NP-MRD: Showing NP-Card for (7S, 8R)-petranine (NP0037627)

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Record Information

Version

2.0

Created at

2021-06-20 20:30:32 UTC

Updated at

2021-06-30 00:09:56 UTC

NP-MRD ID

NP0037627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7S, 8R)-petranine

Provided By

JEOL Database JEOL Logo

Description

(7S, 8R)-petranine is found in Echium glomeratum (Boraginaceae). (7S, 8R)-petranine was first documented in 2008 (Alalli, F. Q., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122303D          

 39 40  0  0  0  0            999 V2000
    3.8259    0.0227   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -0.3623   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.6135   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9721   -4.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -0.6127   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295   -0.9431   -0.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.1502   -2.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -0.2187   -1.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4977    0.9951   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.0861   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    3.0845    0.2691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4354    2.2511    1.3174 N   0  3  2  0  0  4  0  0  0  0  0  0
   -2.4255    1.3953    2.1393 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6653    0.0939    2.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3040    0.4165    1.7755 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2842    1.4567    2.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    2.6771    2.2472 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6103    1.2097    0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6764    1.9873    9.9131 Cl  0  5  0  0  0 15  0  0  0  0  0  0
    4.3402   -0.8309   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5573    0.8264   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742    0.3963   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0109   -0.4261   -3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -0.1705   -4.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -1.8939   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4391   -1.1383   -4.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.2764   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.1369   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758    2.2378   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940    3.8896   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    3.4861    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.9343    3.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408    1.2349    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.1418    3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1481   -0.7372    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741   -0.4326    1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408    3.3306    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983    3.1950    3.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    1.7097    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  6  0  0  0
 11 10  1  0  0  0  0
 10  9  2  0  0  0  0
  9 18  1  0  0  0  0
 12 18  1  0  0  0  0
  3  2  2  0  0  0  0
  7  5  1  0  0  0  0
  2  1  1  0  0  0  0
 18 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
  5  6  2  0  0  0  0
 18 39  1  6  0  0  0
  5  3  1  0  0  0  0
 15 16  1  0  0  0  0
  8  7  1  0  0  0  0
 12 17  1  0  0  0  0
 17 16  1  0  0  0  0
  9  8  1  0  0  0  0
  3  4  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  2 23  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 10 29  1  0  0  0  0
 15 36  1  6  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
M  CHG  2  12   1  19  -1
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8259    0.0227   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -0.3623   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.6135   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9721   -4.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -0.6127   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295   -0.9431   -0.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.1502   -2.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -0.2187   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    0.9951   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.0861   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    3.0845    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354    2.2511    1.3174 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.4255    1.3953    2.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    0.0939    2.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    0.4165    1.7755 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2842    1.4567    2.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    2.6771    2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    1.2097    0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6764    1.9873    9.9131 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    4.3402   -0.8309   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5573    0.8264   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742    0.3963   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0109   -0.4261   -3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -0.1705   -4.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -1.8939   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4391   -1.1383   -4.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.2764   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.1369   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758    2.2378   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940    3.8896   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    3.4861    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.9343    3.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408    1.2349    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.1418    3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1481   -0.7372    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741   -0.4326    1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408    3.3306    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983    3.1950    3.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    1.7097    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  6
 11 10  1  0
 10  9  2  0
  9 18  1  0
 12 18  1  0
  3  2  2  0
  7  5  1  0
  2  1  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
  5  6  2  0
 18 39  1  6
  5  3  1  0
 15 16  1  0
  8  7  1  0
 12 17  1  0
 17 16  1  0
  9  8  1  0
  3  4  1  0
  8 27  1  0
  8 28  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  2 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 11 30  1  0
 11 31  1  0
 10 29  1  0
 15 36  1  6
 14 34  1  0
 14 35  1  0
 13 32  1  0
 13 33  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12   1  19  -1
M  END


