NP-MRD: Showing NP-Card for Chilocorine (NP0069706)

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Record Information

Version

2.0

Created at

2022-04-28 15:03:59 UTC

Updated at

2022-04-28 15:03:59 UTC

NP-MRD ID

NP0069706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chilocorine

Description

(1R,11S,15R,19S,21R)-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁷.0³,¹³.0¹¹,²⁷.0¹⁹,²⁶]Heptacosa-3(13),4,6-trien-8-one belongs to the class of organic compounds known as 9b-azaphenalenes. These are alkaloids with a structure based on the perhydro-9b-azaphenalene skeleton. Perhydro-9b-azaphenalene is a tricyclic compound consisting of quinolizidine that share its only nitrogen atom with a piperidine. In some 9b-azaphenalenes, the resulting tricyclic backbone can be unsaturated. Chilocorine is found in Chilocorus cacti. Based on a literature review very few articles have been published on (1R,11S,15R,19S,21R)-21-methyl-26,27-diazaheptacyclo[13.7.3.1¹,¹⁵.1⁴,⁷.0³,¹³.0¹¹,²⁷.0¹⁹,²⁶]Heptacosa-3(13),4,6-trien-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217042D          

 29 35  0  0  1  0            999 V2000
    1.7858    1.6613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2969    0.9968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117    0.2002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2687   -0.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972    0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    1.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102    1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    1.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5537    0.8054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -0.0054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6233   -0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020    0.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9823    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6866    1.2692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581    1.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0673    2.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450    2.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1320   -0.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827    0.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    1.2091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2850    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674    2.5899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6646    2.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    3.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766    1.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 18  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  2  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
 24 26  1  1  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 63 69  0  0  0  0  0  0  0  0999 V2000
   -4.5722   -2.2520    0.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -1.9136    0.6178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1220   -0.8329    1.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6262    0.4863    1.1880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7670    1.3566    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    2.7631    0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283    2.8328    0.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0117    1.7331   -0.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2755    2.0196   -1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922    0.7907   -2.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318   -0.3419   -1.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962   -0.6684   -0.4058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1114   -1.3081    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -0.5610    0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2827    0.7376    0.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6345    1.1469   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567    0.4503    0.3230 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9753    0.5343   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1848   -0.1145    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387   -1.4006    0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7197   -2.1141    1.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498   -1.8525    0.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075   -3.0685    0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4415   -2.8140    0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746   -1.4422    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4869   -0.9442    0.5096 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4437    1.9054    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943   -1.6914   -0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785    0.5060    0.2658 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6430   -3.3204   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624   -1.6684   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2832   -1.9787    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727   -2.8561    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -1.1390    2.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1851   -0.6821    1.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2911    1.0462    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    1.0093   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5919    1.2495    1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6252    3.3414   -0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271    3.2801    1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3975    3.7987    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    2.8895    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597    2.4964   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0891    2.7465   -1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4408    0.9764   -3.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    0.5202   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3259   -0.1473   -1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9511   -1.2038   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -2.3866    0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4473   -1.2958    1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6612    0.8500   -1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7659    2.2475   -0.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545    0.9420    1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007    1.5781   -0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6782    0.0245   -1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9262   -0.2753   -0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5468    0.5818    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3262   -4.0009    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6463   -3.5374    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8144    2.6953   -0.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5947    2.3410    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7765   -2.6452   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375   -1.4203   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 11  1  6
 12 28  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 15 27  1  0
 12 29  1  0
 28  2  1  0
 25 14  1  0
 29  4  1  0
 27  8  1  0
 29  8  1  0
 26 17  1  0
 26 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  1
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 28 62  1  0
 28 63  1  0
 13 49  1  0
 13 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  1
 18 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 23 58  1  0
 24 59  1  0
 27 60  1  0
 27 61  1  0
M  END


  Mrv1652304282217042D          

 29 35  0  0  1  0            999 V2000
    1.7858    1.6613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2969    0.9968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117    0.2002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2687   -0.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972    0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    1.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6102    1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    1.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5537    0.8054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4016   -0.0054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6233   -0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2977   -0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0020    0.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9823    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6866    1.2692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581    1.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0673    2.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450    2.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1320   -0.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827    0.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    1.2091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2850    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8674    2.5899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6646    2.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    3.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914    0.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766    1.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 18  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  2  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  1 25  1  0  0  0  0
 24 26  1  1  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2CCC[C@@]34CCC[C@@](C1)(CC1=C(C[C@@H]5CCC(=O)C6=CC=C1N56)C3)N24

