NP-MRD: Showing NP-Card for 3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid (NP0289617)

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Record Information

Version

2.0

Created at

2022-09-09 19:53:44 UTC

Updated at

2022-09-09 19:53:44 UTC

NP-MRD ID

NP0289617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid

Description

Sirohydrochlorin belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next. Sirohydrochlorin is a weakly acidic compound (based on its pKa). Sirohydrochlorin exists in both E. 3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid is found in Apis cerana. Coli (prokaryote) and yeast (eukaryote).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241222112D          

 62 66  0  0  0  0            999 V2000
   13.0993    1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3684    1.6396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8509    1.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9654    0.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712    1.0597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3787    2.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5851    1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1487    0.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9442    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4625    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6683    2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2955    1.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7602    0.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7541   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5393    1.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6786    3.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9132    1.0940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2921    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5028    1.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5803    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1487   -1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7157    1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9544    2.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9717    4.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3958    4.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7368    1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058    2.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8892   -0.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9621   -1.3219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1417    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0058    3.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7231    2.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5597   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3649   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9613   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0959   -2.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9687    1.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9167   -1.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7429   -1.3013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3581   -3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6731   -2.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8509   -2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3771    2.5386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3874    1.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3161   -2.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7127   -1.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5920   -2.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6340   -3.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8633   -2.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1948   -3.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3950   -3.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2962   -2.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6306   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1500   -3.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0923   -2.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0903   -3.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9203   -4.9902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3409   -4.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2255   -4.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5494   -4.9594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9839   -4.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  1  0  0  0
  5 10  1  6  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
  9 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  1  0  0  0
 12 19  1  6  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 23  2  0  0  0  0
 16 24  1  0  0  0  0
 16 25  2  0  0  0  0
 17 26  1  6  0  0  0
 18 27  1  0  0  0  0
 20 28  2  0  0  0  0
 21 29  2  0  0  0  0
 21 30  1  0  0  0  0
 26 31  1  0  0  0  0
 27 32  1  0  0  0  0
 27 33  2  0  0  0  0
 28 34  1  0  0  0  0
 29 35  1  0  0  0  0
 29 36  1  0  0  0  0
 30 37  1  0  0  0  0
 31 38  1  0  0  0  0
 34 39  1  0  0  0  0
 34 40  2  0  0  0  0
 35 41  1  0  0  0  0
 36 42  1  0  0  0  0
 37 43  1  0  0  0  0
 38 44  1  0  0  0  0
 38 45  2  0  0  0  0
 39 46  2  0  0  0  0
 39 47  1  0  0  0  0
 40 48  1  0  0  0  0
 41 49  1  0  0  0  0
 42 50  1  0  0  0  0
 42 51  2  0  0  0  0
 46 52  1  0  0  0  0
 47 53  1  0  0  0  0
 49 54  1  0  0  0  0
 52 55  1  0  0  0  0
 53 56  1  0  0  0  0
 53 57  2  0  0  0  0
 54 58  1  0  0  0  0
 54 59  2  0  0  0  0
 55 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
  5  8  1  0  0  0  0
 17 20  1  0  0  0  0
 35 37  2  0  0  0  0
 43 48  2  0  0  0  0
 46 48  1  0  0  0  0
M  END

