NP-MRD: Showing NP-Card for (+)-5-bromohypaphorine (NP0028647)

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Record Information

Version

2.0

Created at

2021-06-19 20:28:38 UTC

Updated at

2021-06-29 23:55:33 UTC

NP-MRD ID

NP0028647

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-5-bromohypaphorine

Provided By

JEOL Database JEOL Logo

Description

(+)-5-bromohypaphorine is found in Smenospongia and Thorectandra. (+)-5-bromohypaphorine was first documented in 2005 (PMID: 16252912). Based on a literature review very few articles have been published on (+)-5-bromohypaphorine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122283D          

 37 38  0  0  0  0            999 V2000
   -1.5298    0.3272   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    1.1055    0.0571 N   0  3  1  0  0  4  0  0  0  0  0  0
   -1.2599    2.5360   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578    1.1354    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    0.3642    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5177    0.4009    1.2566 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1742   -0.4605    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.0281   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -1.1132   -1.4936 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -2.2554   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -3.5802   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -4.5645   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -4.2269    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -5.5825    1.3339 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8997    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8859    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    0.9026    2.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569    2.0505    2.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.0491    3.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    0.7249   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075    0.4769   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472   -0.7284   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    2.5194   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    2.9895   -0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073    3.0982    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917    0.1124    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.7856    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.5347   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.6615    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746    1.4339    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9041    0.0597    2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.9560   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.0919   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -3.8460   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -5.6022   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -2.6667    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817    0.3918    4.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0  0  0  0
  2  1  1  6  0  0  0
 15 13  1  0  0  0  0
 13 12  2  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
  9  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 17 18  2  0  0  0  0
  5 17  1  0  0  0  0
  2  3  1  0  0  0  0
  7 16  1  0  0  0  0
 13 14  1  0  0  0  0
 10 16  1  0  0  0  0
 17 19  1  0  0  0  0
  2  4  1  0  0  0  0
  5  2  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
  5 29  1  1  0  0  0
  9 33  1  0  0  0  0
  8 32  1  0  0  0  0
 15 36  1  0  0  0  0
 12 35  1  0  0  0  0
 11 34  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 19 37  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
M  CHG  1   2   1
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5298    0.3272   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    1.1055    0.0571 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.2599    2.5360   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578    1.1354    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    0.3642    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5177    0.4009    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742   -0.4605    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.0281   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -1.1132   -1.4936 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -2.2554   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -3.5802   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -4.5645   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -4.2269    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -5.5825    1.3339 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8997    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8859    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    0.9026    2.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569    2.0505    2.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.0491    3.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    0.7249   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075    0.4769   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472   -0.7284   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    2.5194   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    2.9895   -0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073    3.0982    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917    0.1124    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.7856    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.5347   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.6615    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746    1.4339    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9041    0.0597    2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.9560   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.0919   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -3.8460   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -5.6022   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -2.6667    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817    0.3918    4.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0
  2  1  1  6
 15 13  1  0
 13 12  2  0
 10  9  1  0
 12 11  1  0
 11 10  2  0
  9  8  1  0
  7  6  1  0
  6  5  1  0
  8  7  2  0
 17 18  2  0
  5 17  1  0
  2  3  1  0
  7 16  1  0
 13 14  1  0
 10 16  1  0
 17 19  1  0
  2  4  1  0
  5  2  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 29  1  1
  9 33  1  0
  8 32  1  0
 15 36  1  0
 12 35  1  0
 11 34  1  0
  6 30  1  0
  6 31  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 19 37  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
M  CHG  1   2   1
M  END


