NP-MRD: Showing NP-Card for (+)-Apateline (NP0067821)

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Record Information

Version

2.0

Created at

2022-04-28 12:39:50 UTC

Updated at

2022-04-28 12:39:50 UTC

NP-MRD ID

NP0067821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Apateline

Description

Apateline belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (+)-Apateline is found in Albertisia laurifolia Yamamoto, Albertisia papuana, Cocculus pendulus, Daphnandra apatela, Guatteria guianensis and Pachygone loyaltiensis Diels. Based on a literature review very few articles have been published on Apateline.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214392D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282214392D          

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    7.8697    0.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4347    1.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1459    1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3360    2.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2408    1.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9671    1.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9866    1.2305    0.0000 O   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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
 22 31  1  0  0  0  0
 31 32  1  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
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 36 39  1  0  0  0  0
  2 39  1  0  0  0  0
 30 40  1  0  0  0  0
  3 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=CC=C(OC5=CC(C[C@H]6NCCC7=C6C=C6OC3=C1OC6=C7)=CC=C5O)C=C4)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C34H32N2O5/c1-36-12-10-22-17-31(38-2)33-34-32(22)26(36)14-19-3-6-23(7-4-19)39-28-15-20(5-8-27(28)37)13-25-24-18-30(41-34)29(40-33)16-21(24)9-11-35-25/h3-8,15-18,25-26,35,37H,9-14H2,1-2H3/t25-,26+/m1/s1

> <INCHI_KEY>
AFGMWONXXNDGGE-FTJBHMTQSA-N

> <FORMULA>
C34H32N2O5

> <MOLECULAR_WEIGHT>
548.639

> <EXACT_MASS>
548.231122138

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
60.367419086916186

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,21S)-27-methoxy-22-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1,3,10,12,14(37),16,18,25(33),26,28(32),30(34),35-dodecaen-13-ol

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
5.099628206221969

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.411138912574119

> <JCHEM_PKA_STRONGEST_BASIC>
9.146471855797776

> <JCHEM_POLAR_SURFACE_AREA>
72.42

> <JCHEM_REFRACTIVITY>
157.59399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R,21S)-27-methoxy-22-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1,3,10,12,14(37),16,18,25(33),26,28(32),30(34),35-dodecaen-13-ol

> <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      17.864   5.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.365   3.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.928   3.723   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.908   4.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.346   6.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.806   6.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.177   8.119   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.238   9.420   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      18.189  10.668   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      17.626  12.106   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.092  12.328   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.085  11.123   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.653   9.660   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.616   8.466   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.072   8.707   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.503  10.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.532  11.357   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.945  10.360   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.960   9.110   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.534   7.640   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.093   7.486   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.568   6.328   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.020   6.647   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.437   8.098   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.399   9.315   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.820  10.742   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.295  10.954   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.926   5.529   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.347   4.034   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       8.864   3.671   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       9.992   4.769   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.347   3.854   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.597   2.829   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.165   1.346   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.690   1.020   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.745   2.174   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.206   3.625   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.694   3.939   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      17.249   2.731   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.272   2.186   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      20.508   2.297   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20   23   31                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   40                                                  
CONECT   31   30   22   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   36    2                                                       
CONECT   40   30                                                            
CONECT   41    3                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₂N₂O₅

Average Mass

548.6390 Da

Monoisotopic Mass

548.23112 Da

IUPAC Name

(8R,21S)-27-methoxy-22-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1,3,10,12,14(37),16,18,25(33),26,28(32),30(34),35-dodecaen-13-ol

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=CC=C(OC5=CC(C[C@H]6NCCC7=C6C=C6OC3=C1OC6=C7)=CC=C5O)C=C4)N(C)CC2

InChI Identifier

InChI=1S/C34H32N2O5/c1-36-12-10-22-17-31(38-2)33-34-32(22)26(36)14-19-3-6-23(7-4-19)39-28-15-20(5-8-27(28)37)13-25-24-18-30(41-34)29(40-33)16-21(24)9-11-35-25/h3-8,15-18,25-26,35,37H,9-14H2,1-2H3/t25-,26+/m1/s1

InChI Key

AFGMWONXXNDGGE-FTJBHMTQSA-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
Albertisia laurifolia Yamamoto	Plant	KNApSAcK
Albertisia papuana	Plant	KNApSAcK
Cocculus pendulus	LOTUS Database	35616633
Daphnandra apatela	Plant	KNApSAcK
Guatteria guianensis	LOTUS Database	35616633
Pachygone loyaltiensis Diels	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Dibenzo-p-dioxin
Diaryl ether
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Secondary amine
Oxacycle
Ether
Secondary aliphatic amine
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
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	4.57	ALOGPS
logP	5.1	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.41	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.42 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	157.59 m³·mol⁻¹	ChemAxon
Polarizability	60.37 Å³	ChemAxon
Number of Rings	8	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

C00025634

Chemspider ID

16735905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560531

PDB ID

Not Available

ChEBI ID

182871

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Apateline (NP0067821)

MOL for NP0067821 ((+)-Apateline)

3D MOL for NP0067821 ((+)-Apateline)

3D SDF for NP0067821 ((+)-Apateline)

3D-SDF for NP0067821 ((+)-Apateline)

PDB for NP0067821 ((+)-Apateline)

3D PDB for NP0067821 ((+)-Apateline)

SMILES for NP0067821 ((+)-Apateline)

INCHI for NP0067821 ((+)-Apateline)

Structure for NP0067821 ((+)-Apateline)

3D Structure for NP0067821 ((+)-Apateline)