NP-MRD: Showing NP-Card for (3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate (NP0200408)

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Record Information

Version

2.0

Created at

2022-09-04 19:14:44 UTC

Updated at

2022-09-04 19:14:44 UTC

NP-MRD ID

NP0200408

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate

Description

Metacridamide A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate is found in Metarhizium acridum. (3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate was first documented in 2012 (PMID: 22292922). Based on a literature review very few articles have been published on Metacridamide A (PMID: 23723893).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221142D          

 44 45  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -4.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6907   -4.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090   -3.9580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9445   -3.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7650   -3.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1006   -2.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9210   -2.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0704   -3.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499   -3.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0215   -4.6725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6467   -5.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.3928   -6.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    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
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
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 17 18  1  0  0  0  0
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 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
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 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
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 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
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 28 30  1  0  0  0  0
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 35 40  1  0  0  0  0
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 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END

     RDKit          3D

 99100  0  0  0  0  0  0  0  0999 V2000
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    5.1480   -1.1509   -0.7708 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.1421   -0.0928   -0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9137   -0.1302    0.0403 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1107   -0.2152    1.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6708   -0.7332   -0.4769 C   0  0  1  0  0  0  0  0  0  0  0  0
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 26 74  1  6
 27 75  1  0
 27 76  1  0
 27 77  1  0
 28 78  1  6
 29 79  1  0
 31 80  1  0
 31 81  1  0
 31 82  1  0
 32 83  1  0
 33 84  1  6
 34 85  1  0
 34 86  1  0
 34 87  1  0
 35 88  1  6
 38 89  1  0
 38 90  1  0
 38 91  1  0
 41 92  1  0
 41 93  1  0
 41 94  1  0
 42 95  1  0
 43 96  1  6
 44 97  1  0
 44 98  1  0
 44 99  1  0
M  END


  Mrv1652309042221142D          

 44 45  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020   -4.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6907   -4.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090   -3.9580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9445   -3.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7650   -3.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1006   -2.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9210   -2.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4060   -2.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0704   -3.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2499   -3.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0215   -4.6725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4694   -5.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6467   -5.2245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1356   -6.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928   -6.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    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
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
  8 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0200408

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C[C@H](C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N=C(O)\C(C)=C\[C@H](C)[C@@H](O)\C(C)=C\[C@H](C)[C@H](OC(C)=O)\C(C)=C\[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C37H55NO6/c1-11-22(2)17-25(5)35-28(8)20-27(7)34(43-30(10)39)26(6)18-23(3)33(40)24(4)19-29(9)36(41)38-32(37(42)44-35)21-31-15-13-12-14-16-31/h12-16,18-20,22,24-26,28,32-35,40H,11,17,21H2,1-10H3,(H,38,41)/b23-18+,27-20+,29-19+/t22-,24-,25-,26-,28-,32-,33-,34-,35+/m0/s1

> <INCHI_KEY>
WIRRTALUVUQONX-HVCDBQLESA-N

> <FORMULA>
C37H55NO6

> <MOLECULAR_WEIGHT>
609.848

> <EXACT_MASS>
609.402938495

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
70.19145920355437

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2S,4S)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate

> <JCHEM_LOGP>
8.245551089666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.837178013216377

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3023204033930895

> <JCHEM_PKA_STRONGEST_BASIC>
2.092290090931192

> <JCHEM_POLAR_SURFACE_AREA>
105.42000000000002

> <JCHEM_REFRACTIVITY>
177.76610000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2S,4S)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.830  -7.708   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.623  -9.234   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.337  -7.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.963  -5.981   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.495  -5.820   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.121  -4.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.653  -4.253   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.558  -5.498   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.931  -6.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.400  -7.066   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      13.107  -8.722   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      12.076  -9.866   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.540  -9.752   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.320 -12.349   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.200 -11.389   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   43                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   12   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42    8   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₅₅NO₆

Average Mass

609.8480 Da

Monoisotopic Mass

609.40294 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C[C@H](C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N=C(O)\C(C)=C\[C@H](C)[C@@H](O)\C(C)=C\[C@H](C)[C@H](OC(C)=O)\C(C)=C\[C@@H]1C

InChI Identifier

InChI=1S/C37H55NO6/c1-11-22(2)17-25(5)35-28(8)20-27(7)34(43-30(10)39)26(6)18-23(3)33(40)24(4)19-29(9)36(41)38-32(37(42)44-35)21-31-15-13-12-14-16-31/h12-16,18-20,22,24-26,28,32-35,40H,11,17,21H2,1-10H3,(H,38,41)/b23-18+,27-20+,29-19+/t22-,24-,25-,26-,28-,32-,33-,34-,35+/m0/s1

InChI Key

WIRRTALUVUQONX-HVCDBQLESA-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
Metarhizium acridum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
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

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

28503676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57332100

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Krasnoff SB, Englich U, Miller PG, Shuler ML, Glahn RP, Donzelli BG, Gibson DM: Metacridamides A and B, macrocycles from conidia of the entomopathogenic fungus Metarhizium acridum. J Nat Prod. 2012 Feb 24;75(2):175-80. doi: 10.1021/np2007044. Epub 2012 Jan 31. [PubMed:22292922 ]
Englich U, Krasnoff SB: Metacridamide B methanol-d 4 monosolvate. Acta Crystallogr Sect E Struct Rep Online. 2013 Apr 17;69(Pt 5):o742. doi: 10.1107/S1600536813009641. Print 2013 May 1. [PubMed:23723893 ]
LOTUS database [Link]

Showing NP-Card for (3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate (NP0200408)

MOL for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

3D MOL for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

3D SDF for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

3D-SDF for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

PDB for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

3D PDB for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

SMILES for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

INCHI for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

Structure for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)

3D Structure for NP0200408 ((3s,6e,8s,9r,10e,12s,13s,14e,16s,17r)-3-benzyl-5,9-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2s,4s)-4-methylhexan-2-yl]-2-oxo-1-oxa-4-azacycloheptadeca-4,6,10,14-tetraen-13-yl acetate)