NP-MRD: Showing NP-Card for n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid (NP0149742)

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Record Information

Version

2.0

Created at

2022-09-02 05:40:28 UTC

Updated at

2022-09-02 05:40:29 UTC

NP-MRD ID

NP0149742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid

Description

N-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-[(1H-indol-3-yl)methyl]-16-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid is found in Xenorhabdus szentirmaii. Based on a literature review very few articles have been published on N-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-[(1H-indol-3-yl)methyl]-16-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207402D          

 61 65  0  0  0  0            999 V2000
    3.0278  -11.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2827  -10.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897  -10.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7307  -10.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -9.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926   -9.0551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0476   -8.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8545   -8.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -8.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6267   -8.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6886   -7.8289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -7.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -8.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9678   -8.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0746   -8.1720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5226   -7.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   -7.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5393   -8.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127   -9.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422   -9.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492  -10.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -9.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -8.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775   -6.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5845   -6.6028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2255   -6.1612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804   -5.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3265   -5.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -4.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815   -6.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716   -4.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -4.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -3.9788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903   -3.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2452   -3.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6932   -2.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138   -2.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -1.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109   -1.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629   -0.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -1.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5423   -4.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874   -5.2050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3493   -4.2489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9013   -4.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083   -4.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633   -3.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633   -2.5710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -4.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7479   -3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -5.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -5.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1984   -6.2597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435   -7.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4955   -7.6574    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  4  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  4  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
 34 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 45 46  1  4  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
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 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 48 56  1  0  0  0  0
 51 56  1  0  0  0  0
 46 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 12 60  1  0  0  0  0
 60 61  1  0  0  0  0
M  END

     RDKit          3D

116120  0  0  0  0  0  0  0  0999 V2000
   -7.0763    2.7777   -2.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9536    2.0077   -0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5836    2.8456    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4908    1.7420   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070    0.9849    0.7423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8382    1.7249    1.8376 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1539    2.3840    2.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7895    2.4748    2.6962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8874    0.5554    0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -0.0997    2.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0309    0.7944    0.0271 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6420    0.4629    0.0321 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.8797    0.5840    2.3727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.4695    1.3037 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6260   -4.5433   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3903   -2.9661   -1.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3346   -2.2000   -1.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7279    3.6626   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022207402D          

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M  END
> <DATABASE_ID>
NP0149742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(N=CO)C(O)=NC1C(C)OC(=O)C(CC2=CNC3=CC=CC=C23)N=C(O)C(CC2=CC=C(O)C=C2)N=C(O)C(N=C(O)C(CC2=CC=CC=C2)N=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C45H55N7O9/c1-25(2)19-34(47-24-53)40(55)52-39-27(5)61-45(60)37(22-30-23-46-33-14-10-9-13-32(30)33)50-41(56)35(21-29-15-17-31(54)18-16-29)48-43(58)38(26(3)4)51-42(57)36(49-44(39)59)20-28-11-7-6-8-12-28/h6-18,23-27,34-39,46,54H,19-22H2,1-5H3,(H,47,53)(H,48,58)(H,49,59)(H,50,56)(H,51,57)(H,52,55)

> <INCHI_KEY>
LVGMCXZPNJMSFE-UHFFFAOYSA-N

> <FORMULA>
C45H55N7O9

> <MOLECULAR_WEIGHT>
837.975

> <EXACT_MASS>
837.406126379

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
88.49925982379683

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-[(1H-indol-3-yl)methyl]-16-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
6.985704737349671

