NP-MRD: Showing NP-Card for Lapatin B (NP0005905)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 03:01:37 UTC

Updated at

2021-07-15 16:53:18 UTC

NP-MRD ID

NP0005905

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lapatin B

Provided By

NPAtlas

Description

(1'S,12'S)-2,15'-dihydroxy-2',10',16'-triazaspiro[indole-3,13'-tetracyclo[10.2.2.0²,¹¹.0⁴,⁹]Hexadecane]-4',6',8',10',15'-pentaen-3'-one belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Lapatin B is found in Penicillium. Based on a literature review very few articles have been published on (1'S,12'S)-2,15'-dihydroxy-2',10',16'-triazaspiro[indole-3,13'-tetracyclo[10.2.2.0²,¹¹.0⁴,⁹]Hexadecane]-4',6',8',10',15'-pentaen-3'-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118233D          

 41 46  0  0  0  0            999 V2000
   -0.3225   -3.6591    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -2.4531    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.8929   -0.8210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737   -0.4336   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9633   -0.2268   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152    0.4415   -1.2774 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    0.5766   -0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    1.2711   -1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271    1.4160   -1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    0.8564   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.1643    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007    0.0217    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -0.6684    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -1.1936    2.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -0.7742    0.6684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.4788    1.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8034   -0.4226    1.5974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2755    0.1306    0.2979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0864    1.6244    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    2.2572    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.2475    0.0215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    1.2490   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031    1.3628   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4789    0.2226   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.0339   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5472   -1.1095    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.0020    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.4268   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    0.0014   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.7166   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690    1.9561   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    0.9575    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -0.2865    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146   -1.9082    2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -0.7968    2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.4030    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    3.2844   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1827    2.3208   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    0.3301   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5177   -1.9466   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264   -2.0984    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16  2  1  0  0  0  0
 27 18  1  0  0  0  0
 18  4  1  0  0  0  0
 27 22  1  0  0  0  0
 15  5  1  0  0  0  0
 12  7  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  6  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 16 34  1  1  0  0  0
 17 35  1  0  0  0  0
 17 36  1  0  0  0  0
 21 37  1  0  0  0  0
 23 38  1  0  0  0  0
 24 39  1  0  0  0  0
 25 40  1  0  0  0  0
 26 41  1  0  0  0  0
M  END

     RDKit          3D

 41 46  0  0  0  0  0  0  0  0999 V2000
   -0.3225   -3.6591    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -2.4531    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.8929   -0.8210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737   -0.4336   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9633   -0.2268   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152    0.4415   -1.2774 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    0.5766   -0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    1.2711   -1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271    1.4160   -1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    0.8564   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.1643    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007    0.0217    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -0.6684    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -1.1936    2.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -0.7742    0.6684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.4788    1.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8034   -0.4226    1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    0.1306    0.2979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0864    1.6244    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    2.2572    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.2475    0.0215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    1.2490   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031    1.3628   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4789    0.2226   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.0339   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5472   -1.1095    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.0020    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.4268   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    0.0014   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.7166   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690    1.9561   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    0.9575    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -0.2865    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146   -1.9082    2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -0.7968    2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.4030    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    3.2844   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1827    2.3208   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    0.3301   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5177   -1.9466   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264   -2.0984    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 16  2  1  0
 27 18  1  0
 18  4  1  0
 27 22  1  0
 15  5  1  0
 12  7  1  0
  3 28  1  0
  4 29  1  6
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 16 34  1  1
 17 35  1  0
 17 36  1  0
 21 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
M  END


  Mrv1652306242118233D          

 41 46  0  0  0  0            999 V2000
   -0.3225   -3.6591    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -2.4531    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.8929   -0.8210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737   -0.4336   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9633   -0.2268   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152    0.4415   -1.2774 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    0.5766   -0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    1.2711   -1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271    1.4160   -1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    0.8564   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.1643    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007    0.0217    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -0.6684    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -1.1936    2.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -0.7742    0.6684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.4788    1.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8034   -0.4226    1.5974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2755    0.1306    0.2979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0864    1.6244    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    2.2572    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.2475    0.0215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    1.2490   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031    1.3628   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4789    0.2226   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.0339   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5472   -1.1095    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.0020    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.4268   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    0.0014   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.7166   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690    1.9561   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    0.9575    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -0.2865    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146   -1.9082    2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -0.7968    2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.4030    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    3.2844   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1827    2.3208   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    0.3301   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5177   -1.9466   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264   -2.0984    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16  2  1  0  0  0  0
 27 18  1  0  0  0  0
 18  4  1  0  0  0  0
 27 22  1  0  0  0  0
 15  5  1  0  0  0  0
 12  7  1  0  0  0  0
  3 28  1  0  0  0  0
  4 29  1  6  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 16 34  1  1  0  0  0
 17 35  1  0  0  0  0
 17 36  1  0  0  0  0
 21 37  1  0  0  0  0
 23 38  1  0  0  0  0
 24 39  1  0  0  0  0
 25 40  1  0  0  0  0
 26 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C([H])C([H])=C2[C@@]2(C1=O)C([H])([H])[C@]1([H])N3C(=O)C4=C([H])C([H])=C([H])C([H])=C4N=C3[C@@]2([H])N([H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H14N4O3/c25-17-14-9-20(11-6-2-4-8-13(11)22-19(20)27)15(23-17)16-21-12-7-3-1-5-10(12)18(26)24(14)16/h1-8,14-15H,9H2,(H,22,27)(H,23,25)/t14-,15+,20-/m0/s1

