NP-MRD: Showing NP-Card for Lyngbyatoxin A (NP0003237)

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Record Information

Version

1.0

Created at

2020-12-09 00:32:12 UTC

Updated at

2021-07-15 16:45:52 UTC

NP-MRD ID

NP0003237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lyngbyatoxin A

Provided By

NPAtlas

Description

Lyngbyatoxin A is found in Kitasatospora mediocidica, Lyngbya majuscula and Streptomyces blastmyceticus. It was first documented in 1979 (PMID: 107586). Based on a literature review very few articles have been published on (10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]Pentadeca-1,4,6,8(15),11-pentaen-11-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 71 73  0  0  0  0            999 V2000
    3.6269   -2.6110   -2.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -1.8661   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -1.3952   -0.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7973   -2.5797    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674   -0.4583    0.0334 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7282    0.6255   -0.9592 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7457    1.6492   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6948    1.8698    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5601    3.1053   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    1.0905    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2663    1.5007    2.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1565    1.0721   -1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1938    2.1619   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.2990   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
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 30 68  1  0  0  0  0
 32 69  1  0  0  0  0
 32 70  1  0  0  0  0
 32 71  1  0  0  0  0
M  END

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
    3.6269   -2.6110   -2.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -1.8661   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 30 68  1  0
 32 69  1  0
 32 70  1  0
 32 71  1  0
M  END


  Mrv1652306242117463D          

 71 73  0  0  0  0            999 V2000
    3.6269   -2.6110   -2.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -1.8661   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -1.3952   -0.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7973   -2.5797    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674   -0.4583    0.0334 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7282    0.6255   -0.9592 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7457    1.6492   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6948    1.8698    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5601    3.1053   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    1.0905    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -0.7518    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    0.4976    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072    1.0106    1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2160    0.2977    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.9391    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401   -1.9077    0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3931   -3.0219   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -2.7088   -0.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972   -1.4582    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4431   -1.8832    0.7859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3195   -1.4463   -0.3484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2137   -2.6240   -0.7479 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4446   -3.6775   -1.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7325    0.6612    1.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041    0.8855    2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165    1.4637    0.8396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2954    1.8779   -0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0329    2.7136   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4546    2.7803   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346    1.0364    1.5494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    1.5007    2.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -2.8724   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988   -2.9783   -3.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6523   -1.1267   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4527    2.7916   -0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9772    3.8189   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561    0.0073    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0130    1.4881    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2954    1.2469    2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    1.0733    0.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    2.0023    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8216   -3.9705   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -3.3603   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138   -1.2491    1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8056   -1.1599   -1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7376   -3.0034    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9461   -2.3536   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565   -3.4253   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1614   -0.3717   -0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1938    2.1619   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.2990   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1385    2.9739   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.7980    3.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    0.7523    3.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859    2.4142    3.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  3  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 19 11  1  0  0  0  0
 31 14  1  0  0  0  0
 19 15  2  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
  7 43  1  0  0  0  0
  9 44  1  0  0  0  0
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 10 49  1  0  0  0  0
 12 50  1  0  0  0  0
 13 51  1  0  0  0  0
 17 52  1  0  0  0  0
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 21 56  1  6  0  0  0
 22 57  1  0  0  0  0
 22 58  1  0  0  0  0
 23 59  1  0  0  0  0
 24 60  1  0  0  0  0
 27 61  1  1  0  0  0
 28 62  1  6  0  0  0
 29 63  1  0  0  0  0
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 30 67  1  0  0  0  0
 30 68  1  0  0  0  0
 32 69  1  0  0  0  0
 32 70  1  0  0  0  0
 32 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])N([H])C(=O)[C@@]([H])(N(C2=C([H])C([H])=C(C3=C2C(=C([H])N3[H])C1([H])[H])[C@](C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27-/m0/s1

> <INCHI_KEY>
KISDGNGREAJPQR-OICBGKIFSA-N

> <FORMULA>
C27H39N3O2

> <MOLECULAR_WEIGHT>
437.6175

> <EXACT_MASS>
437.304227507

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.92116497499104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4(15),5,7-tetraen-11-one