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.099654305573391

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.123830603977415

> <JCHEM_PKA_STRONGEST_BASIC>
5.008450534118747

> <JCHEM_POLAR_SURFACE_AREA>
257.85999999999996

> <JCHEM_REFRACTIVITY>
227.1317

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1H-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.652 -21.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.128 -19.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.634 -19.512   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.097 -18.688   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.573 -17.223   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.080 -16.903   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.555 -15.438   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.062 -15.118   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.543 -16.079   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.036 -16.399   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       5.019 -14.614   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.988 -13.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.512 -14.934   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.673 -16.466   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.006 -15.254   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.975 -14.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.531 -14.430   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.007 -15.895   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.024 -17.039   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.452 -18.504   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.959 -18.824   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.989 -17.680   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.513 -16.215   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.451 -12.645   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.958 -12.325   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       0.421 -11.501   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.897 -10.036   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.610 -10.356   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.640  -9.212   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.085 -11.821   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.134  -8.892   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.541  -8.265   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       0.342  -7.427   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       1.849  -7.107   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.324  -5.642   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.294  -4.498   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.212  -4.818   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.243  -3.674   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.767  -2.209   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.797  -1.065   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.739  -1.889   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.770  -3.033   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.879  -8.251   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.403  -9.716   0.000  0.00  0.00           O+0
HETATM   45  N   UNK     0       4.385  -7.931   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0       5.416  -9.076   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.922  -8.756   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.398  -7.291   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.493  -6.045   0.000  0.00  0.00           C+0
HETATM   50  N   UNK     0       7.398  -4.799   0.000  0.00  0.00           N+0
HETATM   51  C   UNK     0       8.863  -5.275   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.196  -4.505   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.530  -5.275   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      11.530  -6.815   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      10.196  -7.585   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.863  -6.815   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.940 -10.540   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       3.434 -10.861   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       5.970 -11.685   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       5.495 -13.149   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       6.525 -14.294   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   60                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   16   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   43                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
CONECT   43   34   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47   57                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   56                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   56                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   48   51                                                  
CONECT   57   46   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   12   61                                                  
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  130    0
END

View in JSmol

Synonyms

Value	Source
N-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-[(1H-indol-3-yl)methyl]-16-methyl-2-oxo-9-(propan-2-yl)-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidate	Generator

Chemical Formula

C₄₅H₅₅N₇O₉

Average Mass

837.9750 Da

Monoisotopic Mass

837.40613 Da

IUPAC Name

Traditional Name

N-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1H-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(N=CO)C(O)=NC1C(C)OC(=O)C(CC2=CNC3=CC=CC=C23)N=C(O)C(CC2=CC=C(O)C=C2)N=C(O)C(N=C(O)C(CC2=CC=CC=C2)N=C1O)C(C)C

InChI Identifier

InChI=1S/C45H55N7O9/c1-25(2)19-34(47-24-53)40(55)52-39-27(5)61-45(60)37(22-30-23-46-33-14-10-9-13-32(30)33)50-41(56)35(21-29-15-17-31(54)18-16-29)48-43(58)38(26(3)4)51-42(57)36(49-44(39)59)20-28-11-7-6-8-12-28/h6-18,23-27,34-39,46,54H,19-22H2,1-5H3,(H,47,53)(H,48,58)(H,49,59)(H,50,56)(H,51,57)(H,52,55)

InChI Key

LVGMCXZPNJMSFE-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Xenorhabdus szentirmaii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Leucine or derivatives
Alpha-amino acid ester
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-formyl-alpha-amino acid
N-formyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
3-alkylindole
N-substituted-alpha-amino acid
Indole or derivatives
Indole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Fatty amide
N-acyl-amine
Benzenoid
Substituted pyrrole
Monocyclic benzene moiety
Heteroaromatic compound
Pyrrole
Lactam
Carboxylic acid ester
Lactone
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.12	ALOGPS
logP	6.99	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	5.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	257.86 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	227.13 m³·mol⁻¹	ChemAxon
Polarizability	88.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

152772142

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid (NP0149742)

MOL for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

3D MOL for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

3D SDF for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

3D-SDF for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

PDB for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

3D PDB for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

SMILES for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

INCHI for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

Structure for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)

3D Structure for NP0149742 (n-{12-benzyl-5,8,11,14-tetrahydroxy-6-[(4-hydroxyphenyl)methyl]-3-(1h-indol-3-ylmethyl)-9-isopropyl-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl}-2-[(hydroxymethylidene)amino]-4-methylpentanimidic acid)