NP-MRD: Showing NP-Card for Talarolide A (NP0333098)

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Record Information

Version

2.0

Created at

2024-05-09 00:26:45 UTC

Updated at

2025-06-11 03:36:55 UTC

NP-MRD ID

NP0333098

Natural Product DOI

https://doi.org/10.57994/2397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Talarolide A

Description

Talarolide A belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Talarolide A was first documented in 2017 (PMID: 28383269). Based on a literature review a small amount of articles have been published on Talarolide A (PMID: 37755100) (PMID: 29989642) (PMID: 37764483).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212303032D          

 51 52  0  0  1  0            999 V2000
   -0.4224    5.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    4.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    4.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    3.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    3.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    2.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    1.9238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2921    1.0988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4759    0.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988   -0.0184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3668   -0.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.5328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -1.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.9259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1685   -1.7423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -2.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559   -2.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9206   -3.0440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7433   -2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -3.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5627   -3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -1.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6365   -1.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -0.9990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9240   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819   -1.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -1.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172   -2.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7433   -0.2557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9275   -0.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9945   -2.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -3.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210   -2.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    2.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7210    1.9238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    1.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660    2.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1340    2.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    1.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    1.1374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3045    0.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1088    0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224    1.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790    2.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    3.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    3.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    4.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  6  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  2  0  0  0  0
 16 32  2  0  0  0  0
 14 33  1  6  0  0  0
 13 34  2  0  0  0  0
 12 35  1  0  0  0  0
  9 36  2  0  0  0  0
  8 37  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  0  0  0  0
 44 45  1  0  0  0  0
 29 45  1  0  0  0  0
 45 46  2  0  0  0  0
 44 47  1  1  0  0  0
 42 48  2  0  0  0  0
 38 49  2  0  0  0  0
  5 50  1  0  0  0  0
 50 51  2  0  0  0  0
  2 51  1  0  0  0  0
M  END


  Mrv2104 01212303032D          

 51 52  0  0  1  0            999 V2000
   -0.4224    5.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    4.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    4.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    3.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    3.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    2.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    1.9238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2921    1.0988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4759    0.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5988   -0.0184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3668   -0.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.5328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1970   -1.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641   -1.9259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1685   -1.7423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6332   -2.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559   -2.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9206   -3.0440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7433   -2.9823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -3.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5627   -3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -1.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6365   -1.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -0.9990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9240   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819   -1.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1046   -1.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172   -2.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7433   -0.2557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9275   -0.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9945   -2.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2752   -3.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210   -2.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -1.5047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -0.2896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1209    1.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    2.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7210    1.9238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827    1.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660    2.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1340    2.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    1.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    1.1374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3045    0.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1088    0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6224    1.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7790    2.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0066    3.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    3.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    4.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  6  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  2  0  0  0  0
 16 32  2  0  0  0  0
 14 33  1  6  0  0  0
 13 34  2  0  0  0  0
 12 35  1  0  0  0  0
  9 36  2  0  0  0  0
  8 37  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  0  0  0  0
 44 45  1  0  0  0  0
 29 45  1  0  0  0  0
 45 46  2  0  0  0  0
 44 47  1  1  0  0  0
 42 48  2  0  0  0  0
 38 49  2  0  0  0  0
  5 50  1  0  0  0  0
 50 51  2  0  0  0  0
  2 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H]1NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@H](C)NC(=O)CN(O)C(=O)[C@H](CC2=CC=C(O)C=C2)N(C)C(=O)[C@H](C)N(C)C(=O)[C@@H](C)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H55N7O9/c1-11-20(4)29-31(46)37-22(6)32(47)39(8)23(7)34(49)41(10)27(17-24-12-14-25(43)15-13-24)35(50)42(51)18-28(44)36-21(5)33(48)40(9)26(16-19(2)3)30(45)38-29/h12-15,19-23,26-27,29,43,51H,11,16-18H2,1-10H3,(H,36,44)(H,37,46)(H,38,45)/t20-,21-,22+,23-,26+,27-,29+/m0/s1

> <INCHI_KEY>
DWXDJPQNIPFVLN-BIUSABGFSA-N

> <FORMULA>
C35H55N7O9

> <MOLECULAR_WEIGHT>
717.865

> <EXACT_MASS>
717.406126379

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
74.8205793482131

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,9R,12R,15R,18S)-12-[(2S)-butan-2-yl]-1-hydroxy-3-[(4-hydroxyphenyl)methyl]-4,6,7,9,16,18-hexamethyl-15-(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclohenicosane-2,5,8,11,14,17,20-heptone

