NP-MRD: Showing NP-Card for Daechuine S10 (NP0069772)

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Record Information

Version

2.0

Created at

2022-04-28 15:06:58 UTC

Updated at

2022-04-28 15:06:58 UTC

NP-MRD ID

NP0069772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Daechuine S10

Description

(2S)-1-[(3R,7S,10S,13E)-10-[(2R)-butan-2-yl]-8,11-dihydroxy-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.0³,⁷]Nonadeca-1(18),8,11,13,15(19),16-hexaen-6-yl]-2-(dimethylamino)-3-(4-hydroxyphenyl)propan-1-one belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. Daechuine S10 is found in Zizyphus jujuba var.inermis . Based on a literature review very few articles have been published on (2S)-1-[(3R,7S,10S,13E)-10-[(2R)-butan-2-yl]-8,11-dihydroxy-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.0³,⁷]Nonadeca-1(18),8,11,13,15(19),16-hexaen-6-yl]-2-(dimethylamino)-3-(4-hydroxyphenyl)propan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217062D          

 41 44  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304282217062D          

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    5.6426    2.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8673    1.1333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5722    0.3629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0919   -0.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7575    0.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6820    1.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2017    0.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0165    0.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5362    0.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2411   -0.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4264   -0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9067   -0.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7608   -1.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1838    4.6911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8559    4.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2620    5.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0124    5.8552    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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  8 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 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  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 34 37  1  0  0  0  0
  1 38  1  6  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@@H]1NC(=O)[C@@H]2[C@@H](CCN2C(=O)[C@H](CC2=CC=C(O)C=C2)N(C)C)OC2=CC(\C=C\NC1=O)=C(OC)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C31H40N4O6/c1-6-19(2)27-29(37)32-15-13-21-18-23(11-12-25(21)40-5)41-26-14-16-35(28(26)30(38)33-27)31(39)24(34(3)4)17-20-7-9-22(36)10-8-20/h7-13,15,18-19,24,26-28,36H,6,14,16-17H2,1-5H3,(H,32,37)(H,33,38)/b15-13+/t19-,24+,26-,27+,28+/m1/s1

> <INCHI_KEY>
FXMRGUYPWSOTBD-JOWMVAKUSA-N

> <FORMULA>
C31H40N4O6

> <MOLECULAR_WEIGHT>
564.683

> <EXACT_MASS>
564.294785024

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.80269024188048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,7S,10S,13E)-10-[(2R)-butan-2-yl]-6-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.0^{3,7}]nonadeca-1(19),13,15,17-tetraene-8,11-dione

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.7014532753333325

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.211816617654462

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495044974971623

> <JCHEM_PKA_STRONGEST_BASIC>
7.266789592947845

> <JCHEM_POLAR_SURFACE_AREA>
120.44

> <JCHEM_REFRACTIVITY>
155.2096

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,7S,10S,13E)-10-[(2R)-butan-2-yl]-6-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.0^{3,7}]nonadeca-1(19),13,15,17-tetraene-8,11-dione

> <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       6.409   8.117   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.263   6.584   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.518   5.691   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.918   6.331   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.372   4.157   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.000   3.457   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.258   1.978   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.725   2.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.390   3.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.061   4.664   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.207   6.197   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.608   6.837   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.754   8.370   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.154   9.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.300  10.543   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.975   3.511   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.062   1.974   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.437   1.280   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.472   4.039   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.652   3.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.242   1.936   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.763   1.697   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       8.461   3.069   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       9.982   3.312   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.533   4.750   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.952   2.115   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      10.402   0.677   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      11.372  -0.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.881   0.435   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.473   2.358   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.443   1.162   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.964   1.404   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.934   0.208   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.383  -1.231   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.863  -1.473   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.892  -0.277   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.354  -2.427   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.810   8.757   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.064   7.864   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.956  10.290   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.357  10.930   0.000  0.00  0.00           C+0
CONECT    1    2   14   38                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   23                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    1   15                                                  
CONECT   15   14                                                            
CONECT   16   10   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17    8                                                       
CONECT   19   16   20                                                       
CONECT   20   19                                                            
CONECT   21    6   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    5   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   34                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₀N₄O₆

Average Mass

564.6830 Da

Monoisotopic Mass

564.29479 Da

IUPAC Name

(3R,7S,10S,13E)-10-[(2R)-butan-2-yl]-6-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.0^{3,7}]nonadeca-1(19),13,15,17-tetraene-8,11-dione

Traditional Name

(3R,7S,10S,13E)-10-[(2R)-butan-2-yl]-6-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propanoyl]-16-methoxy-2-oxa-6,9,12-triazatricyclo[13.3.1.0^{3,7}]nonadeca-1(19),13,15,17-tetraene-8,11-dione

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@@H]1NC(=O)[C@@H]2[C@@H](CCN2C(=O)[C@H](CC2=CC=C(O)C=C2)N(C)C)OC2=CC(\C=C\NC1=O)=C(OC)C=C2

InChI Identifier

InChI=1S/C31H40N4O6/c1-6-19(2)27-29(37)32-15-13-21-18-23(11-12-25(21)40-5)41-26-14-16-35(28(26)30(38)33-27)31(39)24(34(3)4)17-20-7-9-22(36)10-8-20/h7-13,15,18-19,24,26-28,36H,6,14,16-17H2,1-5H3,(H,32,37)(H,33,38)/b15-13+/t19-,24+,26-,27+,28+/m1/s1

InChI Key

FXMRGUYPWSOTBD-JOWMVAKUSA-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
Zizyphus jujuba var.inermis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Amphetamine or derivatives
Alpha-amino acid or derivatives
N-acylpyrrolidine
Anisole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	2.95	ALOGPS
logP	2.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	7.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	120.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	155.21 m³·mol⁻¹	ChemAxon
Polarizability	59.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

163104068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Daechuine S10 (NP0069772)

MOL for NP0069772 (Daechuine S10)

3D MOL for NP0069772 (Daechuine S10)

3D SDF for NP0069772 (Daechuine S10)

3D-SDF for NP0069772 (Daechuine S10)

PDB for NP0069772 (Daechuine S10)

3D PDB for NP0069772 (Daechuine S10)

SMILES for NP0069772 (Daechuine S10)

INCHI for NP0069772 (Daechuine S10)

Structure for NP0069772 (Daechuine S10)

3D Structure for NP0069772 (Daechuine S10)