NP-MRD: Showing NP-Card for (2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid (NP0155195)

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Record Information

Version

2.0

Created at

2022-09-02 12:12:53 UTC

Updated at

2022-09-02 12:12:54 UTC

NP-MRD ID

NP0155195

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid

Description

(2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid is found in Discaria americana.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214122D          

 35 36  0  0  1  0            999 V2000
    2.0566    5.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537    6.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    6.8301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5822    7.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    7.0198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1570    6.2737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8110    5.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    5.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    5.5751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2161    7.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  2  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022214122D          

 35 36  0  0  1  0            999 V2000
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 10 11  2  0  0  0  0
 11 12  1  4  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  1  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  1  0  0  0
 18 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
 33 32  1  4  0  0  0
 33 34  2  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155195

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@H]1N=C(O)[C@H](N=C(O)[C@H](CC(C)C)NC)[C@H](OC2=CC=C(C=C2)\C=C/N=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42N4O4/c1-8-18(6)22-26(33)29-14-13-19-9-11-20(12-10-19)35-24(17(4)5)23(27(34)30-22)31-25(32)21(28-7)15-16(2)3/h9-14,16-18,21-24,28H,8,15H2,1-7H3,(H,29,33)(H,30,34)(H,31,32)/b14-13-/t18-,21-,22+,23+,24+/m0/s1

> <INCHI_KEY>
XTUMOHUXWFAFRF-VSPPIOTNSA-N

> <FORMULA>
C27H42N4O4

> <MOLECULAR_WEIGHT>
486.657

> <EXACT_MASS>
486.320605848

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.52178900761627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-N-[(3R,4R,7R,10Z)-7-[(2S)-butan-2-yl]-5,8-dihydroxy-3-(propan-2-yl)-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
-1.779470510716614

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
-4.265915465197913

> <JCHEM_PKA_STRONGEST_ACIDIC>
-9.3601182824303

> <JCHEM_PKA_STRONGEST_BASIC>
14.967490857180191

> <JCHEM_POLAR_SURFACE_AREA>
119.03000000000002

> <JCHEM_REFRACTIVITY>
138.04160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N-[(3R,4R,7R,10Z)-7-[(2S)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.839  10.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.340  11.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.897  12.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.953  13.871   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.399  13.104   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.293  11.711   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.514  10.750   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.852   9.360   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.031  10.407   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.031   8.867   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.698   8.097   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.364   8.867   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.698   6.557   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.031   5.787   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.031   4.247   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.365   3.477   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.698   3.477   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -0.364   5.787   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.364   4.247   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.562  10.753   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.207   9.355   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.740   9.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.317   8.097   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.830  11.698   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.323  13.241   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.100  14.614   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.314  15.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.752  16.081   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.036  14.723   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.772  13.374   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.334  16.861   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.735  16.976   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -0.357  16.132   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       0.403  14.701   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.898  15.071   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
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   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18                                                            
CONECT   20    9   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    5   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂N₄O₄

Average Mass

486.6570 Da

Monoisotopic Mass

486.32061 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@H]1N=C(O)[C@H](N=C(O)[C@H](CC(C)C)NC)[C@H](OC2=CC=C(C=C2)\C=C/N=C1O)C(C)C

InChI Identifier

InChI=1S/C27H42N4O4/c1-8-18(6)22-26(33)29-14-13-19-9-11-20(12-10-19)35-24(17(4)5)23(27(34)30-22)31-25(32)21(28-7)15-16(2)3/h9-14,16-18,21-24,28H,8,15H2,1-7H3,(H,29,33)(H,30,34)(H,31,32)/b14-13-/t18-,21-,22+,23+,24+/m0/s1

InChI Key

XTUMOHUXWFAFRF-VSPPIOTNSA-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
Discaria americana	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.44	ALOGPS
logP	-1.8	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	-9.4	ChemAxon
pKa (Strongest Basic)	14.97	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon

External Links

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid (NP0155195)

MOL for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

3D MOL for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

3D SDF for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

3D-SDF for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

PDB for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

3D PDB for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

SMILES for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

INCHI for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

Structure for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)

3D Structure for NP0155195 ((2s)-n-[(3r,4r,7r,10z)-7-[(2s)-butan-2-yl]-5,8-dihydroxy-3-isopropyl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),5,8,10,12,15-hexaen-4-yl]-4-methyl-2-(methylamino)pentanimidic acid)