  Mrv1652306192122283D          

 37 38  0  0  0  0            999 V2000
   -1.5298    0.3272   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    1.1055    0.0571 N   0  3  1  0  0  4  0  0  0  0  0  0
   -1.2599    2.5360   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578    1.1354    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    0.3642    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5177    0.4009    1.2566 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1742   -0.4605    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.0281   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -1.1132   -1.4936 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -2.2554   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -3.5802   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -4.5645   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -4.2269    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -5.5825    1.3339 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8997    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8859    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    0.9026    2.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569    2.0505    2.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.0491    3.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    0.7249   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075    0.4769   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472   -0.7284   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    2.5194   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    2.9895   -0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073    3.0982    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917    0.1124    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.7856    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.5347   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.6615    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746    1.4339    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9041    0.0597    2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.9560   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.0919   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -3.8460   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -5.6022   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -2.6667    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817    0.3918    4.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0  0  0  0
  2  1  1  6  0  0  0
 15 13  1  0  0  0  0
 13 12  2  0  0  0  0
 10  9  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
  9  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 17 18  2  0  0  0  0
  5 17  1  0  0  0  0
  2  3  1  0  0  0  0
  7 16  1  0  0  0  0
 13 14  1  0  0  0  0
 10 16  1  0  0  0  0
 17 19  1  0  0  0  0
  2  4  1  0  0  0  0
  5  2  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
  5 29  1  1  0  0  0
  9 33  1  0  0  0  0
  8 32  1  0  0  0  0
 15 36  1  0  0  0  0
 12 35  1  0  0  0  0
 11 34  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 19 37  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
NP0028647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C(Br)C([H])=C12)[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H17BrN2O2/c1-17(2,3)13(14(18)19)6-9-8-16-12-5-4-10(15)7-11(9)12/h4-5,7-8,13,16H,6H2,1-3H3/p+1/t13-/m0/s1

> <INCHI_KEY>
XFTSJFRJVFXAIB-ZDUSSCGKSA-O

> <FORMULA>
C14H18BrN2O2

> <MOLECULAR_WEIGHT>
326.213

> <EXACT_MASS>
325.054617

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.496107806925025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S)-2-(5-bromo-1H-indol-3-yl)-1-carboxyethyl]trimethylazanium

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
-1.4015786141384123

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.003052178203134

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7589390472474262

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
89.8085

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S)-2-(5-bromo-1H-indol-3-yl)-1-carboxyethyl]trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5298    0.3272   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    1.1055    0.0571 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.2599    2.5360   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578    1.1354    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    0.3642    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5177    0.4009    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742   -0.4605    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.0281   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -1.1132   -1.4936 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -2.2554   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -3.5802   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -4.5645   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -4.2269    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -5.5825    1.3339 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8997    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8859    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    0.9026    2.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569    2.0505    2.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.0491    3.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    0.7249   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075    0.4769   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472   -0.7284   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    2.5194   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    2.9895   -0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073    3.0982    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917    0.1124    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.7856    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.5347   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.6615    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746    1.4339    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9041    0.0597    2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.9560   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.0919   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -3.8460   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -5.6022   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -2.6667    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817    0.3918    4.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0
  2  1  1  6
 15 13  1  0
 13 12  2  0
 10  9  1  0
 12 11  1  0
 11 10  2  0
  9  8  1  0
  7  6  1  0
  6  5  1  0
  8  7  2  0
 17 18  2  0
  5 17  1  0
  2  3  1  0
  7 16  1  0
 13 14  1  0
 10 16  1  0
 17 19  1  0
  2  4  1  0
  5  2  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 29  1  1
  9 33  1  0
  8 32  1  0
 15 36  1  0
 12 35  1  0
 11 34  1  0
  6 30  1  0
  6 31  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 19 37  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
M  CHG  1   2   1
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.530   0.327  -1.240  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.746   1.105   0.057  0.00  0.00           N+1
HETATM    3  C   UNK     0      -1.260   2.536  -0.131  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.258   1.135   0.320  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.027   0.364   1.290  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.518   0.401   1.257  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.174  -0.461   0.223  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.044  -0.028  -0.760  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.446  -1.113  -1.494  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.855  -2.255  -1.007  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.975  -3.580  -1.444  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.285  -4.564  -0.731  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.521  -4.227   0.381  0.00  0.00           C+0
HETATM   14 Br   UNK     0      -0.393  -5.582   1.334  0.00  0.00          Br+0
HETATM   15  C   UNK     0       0.410  -2.900   0.811  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.080  -1.886   0.093  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.440   0.903   2.671  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.757   2.050   2.934  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.427  -0.049   3.624  0.00  0.00           O+0
HETATM   20  H   UNK     0      -2.211   0.725  -1.999  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.507   0.477  -1.583  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.747  -0.728  -1.057  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.205   2.519  -0.413  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.843   2.990  -0.939  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.407   3.098   0.791  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.592   0.112   0.516  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.467   1.786   1.171  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.757   1.535  -0.569  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.408  -0.662   1.227  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.875   1.434   1.170  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.904   0.060   2.228  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.430   0.956  -0.996  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.102  -1.092  -2.264  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.591  -3.846  -2.299  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.367  -5.602  -1.049  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.171  -2.667   1.698  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.682   0.392   4.467  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3    4    5                                             
CONECT    3    2   23   24   25                                             
CONECT    4    2   26   27   28                                             
CONECT    5    6   17    2   29                                             
CONECT    6    7    5   30   31                                             
CONECT    7    6    8   16                                                  
CONECT    8    9    7   32                                                  
CONECT    9   10    8   33                                                  
CONECT   10    9   11   16                                                  
CONECT   11   12   10   34                                                  
CONECT   12   13   11   35                                                  
CONECT   13   15   12   14                                                  
CONECT   14   13                                                            
CONECT   15   16   13   36                                                  
CONECT   16   15    7   10                                                  
CONECT   17   18    5   19                                                  
CONECT   18   17                                                            
CONECT   19   17   37                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   15                                                            
CONECT   37   19                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5298    0.3272   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455    1.1055    0.0571 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.2599    2.5360   -0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2578    1.1354    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    0.3642    1.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5177    0.4009    1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1742   -0.4605    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -0.0281   -0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -1.1132   -1.4936 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8551   -2.2554   -1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -3.5802   -1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2851   -4.5645   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -4.2269    0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -5.5825    1.3339 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8997    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0796   -1.8859    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    0.9026    2.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569    2.0505    2.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4269   -0.0491    3.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    0.7249   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075    0.4769   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472   -0.7284   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    2.5194   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431    2.9895   -0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4073    3.0982    0.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5917    0.1124    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.7856    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.5347   -0.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -0.6615    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8746    1.4339    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9041    0.0597    2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.9560   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.0919   -2.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -3.8460   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -5.6022   -1.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -2.6667    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817    0.3918    4.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  2  0
  2  1  1  6
 15 13  1  0
 13 12  2  0
 10  9  1  0
 12 11  1  0
 11 10  2  0
  9  8  1  0
  7  6  1  0
  6  5  1  0
  8  7  2  0
 17 18  2  0
  5 17  1  0
  2  3  1  0
  7 16  1  0
 13 14  1  0
 10 16  1  0
 17 19  1  0
  2  4  1  0
  5  2  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 29  1  1
  9 33  1  0
  8 32  1  0
 15 36  1  0
 12 35  1  0
 11 34  1  0
  6 30  1  0
  6 31  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 19 37  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
M  CHG  1   2   1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈BrN₂O₂