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
5.285932680333332

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.055983816132237

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.141982181013983

> <JCHEM_PKA_STRONGEST_BASIC>
-0.68286430251608

> <JCHEM_POLAR_SURFACE_AREA>
68.36

> <JCHEM_REFRACTIVITY>
134.25179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4(15),5,7-tetraen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
    3.6269   -2.6110   -2.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -1.8661   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -1.3952   -0.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7973   -2.5797    0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7674   -0.4583    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7282    0.6255   -0.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    1.6492   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6948    1.8698    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5601    3.1053   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    1.0905    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -0.7518    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    0.4976    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072    1.0106    1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2160    0.2977    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.9391    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401   -1.9077    0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3931   -3.0219   -0.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1024   -2.7088   -0.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972   -1.4582    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4159   -2.8724   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7140    1.0092   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6969    2.4193   -1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797    3.4936    0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4527    2.7916   -0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9772    3.8189   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561    0.0073    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0130    1.4881    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2954    1.2469    2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    1.0733    0.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    2.0023    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8216   -3.9705   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -3.3603   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6138   -1.2491    1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8056   -1.1599   -1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9461   -2.3536   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565   -3.4253   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1614   -0.3717   -0.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8019    2.4842    1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1565    1.0721   -1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    3.6597   -1.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882    3.0826    0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938    2.1619   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.2990   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1059    3.7743   -1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385    2.9739   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.7980    3.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    0.7523    3.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859    2.4142    3.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 27 31  1  0
 31 32  1  0
 19 11  1  0
 31 14  1  0
 19 15  2  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
 12 50  1  0
 13 51  1  0
 17 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  6
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 22 58  1  0
 23 59  1  0
 24 60  1  0
 27 61  1  1
 28 62  1  6
 29 63  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 30 68  1  0
 32 69  1  0
 32 70  1  0
 32 71  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.627  -2.611  -2.024  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.616  -1.866  -1.612  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.559  -1.395  -0.227  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.797  -2.580   0.720  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.767  -0.458   0.033  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.728   0.626  -0.959  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.746   1.649  -0.831  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.695   1.870   0.027  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.560   3.105  -0.234  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.040   1.091   1.231  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.318  -0.752   0.215  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.207   0.498   0.772  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.007   1.011   1.206  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.216   0.298   1.117  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.104  -0.939   0.575  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.040  -1.908   0.389  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.393  -3.022  -0.181  0.00  0.00           C+0
HETATM   18  N   UNK     0      -0.102  -2.709  -0.317  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.097  -1.458   0.136  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.443  -1.883   0.786  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.319  -1.446  -0.348  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.214  -2.624  -0.748  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.445  -3.678  -1.236  0.00  0.00           O+0
HETATM   24  N   UNK     0      -5.158  -0.374   0.153  0.00  0.00           N+0
HETATM   25  C   UNK     0      -4.732   0.661   1.021  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.504   0.886   2.034  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.517   1.464   0.840  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.295   1.878  -0.597  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.033   2.714  -0.669  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.455   2.780  -0.990  0.00  0.00           C+0
HETATM   31  N   UNK     0      -2.335   1.036   1.549  0.00  0.00           N+0
HETATM   32  C   UNK     0      -2.266   1.501   2.967  0.00  0.00           C+0
HETATM   33  H   UNK     0       4.416  -2.872  -1.329  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.699  -2.978  -3.051  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.846  -1.627  -2.344  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.850  -2.840   1.275  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.536  -2.354   1.503  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.170  -3.467   0.170  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.795  -0.214   1.084  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.652  -1.127  -0.193  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.714   1.009  -1.218  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.003   0.094  -1.965  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.697   2.419  -1.662  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.880   3.494   0.734  0.00  0.00           H+0
HETATM   45  H   UNK     0       7.453   2.792  -0.801  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.977   3.819  -0.814  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.156   0.007   1.082  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.013   1.488   1.647  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.295   1.247   2.057  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.134   1.073   0.894  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.066   2.002   1.658  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.822  -3.970  -0.468  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.627  -3.360  -0.721  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.614  -1.249   1.700  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.769  -2.907   1.148  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.806  -1.160  -1.267  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.738  -3.003   0.160  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.946  -2.354  -1.507  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.157  -3.425  -2.170  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.161  -0.372  -0.155  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.802   2.484   1.311  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.156   1.072  -1.307  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.235   3.660  -1.258  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.788   3.083   0.345  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.194   2.162  -1.132  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.968   2.299  -1.847  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.106   3.774  -1.348  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.138   2.974  -0.140  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.231   1.798   3.214  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.656   0.752   3.647  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.886   2.414   3.055  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4    5   11                                             
CONECT    4    3   36   37   38                                             
CONECT    5    3    6   39   40                                             
CONECT    6    5    7   41   42                                             
CONECT    7    6    8   43                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   44   45   46                                             
CONECT   10    8   47   48   49                                             
CONECT   11    3   12   19                                                  
CONECT   12   11   13   50                                                  
CONECT   13   12   14   51                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18   52                                                  
CONECT   18   17   19   53                                                  
CONECT   19   18   11   15                                                  
CONECT   20   16   21   54   55                                             
CONECT   21   20   22   24   56                                             
CONECT   22   21   23   57   58                                             
CONECT   23   22   59                                                       
CONECT   24   21   25   60                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31   61                                             
CONECT   28   27   29   30   62                                             
CONECT   29   28   63   64   65                                             
CONECT   30   28   66   67   68                                             
CONECT   31   27   32   14                                                  
CONECT   32   31   69   70   71                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
CONECT   69   32                                                            
CONECT   70   32                                                            
CONECT   71   32                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  146    0
END

