NP-MRD: Showing NP-Card for Protodestruxin (NP0075699)

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Record Information

Version

2.0

Created at

2022-04-28 20:56:56 UTC

Updated at

2022-04-28 20:56:56 UTC

NP-MRD ID

NP0075699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Protodestruxin

Description

(3R,6S,9R,16R,21aR)-3,16-bis[(2R)-butan-2-yl]-1,4,7,10-tetrahydroxy-9-methyl-6-(propan-2-yl)-3H,6H,9H,12H,13H,14H,16H,17H,19H,20H,21H,21aH-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-14,17-dione 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. Protodestruxin is found in Metarrhizium anisopliae (Metchnikoff). Based on a literature review very few articles have been published on (3R,6S,9R,16R,21aR)-3,16-bis[(2R)-butan-2-yl]-1,4,7,10-tetrahydroxy-9-methyl-6-(propan-2-yl)-3H,6H,9H,12H,13H,14H,16H,17H,19H,20H,21H,21aH-pyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-14,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222562D          

 40 41  0  0  1  0            999 V2000
    4.0600    0.0418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282222562D          

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    4.6411    2.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4489    2.6722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7075    1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5153    1.7210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583    1.2731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4169    0.4897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8678   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1264   -0.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506    1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6857    2.7330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2481    3.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8818    2.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194    2.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388    1.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8493    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5103    0.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -1.8052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2203   -1.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8634   -2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556   -2.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3186   -0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735   -1.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7694   -1.3573    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  6  0  0  0
 13 27  1  1  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  9 33  1  0  0  0  0
  5 34  1  1  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
  1 38  1  1  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@H]1NC(=O)[C@H]2CCCN2C(=O)[C@H](OC(=O)CCNC(=O)[C@@H](C)NC(=O)[C@@H](NC1=O)C(C)C)[C@H](C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C28H47N5O7/c1-8-16(5)22-27(38)31-21(15(3)4)26(37)30-18(7)24(35)29-13-12-20(34)40-23(17(6)9-2)28(39)33-14-10-11-19(33)25(36)32-22/h15-19,21-23H,8-14H2,1-7H3,(H,29,35)(H,30,37)(H,31,38)(H,32,36)/t16-,17-,18-,19-,21+,22-,23-/m1/s1

> <INCHI_KEY>
LPNCKOVXGGRIPE-IZDSGKKBSA-N

> <FORMULA>
C28H47N5O7

> <MOLECULAR_WEIGHT>
565.712

> <EXACT_MASS>
565.347548873

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
60.45502433602102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6S,9R,16R,21aR)-3,16-bis[(2R)-butan-2-yl]-9-methyl-6-(propan-2-yl)-icosahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.0025836856666657

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.60892099944083

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.882551674849344

> <JCHEM_PKA_STRONGEST_BASIC>
-2.832417035915086

> <JCHEM_POLAR_SURFACE_AREA>
163.01

> <JCHEM_REFRACTIVITY>
145.91800000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6S,9R,16R,21aR)-3,16-bis[(2R)-butan-2-yl]-6-isopropyl-9-methyl-tetradecahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.579   0.078   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.554  -1.071   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.046  -0.758   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.563   0.704   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.021  -1.907   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.513  -1.594   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.916  -0.018   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.086   0.982   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.578   0.745   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.891   2.253   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.422   2.421   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.492   1.314   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.598   3.629   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.105   3.316   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.131   4.465   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.648   5.928   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.638   4.152   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.663   5.301   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      10.171   4.988   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      10.654   3.526   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.162   3.213   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.629   2.376   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      10.112   0.914   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       9.086  -0.235   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.569  -1.698   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.121   2.690   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.147   5.102   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.197   6.228   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.646   5.447   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.596   4.321   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.446   3.017   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.585   1.981   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.952   0.577   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.503  -3.370   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.011  -3.683   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.478  -4.519   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.970  -4.206   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.061  -1.384   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.097  -2.524   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.036  -2.534   0.000  0.00  0.00           C+0
CONECT    1    2   24   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23    1   25                                                  
CONECT   25   24                                                            
CONECT   26   22                                                            
CONECT   27   13   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   10   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    9                                                       
CONECT   34    5   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₇N₅O₇

Average Mass

565.7120 Da

Monoisotopic Mass

565.34755 Da

IUPAC Name

(3R,6S,9R,16R,21aR)-3,16-bis[(2R)-butan-2-yl]-9-methyl-6-(propan-2-yl)-icosahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone

Traditional Name

(3R,6S,9R,16R,21aR)-3,16-bis[(2R)-butan-2-yl]-6-isopropyl-9-methyl-tetradecahydropyrrolo[1,2-d]1-oxa-4,7,10,13,16-pentaazacyclononadecane-1,4,7,10,14,17-hexone

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@H]1NC(=O)[C@H]2CCCN2C(=O)[C@H](OC(=O)CCNC(=O)[C@@H](C)NC(=O)[C@@H](NC1=O)C(C)C)[C@H](C)CC

InChI Identifier

InChI=1S/C28H47N5O7/c1-8-16(5)22-27(38)31-21(15(3)4)26(37)30-18(7)24(35)29-13-12-20(34)40-23(17(6)9-2)28(39)33-14-10-11-19(33)25(36)32-22/h15-19,21-23H,8-14H2,1-7H3,(H,29,35)(H,30,37)(H,31,38)(H,32,36)/t16-,17-,18-,19-,21+,22-,23-/m1/s1

InChI Key

LPNCKOVXGGRIPE-IZDSGKKBSA-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
Metarrhizium anisopliae (Metchnikoff)	-	KNApSAcK

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
Macrolide
Macrolactam
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.74	ALOGPS
logP	1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	163.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.92 m³·mol⁻¹	ChemAxon
Polarizability	60.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

163104930

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Protodestruxin (NP0075699)

MOL for NP0075699 (Protodestruxin)

3D MOL for NP0075699 (Protodestruxin)

3D SDF for NP0075699 (Protodestruxin)

3D-SDF for NP0075699 (Protodestruxin)

PDB for NP0075699 (Protodestruxin)

3D PDB for NP0075699 (Protodestruxin)

SMILES for NP0075699 (Protodestruxin)

INCHI for NP0075699 (Protodestruxin)

Structure for NP0075699 (Protodestruxin)

3D Structure for NP0075699 (Protodestruxin)