NP-MRD: Showing NP-Card for (+)-1,2-Dehydroapateline (NP0067811)

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Record Information

Version

1.0

Created at

2022-04-28 12:39:21 UTC

Updated at

2022-04-28 12:39:21 UTC

NP-MRD ID

NP0067811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-1,2-Dehydroapateline

Description

Dehydroapateline 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. (+)-1,2-Dehydroapateline is found in Anisocycla cymosa, Anisocyla jollyana, Bacopa monniera, Cocculus orbiculatus, Cocculus pendulus, Cocculus pendulus (Forsk.) Diels , Cocculus trilobus , Daphnandra apatela, Pachygone loyaltiensis Diels, Stephania pierrei and Stephania pierrei Diels(=S.erecta Craib) . It was first documented in 2006 (PMID: 17071017). Based on a literature review a small amount of articles have been published on dehydroapateline (PMID: 18321694) (PMID: 19126303).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214392D          

 41 48  0  0  1  0            999 V2000
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  1  2  2  0  0  0  0
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 40 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282214392D          

 41 48  0  0  1  0            999 V2000
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    8.9730    2.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1982    3.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5916    4.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8839    4.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5270    4.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2148    5.8472    0.0000 C   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
  5  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
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  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
  1 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 30 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4=CC=C(OC5=CC(CC6=NCCC7=C6C=C6OC3=C1OC6=C7)=CC=C5O)C=C4)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C34H30N2O5/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/h3-8,15-18,26,37H,9-14H2,1-2H3/t26-/m0/s1

> <INCHI_KEY>
HUUXXMNWOPUALW-SANMLTNESA-N

> <FORMULA>
C34H30N2O5

> <MOLECULAR_WEIGHT>
546.623

> <EXACT_MASS>
546.215472074

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
60.19382103669406

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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-1,3,7,10,12,14(37),16,18,25(33),26,28(32),30(34),35-tridecaen-13-ol

> <ALOGPS_LOGP>
5.98

> <JCHEM_LOGP>
5.634958136513537

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.429773761071223

> <JCHEM_PKA_STRONGEST_BASIC>
6.5746618454993415

> <JCHEM_POLAR_SURFACE_AREA>
72.75000000000001

> <JCHEM_REFRACTIVITY>
157.3867

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(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-1,3,7,10,12,14(37),16,18,25(33),26,28(32),30(34),35-tridecaen-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      13.034   2.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.951   3.292   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.119   4.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.612   4.608   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.696   3.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.461   2.022   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.151   3.714   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.579   5.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.688   6.309   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.201   6.020   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.168   8.050   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.532   8.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.480   7.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.117   5.763   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.997   4.825   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.468   4.918   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.889   6.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.860   7.577   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.574   3.584   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.528   6.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.972   7.722   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.172   7.003   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.770   7.490   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.371   8.853   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.127   9.891   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.584   9.429   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.017   8.320   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.469   7.354   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.331   5.753   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.266   4.402   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.689   2.483   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.883   0.835   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      15.313   0.347   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0      16.265   1.546   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.691   3.006   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.750   5.086   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.170   6.608   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.038   7.675   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.583   9.182   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      10.317   9.130   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       9.734  10.915   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   40                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31    1   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    2                                                       
CONECT   36   30   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   28   39                                                  
CONECT   39   38                                                            
CONECT   40   11   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₀N₂O₅

Average Mass

546.6230 Da

Monoisotopic Mass

546.21547 Da

IUPAC Name

(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-1,3,7,10,12,14(37),16,18,25(33),26,28(32),30(34),35-tridecaen-13-ol

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4=CC=C(OC5=CC(CC6=NCCC7=C6C=C6OC3=C1OC6=C7)=CC=C5O)C=C4)N(C)CC2

InChI Identifier

InChI=1S/C34H30N2O5/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/h3-8,15-18,26,37H,9-14H2,1-2H3/t26-/m0/s1

InChI Key

HUUXXMNWOPUALW-SANMLTNESA-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
Anisocycla cymosa	Plant	KNApSAcK
Anisocyla jollyana	Plant	KNApSAcK
Bacopa monnieri	Plant	KNApSAcK
Cocculus orbiculatus	LOTUS Database	35616633
Cocculus pendulus	LOTUS Database	35616633
Cocculus pendulus (Forsk.) Diels	Plant	KNApSAcK
Cocculus trilobus	Plant	KNApSAcK
Daphnandra apatela	LOTUS Database	35616633
Pachygone loyaltiensis Diels	Plant	KNApSAcK
Stephania pierrei	LOTUS Database	35616633
Stephania pierrei Diels(=S.erecta Craib)	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
Dihydroisoquinoline
Tetrahydroisoquinoline
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Benzenoid
Ketimine
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Ether
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Amine
Imine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
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	5.98	ALOGPS
logP	5.63	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	6.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.75 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	157.39 m³·mol⁻¹	ChemAxon
Polarizability	60.19 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

23326757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559250

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Murebwayire S, Frederich M, Hannaert V, Jonville MC, Duez P: Antiplasmodial and antitrypanosomal activity of Triclisia sacleuxii (Pierre) Diels. Phytomedicine. 2008 Sep;15(9):728-33. doi: 10.1016/j.phymed.2007.10.005. Epub 2008 Mar 5. [PubMed:18321694 ]
Murebwayire S, Ingkaninan K, Changwijit K, Frederich M, Duez P: Triclisia sacleuxii (Pierre) Diels (Menispermaceae), a potential source of acetylcholinesterase inhibitors. J Pharm Pharmacol. 2009 Jan;61(1):103-7. doi: 10.1211/jpp/61.01.0014. [PubMed:19126303 ]
Murebwayire S, Diallo B, Luhmer M, Vanhaelen-Fastre R, Vanhaelen M, Duez P: Alkaloids and amides from Triclisia sacleuxii. Fitoterapia. 2006 Dec;77(7-8):615-7. doi: 10.1016/j.fitote.2006.09.007. Epub 2006 Sep 22. [PubMed:17071017 ]

Showing NP-Card for (+)-1,2-Dehydroapateline (NP0067811)

MOL for NP0067811 ((+)-1,2-Dehydroapateline)

3D MOL for NP0067811 ((+)-1,2-Dehydroapateline)

3D SDF for NP0067811 ((+)-1,2-Dehydroapateline)

3D-SDF for NP0067811 ((+)-1,2-Dehydroapateline)

PDB for NP0067811 ((+)-1,2-Dehydroapateline)

3D PDB for NP0067811 ((+)-1,2-Dehydroapateline)

SMILES for NP0067811 ((+)-1,2-Dehydroapateline)

INCHI for NP0067811 ((+)-1,2-Dehydroapateline)

Structure for NP0067811 ((+)-1,2-Dehydroapateline)

3D Structure for NP0067811 ((+)-1,2-Dehydroapateline)