NP-MRD: Showing NP-Card for Bulbiferamide A (NP0333120)

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Record Information

Version

1.0

Created at

2024-05-11 03:24:16 UTC

Updated at

2024-05-13 01:11:01 UTC

NP-MRD ID

NP0333120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bulbiferamide A

Description

Based on a literature review very few articles have been published on (2S)-2-{[(Z)-[(1S)-1-[(Z)-[(3S,4Z,6S,7E,9S,10E,12S)-9-[(2S)-butan-2-yl]-6-(3-carbamimidamidopropyl)-5,8,11-trihydroxy-3-(2-methylpropyl)-2-oxo-1,4,7,10-tetraazatricyclo[12.6.1.0¹⁵,²⁰]Henicosa-4,7,10,14(21),15,17,19-heptaen-12-yl]-C-hydroxycarbonimidoyl]-3-methylbutyl]-C-hydroxycarbonimidoyl]amino}-3-phenylpropanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232306002D          

 63 66  0  0  1  0            999 V2000
   -3.9305    8.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    7.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503    6.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9319    7.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0694    6.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5075    5.4825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    5.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    5.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6143    4.4905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3680    4.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911    3.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9267    2.5070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1832    2.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969    1.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6758    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7620    2.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5157    2.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7472    2.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0827    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    3.0882    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0526    3.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3881    2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9032    1.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2086    2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8966    3.8419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3815    4.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2020    4.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0459    5.2630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5309    5.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3513    5.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8363    6.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6567    6.4254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1417    7.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9622    7.0066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8061    7.8465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2254    5.3493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    6.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748    6.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999    4.0780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    4.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    5.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    4.0780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4709    3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    2.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    2.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    4.4905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    4.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429    3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725    4.4905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    4.0780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1014    4.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    5.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    5.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    6.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    6.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    6.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    5.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    2.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725    2.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  2  0  0  0  0
  9 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 44 42  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 44 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 53 52  1  1  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 55 60  1  0  0  0  0
 53 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  2  0  0  0  0
M  END


  Mrv2104 01232306002D          

 63 66  0  0  1  0            999 V2000
   -3.9305    8.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    7.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7503    6.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9319    7.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0694    6.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5075    5.4825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006    5.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    5.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6143    4.4905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3680    4.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    3.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911    3.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9267    2.5070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1832    2.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969    1.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    0.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6758    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7620    2.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5157    2.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7472    2.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0827    1.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2321    3.0882    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0526    3.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3881    2.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9032    1.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2086    2.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8966    3.8419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3815    4.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2020    4.4231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0459    5.2630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5309    5.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3513    5.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8363    6.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6567    6.4254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1417    7.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9622    7.0066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8061    7.8465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2254    5.3493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    6.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748    6.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999    4.0780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    4.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    5.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    4.0780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4709    3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    2.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    2.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    4.4905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580    4.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429    3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725    4.4905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    4.0780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1014    4.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    5.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    5.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    6.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    6.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    6.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    5.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3870    3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1014    2.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725    2.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  2  0  0  0  0
  9 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 44 42  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 44 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 53 52  1  1  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 55 60  1  0  0  0  0
 53 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1NC(=O)[C@H](CC2=CN(C3=CC=CC=C23)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC1=O)NC(=O)[C@H](CC(C)C)NC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C45H64N10O8/c1-7-27(6)37-41(59)49-31(17-13-19-48-44(46)47)38(56)51-34(21-26(4)5)42(60)55-24-29(30-16-11-12-18-36(30)55)23-33(40(58)54-37)50-39(57)32(20-25(2)3)52-45(63)53-35(43(61)62)22-28-14-9-8-10-15-28/h8-12,14-16,18,24-27,31-35,37H,7,13,17,19-23H2,1-6H3,(H,49,59)(H,50,57)(H,51,56)(H,54,58)(H,61,62)(H4,46,47,48)(H2,52,53,63)/t27-,31-,32-,33-,34-,35-,37-/m0/s1

> <INCHI_KEY>
HXPTZHQTKSTIMK-OQYWAUBWSA-N

> <FORMULA>
C45H64N10O8

> <MOLECULAR_WEIGHT>
873.069

> <EXACT_MASS>
872.490859061

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
127

> <JCHEM_AVERAGE_POLARIZABILITY>
93.98685931428395

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-({[(1S)-1-{[(3S,6S,9S,12S)-9-[(2S)-butan-2-yl]-6-(3-carbamimidamidopropyl)-3-(2-methylpropyl)-2,5,8,11-tetraoxo-1,4,7,10-tetraazatricyclo[12.6.1.0^{15,20}]henicosa-14(21),15,17,19-tetraen-12-yl]carbamoyl}-3-methylbutyl]carbamoyl}amino)-3-phenylpropanoic acid

