NP-MRD: Showing NP-Card for [(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid (NP0142362)

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Record Information

Version

2.0

Created at

2022-09-01 20:53:32 UTC

Updated at

2022-09-01 20:53:32 UTC

NP-MRD ID

NP0142362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid

Description

Cylindrospermopsin 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. Cylindrospermopsin (abbreviated to CYN, or CYL) is a cyanotoxin produced by a variety of freshwater cyanobacteria. CYN is a polycyclic uracil derivative containing guanidino and sulfate groups. Cylindrospermopsin is a very strong basic compound (based on its pKa). Cylindrospermopsin is a potentially toxic compound. CYN is toxic to liver and kidney tissue and is thought to inhibit protein synthesis and to covalently modify DNA and/or RNA. It is not known whether cylindrospermopsin is a carcinogen, but it appears to have no tumour initiating activity in mice. It is also zwitterionic, making it highly water soluble.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401552D          

 34 37  0  0  1  0            999 V2000
    4.4186    0.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1699    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5122    0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.6525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4163    1.6224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8227    1.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5984    1.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.3169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8374    1.4730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1796    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690    1.8085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6626    0.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195    1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175   -0.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9089    0.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    1.6592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333    0.3538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3300    0.8019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172    2.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    1.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635    3.4495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4978    2.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568    2.7153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    1.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773    2.6290    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6649   -0.1680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    2.4468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552    0.9881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    1.1374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.9881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7364    2.2935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
  8 13  1  1  0  0  0
 13  9  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 12  2  0  0  0  0
 19 15  1  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 12  1  0  0  0  0
 13 22  1  6  0  0  0
 23 15  1  0  0  0  0
 11 27  1  6  0  0  0
 28 24  1  0  0  0  0
 28 25  2  0  0  0  0
 28 26  2  0  0  0  0
 28 27  1  0  0  0  0
  6 29  1  1  0  0  0
  7 30  1  6  0  0  0
  8 31  1  6  0  0  0
 10 32  1  6  0  0  0
 11 33  1  1  0  0  0
 13 34  1  1  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    3.4441    2.2979   -0.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2330    0.8028   -0.9621 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8051    0.2366    0.3549 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7419    0.6532    1.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240   -0.6376    2.0227 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.7010   -1.2891    3.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9525   -1.6645    1.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9242   -0.0258    2.7569 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4560    0.7321    0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4018    0.6017   -0.2499 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7472   -0.2735    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6585   -0.4960   -1.0096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8943   -1.2496   -0.6386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6133   -2.4830   -0.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -0.5101    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8995   -1.1881    0.7461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8156   -0.5526    1.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8974   -1.2647    2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6556    0.7575    1.8853 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5883    1.4062    1.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602    2.7471    1.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6925    0.7863    0.5583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -1.2948   -1.9657 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.9446   -2.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3314   -1.4009   -3.0567 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759   -0.6817   -2.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238    0.5331   -2.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9939    0.0914   -1.4402 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6840    2.8606   -1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    2.6251   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3408    2.5993    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1789    0.2961   -1.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.8673    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5141    0.3975    2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2095    0.1526    1.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    1.8015    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    1.6050   -0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3331   -1.2369    0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225    0.1778    0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9167    0.4663   -1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417   -1.4703   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -2.5592    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0879   -2.2330    0.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9465   -1.3783    3.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6455    3.5093    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3178   -2.1022   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476   -1.3418   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0240   -0.3954   -3.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194    1.4042   -2.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  3  1  0
  3  4  1  0
  4  5  1  0
  5  8  1  0
  5  6  2  0
  5  7  2  0
  3  2  1  0
  2  1  1  0
  2 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 24 28  1  0
 22 15  1  0
 23 12  1  0
 28 10  1  0
 28 27  1  0
 13 41  1  6
 14 42  1  0
 16 43  1  0
 18 44  1  0
 21 45  1  0
 12 40  1  6
 11 38  1  0
 11 39  1  0
 10 37  1  6
  9 35  1  0
  9 36  1  0
  3 33  1  6
  8 34  1  0
  2 32  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
 27 49  1  6
 26 47  1  0
 26 48  1  0
 23 46  1  0
M  END


  Mrv0541 08291401552D          

 34 37  0  0  1  0            999 V2000
    4.4186    0.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4901    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1699    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5122    0.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.6525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4163    1.6224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8227    1.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5984    1.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    0.3169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8374    1.4730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1796    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0690    1.8085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6626    0.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195    1.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175   -0.4677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9089    0.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    1.6592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333    0.3538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3300    0.8019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172    2.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    1.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635    3.4495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4978    2.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568    2.7153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911    1.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773    2.6290    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6649   -0.1680    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    2.4468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552    0.9881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    1.1374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.9881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7364    2.2935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  7  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
  8 13  1  1  0  0  0
 13  9  1  0  0  0  0
 16  5  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  2  0  0  0  0
 19 12  2  0  0  0  0
 19 15  1  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 12  1  0  0  0  0
 13 22  1  6  0  0  0
 23 15  1  0  0  0  0
 11 27  1  6  0  0  0
 28 24  1  0  0  0  0
 28 25  2  0  0  0  0
 28 26  2  0  0  0  0
 28 27  1  0  0  0  0
  6 29  1  1  0  0  0
  7 30  1  6  0  0  0
  8 31  1  6  0  0  0
 10 32  1  6  0  0  0
 11 33  1  1  0  0  0
 13 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0142362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](O)(C1=CC(O)=NC(O)=N1)[C@@]1([H])C[C@@]2([H])C[C@]([H])(OS(O)(=O)=O)[C@]([H])(C)[C@@]3([H])CN=C(N1)N23