RDKit          3D

71 73  0  0  0  0  0  0  0  0999 V2000
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    2.6164   -1.8661   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7282    0.6255   -0.9592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7457    1.6492   -0.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6948    1.8698    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5601    3.1053   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    1.0905    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -0.7518    0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    0.4976    0.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072    1.0106    1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2160    0.2977    1.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.9391    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4431   -1.8832    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195   -1.4463   -0.3484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2137   -2.6240   -0.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4446   -3.6775   -1.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5041    0.8855    2.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2954    1.8779   -0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0329    2.7136   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3346    1.0364    1.5494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2663    1.5007    2.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -2.8724   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988   -2.9783   -3.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456   -1.6274   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1700   -3.4672    0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7954   -0.2136    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6523   -1.1267   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140    1.0092   -1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    0.0940   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969    2.4193   -1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797    3.4936    0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4527    2.7916   -0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9772    3.8189   -0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561    0.0073    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0130    1.4881    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2954    1.2469    2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    1.0733    0.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    2.0023    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8216   -3.9705   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -3.3603   -0.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7376   -3.0034    0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9461   -2.3536   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565   -3.4253   -2.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1938    2.1619   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.2990   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1059    3.7743   -1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385    2.9739   -0.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.7980    3.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6555    0.7523    3.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8859    2.4142    3.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
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 16 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
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 25 27  1  0
 27 28  1  0
 28 29  1  0
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 27 31  1  0
 31 32  1  0
 19 11  1  0
 31 14  1  0
 19 15  2  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
 12 50  1  0
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 17 52  1  0
 18 53  1  0
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 22 58  1  0
 23 59  1  0
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 29 63  1  0
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 32 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Teleocidin a 1	MeSH
Teleocidin a1	MeSH
Lyngbyatoxin a	MeSH
Teleocidin a-1	MeSH
Teleocidin a	MeSH

Chemical Formula

C₂₇H₃₉N₃O₂

Average Mass

437.6175 Da

Monoisotopic Mass

437.30423 Da

IUPAC Name

(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4(15),5,7-tetraen-11-one

Traditional Name

(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0^{4,15}]pentadeca-1,4(15),5,7-tetraen-11-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N(C)C2=C3C(C[C@@H](CO)NC1=O)=CNC3=C(C=C2)[C@](C)(CCC=C(C)C)C=C

InChI Identifier

InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27-/m0/s1

InChI Key

KISDGNGREAJPQR-OICBGKIFSA-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
Kitasatospora mediocidica	LOTUS Database	35616633
Lyngbya majuscula	NPAtlas	107586
Streptomyces blastmyceticus	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Aromatic monoterpenoid
Monoterpenoid
3-alkylindole
Indole
Indole or derivatives
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organopnictogen compound
Primary alcohol
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.84	ALOGPS
logP	5.29	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.14	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.25 m³·mol⁻¹	ChemAxon
Polarizability	51.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA020374

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10472344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cardellina JH 2nd, Marner FJ, Moore RE: Seaweed dermatitis: structure of lyngbyatoxin A. Science. 1979 Apr 13;204(4389):193-5. doi: 10.1126/science.107586. [PubMed:107586 ]

Showing NP-Card for Lyngbyatoxin A (NP0003237)

MOL for NP0003237 (Lyngbyatoxin A)

3D MOL for NP0003237 (Lyngbyatoxin A)

3D SDF for NP0003237 (Lyngbyatoxin A)

3D-SDF for NP0003237 (Lyngbyatoxin A)

PDB for NP0003237 (Lyngbyatoxin A)

3D PDB for NP0003237 (Lyngbyatoxin A)

SMILES for NP0003237 (Lyngbyatoxin A)

INCHI for NP0003237 (Lyngbyatoxin A)

Structure for NP0003237 (Lyngbyatoxin A)

3D Structure for NP0003237 (Lyngbyatoxin A)