NP-MRD: Showing NP-Card for 2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate (NP0214228)

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Record Information

Version

2.0

Created at

2022-09-05 13:28:08 UTC

Updated at

2022-09-05 13:28:08 UTC

NP-MRD ID

NP0214228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

Description

2,18-Dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3(8),4,6,14-tetraene-2,18-dicarboxylate belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups. 2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate is found in Kopsia singapurensis. 2,18-Dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3(8),4,6,14-tetraene-2,18-dicarboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241505262D          

 33 38  0  0  0  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2930    2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1098    2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7867    1.2767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5605    0.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4119   -0.9051    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


  Mrv1533004241505262D          

 33 38  0  0  0  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841    3.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0214228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(OC)C=CC=C2C23CCN4CC=CC5(CCC12C(O)(C5O)C(=O)OC)C34

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

> <INCHI_KEY>
BSCMCQIYAPFDSL-UHFFFAOYSA-N

> <FORMULA>
C24H28N2O7

> <MOLECULAR_WEIGHT>
456.495

> <EXACT_MASS>
456.18965125

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.26936177785897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
0.5047715880000001

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.962715355362157

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.756952977434239

> <JCHEM_PKA_STRONGEST_BASIC>
7.757507589640881

> <JCHEM_POLAR_SURFACE_AREA>
108.77

> <JCHEM_REFRACTIVITY>
116.4785

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-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      11.372   7.381   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.797   5.952   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.747   4.740   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.272   4.957   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.172   3.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.906   1.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.350   1.400   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.535   2.383   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.980   1.849   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.610  -0.118   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.425  -1.102   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.981  -0.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.721   0.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.108   1.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.213  -0.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.235  -1.690   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.001  -0.682   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.467  -1.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.239  -0.108   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.386   1.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.916   1.999   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.153   2.609   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.474   2.186   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.665   2.817   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.257   3.817   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.458   4.781   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.562   3.610   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.623   4.830   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.658   5.236   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.588   6.464   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.130   5.428   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.532   6.847   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.318   0.927   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   24   33                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27   33                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    5   14   25                                             
CONECT   25   24   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25   21   28                                                  
CONECT   28   27                                                            
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   21   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
2,18-Dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1,.0,.0,.0,]henicosa-3(8),4,6,14-tetraene-2,18-dicarboxylic acid	Generator
2,18-Dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6,14-tetraene-2,18-dicarboxylic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₇

Average Mass

456.4950 Da

Monoisotopic Mass

456.18965 Da

IUPAC Name

2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

Traditional Name

2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(OC)C=CC=C2C23CCN4CC=CC5(CCC12C(O)(C5O)C(=O)OC)C34

InChI Identifier

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

InChI Key

BSCMCQIYAPFDSL-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 oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharide sulfates

Alternative Parents

Substituents

Oligosaccharide sulfate
N-acyl-alpha-hexosamine
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Fatty acyl
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Oxane
Organic sulfuric acid or derivatives
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.98	ALOGPS
logP	0.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.76	ChemAxon
pKa (Strongest Basic)	7.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.48 m³·mol⁻¹	ChemAxon
Polarizability	46.27 Å³	ChemAxon
Number of Rings	6	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

85129309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate (NP0214228)

MOL for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D MOL for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D SDF for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D-SDF for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

PDB for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D PDB for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

SMILES for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

INCHI for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

Structure for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D Structure for NP0214228 (2,18-dimethyl 17,18-dihydroxy-4-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)