  Mrv1652306202122303D          

 39 40  0  0  0  0            999 V2000
    3.8259    0.0227   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -0.3623   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.6135   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9721   -4.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -0.6127   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295   -0.9431   -0.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.1502   -2.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -0.2187   -1.5334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4977    0.9951   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.0861   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    3.0845    0.2691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4354    2.2511    1.3174 N   0  3  2  0  0  4  0  0  0  0  0  0
   -2.4255    1.3953    2.1393 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6653    0.0939    2.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3040    0.4165    1.7755 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2842    1.4567    2.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    2.6771    2.2472 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6103    1.2097    0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6764    1.9873    9.9131 Cl  0  5  0  0  0 15  0  0  0  0  0  0
    4.3402   -0.8309   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5573    0.8264   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742    0.3963   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0109   -0.4261   -3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -0.1705   -4.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -1.8939   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4391   -1.1383   -4.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.2764   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.1369   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758    2.2378   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940    3.8896   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    3.4861    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.9343    3.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408    1.2349    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.1418    3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1481   -0.7372    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741   -0.4326    1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408    3.3306    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983    3.1950    3.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    1.7097    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  6  0  0  0
 11 10  1  0  0  0  0
 10  9  2  0  0  0  0
  9 18  1  0  0  0  0
 12 18  1  0  0  0  0
  3  2  2  0  0  0  0
  7  5  1  0  0  0  0
  2  1  1  0  0  0  0
 18 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  1  0  0  0  0
  5  6  2  0  0  0  0
 18 39  1  6  0  0  0
  5  3  1  0  0  0  0
 15 16  1  0  0  0  0
  8  7  1  0  0  0  0
 12 17  1  0  0  0  0
 17 16  1  0  0  0  0
  9  8  1  0  0  0  0
  3  4  1  0  0  0  0
  8 27  1  0  0  0  0
  8 28  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  2 23  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 10 29  1  0  0  0  0
 15 36  1  6  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
M  CHG  2  12   1  19  -1
M  END
> <DATABASE_ID>
NP0037627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[Cl-].[H]\C(=C(\C(=O)OC([H])([H])C1=C([H])C([H])([H])[N@@+]23C([H])([H])O[C@@]([H])(C([H])([H])C2([H])[H])[C@@]13[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H20NO3.ClH/c1-3-10(2)14(16)17-8-11-4-6-15-7-5-12(13(11)15)18-9-15;/h3-4,12-13H,5-9H2,1-2H3;1H/q+1;/p-1/b10-3-;/t12-,13+,15-;/m0./s1

> <INCHI_KEY>
RHVNAIMJOHRFPD-LEADJJEPSA-M

> <FORMULA>
C14H20ClNO3

> <MOLECULAR_WEIGHT>
285.77

> <EXACT_MASS>
285.1131712

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.970168718163496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5R,6S)-4-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-7-oxa-1lambda5-azatricyclo[4.2.2.0^{1,5}]dec-3-en-1-ylium chloride

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
-2.5413796448050787

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.515621393412107

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
80.2586

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6S)-4-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-7-oxa-1lambda5-azatricyclo[4.2.2.0^{1,5}]dec-3-en-1-ylium chloride

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.8259    0.0227   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -0.3623   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.6135   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9721   -4.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -0.6127   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295   -0.9431   -0.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.1502   -2.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -0.2187   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    0.9951   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.0861   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    3.0845    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354    2.2511    1.3174 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.4255    1.3953    2.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    0.0939    2.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    0.4165    1.7755 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2842    1.4567    2.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    2.6771    2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    1.2097    0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6764    1.9873    9.9131 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    4.3402   -0.8309   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5573    0.8264   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742    0.3963   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0109   -0.4261   -3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -0.1705   -4.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -1.8939   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4391   -1.1383   -4.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.2764   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.1369   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758    2.2378   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940    3.8896   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    3.4861    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.9343    3.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408    1.2349    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.1418    3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1481   -0.7372    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741   -0.4326    1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408    3.3306    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983    3.1950    3.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    1.7097    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  6
 11 10  1  0
 10  9  2  0
  9 18  1  0
 12 18  1  0
  3  2  2  0
  7  5  1  0
  2  1  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
  5  6  2  0
 18 39  1  6
  5  3  1  0
 15 16  1  0
  8  7  1  0
 12 17  1  0
 17 16  1  0
  9  8  1  0
  3  4  1  0
  8 27  1  0
  8 28  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  2 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 11 30  1  0
 11 31  1  0
 10 29  1  0
 15 36  1  6
 14 34  1  0
 14 35  1  0
 13 32  1  0
 13 33  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12   1  19  -1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.826   0.023  -1.209  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.261  -0.362  -2.540  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.977  -0.614  -2.865  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.572  -0.972  -4.266  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.901  -0.613  -1.841  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.030  -0.943  -0.672  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.254  -0.150  -2.380  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.406  -0.219  -1.533  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.498   0.995  -0.674  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.276   2.086  -0.845  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.075   3.084   0.269  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.435   2.251   1.317  0.00  0.00           N+1
HETATM   13  C   UNK     0      -2.426   1.395   2.139  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.665   0.094   2.367  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.304   0.417   1.776  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.284   1.457   2.650  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.370   2.677   2.247  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.610   1.210   0.513  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       1.676   1.987   9.913  0.00  0.00          Cl-1
HETATM   20  H   UNK     0       4.340  -0.831  -0.758  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.557   0.826  -1.345  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.074   0.396  -0.510  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.011  -0.426  -3.329  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.974  -0.171  -4.712  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.980  -1.894  -4.270  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.439  -1.138  -4.914  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.277  -0.276  -2.195  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.416  -1.137  -0.934  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.976   2.238  -1.657  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.394   3.890  -0.023  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.014   3.486   0.661  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.670   1.934   3.061  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.341   1.235   1.559  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.613  -0.142   3.435  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.148  -0.737   1.843  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.374  -0.433   1.694  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.341   3.331   1.729  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.798   3.195   3.111  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.304   1.710   0.152  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    3    1   23                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3   24   25   26                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   27   28                                             
CONECT    9   10   18    8                                                  
CONECT   10   11    9   29                                                  
CONECT   11   12   10   30   31                                             
CONECT   12   11   18   13   17                                             
CONECT   13   14   12   32   33                                             
CONECT   14   15   13   34   35                                             
CONECT   15   18   14   16   36                                             
CONECT   16   15   17                                                       
CONECT   17   12   16   37   38                                             
CONECT   18    9   12   15   39                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    8                                                            
CONECT   28    8                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
    3.8259    0.0227   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -0.3623   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.6135   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.9721   -4.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -0.6127   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0295   -0.9431   -0.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.1502   -2.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -0.2187   -1.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    0.9951   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2760    2.0861   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    3.0845    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354    2.2511    1.3174 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.4255    1.3953    2.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    0.0939    2.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    0.4165    1.7755 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2842    1.4567    2.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3703    2.6771    2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103    1.2097    0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6764    1.9873    9.9131 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    4.3402   -0.8309   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5573    0.8264   -1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742    0.3963   -0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0109   -0.4261   -3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9744   -0.1705   -4.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -1.8939   -4.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4391   -1.1383   -4.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.2764   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.1369   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9758    2.2378   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3940    3.8896   -0.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    3.4861    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6701    1.9343    3.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408    1.2349    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.1418    3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1481   -0.7372    1.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741   -0.4326    1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408    3.3306    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983    3.1950    3.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3036    1.7097    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  6
 11 10  1  0
 10  9  2  0
  9 18  1  0
 12 18  1  0
  3  2  2  0
  7  5  1  0
  2  1  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
  5  6  2  0
 18 39  1  6
  5  3  1  0
 15 16  1  0
  8  7  1  0
 12 17  1  0
 17 16  1  0
  9  8  1  0
  3  4  1  0
  8 27  1  0
  8 28  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  2 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 11 30  1  0
 11 31  1  0
 10 29  1  0
 15 36  1  6
 14 34  1  0
 14 35  1  0
 13 32  1  0
 13 33  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12   1  19  -1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₀ClNO₃