> <INCHI_KEY>
RSCQCCZWYNEMPN-VKWYCSODSA-N

> <FORMULA>
C20H14N4O3

> <MOLECULAR_WEIGHT>
358.357

> <EXACT_MASS>
358.106590327

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.00190603111991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3S,12'S)-1,2-dihydro-2',10',16'-triazaspiro[indole-3,13'-tetracyclo[10.2.2.0^{2,11}.0^{4,9}]hexadecane]-4',6',8',10'-tetraene-2,3',15'-trione

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
0.9523987216666665

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.174293132915743

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.608382475405035

> <JCHEM_PKA_STRONGEST_BASIC>
1.8355364320935468

> <JCHEM_POLAR_SURFACE_AREA>
90.87

> <JCHEM_REFRACTIVITY>
98.4638

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3S,12'S)-1H-2',10',16'-triazaspiro[indole-3,13'-tetracyclo[10.2.2.0^{2,11}.0^{4,9}]hexadecane]-4',6',8',10'-tetraene-2,3',15'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 46  0  0  0  0  0  0  0  0999 V2000
   -0.3225   -3.6591    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -2.4531    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.8929   -0.8210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737   -0.4336   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9633   -0.2268   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152    0.4415   -1.2774 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    0.5766   -0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    1.2711   -1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271    1.4160   -1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    0.8564   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.1643    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007    0.0217    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -0.6684    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -1.1936    2.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -0.7742    0.6684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.4788    1.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8034   -0.4226    1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    0.1306    0.2979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0864    1.6244    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    2.2572    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.2475    0.0215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    1.2490   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031    1.3628   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4789    0.2226   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.0339   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5472   -1.1095    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.0020    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.4268   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    0.0014   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.7166   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690    1.9561   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    0.9575    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -0.2865    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146   -1.9082    2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -0.7968    2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.4030    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    3.2844   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1827    2.3208   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    0.3301   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5177   -1.9466   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264   -2.0984    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 16  2  1  0
 27 18  1  0
 18  4  1  0
 27 22  1  0
 15  5  1  0
 12  7  1  0
  3 28  1  0
  4 29  1  6
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 16 34  1  1
 17 35  1  0
 17 36  1  0
 21 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.323  -3.659   0.731  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.261  -2.453   0.418  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.682  -1.893  -0.821  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.474  -0.434  -0.872  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.963  -0.227  -0.512  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.815   0.442  -1.277  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.094   0.577  -0.868  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.019   1.271  -1.643  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.327   1.416  -1.236  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.711   0.856  -0.035  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.810   0.164   0.748  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.501   0.022   0.336  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.592  -0.668   1.112  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.911  -1.194   2.218  0.00  0.00           O+0
HETATM   15  N   UNK     0       1.350  -0.774   0.668  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.292  -1.479   1.393  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.803  -0.423   1.597  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.276   0.131   0.298  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.086   1.624   0.239  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.006   2.257   0.360  0.00  0.00           O+0
HETATM   21  N   UNK     0      -2.338   2.248   0.022  0.00  0.00           N+0
HETATM   22  C   UNK     0      -3.323   1.249  -0.064  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.703   1.363  -0.271  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.479   0.223  -0.317  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.913  -1.034  -0.163  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.547  -1.109   0.040  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.728  -0.002   0.095  0.00  0.00           C+0
HETATM   28  H   UNK     0      -1.086  -2.427  -1.601  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.758   0.001  -1.821  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.734   1.717  -2.588  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.069   1.956  -1.827  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.732   0.958   0.304  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.085  -0.287   1.698  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.615  -1.908   2.332  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.608  -0.797   2.249  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.306   0.403   2.174  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.537   3.284  -0.067  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.183   2.321  -0.396  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.556   0.330  -0.480  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.518  -1.947  -0.198  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.126  -2.098   0.158  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   18   29                                             
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16    5                                                  
CONECT   16   15   17    2   34                                             
CONECT   17   16   18   35   36                                             
CONECT   18   17   19   27    4                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   37                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   38                                                  
CONECT   24   23   25   39                                                  
CONECT   25   24   26   40                                                  
CONECT   26   25   27   41                                                  
CONECT   27   26   18   22                                                  
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   17                                                            
CONECT   37   21                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   25                                                            
CONECT   41   26                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

