NP-MRD: Showing NP-Card for 2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate (NP0252546)

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Record Information

Version

2.0

Created at

2022-09-07 16:05:48 UTC

Updated at

2022-09-07 16:05:48 UTC

NP-MRD ID

NP0252546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate

Description

Paucifinine belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. 2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate is found in Kopsia pauciflora. Based on a literature review very few articles have been published on Paucifinine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218052D          

 34 40  0  0  1  0            999 V2000
    7.5594    3.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2169    2.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309072218052D          

 34 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0252546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(C=CC3=C2OCO3)[C@@]23CCN4CCC[C@]5(CC[C@]12[C@@](O)(C5)C(=O)OC)[C@@]34O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O8/c1-31-18(27)22(29)12-20-6-3-10-25-11-9-21(24(20,25)30)14-4-5-15-17(34-13-33-15)16(14)26(19(28)32-2)23(21,22)8-7-20/h4-5,29-30H,3,6-13H2,1-2H3/t20-,21+,22-,23+,24-/m1/s1

> <INCHI_KEY>
YYHXESNSRFJOIR-QWQGWLCTSA-N

> <FORMULA>
C24H28N2O8

> <MOLECULAR_WEIGHT>
472.494

> <EXACT_MASS>
472.18456587

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.50307147332262

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,21-dimethyl (1S,12S,19R,21S,24R)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1^{12,15}.0^{1,12}.0^{3,11}.0^{4,8}.0^{19,24}]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate

> <JCHEM_LOGP>
1.2210026233333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.444314919149658

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.529480681478313

> <JCHEM_PKA_STRONGEST_BASIC>
7.735750589546464

> <JCHEM_POLAR_SURFACE_AREA>
118.0

> <JCHEM_REFRACTIVITY>
115.07939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,21-dimethyl (1S,12S,19R,21S,24R)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1^{12,15}.0^{1,12}.0^{3,11}.0^{4,8}.0^{19,24}]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      14.111   6.008   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.472   4.607   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.939   4.460   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.045   5.714   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.299   3.059   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.969   1.649   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.740   0.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.930  -0.807   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.348  -1.407   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.577  -0.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.387   1.049   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.782   1.702   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      15.834   0.577   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      15.089  -0.771   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.136   0.968   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.168  -0.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.137  -1.802   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.949  -0.740   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.397  -1.097   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.216  -0.040   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.436   1.530   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.988   1.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.252   2.542   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.552   2.059   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.771   2.634   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.410   3.698   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.654   4.605   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.877   5.143   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.862   6.327   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.359   5.404   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.826   6.849   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.707   3.568   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.339   0.854   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.820   2.317   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   25                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    7   16   25   33                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32   33                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    5   15   26                                             
CONECT   26   25   27   28   32                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   26   22                                                       
CONECT   33   22   18   15   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈N₂O₈

Average Mass

472.4940 Da

Monoisotopic Mass

472.18457 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(C=CC3=C2OCO3)[C@@]23CCN4CCC[C@]5(CC[C@]12[C@@](O)(C5)C(=O)OC)[C@@]34O

InChI Identifier

InChI=1S/C24H28N2O8/c1-31-18(27)22(29)12-20-6-3-10-25-11-9-21(24(20,25)30)14-4-5-15-17(34-13-33-15)16(14)26(19(28)32-2)23(21,22)8-7-20/h4-5,29-30H,3,6-13H2,1-2H3/t20-,21+,22-,23+,24-/m1/s1

InChI Key

YYHXESNSRFJOIR-QWQGWLCTSA-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

Species Name	Source	Reference
Kopsia pauciflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Carbazole
Indolecarboxylic acid derivative
Indolecarboxylic acid
Quinolidine
Azaspirodecane
Indolizidine
Indole or derivatives
Benzodioxole
Benzenoid
N-alkylpyrrolidine
Piperidine
Methyl ester
Carbamic acid ester
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Carbonic acid derivative
Hemiaminal
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alkanolamine
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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

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

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

101938445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate (NP0252546)

MOL for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

3D MOL for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

3D SDF for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

3D-SDF for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

PDB for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

3D PDB for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

SMILES for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

INCHI for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

Structure for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)

3D Structure for NP0252546 (2,21-dimethyl (1s,12s,19r,21s,24r)-21,24-dihydroxy-5,7-dioxa-2,15-diazaheptacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸.0¹⁹,²⁴]tetracosa-3(11),4(8),9-triene-2,21-dicarboxylate)