NP-MRD: Showing NP-Card for 13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate (NP0313521)

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Record Information

Version

2.0

Created at

2022-09-11 11:07:58 UTC

Updated at

2022-09-11 11:07:58 UTC

NP-MRD ID

NP0313521

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate

Description

13,15-Dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]Docosa-7,9,11-triene-13,15-dicarboxylate 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. 13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate is found in Kopsia singapurensis. 13,15-Dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]Docosa-7,9,11-triene-13,15-dicarboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241503252D          

 33 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241503252D          

 33 39  0  0  0  0            999 V2000
   -0.0639   -1.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0313521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC2OC3C11CCC4(N(C(=O)OC)C5=CC=CC=C5C44CCN2C14)C3(O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O7/c1-30-15-12-16-25-11-10-22-13-6-4-5-7-14(13)26(20(28)32-3)23(22)9-8-21(15,17(22)25)18(33-16)24(23,29)19(27)31-2/h4-7,15-18,29H,8-12H2,1-3H3

> <INCHI_KEY>
BRXMYFHIYLHURN-UHFFFAOYSA-N

> <FORMULA>
C24H28N2O7

> <MOLECULAR_WEIGHT>
456.495

> <EXACT_MASS>
456.18965125

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.520539680407694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
1.215801493666666

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.750415739952421

> <JCHEM_PKA_STRONGEST_BASIC>
6.603886092111351

> <JCHEM_POLAR_SURFACE_AREA>
97.77

> <JCHEM_REFRACTIVITY>
112.38199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.119  -2.534   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.161  -1.678   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.061  -0.142   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.276   0.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.263   0.912   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.057   2.496   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.605   2.744   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.487   1.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.989   1.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.972   2.686   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.427   2.711   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.719   3.699   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       6.830   5.235   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.555   6.099   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.215   5.907   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.326   7.443   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.807   2.586   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.346   2.652   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.172   1.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.460  -0.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.921  -0.079   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.095   1.221   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.485   0.917   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.310  -0.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.821  -1.449   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.492  -0.448   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       3.940   0.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.048   3.769   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.831   5.095   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.314   5.123   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.120   6.436   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.775   5.165   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.041   6.519   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    3    9   27                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23   28                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   11   24   27                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26    8   23                                                  
CONECT   28   11    7   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Value	Source
13,15-Dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0,.0,.0,.0,.0,]docosa-7,9,11-triene-13,15-dicarboxylic acid	Generator
13,15-Dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₇

Average Mass

456.4950 Da

Monoisotopic Mass

456.18965 Da

IUPAC Name

13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate

Traditional Name

13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC1CC2OC3C11CCC4(N(C(=O)OC)C5=CC=CC=C5C44CCN2C14)C3(O)C(=O)OC

InChI Identifier

InChI=1S/C24H28N2O7/c1-30-15-12-16-25-11-10-22-13-6-4-5-7-14(13)26(20(28)32-3)23(22)9-8-21(15,17(22)25)18(33-16)24(23,29)19(27)31-2/h4-7,15-18,29H,8-12H2,1-3H3

InChI Key

BRXMYFHIYLHURN-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

Species Name	Source	Reference
Kopsia singapurensis	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
Aspidosperma alkaloid
Carbazole
Indolecarboxylic acid derivative
Indolecarboxylic acid
Azaspirodecane
Quinolidine
Indolizidine
Indole or derivatives
1,3-oxazinane
Oxane
Oxazinane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Cyclic alcohol
Tertiary alcohol
Carbamic acid ester
Methyl ester
Carbonic acid derivative
Carboxylic acid ester
Hemiaminal
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	1.06	ALOGPS
logP	1.22	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.75	ChemAxon
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.38 m³·mol⁻¹	ChemAxon
Polarizability	46.52 Å³	ChemAxon
Number of Rings	7	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate (NP0313521)

MOL for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

3D MOL for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

3D SDF for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

3D-SDF for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

PDB for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

3D PDB for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

SMILES for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

INCHI for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

Structure for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)

3D Structure for NP0313521 (13,15-dimethyl 15-hydroxy-20-methoxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]docosa-7,9,11-triene-13,15-dicarboxylate)