NP-MRD: Showing NP-Card for (+)-Taumycin A (NP0082103)

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Record Information

Version

2.0

Created at

2022-04-29 03:09:39 UTC

Updated at

2022-04-29 03:09:39 UTC

NP-MRD ID

NP0082103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Taumycin A

Description

(3S,6R,11R,12S)-6-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]-5,8-dihydroxy-11-methyl-12-[(1E,4R,6E)-2,4,6-trimethyl-7-(1,3-oxazol-4-yl)hepta-1,6-dien-1-yl]-1-oxa-4,7-diazacyclododeca-4,7-diene-2,10-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. Based on a literature review very few articles have been published on (3S,6R,11R,12S)-6-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]-5,8-dihydroxy-11-methyl-12-[(1E,4R,6E)-2,4,6-trimethyl-7-(1,3-oxazol-4-yl)hepta-1,6-dien-1-yl]-1-oxa-4,7-diazacyclododeca-4,7-diene-2,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205092D          

 40 41  0  0  1  0            999 V2000
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  3 40  1  6  0  0  0
M  END

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M  END


  Mrv1652304292205092D          

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   -9.3941   13.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   14.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   15.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   10.8911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5737   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    9.6536    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904    6.6937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    5.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5253    6.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   13.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  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
  6  8  1  0  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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  1 16  1  0  0  0  0
 12 17  1  6  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  1  0  0  0
  4 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  2  0  0  0  0
 31 38  1  0  0  0  0
 29 39  1  1  0  0  0
  3 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@H]1NC(=O)CC(=O)[C@H](C)[C@@H](OC(=O)[C@@H](NC1=O)[C@@H](C)CC)\C=C(/C)C[C@H](C)C\C(C)=C\C1=COC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C31H47N3O6/c1-9-21(6)28-30(37)34-29(22(7)10-2)31(38)40-26(23(8)25(35)15-27(36)33-28)14-20(5)12-18(3)11-19(4)13-24-16-39-17-32-24/h13-14,16-18,21-23,26,28-29H,9-12,15H2,1-8H3,(H,33,36)(H,34,37)/b19-13+,20-14+/t18-,21-,22+,23+,26+,28-,29+/m1/s1

> <INCHI_KEY>
OGFGKSZURZDTME-WCFWLGDISA-N

> <FORMULA>
C31H47N3O6

> <MOLECULAR_WEIGHT>
557.732

> <EXACT_MASS>
557.346486245

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
61.381721538190874

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R,11R,12S)-6-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]-11-methyl-12-[(1E,4R,6E)-2,4,6-trimethyl-7-(1,3-oxazol-4-yl)hepta-1,6-dien-1-yl]-1-oxa-4,7-diazacyclododecane-2,5,8,10-tetrone

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
5.421191786999998

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.574765993686842

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.805106916696715

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21164506158853935

> <JCHEM_POLAR_SURFACE_AREA>
127.6

> <JCHEM_REFRACTIVITY>
153.90870000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,11R,12S)-6-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]-11-methyl-12-[(1E,4R,6E)-2,4,6-trimethyl-7-(1,3-oxazol-4-yl)hepta-1,6-dien-1-yl]-1-oxa-4,7-diazacyclododecane-2,5,8,10-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0     -12.003  24.950   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -13.337  24.180   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -10.669  24.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  22.640   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -12.003  21.870   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0     -13.337  22.640   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -14.242  23.886   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -14.670  21.870   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0     -16.004  22.640   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0     -16.004  24.180   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -17.338  24.950   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -14.670  24.950   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0     -14.670  26.490   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0     -13.337  27.260   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -13.337  28.800   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -12.003  26.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -16.004  25.720   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -17.536  25.881   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -16.004  27.260   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -17.338  28.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.670  20.330   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -16.004  19.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -17.338  20.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.337  19.560   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336  21.870   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.336  20.330   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669  19.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002  19.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.002  18.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.668  17.250   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.668  15.710   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335  14.940   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335  13.400   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -4.089  12.495   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      -4.565  11.030   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.105  11.030   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.581  12.495   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.002  14.940   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.336  17.250   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.336  24.950   0.000  0.00  0.00           C+0
CONECT    1    2    3   16                                                  
CONECT    2    1                                                            
CONECT    3    1    4   40                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    1                                                       
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21    8   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25    4   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33                                                       
CONECT   38   31                                                            
CONECT   39   29                                                            
CONECT   40    3                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₇N₃O₆

Average Mass

557.7320 Da

Monoisotopic Mass

557.34649 Da

IUPAC Name

(3S,6R,11R,12S)-6-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]-11-methyl-12-[(1E,4R,6E)-2,4,6-trimethyl-7-(1,3-oxazol-4-yl)hepta-1,6-dien-1-yl]-1-oxa-4,7-diazacyclododecane-2,5,8,10-tetrone

Traditional Name

(3S,6R,11R,12S)-6-[(2R)-butan-2-yl]-3-[(2S)-butan-2-yl]-11-methyl-12-[(1E,4R,6E)-2,4,6-trimethyl-7-(1,3-oxazol-4-yl)hepta-1,6-dien-1-yl]-1-oxa-4,7-diazacyclododecane-2,5,8,10-tetrone

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@H]1NC(=O)CC(=O)[C@H](C)[C@@H](OC(=O)[C@@H](NC1=O)[C@@H](C)CC)\C=C(/C)C[C@H](C)C\C(C)=C\C1=COC=N1

InChI Identifier

InChI=1S/C31H47N3O6/c1-9-21(6)28-30(37)34-29(22(7)10-2)31(38)40-26(23(8)25(35)15-27(36)33-28)14-20(5)12-18(3)11-19(4)13-24-16-39-17-32-24/h13-14,16-18,21-23,26,28-29H,9-12,15H2,1-8H3,(H,33,36)(H,34,37)/b19-13+,20-14+/t18-,21-,22+,23+,26+,28-,29+/m1/s1

InChI Key

OGFGKSZURZDTME-WCFWLGDISA-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

Not Available

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
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
Heteroaromatic compound
Cyclic carboximidic acid
Oxazole
Azole
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
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
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	3.91	ALOGPS
logP	5.42	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.81	ChemAxon
pKa (Strongest Basic)	-0.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	153.91 m³·mol⁻¹	ChemAxon
Polarizability	61.38 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

163105351

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Taumycin A (NP0082103)

MOL for NP0082103 ((+)-Taumycin A)

3D MOL for NP0082103 ((+)-Taumycin A)

3D SDF for NP0082103 ((+)-Taumycin A)

3D-SDF for NP0082103 ((+)-Taumycin A)

PDB for NP0082103 ((+)-Taumycin A)

3D PDB for NP0082103 ((+)-Taumycin A)

SMILES for NP0082103 ((+)-Taumycin A)

INCHI for NP0082103 ((+)-Taumycin A)

Structure for NP0082103 ((+)-Taumycin A)

3D Structure for NP0082103 ((+)-Taumycin A)