NP-MRD: Showing NP-Card for 4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate (NP0231925)

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Record Information

Version

2.0

Created at

2022-09-06 12:58:42 UTC

Updated at

2022-09-06 12:58:42 UTC

NP-MRD ID

NP0231925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate

Description

4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]Icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group. Based on a literature review very few articles have been published on 4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]Icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062214582D          

 39 44  0  0  0  0            999 V2000
    4.2590    5.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309062214582D          

 39 44  0  0  0  0            999 V2000
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    6.6630   -0.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0472   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4717    0.5026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 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
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 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
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  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
 19 32  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 22 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(O)(CC1=CC=CC=C1)C(=O)OC1=C2C3=CC4=C(OCO4)C=C3CCN3CCCC23C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H31NO8/c1-35-24-16-29-10-6-11-31(29)12-9-20-13-22-23(38-18-37-22)14-21(20)26(29)27(24)39-28(33)30(34,17-25(32)36-2)15-19-7-4-3-5-8-19/h3-5,7-8,13-14,16,34H,6,9-12,15,17-18H2,1-2H3

> <INCHI_KEY>
WAHNMIKDNXYEDN-UHFFFAOYSA-N

> <FORMULA>
C30H31NO8

> <MOLECULAR_WEIGHT>
533.577

> <EXACT_MASS>
533.204966962

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.06207157167621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate

> <JCHEM_LOGP>
2.6680801543333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.966115944111928

> <JCHEM_PKA_STRONGEST_BASIC>
8.368176536919064

> <JCHEM_POLAR_SURFACE_AREA>
103.76

> <JCHEM_REFRACTIVITY>
143.2308

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       7.950  10.921   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.401   9.482   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.372   8.287   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.893   8.531   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.822   6.849   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.794   5.653   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.989   6.625   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.765   4.458   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.285   4.702   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.835   6.141   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.356   6.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.327   5.189   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.777   3.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.257   3.507   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.599   4.682   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.160   5.232   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.842   3.162   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.647   2.190   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.730   0.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.059  -0.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.269   0.828   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.699   0.257   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.920  -1.267   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.710  -2.220   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.280  -1.649   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.226  -2.772   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.691  -2.648   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       4.831  -1.371   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       3.291  -1.385   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.802   0.075   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.909   0.818   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.293   0.098   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.322   1.294   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.159   2.586   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.604   4.023   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.083   4.262   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.438  -1.528   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      13.155  -0.165   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.080   0.938   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                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   32                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   39                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   19   28   33                                             
CONECT   33   32   34                                                       
CONECT   34   33   18   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   23   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   22                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
4-Methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioic acid	Generator

Chemical Formula

C₃₀H₃₁NO₈

Average Mass

533.5770 Da

Monoisotopic Mass

533.20497 Da

IUPAC Name

4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate

Traditional Name

4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)CC(O)(CC1=CC=CC=C1)C(=O)OC1=C2C3=CC4=C(OCO4)C=C3CCN3CCCC23C=C1OC

InChI Identifier

InChI=1S/C30H31NO8/c1-35-24-16-29-10-6-11-31(29)12-9-20-13-22-23(38-18-37-22)14-21(20)26(29)27(24)39-28(33)30(34,17-25(32)36-2)15-19-7-4-3-5-8-19/h3-5,7-8,13-14,16,34H,6,9-12,15,17-18H2,1-2H3

InChI Key

WAHNMIKDNXYEDN-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, 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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cephalotaxus alkaloids

Sub Class

Not Available

Direct Parent

Cephalotaxus alkaloids

Alternative Parents

Substituents

Cephalotaxine
Benzazepine
Benzodioxole
Azepine
Fatty acid ester
Aralkylamine
Fatty acid methyl ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
N-alkylpyrrolidine
Enol ester
Pyrrolidine
Tertiary alcohol
Methyl ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Oxacycle
Azacycle
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
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	2.67	ChemAxon
pKa (Strongest Acidic)	11.97	ChemAxon
pKa (Strongest Basic)	8.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	143.23 m³·mol⁻¹	ChemAxon
Polarizability	55.06 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4478247

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320085

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate (NP0231925)

MOL for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

3D MOL for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

3D SDF for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

3D-SDF for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

PDB for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

3D PDB for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

SMILES for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

INCHI for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

Structure for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)

3D Structure for NP0231925 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),2,4,13,15(19)-pentaen-3-yl 1-methyl 3-benzyl-3-hydroxybutanedioate)