NP-MRD: Showing NP-Card for casuarinine A (NP0043579)

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Record Information

Version

1.0

Created at

2021-06-21 00:56:51 UTC

Updated at

2021-06-30 00:19:20 UTC

NP-MRD ID

NP0043579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

casuarinine A

Provided By

JEOL Database JEOL Logo

Description

(1R,9R,10R,11R)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]Heptadeca-2(7),3,5,16-tetraene-5,11-diol belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring. casuarinine A is found in Lycopodiastrum casuarinoides. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on (1R,9R,10R,11R)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]Heptadeca-2(7),3,5,16-tetraene-5,11-diol (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102563D          

 43 46  0  0  0  0            999 V2000
   -3.9024   -3.3305    2.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -2.2867    2.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -2.5372    2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -1.4985    2.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3852   -1.7242    1.5089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2633   -1.1641    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -1.5254   -0.9382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -1.1470   -2.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.4800   -3.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -0.3056   -2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    0.0447   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -0.3721    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    0.0919    1.6047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2327   -0.9177    1.8679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0495   -0.0607    2.7999 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0584    1.0083    2.8076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8006    0.9037    4.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279    2.4056    2.6895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4127    2.4868    1.4550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5159    1.5137    1.4648 N   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5567    1.9276    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6055    0.0468    3.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2820    3.1420    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828    2.6678    3.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982    2.3363    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    3.5057    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    2.9982    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060    1.4310    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    1.7352    3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 13  1  0  0  0  0
 18 19  1  0  0  0  0
 18 16  1  0  0  0  0
  6  7  1  0  0  0  0
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  5  4  1  0  0  0  0
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  4 26  1  1  0  0  0
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  7 29  1  0  0  0  0
 17 36  1  0  0  0  0
  3 25  1  0  0  0  0
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  1 22  1  0  0  0  0
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 21 43  1  0  0  0  0
M  END

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.9024   -3.3305    2.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -2.2867    2.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -2.5372    2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -1.4985    2.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3852   -1.7242    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633   -1.1641    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -1.5254   -0.9382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -1.1470   -2.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.4800   -3.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -0.3056   -2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    0.0447   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -0.3721    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    0.0919    1.6047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2327   -0.9177    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -0.0607    2.7999 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0584    1.0083    2.8076 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5279    2.4056    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4127    2.4868    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5567    1.9276    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -3.0006    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3691   -1.2560    1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8349   -1.0299    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
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 15 13  1  0
 18 19  1  0
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 21 43  1  0
M  END


  Mrv1652306212102563D          

 43 46  0  0  0  0            999 V2000
   -3.9024   -3.3305    2.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -2.2867    2.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -2.5372    2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -1.4985    2.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3852   -1.7242    1.5089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2633   -1.1641    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -1.5254   -0.9382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -1.1470   -2.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.4800   -3.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -0.3056   -2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    0.0447   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -0.3721    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    0.0919    1.6047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2327   -0.9177    1.8679 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0495   -0.0607    2.7999 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0584    1.0083    2.8076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8006    0.9037    4.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279    2.4056    2.6895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4127    2.4868    1.4550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5159    1.5137    1.4648 N   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5567    1.9276    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -3.0006    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -4.2850    2.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1279   -2.1185   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8301    0.6554   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.0299    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7681    0.8639    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2820    3.1420    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828    2.6678    3.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8066    3.5057    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    2.9982    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2886    1.7352    3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 13  1  0  0  0  0
 18 19  1  0  0  0  0
 18 16  1  0  0  0  0
  6  7  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
 10  8  1  0  0  0  0
  8  7  1  0  0  0  0
 19 20  1  0  0  0  0
  8  9  2  0  0  0  0
 15  4  1  0  0  0  0
 16 17  1  0  0  0  0
 13 12  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 13 14  1  0  0  0  0
  5  4  1  0  0  0  0
 15 34  1  1  0  0  0
  6 12  2  0  0  0  0
  3  2  2  0  0  0  0
  2 14  1  0  0  0  0
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  2  1  1  0  0  0  0
 15 16  1  0  0  0  0
 20 21  1  0  0  0  0
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 16 35  1  6  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  4 26  1  1  0  0  0
 11 31  1  0  0  0  0
 10 30  1  0  0  0  0
  7 29  1  0  0  0  0
 17 36  1  0  0  0  0
  3 25  1  0  0  0  0
 14 32  1  0  0  0  0
 14 33  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 21 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]23C4=C(N([H])C(=O)C([H])=C4[H])C([H])([H])[C@]([H])(C([H])=C(C([H])([H])[H])C2([H])[H])[C@@]13[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O2/c1-10-7-11-8-13-12(3-4-15(21)18-13)17(9-10)16(11)14(20)5-6-19(17)2/h3-4,7,11,14,16,20H,5-6,8-9H2,1-2H3,(H,18,21)/t11-,14+,16-,17-/m0/s1

