NP-MRD: Showing NP-Card for casuarinine E (NP0043581)

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Record Information

Version

1.0

Created at

2021-06-21 00:56:55 UTC

Updated at

2021-06-30 00:19:20 UTC

NP-MRD ID

NP0043581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

casuarinine E

Provided By

JEOL Database JEOL Logo

Description

(1R,9R,13R)-13-ethenyl-11-(hydroxymethyl)-1-(methylamino)-6-azatricyclo[7.3.1.0²,⁷]Trideca-2(7),3,5,10-tetraen-5-ol belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. casuarinine E is found in Lycopodiastrum casuarinoides. It was first documented in 2013 (Tang, Y., et al.). Based on a literature review very few articles have been published on (1R,9R,13R)-13-ethenyl-11-(hydroxymethyl)-1-(methylamino)-6-azatricyclo[7.3.1.0²,⁷]Trideca-2(7),3,5,10-tetraen-5-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102563D          

 40 42  0  0  0  0            999 V2000
   -1.4169   -3.2329   -2.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.1693   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.9860   -1.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4381    0.2838   -2.2327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2640    1.4339   -1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.5178   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758    2.6643    0.1165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7206    3.3913    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    0.4419    0.6155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5971    0.1220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1440   -1.7932    1.0097 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3899   -2.5034    1.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    0.1149    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.2038    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    0.7889    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    1.3723    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026    1.9106    0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    1.2766   -0.8719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169    0.6742   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.7115   -2.3018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8170   -4.0495   -2.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -3.3177   -2.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -2.1473   -1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723   -1.2564   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    0.0729   -3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.2232   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694    3.3534   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897    2.2991    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    3.5217    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -0.0634    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    0.9077    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785   -2.4452    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -1.9283    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059   -2.7872    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -3.4275    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.2153    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.8665    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.6916   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.7217   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    0.0494   -2.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
 12 11  1  0  0  0  0
 10 11  1  1  0  0  0
 19 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
  3  4  1  0  0  0  0
 16 17  2  0  0  0  0
 10 13  1  0  0  0  0
  4  5  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 20  4  1  0  0  0  0
  3 24  1  1  0  0  0
 19 13  2  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  3  2  1  0  0  0  0
  6  7  1  0  0  0  0
  3 10  1  0  0  0  0
  7  8  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 11 32  1  0  0  0  0
  2 23  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
  4 25  1  6  0  0  0
 14 36  1  0  0  0  0
 15 37  1  0  0  0  0
 18 38  1  0  0  0  0
  5 26  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.4169   -3.2329   -2.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.1693   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.9860   -1.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4381    0.2838   -2.2327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2640    1.4339   -1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.5178   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758    2.6643    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206    3.3913    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    0.4419    0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5971    0.1220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1440   -1.7932    1.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3899   -2.5034    1.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    0.1149    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.2038    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    0.7889    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    1.3723    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026    1.9106    0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    1.2766   -0.8719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169    0.6742   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.7115   -2.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -4.0495   -2.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -3.3177   -2.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -2.1473   -1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723   -1.2564   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    0.0729   -3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.2232   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694    3.3534   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897    2.2991    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    3.5217    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -0.0634    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    0.9077    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785   -2.4452    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -1.9283    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059   -2.7872    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -3.4275    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.2153    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.8665    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.6916   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.7217   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    0.0494   -2.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
 12 11  1  0
 10 11  1  1
 19 18  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 18  1  0
  3  4  1  0
 16 17  2  0
 10 13  1  0
  4  5  1  0
 19 20  1  0
 10  9  1  0
 20  4  1  0
  3 24  1  1
 19 13  2  0
  5  6  2  0
  6  9  1  0
  3  2  1  0
  6  7  1  0
  3 10  1  0
  7  8  1  0
  1 21  1  0
  1 22  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 11 32  1  0
  2 23  1  0
 20 39  1  0
 20 40  1  0
  4 25  1  6
 14 36  1  0
 15 37  1  0
 18 38  1  0
  5 26  1  0
  9 30  1  0
  9 31  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
M  END