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/t6-,7+,8-,10-,11+,13-/m1/s1

> <INCHI_KEY>
LHJPHMKIGRLKDR-VDPNAHCISA-N

> <FORMULA>
C15H21N5O7S

> <MOLECULAR_WEIGHT>
415.422

> <EXACT_MASS>
415.116168741

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.69774681404292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4S,5R,6S,8S,10R)-10-[(R)-(2,6-dihydroxypyrimidin-4-yl)(hydroxy)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-0.768845107300849

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.814769309842585

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.6360566888155859

> <JCHEM_PKA_STRONGEST_BASIC>
10.256846423583166

> <JCHEM_POLAR_SURFACE_AREA>
177.7

> <JCHEM_REFRACTIVITY>
94.26859999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4S,5R,6S,8S,10R)-10-[(R)-(2,6-dihydroxypyrimidin-4-yl)(hydroxy)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       8.248   0.313   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.782   3.655   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.917   3.655   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.956   0.939   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.119  -0.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.002   1.218   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.510   3.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.536   2.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.117   2.471   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.595   0.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.163   2.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.202   0.034   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.129   3.376   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.104   0.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.770   2.192   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.579  -0.873   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       1.697   1.218   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -2.524   3.097   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -3.609   0.660   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       4.349   1.497   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -2.041  -1.498   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.032   4.908   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.177   2.818   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.892   6.439   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.263   4.747   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.199   5.068   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.570   3.376   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0       8.731   4.908   0.000  0.00  0.00           S+0
HETATM   29  H   UNK     0       6.841  -0.314   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.455   4.567   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.290   1.844   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.756   2.123   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.409   1.844   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.375   4.281   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7    8                                                       
CONECT    3    7   11                                                       
CONECT    4    9   12                                                       
CONECT    5   10   16                                                       
CONECT    6    1   10   11   29                                             
CONECT    7    2    3   20   30                                             
CONECT    8    2   13   17   31                                             
CONECT    9    4   13   18                                                  
CONECT   10    5    6   20   32                                             
CONECT   11    3    6   27   33                                             
CONECT   12    4   19   21                                                  
CONECT   13    8    9   22   34                                             
CONECT   14   16   17   20                                                  
CONECT   15   18   19   23                                                  
CONECT   16    5   14                                                       
CONECT   17    8   14                                                       
CONECT   18    9   15                                                       
CONECT   19   12   15                                                       
CONECT   20    7   10   14                                                  
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   15                                                            
CONECT   24   28                                                            
CONECT   25   28                                                            
CONECT   26   28                                                            
CONECT   27   11   28                                                       
CONECT   28   24   25   26   27                                             
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   13                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
7-Epicylindrospermopsin	MeSH
7-Epi-cylindrospermopsin	MeSH

Chemical Formula

C₁₅H₂₁N₅O₇S

Average Mass

415.4220 Da

Monoisotopic Mass

415.11617 Da

IUPAC Name

[(4S,5R,6S,8S,10R)-10-[(R)-(2,6-dihydroxypyrimidin-4-yl)(hydroxy)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid

Traditional Name

[(4S,5R,6S,8S,10R)-10-[(R)-(2,6-dihydroxypyrimidin-4-yl)(hydroxy)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C1=CC(O)=NC(O)=N1)[C@@]1([H])C[C@@]2([H])C[C@]([H])(OS(O)(=O)=O)[C@]([H])(C)[C@@]3([H])CN=C(N1)N23

InChI Identifier

InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/t6-,7+,8-,10-,11+,13-/m1/s1

InChI Key

LHJPHMKIGRLKDR-VDPNAHCISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Pyridopyrimidine
Imidazopyrimidine
Pyrimidone
1,3-diazinane
Hydropyrimidine
Piperidine
Pyridine
Pyrimidine
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
2-imidazoline
Organic sulfuric acid or derivatives
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Guanidine
Urea
Lactam
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Carboximidamide
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Organic nitrogen compound
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	-1.1	ALOGPS
logP	-0.77	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	10.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	177.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.27 m³·mol⁻¹	ChemAxon
Polarizability	37.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19999

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cylindrospermopsin

METLIN ID

Not Available

PubChem Compound

42628600

PDB ID

Not Available

ChEBI ID

88044

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid (NP0142362)

MOL for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

3D MOL for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

3D SDF for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

3D-SDF for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

PDB for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

3D PDB for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

SMILES for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

INCHI for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

Structure for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)

3D Structure for NP0142362 ([(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid)