NP-MRD: Showing NP-Card for (+)-Daphniphylline (NP0077939)

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Record Information

Version

2.0

Created at

2022-04-28 23:05:22 UTC

Updated at

2022-04-28 23:05:22 UTC

NP-MRD ID

NP0077939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Daphniphylline

Description

(+)-Daphniphylline is found in Daphniphyllum bancanum, Daphniphyllum longeracemosum and Hibiscus sabdariffa .

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201052D          

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M  END

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M  END


  Mrv1652304292201052D          

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    2.7251    1.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7951    3.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6765    3.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    4.1290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5069    4.6081    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4628    5.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794    5.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    5.8398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2896    5.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9719    4.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0457    5.3971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3716    6.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233    3.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  6  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  9  7  1  1  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 14 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  5 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  1  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
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 34  1  0  0  0  0
 32 35  1  0  0  0  0
 29 35  1  1  0  0  0
 32 36  1  1  0  0  0
 28 37  1  6  0  0  0
  4 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@]45CCC[C@H]4[C@@]2(C[C@@H](OC(C)=O)C(=O)[C@]2(C)CO[C@@]4(C)CC[C@@H]2O4)[C@H]1N5C3

> <INCHI_IDENTIFIER>
InChI=1S/C32H49NO5/c1-19(2)22-10-13-29(5)21-9-15-31-12-7-8-24(31)32(29,26(22)33(31)17-21)16-23(37-20(3)34)27(35)28(4)18-36-30(6)14-11-25(28)38-30/h19,21-26H,7-18H2,1-6H3/t21-,22-,23-,24-,25+,26+,28-,29+,30-,31-,32-/m1/s1

> <INCHI_KEY>
LFLWRPZTBUUBEQ-PZRINQKTSA-N

> <FORMULA>
C32H49NO5

> <MOLECULAR_WEIGHT>
527.746

> <EXACT_MASS>
527.361073682

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.07323774607961

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7R,10S,13S,14R)-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-2-yl]-1-oxopropan-2-yl acetate

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
5.201202998999999

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.207513803577903

> <JCHEM_PKA_STRONGEST_BASIC>
11.785402443956604

> <JCHEM_POLAR_SURFACE_AREA>
65.07000000000001

> <JCHEM_REFRACTIVITY>
144.82489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.46e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7R,10S,13S,14R)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-2-yl]-1-oxopropan-2-yl acetate

> <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       2.726  -0.461   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.702  -1.597   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.433   0.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.194   1.690   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.820   2.374   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.653   0.712   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.498  -0.232   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.296  -1.370   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.786   0.856   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.184   1.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.985   3.286   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.708   2.410   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.163   0.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.128   0.825   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.181   2.373   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.652   3.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.332  -0.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.902  -0.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.205  -1.870   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.247   4.109   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.736   5.648   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.136   5.995   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.711   4.470   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.789   4.927   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.087   3.381   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.084   6.551   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.730   6.376   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.933   7.707   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.680   8.602   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.597  10.140   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.748  11.163   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.266  10.901   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.007   9.551   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.414   8.130   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.685  10.075   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.160  12.155   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.337   7.192   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.481   2.445   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   16   38                                             
CONECT    5    4    6   10   20                                             
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7    1   10   13                                             
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
CONECT   14    6   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    4                                                       
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    5   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34   37                                             
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   35   36                                             
CONECT   33   32   34                                                       
CONECT   34   33   28                                                       
CONECT   35   32   29                                                       
CONECT   36   32                                                            
CONECT   37   28                                                            
CONECT   38    4                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₉NO₅

Average Mass

527.7460 Da

Monoisotopic Mass

527.36107 Da

IUPAC Name

(2R)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7R,10S,13S,14R)-1-methyl-14-(propan-2-yl)-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-2-yl]-1-oxopropan-2-yl acetate

Traditional Name

(2R)-1-[(1R,4R,5S)-1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octan-4-yl]-3-[(1S,2R,3S,7R,10S,13S,14R)-14-isopropyl-1-methyl-12-azapentacyclo[8.6.0.0^{2,13}.0^{3,7}.0^{7,12}]hexadecan-2-yl]-1-oxopropan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@]45CCC[C@H]4[C@@]2(C[C@@H](OC(C)=O)C(=O)[C@]2(C)CO[C@@]4(C)CC[C@@H]2O4)[C@H]1N5C3

InChI Identifier

InChI=1S/C32H49NO5/c1-19(2)22-10-13-29(5)21-9-15-31-12-7-8-24(31)32(29,26(22)33(31)17-21)16-23(37-20(3)34)27(35)28(4)18-36-30(6)14-11-25(28)38-30/h19,21-26H,7-18H2,1-6H3/t21-,22-,23-,24-,25+,26+,28-,29+,30-,31-,32-/m1/s1

InChI Key

LFLWRPZTBUUBEQ-PZRINQKTSA-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
Daphniphyllum bancanum	Plant	KNApSAcK
Daphniphyllum longeracemosum	Plant	KNApSAcK
Hibiscus sabbariffa	Plant	KNApSAcK

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	4.33	ALOGPS
logP	5.2	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	16.21	ChemAxon
pKa (Strongest Basic)	11.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	144.82 m³·mol⁻¹	ChemAxon
Polarizability	59.07 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Daphniphylline (NP0077939)

MOL for NP0077939 ((+)-Daphniphylline)

3D MOL for NP0077939 ((+)-Daphniphylline)

3D SDF for NP0077939 ((+)-Daphniphylline)

3D-SDF for NP0077939 ((+)-Daphniphylline)

PDB for NP0077939 ((+)-Daphniphylline)

3D PDB for NP0077939 ((+)-Daphniphylline)

SMILES for NP0077939 ((+)-Daphniphylline)

INCHI for NP0077939 ((+)-Daphniphylline)

Structure for NP0077939 ((+)-Daphniphylline)

3D Structure for NP0077939 ((+)-Daphniphylline)