NP-MRD: Showing NP-Card for Jamaicamide A (NP0005404)

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Record Information

Version

2.0

Created at

2020-12-09 02:39:16 UTC

Updated at

2021-07-15 16:51:54 UTC

NP-MRD ID

NP0005404

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jamaicamide A

Provided By

NPAtlas

Description

Jamaicamide A is found in Lyngbya and Lyngbya majuscula. Jamaicamide A was first documented in 2004 (PMID: 15217615). Based on a literature review very few articles have been published on (4E,9E)-14-bromo-9-(chloromethylidene)-N-[(3E)-3-methoxy-5-(2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-5-oxopent-3-en-1-yl]-6-methyltetradec-4-en-13-ynimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118183D          

 71 71  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 71 71  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118183D          

 71 71  0  0  0  0            999 V2000
   -6.6700   -2.1684   -2.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0273   -2.5693   -1.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7391   -1.4793   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7179   -0.7905    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5703    0.3145    1.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4998    0.7897    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7740    0.9636    1.6192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8249    2.0755    2.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8425    2.6755    3.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2061    2.4474    2.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9492    1.6168    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520    0.6284    1.3014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5087   -0.7796    1.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340   -1.2035    0.0663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5622   -0.7484   -1.1648 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1998   -0.5031   -0.7713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180   -0.0645   -1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626    0.1115   -2.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    0.1851   -1.2847 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0308    0.6463   -2.4461 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4227    0.8990   -2.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903    0.7464   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3089    1.0198   -0.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4422    2.1556    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -0.2649    0.0271 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3980    0.0441    0.3530 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1075   -1.1225    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757   -2.3165    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3359   -3.7049    1.6508 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4822   -1.0624    1.3561 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5075   -1.0469    0.2901 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5098    0.0464   -0.6998 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6228    1.3878   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6995    2.4932    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8437    4.1988    1.1612 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.8712   -3.0249   -2.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6448   -1.7234   -2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0581   -1.3727   -2.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7661   -1.0719   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5972    3.2624    3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0490    1.6227    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3001    0.7416    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5846   -1.1959    2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9259   -1.4011    0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2675   -0.6905    2.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1058   -0.6346    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455   -2.2321    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5484   -1.5782   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0410    0.1085   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188   -0.6493    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -0.7354   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    0.9787   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455   -0.1165   -3.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    1.5485   -2.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085    1.2338   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    0.4069   -0.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8157    1.3476   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2911    1.8511    1.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4408    2.6520    0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6868    2.9285    0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -1.0230   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -0.5129    0.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9075    0.4911   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3896    0.8289    1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405   -2.3662    0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6438   -0.1810    2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6925   -1.9710    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5062   -2.0157   -0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5474   -1.0491    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7849   -0.0120   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5264   -0.0654   -1.2490 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  3  0  0  0  0
 34 35  1  0  0  0  0
 12  7  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  4 39  1  0  0  0  0
 10 40  1  0  0  0  0
 11 41  1  0  0  0  0
 12 42  1  6  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 16 50  1  0  0  0  0
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 21 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 57  1  6  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  0  0  0  0
 25 62  1  0  0  0  0
 26 63  1  0  0  0  0
 26 64  1  0  0  0  0
 28 65  1  0  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 31 68  1  0  0  0  0
 31 69  1  0  0  0  0
 32 70  1  0  0  0  0
 32 71  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005404

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C([H])([H])C([H])([H])C(\[H])=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C(=C(/[H])Cl)\C([H])([H])C([H])([H])C([H])([H])C#CBr)C([H])([H])C([H])([H])C(\OC([H])([H])[H])=C(\[H])C(=O)N1C(=O)C([H])=C([H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H36BrClN2O4/c1-21(12-14-23(20-29)10-5-4-8-17-28)9-6-7-11-25(32)30-18-16-24(35-3)19-27(34)31-22(2)13-15-26(31)33/h6,9,13,15,19-22H,4-5,7,10-12,14,16,18H2,1-3H3,(H,30,32)/b9-6+,23-20+,24-19+/t21-,22+/m1/s1