  Mrv1652306212102563D          

 40 42  0  0  0  0            999 V2000
   -1.4169   -3.2329   -2.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.1693   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.9860   -1.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4381    0.2838   -2.2327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2640    1.4339   -1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.5178   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758    2.6643    0.1165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7206    3.3913    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    0.4419    0.6155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5971    0.1220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1440   -1.7932    1.0097 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3899   -2.5034    1.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    0.1149    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.2038    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    0.7889    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    1.3723    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026    1.9106    0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    1.2766   -0.8719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169    0.6742   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.7115   -2.3018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8170   -4.0495   -2.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -3.3177   -2.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -2.1473   -1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723   -1.2564   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    0.0729   -3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.2232   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694    3.3534   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897    2.2991    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    3.5217    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -0.0634    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    0.9077    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785   -2.4452    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -1.9283    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059   -2.7872    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -3.4275    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.2153    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.8665    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.6916   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.7217   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    0.0494   -2.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
 12 11  1  0  0  0  0
 10 11  1  1  0  0  0
 19 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
  3  4  1  0  0  0  0
 16 17  2  0  0  0  0
 10 13  1  0  0  0  0
  4  5  1  0  0  0  0
 19 20  1  0  0  0  0
 10  9  1  0  0  0  0
 20  4  1  0  0  0  0
  3 24  1  1  0  0  0
 19 13  2  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  3  2  1  0  0  0  0
  6  7  1  0  0  0  0
  3 10  1  0  0  0  0
  7  8  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 11 32  1  0  0  0  0
  2 23  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
  4 25  1  6  0  0  0
 14 36  1  0  0  0  0
 15 37  1  0  0  0  0
 18 38  1  0  0  0  0
  5 26  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])[C@@]2([H])C([H])([H])C3=C(C([H])=C([H])C(=O)N3[H])[C@@](N([H])C([H])([H])[H])(C1([H])[H])[C@]2([H])C([H])=C([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O2/c1-3-12-11-6-10(9-19)8-16(12,17-2)13-4-5-15(20)18-14(13)7-11/h3-6,11-12,17,19H,1,7-9H2,2H3,(H,18,20)/t11-,12+,16+/m0/s1

> <INCHI_KEY>
CARBLNGQAWBJFV-HWWQOWPSSA-N

> <FORMULA>
C16H20N2O2

> <MOLECULAR_WEIGHT>
272.348

> <EXACT_MASS>
272.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.63148114099377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,13R)-13-ethenyl-11-(hydroxymethyl)-1-(methylamino)-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
-0.3757910392827308

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.15688864255766

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.192778382070053

> <JCHEM_PKA_STRONGEST_BASIC>
9.581938788806603

> <JCHEM_POLAR_SURFACE_AREA>
61.36

> <JCHEM_REFRACTIVITY>
81.61539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,13R)-13-ethenyl-11-(hydroxymethyl)-1-(methylamino)-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.4169   -3.2329   -2.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.1693   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.9860   -1.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4381    0.2838   -2.2327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2640    1.4339   -1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.5178   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758    2.6643    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206    3.3913    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    0.4419    0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5971    0.1220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1440   -1.7932    1.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3899   -2.5034    1.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    0.1149    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.2038    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    0.7889    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    1.3723    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026    1.9106    0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    1.2766   -0.8719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169    0.6742   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.7115   -2.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -4.0495   -2.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -3.3177   -2.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -2.1473   -1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723   -1.2564   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    0.0729   -3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.2232   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694    3.3534   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897    2.2991    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    3.5217    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -0.0634    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    0.9077    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785   -2.4452    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -1.9283    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059   -2.7872    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -3.4275    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.2153    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.8665    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.6916   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.7217   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    0.0494   -2.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
 12 11  1  0
 10 11  1  1
 19 18  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 18  1  0
  3  4  1  0
 16 17  2  0
 10 13  1  0
  4  5  1  0
 19 20  1  0
 10  9  1  0
 20  4  1  0
  3 24  1  1
 19 13  2  0
  5  6  2  0
  6  9  1  0
  3  2  1  0
  6  7  1  0
  3 10  1  0
  7  8  1  0
  1 21  1  0
  1 22  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 11 32  1  0
  2 23  1  0
 20 39  1  0
 20 40  1  0
  4 25  1  6
 14 36  1  0
 15 37  1  0
 18 38  1  0
  5 26  1  0
  9 30  1  0
  9 31  1  0
  7 27  1  0
  7 28  1  0
  8 29  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  C   UNK     0      -1.417  -3.233  -2.510  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.836  -2.169  -1.939  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.605  -0.986  -1.359  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.438   0.284  -2.233  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.264   1.434  -1.686  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.653   1.518  -0.399  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.476   2.664   0.117  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.721   3.391   1.072  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.295   0.442   0.616  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.225  -0.597   0.122  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.144  -1.793   1.010  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.390  -2.503   1.252  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.160   0.115   0.146  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.891   0.204   1.408  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.094   0.789   1.489  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.703   1.372   0.274  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.803   1.911   0.304  0.00  0.00           O+0
HETATM   18  N   UNK     0       1.954   1.277  -0.872  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.717   0.674  -0.952  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.041   0.712  -2.302  0.00  0.00           C+0
HETATM   21  H   UNK     0      -0.817  -4.050  -2.901  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.495  -3.318  -2.603  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.251  -2.147  -1.873  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.672  -1.256  -1.374  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.797   0.073  -3.248  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.522   2.223  -2.390  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.769   3.353  -0.682  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.390   2.299   0.595  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.834   3.522   0.693  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.240  -0.063   0.848  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.954   0.908   1.549  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.479  -2.445   0.592  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.067  -1.928   1.889  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.906  -2.787   0.332  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.169  -3.428   1.797  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.435  -0.215   2.301  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.653   0.867   2.410  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.375   1.692  -1.694  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.116   1.722  -2.726  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.587   0.049  -2.986  0.00  0.00           H+0
CONECT    1    2   21   22                                                  
CONECT    2    1    3   23                                                  
CONECT    3    4   24    2   10                                             
CONECT    4    3    5   20   25                                             
CONECT    5    4    6   26                                                  
CONECT    6    5    9    7                                                  
CONECT    7    6    8   27   28                                             
CONECT    8    7   29                                                       
CONECT    9   10    6   30   31                                             
CONECT   10   11   13    9    3                                             
CONECT   11   12   10   32                                                  
CONECT   12   11   33   34   35                                             
CONECT   13   14   10   19                                                  
CONECT   14   13   15   36                                                  
CONECT   15   14   16   37                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   19   16   38                                                  
CONECT   19   18   20   13                                                  
CONECT   20   19    4   39   40                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   18                                                            
CONECT   39   20                                                            
CONECT   40   20                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
   -1.4169   -3.2329   -2.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363   -2.1693   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -0.9860   -1.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4381    0.2838   -2.2327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2640    1.4339   -1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6533    1.5178   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758    2.6643    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206    3.3913    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    0.4419    0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2247   -0.5971    0.1220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1440   -1.7932    1.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3899   -2.5034    1.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1603    0.1149    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909    0.2038    1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935    0.7889    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025    1.3723    0.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8026    1.9106    0.3044 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    1.2766   -0.8719 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7169    0.6742   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.7115   -2.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -4.0495   -2.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4953   -3.3177   -2.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2505   -2.1473   -1.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723   -1.2564   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7974    0.0729   -3.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.2232   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7694    3.3534   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897    2.2991    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    3.5217    0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -0.0634    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9543    0.9077    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785   -2.4452    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -1.9283    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9059   -2.7872    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687   -3.4275    1.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4353   -0.2153    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.8665    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    1.6916   -1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1155    1.7217   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    0.0494   -2.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
 12 11  1  0
 10 11  1  1
 19 18  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 18  1  0
  3  4  1  0
 16 17  2  0
 10 13  1  0
  4  5  1  0
 19 20  1  0
 10  9  1  0
 20  4  1  0
  3 24  1  1
 19 13  2  0
  5  6  2  0
  6  9  1  0
  3  2  1  0
  6  7  1  0
  3 10  1  0
  7  8  1  0
  1 21  1  0
  1 22  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 11 32  1  0
  2 23  1  0
 20 39  1  0
 20 40  1  0
  4 25  1  6
 14 36  1  0
 15 37  1  0
 18 38  1  0
  5 26  1  0
  9 30  1  0
  9 31  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀N₂O₂