> <INCHI_KEY>
WCOFIHGHNUFZAO-ISGYEWALSA-N

> <FORMULA>
C17H22N2O2

> <MOLECULAR_WEIGHT>
286.375

> <EXACT_MASS>
286.168127956

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.263342256854788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10R,11R)-11-hydroxy-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,16-trien-5-one

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
-0.2589208712185082

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.832334571163933

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.181197458135461

> <JCHEM_PKA_STRONGEST_BASIC>
9.418171949696108

> <JCHEM_POLAR_SURFACE_AREA>
52.57

> <JCHEM_REFRACTIVITY>
84.8868

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10R,11R)-11-hydroxy-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,16-trien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -3.9024   -3.3305    2.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -2.2867    2.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -2.5372    2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -1.4985    2.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3852   -1.7242    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633   -1.1641    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -1.5254   -0.9382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -1.1470   -2.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.4800   -3.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -0.3056   -2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    0.0447   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -0.3721    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    0.0919    1.6047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2327   -0.9177    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -0.0607    2.7999 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0584    1.0083    2.8076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8006    0.9037    4.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279    2.4056    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4127    2.4868    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    1.5137    1.4648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567    1.9276    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -3.0006    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -4.2850    2.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800   -3.5108    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -3.5292    3.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1540   -1.6574    3.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -1.2560    1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755   -2.7977    1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -2.1185   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806   -0.0082   -3.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8301    0.6554   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.0299    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043   -0.5297    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055    0.0468    3.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681    0.8639    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.6067    4.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2820    3.1420    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828    2.6678    3.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982    2.3363    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    3.5057    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    2.9982    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060    1.4310    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    1.7352    3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 13  1  0
 18 19  1  0
 18 16  1  0
  6  7  1  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
  8  7  1  0
 19 20  1  0
  8  9  2  0
 15  4  1  0
 16 17  1  0
 13 12  1  0
  4  3  1  0
  6  5  1  0
 13 14  1  0
  5  4  1  0
 15 34  1  1
  6 12  2  0
  3  2  2  0
  2 14  1  0
 13 20  1  6
  2  1  1  0
 15 16  1  0
 20 21  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 16 35  1  6
  5 27  1  0
  5 28  1  0
  4 26  1  1
 11 31  1  0
 10 30  1  0
  7 29  1  0
 17 36  1  0
  3 25  1  0
 14 32  1  0
 14 33  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 41  1  0
 21 42  1  0
 21 43  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      -3.902  -3.330   2.408  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.825  -2.287   2.382  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.572  -2.537   2.799  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.469  -1.498   2.773  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.385  -1.724   1.509  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.263  -1.164   0.264  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.308  -1.525  -0.938  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.162  -1.147  -2.170  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.378  -1.480  -3.218  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.379  -0.306  -2.163  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.932   0.045  -0.995  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.360  -0.372   0.283  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.045   0.092   1.605  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.233  -0.918   1.868  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.050  -0.061   2.800  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.058   1.008   2.808  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.801   0.904   4.023  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.528   2.406   2.689  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.413   2.487   1.455  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.516   1.514   1.465  0.00  0.00           N+0
HETATM   21  C   UNK     0      -3.557   1.928   2.407  0.00  0.00           C+0
HETATM   22  H   UNK     0      -4.735  -3.001   3.037  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.541  -4.285   2.804  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.280  -3.511   1.396  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.300  -3.529   3.154  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.154  -1.657   3.662  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.369  -1.256   1.636  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.576  -2.798   1.374  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.128  -2.119  -0.954  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.781  -0.008  -3.122  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.830   0.655  -0.984  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.835  -1.030   0.957  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.904  -0.530   2.642  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.605   0.047   3.744  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.768   0.864   1.987  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.474   1.607   4.021  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.282   3.142   2.619  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.083   2.668   3.599  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.798   2.336   0.559  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.807   3.506   1.351  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.773   2.998   2.309  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.506   1.431   2.183  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.289   1.735   3.451  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3   14    1                                                  
CONECT    3    4    2   25                                                  
CONECT    4   15    3    5   26                                             
CONECT    5    6    4   27   28                                             
CONECT    6    7    5   12                                                  
CONECT    7    6    8   29                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11    8   30                                                  
CONECT   11   12   10   31                                                  
CONECT   12   11   13    6                                                  
CONECT   13   15   12   14   20                                             
CONECT   14   13    2   32   33                                             
CONECT   15   13    4   34   16                                             
CONECT   16   18   17   15   35                                             
CONECT   17   16   36                                                       
CONECT   18   19   16   37   38                                             
CONECT   19   18   20   39   40                                             
CONECT   20   19   13   21                                                  
CONECT   21   20   41   42   43                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   14                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   19                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
CONECT   43   21                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