> <INCHI_KEY>
NAIKIJSSBJHCBL-IPUGVWFUSA-N

> <FORMULA>
C27H36BrClN2O4

> <MOLECULAR_WEIGHT>
567.95

> <EXACT_MASS>
566.154698

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
59.45212246192048

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E,6S,9E)-14-bromo-9-(chloromethylidene)-N-[(3E)-3-methoxy-5-[(2S)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-5-oxopent-3-en-1-yl]-6-methyltetradec-4-en-13-ynamide

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
3.9179999999999975

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.917116519442253

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.475445480501188

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1608126834591586

> <JCHEM_POLAR_SURFACE_AREA>
75.71000000000001

> <JCHEM_REFRACTIVITY>
147.53259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E,6S,9E)-14-bromo-9-(chloromethylidene)-N-[(3E)-3-methoxy-5-[(2S)-2-methyl-5-oxo-2H-pyrrol-1-yl]-5-oxopent-3-en-1-yl]-6-methyltetradec-4-en-13-ynamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 71  0  0  0  0  0  0  0  0999 V2000
   -6.6700   -2.1684   -2.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0273   -2.5693   -1.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7391   -1.4793   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7179   -0.7905    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5703    0.3145    1.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4998    0.7897    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7740    0.9636    1.6192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8249    2.0755    2.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8425    2.6755    3.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2061    2.4474    2.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9492    1.6168    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520    0.6284    1.3014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5087   -0.7796    1.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340   -1.2035    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5622   -0.7484   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1998   -0.5031   -0.7713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180   -0.0645   -1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626    0.1115   -2.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    0.1851   -1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    0.6463   -2.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4227    0.8990   -2.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903    0.7464   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3089    1.0198   -0.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4422    2.1556    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -0.2649    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3980    0.0441    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1075   -1.1225    0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757   -2.3165    1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3359   -3.7049    1.6508 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4822   -1.0624    1.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5075   -1.0469    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5098    0.0464   -0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6228    1.3878   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6995    2.4932    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8437    4.1988    1.1612 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.8712   -3.0249   -2.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6448   -1.7234   -2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0581   -1.3727   -2.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7661   -1.0719   -0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5972    3.2624    3.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0490    1.6227    2.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3001    0.7416    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5846   -1.1959    2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9259   -1.4011    0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2675   -0.6905    2.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1058   -0.6346    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455   -2.2321    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5484   -1.5782   -1.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0410    0.1085   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188   -0.6493    0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -0.7354   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    0.9787   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455   -0.1165   -3.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660    1.5485   -2.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085    1.2338   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    0.4069   -0.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8157    1.3476   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2911    1.8511    1.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4408    2.6520    0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6868    2.9285    0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413   -1.0230   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4420   -0.5129    0.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9075    0.4911   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3896    0.8289    1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405   -2.3662    0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6438   -0.1810    2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6925   -1.9710    2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5062   -2.0157   -0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5474   -1.0491    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7849   -0.0120   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5264   -0.0654   -1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  3 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  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  3  0
 34 35  1  0
 12  7  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  6
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 22 56  1  0
 23 57  1  6
 24 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
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 26 63  1  0
 26 64  1  0
 28 65  1  0
 30 66  1  0
 30 67  1  0
 31 68  1  0
 31 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      -6.670  -2.168  -2.335  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.027  -2.569  -1.119  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.739  -1.479  -0.233  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.718  -0.791   0.264  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.570   0.315   1.151  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.500   0.790   1.572  0.00  0.00           O+0
HETATM    7  N   UNK     0      -7.774   0.964   1.619  0.00  0.00           N+0
