NP-MRD: Showing NP-Card for (S)-Dicentrine (NP0045877)

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Record Information

Version

2.0

Created at

2022-03-17 19:44:43 UTC

Updated at

2022-03-17 19:44:43 UTC

NP-MRD ID

NP0045877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-Dicentrine

Description

(S)-Dicentrine is found in Cassytha filiformis , Cissampelos capensis, Dasymaschalon sootepense, Dicentra eximia, Dicentra formosa, Dicentra pusilla, Glaucium flavum, Illigera luzonensis, Lindera megaphylla, Litsea deccanensis, Ocotea leucoxylon, Ocotea velloziana, Scolopia chinensis, Stephania brachyandra Diels, Stephania delavayi Diels, Stephania dicentrinifera H.S.Lo.et.M.Yang, Stephania epigaea H.S.Lo, Stephania kuinanensis H.S.Lo & M.Yang, Stephania mashanica H.S.Lo.et.B.N.Chang, Stephania pierrei and Stephania pierrei Diels .

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219292D          

 25 29  0  0  0  0            999 V2000
   -0.1224    0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537    0.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493   -1.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396   -0.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5261   -1.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -1.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977   -0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500    0.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    2.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7112   -1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022   -1.5784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    0.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  2  0  0  0  0
  4 22  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  1  0  0  0  0
  8 20  1  0  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv0541 02241219292D          

 25 29  0  0  0  0            999 V2000
   -0.1224    0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537    0.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493   -1.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396   -0.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5261   -1.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -1.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977   -0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8500    0.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    1.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    2.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7112   -1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022   -1.5784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    0.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  2  0  0  0  0
  4 22  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  1  0  0  0  0
  8 20  1  0  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1=C3C(C2)N(C)CCC3=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3

> <INCHI_KEY>
YJWBWQWUHVXPNC-UHFFFAOYSA-N

> <FORMULA>
C20H21NO4

> <MOLECULAR_WEIGHT>
339.385

> <EXACT_MASS>
339.147058165

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.52863078509223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaene

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.0093029640000006

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.062561297435809

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
94.71959999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.228   0.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.981   1.133   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.340   0.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.794  -0.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.585  -1.888   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.074  -1.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.982  -2.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.493  -1.888   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.796  -0.377   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.587   0.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.040   2.040   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.133   3.249   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.040   4.456   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.399   4.004   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.399   2.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.608   1.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.306   0.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.363  -0.981   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.061  -2.492   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -3.551  -2.946   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -3.249  -4.456   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.154  -1.283   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.363  -0.377   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.549   1.737   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.247   3.249   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   17                                                  
CONECT   10    1    9   11                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17    9   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    8   19   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23                                                       
CONECT   23   22                                                            
CONECT   24    3   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Dicentrine nitrate, (S)-isomer	MeSH
Dicentrine	MeSH
Dicentrine, (R)-isomer	MeSH
(R)-(-)-Dicentrine	MeSH

Chemical Formula

C₂₀H₂₁NO₄

Average Mass

339.3850 Da

Monoisotopic Mass

339.14706 Da

IUPAC Name

16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaene

Traditional Name

16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaene

CAS Registry Number

517-66-8

SMILES

COC1=CC2=C(C=C1OC)C1=C3C(C2)N(C)CCC3=CC2=C1OCO2

InChI Identifier

InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3

InChI Key

YJWBWQWUHVXPNC-UHFFFAOYSA-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
Cassytha filiformis	Plant	KNApSAcK
Cissampelos capensis	LOTUS Database	35616633
Dasymaschalon sootepense	LOTUS Database	35616633
Dicentra eximia	LOTUS Database	35616633
Dicentra formosa	LOTUS Database	35616633
Dicentra pusilla	Plant	KNApSAcK
Glaucium flavum	LOTUS Database	35616633
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Illigera luzonensis	LOTUS Database	35616633
Lindera megaphylla	LOTUS Database	35616633
Litsea deccanensis	LOTUS Database	35616633
Ocotea leucoxylon	LOTUS Database	35616633
Ocotea velloziana	LOTUS Database	35616633
Scolopia chinensis	LOTUS Database	35616633
Stephania brachyandra Diels	Plant	KNApSAcK
Stephania delavayi	Plant	KNApSAcK
Stephania dicentrinifera H.S.Lo.et.M.Yang	Plant	KNApSAcK
Stephania epigaea	Plant	KNApSAcK
Stephania kuinanensis H.S.Lo & M.Yang	Plant	KNApSAcK
Stephania mashanica H.S.Lo.et.B.N.Chang	Plant	KNApSAcK
Stephania pierrei	LOTUS Database	35616633
Stephania pierrei Diels	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organooxygen 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	2.76	ALOGPS
logP	3.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	7.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.72 m³·mol⁻¹	ChemAxon
Polarizability	37.53 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

FDB002141

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

630859

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (S)-Dicentrine (NP0045877)

MOL for NP0045877 ((S)-Dicentrine)

3D MOL for NP0045877 ((S)-Dicentrine)

3D SDF for NP0045877 ((S)-Dicentrine)

3D-SDF for NP0045877 ((S)-Dicentrine)

PDB for NP0045877 ((S)-Dicentrine)

3D PDB for NP0045877 ((S)-Dicentrine)

SMILES for NP0045877 ((S)-Dicentrine)

INCHI for NP0045877 ((S)-Dicentrine)

Structure for NP0045877 ((S)-Dicentrine)

3D Structure for NP0045877 ((S)-Dicentrine)