     RDKit          3D

108112  0  0  0  0  0  0  0  0999 V2000
   -2.5028   -5.3341    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2844   -3.9477    0.7250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8794   -3.9572    2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8642   -4.5685    3.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -5.8086    3.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -3.8239    3.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035   -3.2922   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0948   -3.6137   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2382   -2.7989   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3973   -1.5228   -0.8657 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6913   -1.2071   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769    0.0055   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532    1.2807   -0.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    1.4139   -0.2873 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532    2.6764   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735    3.0382    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880    2.3164    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899    1.2642   -0.5551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5599    0.7679    0.1500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9207   -0.4217    0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329   -1.7196    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7635   -2.1245   -0.5595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165   -3.0005    0.6142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4716   -3.3194   -0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -3.4678   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1609   -3.7841   -2.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3170   -3.8851   -2.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865   -3.9497   -4.0279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3770    2.0680    0.3198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7349    2.6270   -0.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6391    1.8757    1.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5357    0.9334    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383    0.3751   -0.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8034    0.6030    0.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848    2.7077    1.0638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3858    4.0712    1.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5682    5.1708    0.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6303    6.4581    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    6.4804    2.5198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7965    7.6781    0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5957    3.4500   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6214    4.9216   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921    5.5722   -1.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5407    6.8130   -1.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804    4.7608   -1.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564    2.6410   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9540    2.8589   -1.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5136    4.2189   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9655    4.1904   -1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4005   -2.3081   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8755   -2.4483    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1316   -2.8017   -0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6085   -3.8528   -0.2179 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9342   -1.6840   -0.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4868   -3.3229   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124   -4.7065    0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -4.5854    1.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8466   -3.5226    2.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -5.7465    2.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -5.6014    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073   -5.5646   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1790   -6.0441    1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -4.4734    2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -2.8981    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356   -3.3583    4.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1812   -4.7080   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964   -0.8531   -1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.0048   -1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    4.0468    0.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1471    0.8393   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5138   -0.3641    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395   -2.8309    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0673   -4.1887   -0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1933   -2.4509   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2888   -4.2854   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7337    3.0571   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7275    1.7811   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9376    3.3111   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4774    1.5646    2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    2.8509    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1054    2.0657    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752    4.3213    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5817    5.0623    0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241222112D          

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 40 48  1  0  0  0  0
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 46 52  1  0  0  0  0
 47 53  1  0  0  0  0
 49 54  1  0  0  0  0
 52 55  1  0  0  0  0
 53 56  1  0  0  0  0
 53 57  2  0  0  0  0
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  5  8  1  0  0  0  0
 17 20  1  0  0  0  0
 35 37  2  0  0  0  0
 43 48  2  0  0  0  0
 46 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=N\C(=C/C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)\C=C4/N=C(/C=C1\N2)[C@@H](CCC(O)=O)[C@]4(C)CC(O)=O)\C(CCC(O)=O)=C3CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H46N4O16/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29/h13-16,23-24,44-45H,3-12,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)/b25-13-,29-14-,31-15-,32-16-/t23-,24-,41+,42+/m1/s1

> <INCHI_KEY>
KWIZRXMMFRBUML-AHGFGAHVSA-N

> <FORMULA>
C42H46N4O16

> <MOLECULAR_WEIGHT>
862.8318

> <EXACT_MASS>
862.290881444

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
89.44342006533834

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4S,5S,9S,10S)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,6,8(23),11,13,15,17,19-nonaen-4-yl]propanoic acid