HETATM    8  C   UNK     0      -7.825   2.075   2.493  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.843   2.676   3.006  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.206   2.447   2.731  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.949   1.617   2.047  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.152   0.628   1.301  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.509  -0.780   1.783  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.334  -1.204   0.066  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.562  -0.748  -1.165  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.200  -0.503  -0.771  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.218  -0.065  -1.693  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.563   0.112  -2.887  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.176   0.185  -1.285  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.031   0.646  -2.446  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.423   0.899  -2.055  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.890   0.746  -0.837  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.309   1.020  -0.511  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.442   2.156   0.479  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.944  -0.265   0.027  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.398   0.044   0.353  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.107  -1.123   0.879  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.476  -2.317   1.020  0.00  0.00           C+0
HETATM   29 Cl   UNK     0       7.336  -3.705   1.651  0.00  0.00          Cl+0
HETATM   30  C   UNK     0       8.482  -1.062   1.356  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.508  -1.047   0.290  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.510   0.046  -0.700  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.623   1.388  -0.116  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.700   2.493   0.380  0.00  0.00           C+0
HETATM   35 Br   UNK     0       9.844   4.199   1.161  0.00  0.00          Br+0
HETATM   36  H   UNK     0      -6.871  -3.025  -2.979  0.00  0.00           H+0
HETATM   37  H   UNK     0      -7.645  -1.723  -2.046  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.058  -1.373  -2.811  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.766  -1.072  -0.015  0.00  0.00           H+0
HETATM   40  H   UNK     0      -9.597   3.262   3.356  0.00  0.00           H+0
HETATM   41  H   UNK     0     -11.049   1.623   2.006  0.00  0.00           H+0
HETATM   42  H   UNK     0      -9.300   0.742   0.215  0.00  0.00           H+0
HETATM   43  H   UNK     0      -8.585  -1.196   2.233  0.00  0.00           H+0
HETATM   44  H   UNK     0      -9.926  -1.401   0.968  0.00  0.00           H+0
HETATM   45  H   UNK     0     -10.268  -0.691   2.615  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.106  -0.635   0.963  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.845  -2.232   0.301  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.548  -1.578  -1.915  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.041   0.109  -1.667  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.919  -0.649   0.215  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.592  -0.735  -0.828  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.248   0.979  -0.508  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.046  -0.117  -3.264  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.566   1.549  -2.886  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.108   1.234  -2.826  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.170   0.407  -0.084  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.816   1.348  -1.439  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.291   1.851   1.519  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.441   2.652   0.308  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.687   2.929   0.216  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.841  -1.023  -0.748  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.442  -0.513   0.983  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.907   0.491  -0.486  0.00  0.00           H+0
HETATM   64  H   UNK     0       6.390   0.829   1.164  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.441  -2.366   0.730  0.00  0.00           H+0
HETATM   66  H   UNK     0       8.644  -0.181   2.054  0.00  0.00           H+0
HETATM   67  H   UNK     0       8.693  -1.971   2.015  0.00  0.00           H+0
HETATM   68  H   UNK     0       9.506  -2.016  -0.299  0.00  0.00           H+0
HETATM   69  H   UNK     0      10.547  -1.049   0.762  0.00  0.00           H+0
HETATM   70  H   UNK     0       8.785  -0.012  -1.524  0.00  0.00           H+0
HETATM   71  H   UNK     0      10.526  -0.065  -1.249  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   39                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   40                                                  
CONECT   11   10   12   41                                                  
CONECT   12   11   13    7   42                                             
CONECT   13   12   43   44   45                                             
CONECT   14    3   15   46   47                                             
CONECT   15   14   16   48   49                                             
CONECT   16   15   17   50                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   51   52                                             
CONECT   20   19   21   53   54                                             
CONECT   21   20   22   55                                                  
CONECT   22   21   23   56                                                  
CONECT   23   22   24   25   57                                             
CONECT   24   23   58   59   60                                             
CONECT   25   23   26   61   62                                             
CONECT   26   25   27   63   64                                             
CONECT   27   26   28   30                                                  
CONECT   28   27   29   65                                                  
CONECT   29   28                                                            
CONECT   30   27   31   66   67                                             
CONECT   31   30   32   68   69                                             
CONECT   32   31   33   70   71                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    4                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   25                                                            
CONECT   63   26                                                            
CONECT   64   26                                                            
CONECT   65   28                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   31                                                            
CONECT   69   31                                                            
CONECT   70   32                                                            
CONECT   71   32                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  142    0
END