> <JCHEM_LOGP>
1.270416494634018

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.69682987425599

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5604002026636326

> <JCHEM_PKA_STRONGEST_BASIC>
12.208740171552572

> <JCHEM_POLAR_SURFACE_AREA>
278.72999999999996

> <JCHEM_REFRACTIVITY>
244.60330000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-({[(1S)-1-{[(3S,6S,9S,12S)-9-[(2S)-butan-2-yl]-6-(3-carbamimidamidopropyl)-3-(2-methylpropyl)-2,5,8,11-tetraoxo-1,4,7,10-tetraazatricyclo[12.6.1.0^{15,20}]henicosa-14(21),15,17,19-tetraen-12-yl]carbamoyl}-3-methylbutyl]carbamoyl}amino)-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  C   UNK     0      -7.337  15.619   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.933  14.199   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.001  12.973   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.473  13.167   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.596  11.553   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -6.547  10.234   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -5.041   9.914   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.897  10.944   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.880   8.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.287   7.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.039   6.248   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.570   6.087   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -9.196   4.680   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -7.809   3.878   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.648   2.346   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.241   1.720   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.995   2.625   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.156   4.157   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.563   4.783   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.728   4.519   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -11.354   3.112   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -11.633   5.765   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.165   5.604   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.791   4.197   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.886   2.951   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -15.323   4.036   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0     -11.007   7.172   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0     -11.912   8.417   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -13.444   8.256   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.286   9.824   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.191  11.070   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -13.722  10.909   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -14.628  12.155   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0     -16.159  11.994   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0     -17.064  13.240   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0     -18.596  13.079   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0     -16.438  14.647   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0      -9.754   9.985   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -9.128  11.392   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -10.033  12.638   0.000  0.00  0.00           O+0
HETATM   41  N   UNK     0      -3.546   7.612   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      -2.213   8.382   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.213   9.922   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.879   7.612   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.879   6.072   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.455   5.302   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.455   3.762   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.788   6.072   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0       0.455   8.382   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0       1.788   7.612   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       2.694   6.366   0.000  0.00  0.00           O+0
HETATM   52  N   UNK     0       3.122   8.382   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0       4.456   7.612   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.789   8.382   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.789   9.922   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.456  10.692   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.456  12.232   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       5.789  13.002   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       7.123  12.232   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       7.123  10.692   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       4.456   6.072   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       5.789   5.302   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       3.122   5.302   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   41                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   14                                                  
CONECT   20   13   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   30   39                                                       
CONECT   39   38    5   40                                                  
CONECT   40   39                                                            
CONECT   41    9   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   44   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54   61                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   55                                                       
CONECT   61   53   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(Z)-[(1S)-1-[(Z)-[(3S,4Z,6S,7E,9S,10E,12S)-9-[(2S)-butan-2-yl]-6-(3-carbamimidamidopropyl)-5,8,11-trihydroxy-3-(2-methylpropyl)-2-oxo-1,4,7,10-tetraazatricyclo[12.6.1.0,]henicosa-4,7,10,14(21),15,17,19-heptaen-12-yl]-C-hydroxycarbonimidoyl]-3-methylbutyl]-C-hydroxycarbonimidoyl]amino}-3-phenylpropanoate	Generator

Chemical Formula

C₄₅H₆₄N₁₀O₈

Average Mass

873.0690 Da

Monoisotopic Mass

872.49086 Da

IUPAC Name

(2S)-2-({[(1S)-1-{[(3S,6S,9S,12S)-9-[(2S)-butan-2-yl]-6-(3-carbamimidamidopropyl)-3-(2-methylpropyl)-2,5,8,11-tetraoxo-1,4,7,10-tetraazatricyclo[12.6.1.0^{15,20}]henicosa-14(21),15,17,19-tetraen-12-yl]carbamoyl}-3-methylbutyl]carbamoyl}amino)-3-phenylpropanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1NC(=O)[C@H](CC2=CN(C3=CC=CC=C23)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC1=O)NC(=O)[C@H](CC(C)C)NC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C45H64N10O8/c1-7-27(6)37-41(59)49-31(17-13-19-48-44(46)47)38(56)51-34(21-26(4)5)42(60)55-24-29(30-16-11-12-18-36(30)55)23-33(40(58)54-37)50-39(57)32(20-25(2)3)52-45(63)53-35(43(61)62)22-28-14-9-8-10-15-28/h8-12,14-16,18,24-27,31-35,37H,7,13,17,19-23H2,1-6H3,(H,49,59)(H,50,57)(H,51,56)(H,54,58)(H,61,62)(H4,46,47,48)(H2,52,53,63)/t27-,31-,32-,33-,34-,35-,37-/m0/s1

InChI Key

HXPTZHQTKSTIMK-OQYWAUBWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 176 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, C2D6OS, experimental)	wzhong49@gatech.edu	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp. MLAF003		Not Available

Chemical Taxonomy

Classification

Not classified

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	1.27	ChemAxon
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	12.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	278.73 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	244.6 m³·mol⁻¹	ChemAxon
Polarizability	93.99 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171342075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhong W, Deutsch JM, Yi D, Abrahamse NH, Mohanty I, Moore SG, McShan AC, Garg N, Agarwal V: Discovery and Biosynthesis of Ureidopeptide Natural Products Macrocyclized via Indole N-acylation in Marine Microbulbifer spp. Bacteria. Chembiochem. 2023 Jun 15;24(12):e202300190. doi: 10.1002/cbic.202300190. Epub 2023 May 11. [PubMed:37092875 ]

Showing NP-Card for Bulbiferamide A (NP0333120)

MOL for NP0333120 (Bulbiferamide A)

3D MOL for NP0333120 (Bulbiferamide A)

3D SDF for NP0333120 (Bulbiferamide A)

3D-SDF for NP0333120 (Bulbiferamide A)

PDB for NP0333120 (Bulbiferamide A)

3D PDB for NP0333120 (Bulbiferamide A)

SMILES for NP0333120 (Bulbiferamide A)

INCHI for NP0333120 (Bulbiferamide A)

Structure for NP0333120 (Bulbiferamide A)

3D Structure for NP0333120 (Bulbiferamide A)