_PKA_STRONGEST_BASIC>
7.685838074643983

> <JCHEM_POLAR_SURFACE_AREA>
64.01

> <JCHEM_REFRACTIVITY>
98.9518

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,14E,19R,21S)-19-hydroxy-14-(2-hydroxyethylidene)-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

$$$$

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
    5.0773   -2.1286   -1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -2.4829   -1.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.9245   -2.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -4.3508   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -3.4800   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.8267   -0.4117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1716   -2.6812    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -1.4353   -0.2184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0039   -0.4549    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -1.6313   -1.1073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126   -1.1125   -2.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377   -0.1794   -2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5622   -0.9083   -1.1312 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6270   -0.0002   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652    1.1878    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.8958    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784    1.4188    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400    0.2282   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -0.4637   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -1.6832   -1.5456 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.0611   -1.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2523   -2.9902   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -4.0492   -1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3936   -5.1121   -2.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -6.3118   -2.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -6.2136   -3.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -4.0288   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -4.5671   -1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -5.3721   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507   -4.7340    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7246   -2.4809    1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -2.9457    1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.3172    0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.9072   -3.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -0.5839   -2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5987    0.7963   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -0.0070   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    1.5693    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4843    2.8232    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.9761    0.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0390   -0.1321   -0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765   -2.1025   -2.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -3.0799   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7882   -3.1705   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -5.1576   -2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -7.2172   -2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -6.4292   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -5.3753   -3.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  5  4  2  0
 20  2  1  0
  2  3  1  0
  3  4  1  0
 13 14  1  0
  2  1  2  0
 13 21  1  0
 13 12  1  6
 16 17  2  0
 12 11  1  0
 14 15  2  0
 15 16  1  0
 11 10  1  0
 22 10  1  0
 14 19  1  0
 22 23  1  0
 13  8  1  0
 23 24  2  0
  5  6  1  0
 24 25  1  0
  6  7  1  0
 25 26  1  0
  7  8  1  0
  6 30  1  1
  5 21  1  0
  8  9  1  1
 23  6  1  0
 21 42  1  6
  8 10  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 15 38  1  0
  7 31  1  0
  7 32  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
 12 36  1  0
 12 37  1  0
 11 34  1  0
 11 35  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 25 46  1  0
 25 47  1  0
 26 48  1  0
  9 33  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       5.077  -2.129  -1.987  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.902  -2.483  -1.921  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.508  -3.925  -2.248  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.281  -4.351  -1.485  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.280  -3.480  -1.238  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.062  -3.827  -0.412  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.172  -2.681   0.573  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.571  -1.435  -0.218  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.004  -0.455   0.707  0.00  0.00           O+0
HETATM   10  N   UNK     0      -1.727  -1.631  -1.107  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.413  -1.113  -2.442  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.238  -0.179  -2.221  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.562  -0.908  -1.131  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.627  -0.000  -0.561  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.465   1.188   0.144  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.598   1.896   0.551  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.878   1.419   0.249  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.040   0.228  -0.462  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.908  -0.464  -0.864  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.837  -1.683  -1.546  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.425  -2.061  -1.760  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.252  -2.990  -1.128  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.178  -4.049  -1.271  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.394  -5.112  -2.075  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.529  -6.312  -2.273  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.083  -6.214  -3.547  0.00  0.00           O+0
HETATM   27  H   UNK     0       3.352  -4.029  -3.326  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.345  -4.567  -1.954  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.254  -5.372  -1.118  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.251  -4.734   0.177  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.725  -2.481   1.176  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.951  -2.946   1.301  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.933  -0.317   0.450  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.124  -1.907  -3.141  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.269  -0.584  -2.871  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.599   0.796  -1.870  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.332  -0.007  -3.141  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.477   1.569   0.383  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.484   2.823   1.107  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.754   1.976   0.572  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.039  -0.132  -0.683  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.276  -2.103  -2.848  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.018  -3.080  -1.910  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.788  -3.171  -0.187  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.322  -5.158  -2.644  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.143  -7.217  -2.255  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.240  -6.429  -1.507  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.575  -5.375  -3.553  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   20    3    1                                                  
CONECT    3    2    4   27   28                                             
CONECT    4    5    3   29                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   30   23                                             
CONECT    7    6    8   31   32                                             
CONECT    8   13    7    9   10                                             
CONECT    9    8   33                                                       
CONECT   10   11   22    8                                                  
CONECT   11   12   10   34   35                                             
CONECT   12   13   11   36   37                                             
CONECT   13   14   21   12    8                                             
CONECT   14   13   15   19                                                  
CONECT   15   14   16   38                                                  
CONECT   16   17   15   39                                                  
CONECT   17   18   16   40                                                  
CONECT   18   17   19   41                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21    2                                                  
CONECT   21   20   13    5   42                                             
CONECT   22   10   23   43   44                                             
CONECT   23   22   24    6                                                  
CONECT   24   23   25   45                                                  
CONECT   25   24   26   46   47                                             
CONECT   26   25   48                                                       
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   22                                                            
CONECT   45   24                                                            
CONECT   46   25                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