RDKit          3D

71 71  0  0  0  0  0  0  0  0999 V2000
   -6.6700   -2.1684   -2.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0273   -2.5693   -1.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7179   -0.7905    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5703    0.3145    1.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4998    0.7897    1.5720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7740    0.9636    1.6192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8249    2.0755    2.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8425    2.6755    3.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2061    2.4474    2.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9492    1.6168    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520    0.6284    1.3014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5087   -0.7796    1.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340   -1.2035    0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5622   -0.7484   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5626    0.1115   -2.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0308    0.6463   -2.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4227    0.8990   -2.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8903    0.7464   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3089    1.0198   -0.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.8712   -3.0249   -2.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1058   -0.6346    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7849   -0.0120   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5264   -0.0654   -1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
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  3 14  1  0
 14 15  1  0
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 16 17  1  0
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 23 25  1  0
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 27 28  2  0
 28 29  1  0
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  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
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 32 71  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(4E,9E)-14-Bromo-9-(chloromethylidene)-N-[(3E)-3-methoxy-5-(2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-5-oxopent-3-en-1-yl]-6-methyltetradec-4-en-13-ynimidate	Generator

Chemical Formula

C₂₇H₃₆BrClN₂O₄

Average Mass

567.9500 Da

Monoisotopic Mass

566.15470 Da

IUPAC Name

(4E,6S,9E)-14-bromo-9-(chloromethylidene)-N-[(3E)-3-methoxy-5-[(2S)-2-methyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]-5-oxopent-3-en-1-yl]-6-methyltetradec-4-en-13-ynamide

Traditional Name

(4E,6S,9E)-14-bromo-9-(chloromethylidene)-N-[(3E)-3-methoxy-5-[(2S)-2-methyl-5-oxo-2H-pyrrol-1-yl]-5-oxopent-3-en-1-yl]-6-methyltetradec-4-en-13-ynamide

CAS Registry Number

Not Available

SMILES

CO\C(CCNC(=O)CC\C=C\C(C)CC\C(CCCC#CBr)=C\Cl)=C\C(=O)N1C(C)C=CC1=O

InChI Identifier

InChI=1S/C27H36BrClN2O4/c1-21(12-14-23(20-29)10-5-4-8-17-28)9-6-7-11-25(32)30-18-16-24(35-3)19-27(34)31-22(2)13-15-26(31)33/h6,9,13,15,19-22H,4-5,7,10-12,14,16,18H2,1-3H3,(H,30,32)/b9-6+,23-20+,24-19+

InChI Key

NAIKIJSSBJHCBL-IPUGVWFUSA-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
Lyngbya	NPAtlas	15217615
Lyngbya majuscula	-	KNApSAcK

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	5.35	ALOGPS
logP	3.92	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.48	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	75.71 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	147.53 m³·mol⁻¹	ChemAxon
Polarizability	59.45 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013036

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10207718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21589265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Edwards DJ, Marquez BL, Nogle LM, McPhail K, Goeger DE, Roberts MA, Gerwick WH: Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula. Chem Biol. 2004 Jun;11(6):817-33. doi: 10.1016/j.chembiol.2004.03.030. [PubMed:15217615 ]

Showing NP-Card for Jamaicamide A (NP0005404)

MOL for NP0005404 (Jamaicamide A)

3D MOL for NP0005404 (Jamaicamide A)

3D SDF for NP0005404 (Jamaicamide A)

3D-SDF for NP0005404 (Jamaicamide A)

PDB for NP0005404 (Jamaicamide A)

3D PDB for NP0005404 (Jamaicamide A)

SMILES for NP0005404 (Jamaicamide A)

INCHI for NP0005404 (Jamaicamide A)

Structure for NP0005404 (Jamaicamide A)

3D Structure for NP0005404 (Jamaicamide A)