Average Mass

272.3480 Da

Monoisotopic Mass

272.15248 Da

IUPAC Name

(1R,9R,13R)-13-ethenyl-11-(hydroxymethyl)-1-(methylamino)-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

Traditional Name

(1R,9R,13R)-13-ethenyl-11-(hydroxymethyl)-1-(methylamino)-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,10-trien-5-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])[C@@]2([H])C([H])([H])C3=C(C([H])=C([H])C(=O)N3[H])[C@@](N([H])C([H])([H])[H])(C1([H])[H])[C@]2([H])C([H])=C([H])[H]

InChI Identifier

InChI=1S/C16H20N2O2/c1-3-12-11-6-10(9-19)8-16(12,17-2)13-4-5-15(20)18-14(13)7-11/h3-6,11-12,17,19H,1,7-9H2,2H3,(H,18,20)/t11-,12+,16+/m0/s1

InChI Key

CARBLNGQAWBJFV-HWWQOWPSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Lycopodiastrum casuarinoides	JEOL database	Tang, Y., et al, J. Nat. Prod. 76, 1475 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Quinolones and derivatives

Alternative Parents

Substituents

Quinolone
Pyridinone
Aralkylamine
Pyridine
Heteroaromatic compound
Lactam
Secondary amine
Secondary aliphatic amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.47	ALOGPS
logP	-0.38	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	11.19	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.62 m³·mol⁻¹	ChemAxon
Polarizability	29.63 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72192860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang, Y., et al. (2013). Tang, Y., et al, J. Nat. Prod. 76, 1475 (2013). J. Nat. Prod..

Showing NP-Card for casuarinine E (NP0043581)

MOL for NP0043581 (casuarinine E)

3D MOL for NP0043581 (casuarinine E)

3D SDF for NP0043581 (casuarinine E)

3D-SDF for NP0043581 (casuarinine E)

PDB for NP0043581 (casuarinine E)

3D PDB for NP0043581 (casuarinine E)

SMILES for NP0043581 (casuarinine E)

INCHI for NP0043581 (casuarinine E)

Structure for NP0043581 (casuarinine E)

3D Structure for NP0043581 (casuarinine E)