Average Mass

326.2130 Da

Monoisotopic Mass

325.05462 Da

IUPAC Name

[(1S)-2-(5-bromo-1H-indol-3-yl)-1-carboxyethyl]trimethylazanium

Traditional Name

[(1S)-2-(5-bromo-1H-indol-3-yl)-1-carboxyethyl]trimethylazanium

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]([H])(C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C(Br)C([H])=C12)[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C14H17BrN2O2/c1-17(2,3)13(14(18)19)6-9-8-16-12-5-4-10(15)7-11(9)12/h4-5,7-8,13,16H,6H2,1-3H3/p+1/t13-/m0/s1

InChI Key

XFTSJFRJVFXAIB-ZDUSSCGKSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Smenospongia	JEOL database	Segraves, N. L., et al, J. Nat. Prod. 68, 1484 (2001)
Thorectandra	JEOL database	Segraves, N. L., et al, J. Nat. Prod. 68, 1484 (2001)

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	0.78	ALOGPS
logP	-1.4	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	89.81 m³·mol⁻¹	ChemAxon
Polarizability	30.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9784285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11609530

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Segraves NL, Crews P: Investigation of brominated tryptophan alkaloids from two thorectidae sponges: Thorectandra and Smenospongia. J Nat Prod. 2005 Oct;68(10):1484-8. doi: 10.1021/np0501334. [PubMed:16252912 ]
Segraves, N. L., et al. (2001). Segraves, N. L., et al, J. Nat. Prod. 68, 1484 (2001). J. Nat. Prod..

Showing NP-Card for (+)-5-bromohypaphorine (NP0028647)

MOL for NP0028647 ((+)-5-bromohypaphorine)

3D MOL for NP0028647 ((+)-5-bromohypaphorine)

3D SDF for NP0028647 ((+)-5-bromohypaphorine)

3D-SDF for NP0028647 ((+)-5-bromohypaphorine)

PDB for NP0028647 ((+)-5-bromohypaphorine)

3D PDB for NP0028647 ((+)-5-bromohypaphorine)

SMILES for NP0028647 ((+)-5-bromohypaphorine)

INCHI for NP0028647 ((+)-5-bromohypaphorine)

Structure for NP0028647 ((+)-5-bromohypaphorine)

3D Structure for NP0028647 ((+)-5-bromohypaphorine)