NP-MRD: Showing NP-Card for Ageliferin (NP0069540)

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Record Information

Version

2.0

Created at

2022-04-28 14:54:04 UTC

Updated at

2022-04-28 14:54:04 UTC

NP-MRD ID

NP0069540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ageliferin

Description

Ageliferin belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group. Ageliferin is found in Agelas conifera, Agelas nakamurai, Agelas novaecaledoniae and Stylissa caribica. Ageliferin was first documented in 2018 (PMID: 29708748). Based on a literature review a small amount of articles have been published on ageliferin (PMID: 32585891) (PMID: 35427139) (PMID: 32880173) (PMID: 34202500).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216542D          

 36 40  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    3.6579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    4.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    5.1099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487   -1.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138   -1.8495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -3.3015    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138    4.8954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687    5.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937    5.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487    4.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786    6.3474    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  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
  7 11  2  0  0  0  0
  9 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  4 15  1  0  0  0  0
 14 16  1  0  0  0  0
  2 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 19 21  1  0  0  0  0
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 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 23 26  1  0  0  0  0
  1 27  1  6  0  0  0
 27 28  1  0  0  0  0
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 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 31 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
    4.4210    4.3260    1.9461 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5949    3.7015    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7465    3.0416   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9818    2.5041    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    1.6393   -0.1263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4242    2.5410   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5939    3.6981   -0.9463 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465    4.1402   -0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    5.3114   -1.2857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4625    3.2649    0.0482 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045    2.2996    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8222    1.0856    1.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    0.0360    0.8165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0214   -1.1407    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309   -1.6712    1.4269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674   -2.1671    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -2.1651   -0.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046   -2.7088   -0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0649   -2.8032    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1512   -3.3611    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8803   -3.7466    0.7726 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.7332   -3.6039   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -3.2080   -1.3068 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5785    0.6968    1.0086 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6369   -0.2502    1.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1245   -1.2436    0.5338 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -1.1953   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -0.1268   -1.2305 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1941   -2.4456   -1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9311   -3.6967   -0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475   -4.5941   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3735   -6.4835   -1.6773 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0203   -3.8451   -2.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8481   -2.5500   -2.5421 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5058    2.9115    1.2134 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7838    5.3112    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6929    3.8571    2.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127    2.9208   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7831    1.0753   -1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    4.1580   -1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6143    5.4501   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7758    6.0601   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398    0.7035    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464    1.4031    2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8897   -0.1439   -0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0269   -0.8282    2.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437   -1.9290    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0631   -1.7014    2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -2.4941    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3410   -4.0467   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8631   -3.2687   -2.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213    1.3618    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3477   -0.6590    2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    0.4084    1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -2.2655    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4221   -4.0252    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010   -4.2774   -3.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1872   -1.7410   -3.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    2.7117    2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  5 36  1  0
  5  6  1  0
  6 25  1  0
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 27 28  1  0
 28 29  2  0
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 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 25 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 14 13  1  0
 13 12  1  0
 12  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 36  2  1  0
  7  6  1  0
 35 30  1  0
 24 19  1  0
 11 12  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
 36 60  1  0
  6 40  1  6
 25 53  1  1
 26 54  1  0
 26 55  1  0
 27 56  1  0
 31 57  1  0
 34 58  1  0
 35 59  1  0
 14 46  1  6
 15 47  1  0
 15 48  1  0
 16 49  1  0
 20 50  1  0
 23 51  1  0
 24 52  1  0
 13 44  1  0
 13 45  1  0
  8 41  1  0
 10 42  1  0
 10 43  1  0
M  END


  Mrv1652304282216542D          

 36 40  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    3.6579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    4.4425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    5.1099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1712    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487   -1.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687   -2.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138   -1.8495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -3.3015    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1138    4.8954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687    5.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937    5.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487    4.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786    6.3474    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  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
  7 11  2  0  0  0  0
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  5 13  1  0  0  0  0
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 14 15  2  0  0  0  0
  4 15  1  0  0  0  0
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  2 17  1  1  0  0  0
 17 18  1  0  0  0  0
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 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
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 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 23 26  1  0  0  0  0
  1 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 31 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(N1)[C@H]1[C@H](CNC(=O)C2=CC(Br)=CN2)[C@@H](CNC(=O)C2=CC(Br)=CN2)CC2=C1NC(N)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C22H24Br2N10O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t9-,12-,17-/m1/s1

> <INCHI_KEY>
DMMLTRAQSJWUHT-OGTWGDGJSA-N

> <FORMULA>
C22H24Br2N10O2

> <MOLECULAR_WEIGHT>
620.31

> <EXACT_MASS>
618.045046

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
56.97015565977806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{[(5S,6R,7R)-2-amino-7-(2-amino-1H-imidazol-5-yl)-6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-1H-1,3-benzodiazol-5-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
0.3677875249999999

