NP-MRD: Showing NP-Card for 6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one (NP0210705)

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Record Information

Version

2.0

Created at

2022-09-05 08:38:44 UTC

Updated at

2022-09-05 08:38:44 UTC

NP-MRD ID

NP0210705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one

Description

6,20-Difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]Tricosa-1,4(9),5,7,10,13,15,17(22),18,20-decaen-12-one belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole. 6,20-Difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]Tricosa-1,4(9),5,7,10,13,15,17(22),18,20-decaen-12-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181501212D          

 38 44  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004181501212D          

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 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 28 37  2  0  0  0  0
 37 38  1  0  0  0  0
 12 38  1  0  0  0  0
 20 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0210705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C(O)C1O)N1C2=C(C=CC(F)=C2)C2=C1C1=C(C3=CC=C(F)C=C3N1)C1=C2C(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H19F2N3O7/c27-8-1-3-10-12(5-8)29-19-15(10)17-18(25(37)30-24(17)36)16-11-4-2-9(28)6-13(11)31(20(16)19)26-23(35)22(34)21(33)14(7-32)38-26/h1-6,14,21-23,26,29,32-35H,7H2,(H,30,36,37)

> <INCHI_KEY>
NKNQTGRKBYNURK-UHFFFAOYSA-N

> <FORMULA>
C26H19F2N3O7

> <MOLECULAR_WEIGHT>
523.449

> <EXACT_MASS>
523.11910629

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
50.49652420225645

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,20-difluoro-23-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.0238205739999995

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.332354936568066

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.102953628012608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9804971885313973

> <JCHEM_POLAR_SURFACE_AREA>
157.04

> <JCHEM_REFRACTIVITY>
127.13479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,20-difluoro-23-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0       6.281 -15.478   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.960 -13.972   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.105 -12.941   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.785 -11.435   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.929 -10.404   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.394 -10.880   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.538  -9.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.714 -12.387   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.179 -12.862   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.570 -13.417   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.890 -14.923   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       7.609  -8.898   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       6.202  -8.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.795  -8.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.549  -7.993   0.000  0.00  0.00           C+0
HETATM   16  F   UNK     0       2.143  -8.619   0.000  0.00  0.00           F+0
HETATM   17  C   UNK     0       3.710  -6.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.117  -5.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.363  -6.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.869  -6.420   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.639  -5.086   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.164  -3.622   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.699  -3.146   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       9.409  -2.716   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      10.655  -3.622   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.120  -3.146   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.179  -5.086   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.949  -6.420   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.456  -6.740   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.702  -5.835   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.109  -6.461   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.270  -7.993   0.000  0.00  0.00           C+0
HETATM   33  F   UNK     0      16.676  -8.619   0.000  0.00  0.00           F+0
HETATM   34  C   UNK     0      14.024  -8.898   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.617  -8.272   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      11.210  -8.898   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      10.179  -7.754   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.639  -7.754   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   38                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28                                                  
CONECT   28   27   29   37                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   28   38                                                  
CONECT   38   37   12   20                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₁₉F₂N₃O₇

Average Mass

523.4490 Da

Monoisotopic Mass

523.11911 Da

IUPAC Name

6,20-difluoro-23-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C(O)C1O)N1C2=C(C=CC(F)=C2)C2=C1C1=C(C3=CC=C(F)C=C3N1)C1=C2C(=O)NC1=O

InChI Identifier

InChI=1S/C26H19F2N3O7/c27-8-1-3-10-12(5-8)29-19-15(10)17-18(25(37)30-24(17)36)16-11-4-2-9(28)6-13(11)31(20(16)19)26-23(35)22(34)21(33)14(7-32)38-26/h1-6,14,21-23,26,29,32-35H,7H2,(H,30,36,37)

InChI Key

NKNQTGRKBYNURK-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 indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Indolocarbazoles

Alternative Parents

Substituents

Indolocarbazole
Pyrrolo[2,3-a]carbazole
Hexose monosaccharide
Pyrroloindole
Glycosyl compound
Phthalimide
N-glycosyl compound
N-alkylindole
Isoindolone
Indole
Isoindoline
Isoindole or derivatives
Aryl fluoride
Aryl halide
Benzenoid
Monosaccharide
Oxane
Substituted pyrrole
Pyrrole
Carboxylic acid imide, n-unsubstituted
Carboxylic acid imide
Heteroaromatic compound
Secondary alcohol
1,2-diol
Carboxylic acid derivative
Polyol
Azacycle
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organohalogen compound
Primary alcohol
Organofluoride
Organonitrogen 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	1.39	ALOGPS
logP	1.02	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	157.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.13 m³·mol⁻¹	ChemAxon
Polarizability	50.5 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

23442827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one (NP0210705)

MOL for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

3D MOL for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

3D SDF for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

3D-SDF for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

PDB for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

3D PDB for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

SMILES for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

INCHI for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

Structure for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)

3D Structure for NP0210705 (6,20-difluoro-14-hydroxy-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]tricosa-1(16),2(10),4(9),5,7,11(15),13,17(22),18,20-decaen-12-one)