> <JCHEM_LOGP>
0.28238433466666524

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.510417730792684

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.724619351902009

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7941821122894006

> <JCHEM_POLAR_SURFACE_AREA>
208.99999999999997

> <JCHEM_REFRACTIVITY>
186.91270000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,9R,12R,15R,18S)-12-[(2S)-butan-2-yl]-1-hydroxy-3-[(4-hydroxyphenyl)methyl]-4,6,7,9,16,18-hexamethyl-15-(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclohenicosane-2,5,8,11,14,17,20-heptone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-23         0                                  
HETATM    1  O   UNK     0      -0.788  10.521   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.788   8.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.545   8.211   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.545   6.671   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.788   5.901   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.788   4.361   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.545   3.591   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.545   2.051   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.888   1.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.118  -0.034   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.551  -0.597   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.086  -0.995   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.368  -2.466   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.680  -3.595   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.181  -3.252   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.049  -4.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.584  -4.410   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.452  -5.682   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.988  -5.567   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.855  -6.839   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.784  -7.070   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.253  -3.022   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.788  -3.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.656  -1.865   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.191  -1.980   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.860  -3.367   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.395  -3.483   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.992  -4.640   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       6.988  -0.477   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.465  -0.248   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.456  -4.525   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.380  -5.912   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.226  -5.067   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.869  -2.809   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.558  -0.541   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.092   2.449   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.818   1.184   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.879   4.361   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       3.213   3.591   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0       3.328   2.055   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.417   4.551   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.850   3.989   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0       6.080   2.466   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0       7.581   2.123   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.035   0.652   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.536   0.309   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       8.629   3.252   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.054   4.949   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       1.879   5.901   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -2.122   6.671   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.122   8.211   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   50                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   38                                                  
CONECT    8    7    9   37                                                  
CONECT    9    8   10   36                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   35                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   45                                                  
CONECT   30   29                                                            
CONECT   31   23                                                            
CONECT   32   16                                                            
CONECT   33   14                                                            
CONECT   34   13                                                            
CONECT   35   12                                                            
CONECT   36    9                                                            
CONECT   37    8                                                            
CONECT   38    7   39   49                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   47                                                  
CONECT   45   44   29   46                                                  
CONECT   46   45                                                            
CONECT   47   44                                                            
CONECT   48   42                                                            
CONECT   49   38                                                            
CONECT   50    5   51                                                       
CONECT   51   50    2                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₅₅N₇O₉

Average Mass

717.8650 Da

Monoisotopic Mass

717.40613 Da

IUPAC Name

(3S,6S,9R,12R,15R,18S)-12-[(2S)-butan-2-yl]-1-hydroxy-3-[(4-hydroxyphenyl)methyl]-4,6,7,9,16,18-hexamethyl-15-(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclohenicosane-2,5,8,11,14,17,20-heptone

Traditional Name

(3S,6S,9R,12R,15R,18S)-12-[(2S)-butan-2-yl]-1-hydroxy-3-[(4-hydroxyphenyl)methyl]-4,6,7,9,16,18-hexamethyl-15-(2-methylpropyl)-1,4,7,10,13,16,19-heptaazacyclohenicosane-2,5,8,11,14,17,20-heptone

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H]1NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@H](C)NC(=O)CN(O)C(=O)[C@H](CC2=CC=C(O)C=C2)N(C)C(=O)[C@H](C)N(C)C(=O)[C@@H](C)NC1=O

InChI Identifier

InChI=1S/C35H55N7O9/c1-11-20(4)29-31(46)37-22(6)32(47)39(8)23(7)34(49)41(10)27(17-24-12-14-25(43)15-13-24)35(50)42(51)18-28(44)36-21(5)33(48)40(9)26(16-19(2)3)30(45)38-29/h12-15,19-23,26-27,29,43,51H,11,16-18H2,1-10H3,(H,36,44)(H,37,46)(H,38,45)/t20-,21-,22+,23-,26+,27-,29+/m0/s1

InChI Key

DWXDJPQNIPFVLN-BIUSABGFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2024-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Talaromyces sp. CMB-TU011		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Leucine or derivatives
Isoleucine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.28	ChemAxon
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	209 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	186.91 m³·mol⁻¹	ChemAxon
Polarizability	74.82 Å³	ChemAxon
Number of Rings	2	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dewapriya P, Prasad P, Damodar R, Salim AA, Capon RJ: Talarolide A, a Cyclic Heptapeptide Hydroxamate from an Australian Marine Tunicate-Associated Fungus, Talaromyces sp. (CMB-TU011). Org Lett. 2017 Apr 21;19(8):2046-2049. doi: 10.1021/acs.orglett.7b00638. Epub 2017 Apr 6. [PubMed:28383269 ]
Salim AA, Hussein WM, Dewapriya P, Hoang HN, Zhou Y, Samarasekera K, Khalil ZG, Fairlie DP, Capon RJ: Talarolides Revisited: Cyclic Heptapeptides from an Australian Marine Tunicate-Associated Fungus, Talaromyces sp. CMB-TU011. Mar Drugs. 2023 Sep 11;21(9):487. doi: 10.3390/md21090487. [PubMed:37755100 ]
Zhang S, De Leon Rodriguez LM, Huang R, Leung IKH, Harris PWR, Brimble MA: Total synthesis of the proposed structure of talarolide A. Org Biomol Chem. 2018 Jul 25;16(29):5286-5293. doi: 10.1039/c8ob01230j. [PubMed:29989642 ]
Flores-Holguin N, Salas-Leiva JS, Glossman-Mitnik D: Talarolide A and Talaropeptides A-D: Potential Marine-Derived Therapeutic Peptides with Interesting Chemistry and Biological Activity Studied through Density Functional Theory (DFT) and Conceptual DFT. Molecules. 2023 Sep 20;28(18):6708. doi: 10.3390/molecules28186708. [PubMed:37764483 ]
DOI: 10.3390/md21090487

Showing NP-Card for Talarolide A (NP0333098)

MOL for NP0333098 (Talarolide A)

3D MOL for NP0333098 (Talarolide A)

3D SDF for NP0333098 (Talarolide A)

3D-SDF for NP0333098 (Talarolide A)

PDB for NP0333098 (Talarolide A)

3D PDB for NP0333098 (Talarolide A)

SMILES for NP0333098 (Talarolide A)

INCHI for NP0333098 (Talarolide A)

Structure for NP0333098 (Talarolide A)

3D Structure for NP0333098 (Talarolide A)