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.423388244617993

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.804018729741905

> <JCHEM_PKA_STRONGEST_BASIC>
9.156065474367201

> <JCHEM_POLAR_SURFACE_AREA>
199.17999999999998

> <JCHEM_REFRACTIVITY>
142.76659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{[(5S,6R,7R)-2-amino-7-(2-amino-3H-imidazol-4-yl)-6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-1H-1,3-benzodiazol-5-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.678   6.828   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.154   8.293   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.694   8.293   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.170   6.828   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.249   9.539   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -0.320   2.843   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.591  -0.237   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.925  -1.007   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.259  -0.237   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.925  -2.547   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.171  -3.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.695  -4.917   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.155  -4.917   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       7.679  -3.452   0.000  0.00  0.00           N+0
HETATM   26 Br   UNK     0      10.600  -6.163   0.000  0.00  0.00          Br+0
HETATM   27  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       7.591   5.923   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       7.679   9.138   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       8.155  10.603   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.695  10.603   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.171   9.138   0.000  0.00  0.00           C+0
HETATM   36 Br   UNK     0      10.600  11.849   0.000  0.00  0.00          Br+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7                                                       
CONECT   12    9                                                            
CONECT   13    5   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14    4                                                       
CONECT   16   14                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
CONECT   26   23                                                            
CONECT   27    1   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34   31                                                       
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄Br₂N₁₀O₂

Average Mass

620.3100 Da

Monoisotopic Mass

618.04505 Da

IUPAC Name

N-{[(5S,6R,7R)-2-amino-7-(2-amino-1H-imidazol-5-yl)-6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-1H-1,3-benzodiazol-5-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

Traditional Name

N-{[(5S,6R,7R)-2-amino-7-(2-amino-3H-imidazol-4-yl)-6-{[(4-bromo-1H-pyrrol-2-yl)formamido]methyl}-4,5,6,7-tetrahydro-1H-1,3-benzodiazol-5-yl]methyl}-4-bromo-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

NC1=NC=C(N1)[C@H]1[C@H](CNC(=O)C2=CC(Br)=CN2)[C@@H](CNC(=O)C2=CC(Br)=CN2)CC2=C1NC(N)=N2

InChI Identifier

InChI=1S/C22H24Br2N10O2/c23-10-2-14(27-5-10)19(35)29-4-9-1-13-18(34-22(26)32-13)17(16-8-31-21(25)33-16)12(9)7-30-20(36)15-3-11(24)6-28-15/h2-3,5-6,8-9,12,17,27-28H,1,4,7H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t9-,12-,17-/m1/s1

InChI Key

DMMLTRAQSJWUHT-OGTWGDGJSA-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
Agelas conifera	LOTUS Database	35616633
Agelas nakamurai	LOTUS Database	35616633
Agelas novaecaledoniae	LOTUS Database	35616633
Stylissa caribica	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-heteroaryl carboxamides

Alternative Parents

Substituents

2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Azole
Imidazole
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
Organic oxide
Organic oxygen 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	2.29	ALOGPS
logP	0.37	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.18 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.77 m³·mol⁻¹	ChemAxon
Polarizability	56.97 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

C00027817

Chemspider ID

9344613

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ageliferin

METLIN ID

Not Available

PubChem Compound

11169518

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pech-Puch D, Perez-Povedano M, Martinez-Guitian M, Lasarte-Monterrubio C, Vazquez-Ucha JC, Bou G, Rodriguez J, Beceiro A, Jimenez C: In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa. Mar Drugs. 2020 Jun 23;18(6). pii: md18060326. doi: 10.3390/md18060326. [PubMed:32585891 ]
Ding H, Roberts AG, Chiang R, Harran PG: Cascading Auto-oxidative Biproline Guanylations Form Optically Active Dispacamide Dimers and Permit an Eight-Step Synthesis of (-)-Ageliferin. J Org Chem. 2018 Jul 6;83(13):7231-7238. doi: 10.1021/acs.joc.8b00631. Epub 2018 May 7. [PubMed:29708748 ]
Freire VF, Gubiani JR, Spencer TM, Hajdu E, Ferreira AG, Ferreira DAS, de Castro Levatti EV, Burdette JE, Camargo CH, Tempone AG, Berlinck RGS: Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar. J Nat Prod. 2022 May 27;85(5):1340-1350. doi: 10.1021/acs.jnatprod.2c00094. Epub 2022 Apr 15. [PubMed:35427139 ]
Bhandari MR, Herath AK, Rasapalli S, Yousufuddin M, Lovely CJ: Total Synthesis of the Nagelamides - Synthetic Studies toward the Reported Structure of Nagelamide D and Nagelamide E Framework. J Org Chem. 2020 Oct 16;85(20):12971-12987. doi: 10.1021/acs.joc.0c01617. Epub 2020 Sep 30. [PubMed:32880173 ]
Jiang W, Wang D, Wilson BAP, Kang U, Bokesch HR, Smith EA, Wamiru A, Goncharova EI, Voeller D, Lipkowitz S, O'Keefe BR, Gustafson KR: Agelasine Diterpenoids and Cbl-b Inhibitory Ageliferins from the Coralline Demosponge Astrosclera willeyana. Mar Drugs. 2021 Jun 24;19(7). pii: md19070361. doi: 10.3390/md19070361. [PubMed:34202500 ]

Showing NP-Card for Ageliferin (NP0069540)

MOL for NP0069540 (Ageliferin)

3D MOL for NP0069540 (Ageliferin)

3D SDF for NP0069540 (Ageliferin)

3D-SDF for NP0069540 (Ageliferin)

PDB for NP0069540 (Ageliferin)

3D PDB for NP0069540 (Ageliferin)

SMILES for NP0069540 (Ageliferin)

INCHI for NP0069540 (Ageliferin)

Structure for NP0069540 (Ageliferin)

3D Structure for NP0069540 (Ageliferin)