RDKit          3D

41 46  0  0  0  0  0  0  0  0999 V2000
   -0.3225   -3.6591    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -2.4531    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6819   -1.8929   -0.8210 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737   -0.4336   -0.8718 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9633   -0.2268   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152    0.4415   -1.2774 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    0.5766   -0.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187    1.2711   -1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271    1.4160   -1.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109    0.8564   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.1643    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007    0.0217    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -0.6684    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -1.1936    2.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -0.7742    0.6684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2923   -1.4788    1.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8034   -0.4226    1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    0.1306    0.2979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0864    1.6244    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059    2.2572    0.3596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3378    2.2475    0.0215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234    1.2490   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031    1.3628   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4789    0.2226   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126   -1.0339   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5472   -1.1095    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.0020    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0859   -2.4268   -1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7577    0.0014   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    1.7166   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0690    1.9561   -1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    0.9575    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0847   -0.2865    1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146   -1.9082    2.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6081   -0.7968    2.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3062    0.4030    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    3.2844   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1827    2.3208   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5563    0.3301   -0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5177   -1.9466   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264   -2.0984    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 16  2  1  0
 27 18  1  0
 18  4  1  0
 27 22  1  0
 15  5  1  0
 12  7  1  0
  3 28  1  0
  4 29  1  6
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 16 34  1  1
 17 35  1  0
 17 36  1  0
 21 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₁₄N₄O₃

Average Mass

358.3570 Da

Monoisotopic Mass

358.10659 Da

IUPAC Name

(1'S,3S,12'S)-1,2-dihydro-2',10',16'-triazaspiro[indole-3,13'-tetracyclo[10.2.2.0^{2,11}.0^{4,9}]hexadecane]-4',6',8',10'-tetraene-2,3',15'-trione

Traditional Name

(1'S,3S,12'S)-1H-2',10',16'-triazaspiro[indole-3,13'-tetracyclo[10.2.2.0^{2,11}.0^{4,9}]hexadecane]-4',6',8',10'-tetraene-2,3',15'-trione

CAS Registry Number

Not Available

SMILES

O=C1NC2=CC=CC=C2C11C[C@@H]2N3C(=O)C4=CC=CC=C4N=C3[C@H]1NC2=O

InChI Identifier

InChI=1S/C20H14N4O3/c25-17-14-9-20(11-6-2-4-8-13(11)22-19(20)27)15(23-17)16-21-12-7-3-1-5-10(12)18(26)24(14)16/h1-8,14-15H,9H2,(H,22,27)(H,23,25)/t14-,15+,20?/m0/s1

InChI Key

RSCQCCZWYNEMPN-VKWYCSODSA-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
Penicillium	NPAtlas	15974610

Species Where Detected

Species Name	Source	Reference
Penicillium lapatayae	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridopyrimidines. Pyridopyrimidines are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridopyrimidines

Sub Class

Not Available

Direct Parent

Pyridopyrimidines

Alternative Parents

Substituents

Diazanaphthalene
Pyridopyrimidine
Quinazoline
Indole or derivatives
Dihydroindole
Pyrimidone
Delta-lactam
Piperidinone
Benzenoid
Pyrimidine
Pyridine
Piperidine
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Lactam
Azacycle
Carboxylic acid derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	1.01	ALOGPS
logP	0.95	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	10.61	ChemAxon
pKa (Strongest Basic)	1.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.87 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	98.46 m³·mol⁻¹	ChemAxon
Polarizability	36 Å³	ChemAxon
Number of Rings	6	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

NPAtlas ID

NPA003916

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lapatin B (NP0005905)

MOL for NP0005905 (Lapatin B)

3D MOL for NP0005905 (Lapatin B)

3D SDF for NP0005905 (Lapatin B)

3D-SDF for NP0005905 (Lapatin B)

PDB for NP0005905 (Lapatin B)

3D PDB for NP0005905 (Lapatin B)

SMILES for NP0005905 (Lapatin B)

INCHI for NP0005905 (Lapatin B)

Structure for NP0005905 (Lapatin B)

3D Structure for NP0005905 (Lapatin B)