RDKit          3D

43 46  0  0  0  0  0  0  0  0999 V2000
   -3.9024   -3.3305    2.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -2.2867    2.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -2.5372    2.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4686   -1.4985    2.7726 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3852   -1.7242    1.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2633   -1.1641    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3078   -1.5254   -0.9382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615   -1.1470   -2.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -1.4800   -3.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -0.3056   -2.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    0.0447   -0.9949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -0.3721    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    0.0919    1.6047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2327   -0.9177    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -0.0607    2.7999 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0584    1.0083    2.8076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8006    0.9037    4.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279    2.4056    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4127    2.4868    1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    1.5137    1.4648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567    1.9276    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -3.0006    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -4.2850    2.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800   -3.5108    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -3.5292    3.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1540   -1.6574    3.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691   -1.2560    1.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755   -2.7977    1.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -2.1185   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806   -0.0082   -3.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8301    0.6554   -0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.0299    0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043   -0.5297    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055    0.0468    3.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681    0.8639    1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.6067    4.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2820    3.1420    2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0828    2.6678    3.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982    2.3363    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    3.5057    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    2.9982    2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060    1.4310    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    1.7352    3.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 13  1  0
 18 19  1  0
 18 16  1  0
  6  7  1  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
  8  7  1  0
 19 20  1  0
  8  9  2  0
 15  4  1  0
 16 17  1  0
 13 12  1  0
  4  3  1  0
  6  5  1  0
 13 14  1  0
  5  4  1  0
 15 34  1  1
  6 12  2  0
  3  2  2  0
  2 14  1  0
 13 20  1  6
  2  1  1  0
 15 16  1  0
 20 21  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 16 35  1  6
  5 27  1  0
  5 28  1  0
  4 26  1  1
 11 31  1  0
 10 30  1  0
  7 29  1  0
 17 36  1  0
  3 25  1  0
 14 32  1  0
 14 33  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂N₂O₂

Average Mass

286.3750 Da

Monoisotopic Mass

286.16813 Da

IUPAC Name

(1R,9R,10R,11R)-11-hydroxy-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,16-trien-5-one

Traditional Name

(1R,9R,10R,11R)-11-hydroxy-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,16-trien-5-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])C([H])([H])N(C([H])([H])[H])[C@]23C4=C(N([H])C(=O)C([H])=C4[H])C([H])([H])[C@]([H])(C([H])=C(C([H])([H])[H])C2([H])[H])[C@@]13[H]

InChI Identifier

InChI=1S/C17H22N2O2/c1-10-7-11-8-13-12(3-4-15(21)18-13)17(9-10)16(11)14(20)5-6-19(17)2/h3-4,7,11,14,16,20H,5-6,8-9H2,1-2H3,(H,18,21)/t11-,14+,16-,17-/m0/s1

InChI Key

WCOFIHGHNUFZAO-ISGYEWALSA-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 phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Phenanthrolines

Sub Class

Not Available

Direct Parent

Phenanthrolines

Alternative Parents

Substituents

1,7-phenanthroline
Quinolone
Pyridinone
Aralkylamine
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.88	ALOGPS
logP	-0.26	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.18	ChemAxon
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.57 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.89 m³·mol⁻¹	ChemAxon
Polarizability	31.26 Å³	ChemAxon
Number of Rings	4	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

72192856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
Tang, Y., et al. (2013). Tang, Y., et al, J. Nat. Prod. 76, 1475 (2013). J. Nat. Prod..

Showing NP-Card for casuarinine A (NP0043579)

MOL for NP0043579 (casuarinine A)

3D MOL for NP0043579 (casuarinine A)

3D SDF for NP0043579 (casuarinine A)

3D-SDF for NP0043579 (casuarinine A)

PDB for NP0043579 (casuarinine A)

3D PDB for NP0043579 (casuarinine A)

SMILES for NP0043579 (casuarinine A)

INCHI for NP0043579 (casuarinine A)

Structure for NP0043579 (casuarinine A)

3D Structure for NP0043579 (casuarinine A)