Average Mass

285.7700 Da

Monoisotopic Mass

285.11317 Da

IUPAC Name

(1S,5R,6S)-4-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-7-oxa-1lambda5-azatricyclo[4.2.2.0^{1,5}]dec-3-en-1-ylium chloride

Traditional Name

(1S,5R,6S)-4-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-7-oxa-1lambda5-azatricyclo[4.2.2.0^{1,5}]dec-3-en-1-ylium chloride

CAS Registry Number

Not Available

SMILES

[Cl-].[H]\C(=C(\C(=O)OC([H])([H])C1=C([H])C([H])([H])[N@@+]23C([H])([H])O[C@@]([H])(C([H])([H])C2([H])[H])[C@@]13[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C14H20NO3.ClH/c1-3-10(2)14(16)17-8-11-4-6-15-7-5-12(13(11)15)18-9-15;/h3-4,12-13H,5-9H2,1-2H3;1H/q+1;/p-1/b10-3-;/t12-,13+,15-;/m0./s1

InChI Key

RHVNAIMJOHRFPD-LEADJJEPSA-M

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Echium glomeratum (Boraginaceae)	JEOL database	Alalli, F. Q., et al, Phytochem. 69, 2341 (2008)

Chemical Taxonomy

Classification

Not classified

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	0.07	ALOGPS
logP	-2.5	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.26 m³·mol⁻¹	ChemAxon
Polarizability	26.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Alalli, F. Q., et al. (2008). Alalli, F. Q., et al, Phytochem. 69, 2341 (2008). Phytochem..

Showing NP-Card for (7S, 8R)-petranine (NP0037627)

MOL for NP0037627 ((7S, 8R)-petranine)

3D MOL for NP0037627 ((7S, 8R)-petranine)

3D SDF for NP0037627 ((7S, 8R)-petranine)

3D-SDF for NP0037627 ((7S, 8R)-petranine)

PDB for NP0037627 ((7S, 8R)-petranine)

3D PDB for NP0037627 ((7S, 8R)-petranine)

SMILES for NP0037627 ((7S, 8R)-petranine)

INCHI for NP0037627 ((7S, 8R)-petranine)

Structure for NP0037627 ((7S, 8R)-petranine)

3D Structure for NP0037627 ((7S, 8R)-petranine)