> <INCHI_IDENTIFIER>
InChI=1S/C26H34N2O/c1-17-12-20-4-2-9-25-10-3-11-26(14-17,28(20)25)16-21-18(15-25)13-19-5-8-24(29)23-7-6-22(21)27(19)23/h6-7,17,19-20H,2-5,8-16H2,1H3/t17-,19+,20+,25-,26-/m1/s1

> <INCHI_KEY>
GRKJCRLHWHVJKZ-AHPZKRJMSA-N

> <FORMULA>
C26H34N2O

> <MOLECULAR_WEIGHT>
390.571

> <EXACT_MASS>
390.267113723

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.391492228770716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,11S,15R,19S,21R)-21-methyl-26,27-diazaheptacyclo[13.7.3.1^{1,15}.1^{4,7}.0^{3,13}.0^{11,27}.0^{19,26}]heptacosa-3(13),4,6-trien-8-one

> <JCHEM_LOGP>
4.261845678999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.33497133701837

> <JCHEM_PKA_STRONGEST_BASIC>
10.240432190028361

> <JCHEM_POLAR_SURFACE_AREA>
25.240000000000002

> <JCHEM_REFRACTIVITY>
116.91829999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,11S,15R,19S,21R)-21-methyl-26,27-diazaheptacyclo[13.7.3.1^{1,15}.1^{4,7}.0^{3,13}.0^{11,27}.0^{19,26}]heptacosa-3(13),4,6-trien-8-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.334   3.101   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.421   1.861   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.822   0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.235  -0.676   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.595   0.482   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.879   1.995   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.872   3.161   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.331   2.506   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.500   1.503   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.216  -0.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.764  -0.521   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.889  -0.774   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.204   0.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.167   1.567   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.482   2.369   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.815   2.305   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.459   3.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.924   3.928   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.735  -0.717   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.246  -0.321   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.154   1.166   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.933   2.257   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.532   3.744   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.619   4.834   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.107   4.438   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.218   6.321   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.310  -0.023   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.397   1.068   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.996   2.555   0.000  0.00  0.00           C+0
CONECT    1    2    7   25   29                                             
CONECT    2    1    3   22                                                  
CONECT    3    2    4   19   27                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   18                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    8                                                       
CONECT   19    3   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24    1                                                       
CONECT   26   24                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    1                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄N₂O

Average Mass

390.5710 Da

Monoisotopic Mass

390.26711 Da

IUPAC Name

(1R,11S,15R,19S,21R)-21-methyl-26,27-diazaheptacyclo[13.7.3.1^{1,15}.1^{4,7}.0^{3,13}.0^{11,27}.0^{19,26}]heptacosa-3(13),4,6-trien-8-one

Traditional Name

(1R,11S,15R,19S,21R)-21-methyl-26,27-diazaheptacyclo[13.7.3.1^{1,15}.1^{4,7}.0^{3,13}.0^{11,27}.0^{19,26}]heptacosa-3(13),4,6-trien-8-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2CCC[C@@]34CCC[C@@](C1)(CC1=C(C[C@@H]5CCC(=O)C6=CC=C1N56)C3)N24

InChI Identifier

InChI=1S/C26H34N2O/c1-17-12-20-4-2-9-25-10-3-11-26(14-17,28(20)25)16-21-18(15-25)13-19-5-8-24(29)23-7-6-22(21)27(19)23/h6-7,17,19-20H,2-5,8-16H2,1H3/t17-,19+,20+,25-,26-/m1/s1

InChI Key

GRKJCRLHWHVJKZ-AHPZKRJMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chilocorus cacti	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9b-azaphenalenes. These are alkaloids with a structure based on the perhydro-9b-azaphenalene skeleton. Perhydro-9b-azaphenalene is a tricyclic compound consisting of quinolizidine that share its only nitrogen atom with a piperidine. In some 9b-azaphenalenes, the resulting tricyclic backbone can be unsaturated.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

9b-azaphenalenes

Sub Class

Not Available

Direct Parent

9b-azaphenalenes

Alternative Parents

Substituents

9b-azaphenalene skeleton
Quinolizidine
Aryl alkyl ketone
Aryl ketone
Azepine
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	4.26	ChemAxon
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	10.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.24 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	116.92 m³·mol⁻¹	ChemAxon
Polarizability	46.39 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

162975445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chilocorine (NP0069706)

MOL for NP0069706 (Chilocorine)

3D MOL for NP0069706 (Chilocorine)

3D SDF for NP0069706 (Chilocorine)

3D-SDF for NP0069706 (Chilocorine)

PDB for NP0069706 (Chilocorine)

3D PDB for NP0069706 (Chilocorine)

SMILES for NP0069706 (Chilocorine)

INCHI for NP0069706 (Chilocorine)

Structure for NP0069706 (Chilocorine)

3D Structure for NP0069706 (Chilocorine)