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
3.116881802

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-8

> <JCHEM_PKA>
3.4318325811550707

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.05614721406891

> <JCHEM_POLAR_SURFACE_AREA>
355.76

> <JCHEM_REFRACTIVITY>
209.3843000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sirohydrochlorin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      24.452   2.331   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.088   3.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.855   2.855   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      24.202   0.819   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      21.973   1.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.107   4.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.226   2.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.678   0.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.429   1.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.397   3.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.781   5.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.552   3.067   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      27.552   0.774   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      21.941  -0.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.673   3.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.800   6.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.705   2.042   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.545   4.624   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.072   3.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.083   0.633   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.678  -2.243   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.136   3.336   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      20.448   4.656   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.481   7.698   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      23.139   7.673   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      31.242   2.048   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.877   5.392   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.660  -0.796   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.973  -3.627   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      24.196  -2.468   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0      31.998   3.387   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      29.877   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      31.216   4.630   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      29.045  -2.218   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.081  -4.690   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.461  -3.877   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      24.446  -3.992   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      33.542   3.400   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      29.711  -3.620   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      27.520  -2.429   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      23.068  -6.234   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.923  -5.311   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.855  -4.517   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      34.304   4.739   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      34.323   2.068   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      28.590  -4.665   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      31.197  -3.210   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      27.238  -3.941   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      21.717  -7.009   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      18.411  -5.568   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      20.897  -6.497   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      28.737  -6.195   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      32.286  -4.287   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      21.710  -8.559   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      30.147  -6.836   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      33.772  -3.883   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      31.902  -5.779   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      20.385  -9.315   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      23.036  -9.328   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      30.288  -8.373   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      29.026  -9.258   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      31.703  -9.008   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9   10    8                                             
CONECT    6    2   11                                                       
CONECT    7    3   12   13                                                  
CONECT    8    4   14    5                                                  
CONECT    9    5   15                                                       
CONECT   10    5                                                            
CONECT   11    6   16                                                       
CONECT   12    7   17   18   19                                             
CONECT   13    7   20                                                       
CONECT   14    8   21                                                       
CONECT   15    9   22   23                                                  
CONECT   16   11   24   25                                                  
CONECT   17   12   26   20                                                  
CONECT   18   12   27                                                       
CONECT   19   12                                                            
CONECT   20   13   28   17                                                  
CONECT   21   14   29   30                                                  
CONECT   22   15                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   16                                                            
CONECT   26   17   31                                                       
CONECT   27   18   32   33                                                  
CONECT   28   20   34                                                       
CONECT   29   21   35   36                                                  
CONECT   30   21   37                                                       
CONECT   31   26   38                                                       
CONECT   32   27                                                            
CONECT   33   27                                                            
CONECT   34   28   39   40                                                  
CONECT   35   29   41   37                                                  
CONECT   36   29   42                                                       
CONECT   37   30   43   35                                                  
CONECT   38   31   44   45                                                  
CONECT   39   34   46   47                                                  
CONECT   40   34   48                                                       
CONECT   41   35   49                                                       
CONECT   42   36   50   51                                                  
CONECT   43   37   48                                                       
CONECT   44   38                                                            
CONECT   45   38                                                            
CONECT   46   39   52   48                                                  
CONECT   47   39   53                                                       
CONECT   48   40   43   46                                                  
CONECT   49   41   54                                                       
CONECT   50   42                                                            
CONECT   51   42                                                            
CONECT   52   46   55                                                       
CONECT   53   47   56   57                                                  
CONECT   54   49   58   59                                                  
CONECT   55   52   60                                                       
CONECT   56   53                                                            
CONECT   57   53                                                            
CONECT   58   54                                                            
CONECT   59   54                                                            
CONECT   60   55   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  132    0
END

View in JSmol

Synonyms

Value	Source
(7S,8S,12S,13S)-3,8,13,17-Tetrakis(carboxymethyl)-8,13-dimethyl-7,8,12,13-tetrahydroporphyrin-2,7,12,18-tetrapropionic acid	ChEBI
(7S,8S,12S,13S)-3,8,13,17-Tetrakis(carboxymethyl)-8,13-dimethyl-7,8,12,13-tetrahydroporphyrin-2,7,12,18-tetrapropionate	Generator

Chemical Formula

C₄₂H₄₆N₄O₁₆

Average Mass

862.8318 Da

Monoisotopic Mass

862.29088 Da

IUPAC Name

3-[(4S,5S,9S,10S)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,6,8(23),11,13,15,17,19-nonaen-4-yl]propanoic acid

Traditional Name

sirohydrochlorin

CAS Registry Number

Not Available

SMILES

C[C@]1(CC(O)=O)[C@H](CCC(O)=O)\C2=C\C3=N\C(=C/C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)\C=C4/N=C(/C=C1\N2)[C@@H](CCC(O)=O)[C@]4(C)CC(O)=O)\C(CCC(O)=O)=C3CC(O)=O

InChI Identifier

InChI=1S/C42H46N4O16/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29/h13-16,23-24,44-45H,3-12,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)/b25-13-,29-14-,31-15-,32-16-/t23-,24-,41+,42+/m1/s1

InChI Key

KWIZRXMMFRBUML-AHGFGAHVSA-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

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Not Available

Direct Parent

Tetrapyrroles and derivatives

Alternative Parents

Substituents

Tetrapyrrole skeleton
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isobacteriochlorins (CHEBI:18023 )

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	1.04	ALOGPS
logP	3.12	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
Physiological Charge	-8	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	355.76 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	209.38 m³·mol⁻¹	ChemAxon
Polarizability	89.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007315

Chemspider ID

Not Available

KEGG Compound ID

C05778

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sirohydrochlorin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18023

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid (NP0289617)

MOL for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

3D MOL for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

3D SDF for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

3D-SDF for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

PDB for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

3D PDB for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

SMILES for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

INCHI for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

Structure for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)

3D Structure for NP0289617 (3-[(4s,5s,19s,20s)-10,14,19-tris(2-carboxyethyl)-5,9,15,20-tetrakis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),6,8,10,12,14,16(22),17-nonaen-4-yl]propanoic acid)