RDKit          3D

48 53  0  0  0  0  0  0  0  0999 V2000
    5.0773   -2.1286   -1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -2.4829   -1.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081   -3.9245   -2.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -4.3508   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -3.4800   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -3.8267   -0.4117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1716   -2.6812    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -1.4353   -0.2184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0039   -0.4549    0.7068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -1.6313   -1.1073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126   -1.1125   -2.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377   -0.1794   -2.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5622   -0.9083   -1.1312 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6270   -0.0002   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652    1.1878    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978    1.8958    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8784    1.4188    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400    0.2282   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -0.4637   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -1.6832   -1.5456 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -2.0611   -1.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2523   -2.9902   -1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -4.0492   -1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3936   -5.1121   -2.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -6.3118   -2.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826   -6.2136   -3.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -4.0288   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -4.5671   -1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -5.3721   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507   -4.7340    0.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7246   -2.4809    1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507   -2.9457    1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -0.3172    0.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.9072   -3.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -0.5839   -2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5987    0.7963   -1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -0.0070   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    1.5693    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4843    2.8232    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.9761    0.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0390   -0.1321   -0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765   -2.1025   -2.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -3.0799   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7882   -3.1705   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -5.1576   -2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -7.2172   -2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2395   -6.4292   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -5.3753   -3.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  5  4  2  0
 20  2  1  0
  2  3  1  0
  3  4  1  0
 13 14  1  0
  2  1  2  0
 13 21  1  0
 13 12  1  6
 16 17  2  0
 12 11  1  0
 14 15  2  0
 15 16  1  0
 11 10  1  0
 22 10  1  0
 14 19  1  0
 22 23  1  0
 13  8  1  0
 23 24  2  0
  5  6  1  0
 24 25  1  0
  6  7  1  0
 25 26  1  0
  7  8  1  0
  6 30  1  1
  5 21  1  0
  8  9  1  1
 23  6  1  0
 21 42  1  6
  8 10  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 15 38  1  0
  7 31  1  0
  7 32  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
 12 36  1  0
 12 37  1  0
 11 34  1  0
 11 35  1  0
 22 43  1  0
 22 44  1  0
 24 45  1  0
 25 46  1  0
 25 47  1  0
 26 48  1  0
  9 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂N₂O₃

Average Mass

350.4180 Da

Monoisotopic Mass

350.16304 Da

IUPAC Name

(1S,13S,14E,19R,21S)-19-hydroxy-14-(2-hydroxyethylidene)-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

(1S,13S,14E,19R,21S)-19-hydroxy-14-(2-hydroxyethylidene)-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

[H]OC([H])([H])C(\[H])=C1\C([H])([H])N2C([H])([H])C([H])([H])[C@]34C5=C([H])C([H])=C([H])C([H])=C5N5C(=O)C([H])([H])C([H])=C([C@@]35[H])[C@@]1([H])C([H])([H])[C@]24O[H]

InChI Identifier

InChI=1S/C21H22N2O3/c24-10-7-13-12-22-9-8-20-16-3-1-2-4-17(16)23-18(25)6-5-14(19(20)23)15(13)11-21(20,22)26/h1-5,7,15,19,24,26H,6,8-12H2/b13-7-/t15-,19-,20-,21+/m0/s1

InChI Key

FHSINSSEIZLFHR-AKQJGEJZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Strychnos nux-vomica L.	JEOL database	Zhao, N., et al, Tetrahedron 68, 3288 (2012)

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
Piperidine
Benzenoid
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Hemiaminal
Lactam
Organoheterocyclic compound
Alkanolamine
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Alcohol
Organooxygen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Primary alcohol
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	1.19	ALOGPS
logP	0.21	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	7.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.01 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.95 m³·mol⁻¹	ChemAxon
Polarizability	36.92 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

Not Available

Chemspider ID

28289885

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57412267

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao, N., et al. (2012). Zhao, N., et al, Tetrahedron 68, 3288 (2012). Tetrahedron.

Showing NP-Card for isopseudostrychnine (NP0041374)

MOL for NP0041374 (isopseudostrychnine)

3D MOL for NP0041374 (isopseudostrychnine)

3D SDF for NP0041374 (isopseudostrychnine)

3D-SDF for NP0041374 (isopseudostrychnine)

PDB for NP0041374 (isopseudostrychnine)

3D PDB for NP0041374 (isopseudostrychnine)

SMILES for NP0041374 (isopseudostrychnine)

INCHI for NP0041374 (isopseudostrychnine)

Structure for NP0041374 (isopseudostrychnine)

3D Structure for NP0041374 (isopseudostrychnine)