NP-MRD: Showing NP-Card for (3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one (NP0292153)

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Record Information

Version

2.0

Created at

2022-09-09 23:33:30 UTC

Updated at

2022-09-09 23:33:30 UTC

NP-MRD ID

NP0292153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one

Description

(3R,6S)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-6-methyl-11-methylidene-3-(propan-2-yl)-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one 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 (3R,6S)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-6-methyl-11-methylidene-3-(propan-2-yl)-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102201332D          

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M  END


  Mrv1652309102201332D          

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    0.2531   -2.6211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  4  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 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  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35  2  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0292153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(C)C(CCO)C1OC(=O)[C@H](N=C(O)[C@H](C)N=C(O)\C=C\C(=C)N=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H43N3O6/c1-7-8-9-10-11-17(4)20(14-15-30)23-25(33)27-18(5)12-13-21(31)28-19(6)24(32)29-22(16(2)3)26(34)35-23/h12-13,16-17,19-20,22-23,30H,5,7-11,14-15H2,1-4,6H3,(H,27,33)(H,28,31)(H,29,32)/b13-12+/t17?,19-,20?,22+,23?/m0/s1

> <INCHI_KEY>
QWBWNXCMGNCVQC-OIXFFAKGSA-N

> <FORMULA>
C26H43N3O6

> <MOLECULAR_WEIGHT>
493.645

> <EXACT_MASS>
493.315186117

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.947258403778946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6S,9E)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-6-methyl-11-methylidene-3-(propan-2-yl)-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one

> <JCHEM_LOGP>
0.018450931202347122

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
0.3833322603480518

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.010076536995277

> <JCHEM_PKA_STRONGEST_BASIC>
11.299002030272126

> <JCHEM_POLAR_SURFACE_AREA>
144.3

> <JCHEM_REFRACTIVITY>
136.14290000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6S,9E)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.544  -6.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.040  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.048  -4.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.560  -4.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.568  -3.147   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.081  -3.438   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -4.064  -1.691   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.552  -1.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.544  -2.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.048   0.055   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.056   1.219   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -0.536   0.346   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.472  -0.818   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.977   0.637   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.489   0.928   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.032   1.801   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.985  -0.527   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.248   0.354   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.993  -1.691   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.489  -3.147   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.497  -4.311   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.993  -5.766   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.497  -8.385   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.009  -4.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.513  -2.565   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.017  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.530  -4.893   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.538  -6.057   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.050  -5.766   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.058  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.570  -6.639   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.977  -3.438   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.032  -2.273   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0       0.472  -4.893   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   20   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₃N₃O₆

Average Mass

493.6450 Da

Monoisotopic Mass

493.31519 Da

IUPAC Name

(3R,6S,9E)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-6-methyl-11-methylidene-3-(propan-2-yl)-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one

Traditional Name

(3R,6S,9E)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)C(CCO)C1OC(=O)[C@H](N=C(O)[C@H](C)N=C(O)\C=C\C(=C)N=C1O)C(C)C

InChI Identifier

InChI=1S/C26H43N3O6/c1-7-8-9-10-11-17(4)20(14-15-30)23-25(33)27-18(5)12-13-21(31)28-19(6)24(32)29-22(16(2)3)26(34)35-23/h12-13,16-17,19-20,22-23,30H,5,7-11,14-15H2,1-4,6H3,(H,27,33)(H,28,31)(H,29,32)/b13-12+/t17?,19-,20?,22+,23?/m0/s1

InChI Key

QWBWNXCMGNCVQC-OIXFFAKGSA-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

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
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Cyclic carboximidic acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary alcohol
Alcohol
Organopnictogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.018	ChemAxon
pKa (Strongest Acidic)	-4	ChemAxon
pKa (Strongest Basic)	11.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	136.14 m³·mol⁻¹	ChemAxon
Polarizability	53.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78445015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583249

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one (NP0292153)

MOL for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

3D MOL for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

3D SDF for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

3D-SDF for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

PDB for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

3D PDB for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

SMILES for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

INCHI for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

Structure for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)

3D Structure for NP0292153 ((3r,6s,9e)-5,8,13-trihydroxy-14-(1-hydroxy-4-methyldecan-3-yl)-3-isopropyl-6-methyl-11-methylidene-1-oxa-4,7,12-triazacyclotetradeca-4,7,9,12-tetraen-2-one)