NP-MRD: Showing NP-Card for 10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile (NP0208858)

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Record Information

Version

2.0

Created at

2022-09-05 06:02:11 UTC

Updated at

2022-09-05 06:02:11 UTC

NP-MRD ID

NP0208858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile

Description

10-(Hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]Henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton. 10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile is found in Jorunna funebris. 10-(Hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]Henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251514432D          

 36 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251514432D          

 36 40  0  0  0  0            999 V2000
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 32 33  1  0  0  0  0
 33 34  3  0  0  0  0
  9 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0208858

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C2=C(C(CO)N3C(C2)C2N(C)C(CC4=C2C(=O)C(OC)=C(C)C4=O)C3C#N)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H27N3O7/c1-10-21(31)12-7-15-20-19-13(22(32)11(2)26(36-5)24(19)34)6-14(28(20)3)16(8-27)29(15)17(9-30)18(12)23(33)25(10)35-4/h14-17,20,30H,6-7,9H2,1-5H3

> <INCHI_KEY>
JHAXVYBLQNHGFS-UHFFFAOYSA-N

> <FORMULA>
C26H27N3O7

> <MOLECULAR_WEIGHT>
493.516

> <EXACT_MASS>
493.184900221

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.44179939738675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
0.4725598079999992

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.039647201134194

> <JCHEM_PKA_STRONGEST_BASIC>
2.6516961291328167

> <JCHEM_POLAR_SURFACE_AREA>
137.24

> <JCHEM_REFRACTIVITY>
131.02149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      17.538   1.100   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.460   0.001   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.968   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.556   1.869   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.634   2.968   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.065   2.254   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.652   3.737   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.986   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.399  -0.329   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.320  -1.428   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.733  -2.912   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.224  -3.297   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       9.829  -1.044   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       9.416   0.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.495   1.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.075   1.197   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.331  -0.861   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       9.458  -1.911   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.588  -2.797   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.247  -2.040   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.834  -0.556   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.591   0.785   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.809   2.111   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.566   3.452   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.269   2.096   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.512   0.755   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.972   0.741   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.294  -0.571   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.537  -1.912   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.486   3.423   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.946   3.408   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.071  -2.385   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.020  -3.598   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      10.969  -4.810   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      13.890  -0.714   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.302  -2.197   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   32                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    8                                                       
CONECT   16   14   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30                                                            
CONECT   32   19   13   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35    9    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₇N₃O₇

Average Mass

493.5160 Da

Monoisotopic Mass

493.18490 Da

IUPAC Name

10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile

Traditional Name

10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C(C(CO)N3C(C2)C2N(C)C(CC4=C2C(=O)C(OC)=C(C)C4=O)C3C#N)C1=O

InChI Identifier

InChI=1S/C26H27N3O7/c1-10-21(31)12-7-15-20-19-13(22(32)11(2)26(36-5)24(19)34)6-14(28(20)3)16(8-27)29(15)17(9-30)18(12)23(33)25(10)35-4/h14-17,20,30H,6-7,9H2,1-5H3

InChI Key

JHAXVYBLQNHGFS-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
Jorunna funebris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinoline quinones

Direct Parent

Isoquinoline quinones

Alternative Parents

Substituents

Isoquinoline quinone
Isoquinolone
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Piperazine
Vinylogous ester
Alpha-aminonitrile
Ketone
Tertiary amine
Tertiary aliphatic amine
Carbonitrile
Nitrile
Azacycle
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxide
Cyanide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.22	ALOGPS
logP	0.47	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.04	ChemAxon
pKa (Strongest Basic)	2.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.24 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.02 m³·mol⁻¹	ChemAxon
Polarizability	50.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

56667302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile (NP0208858)

MOL for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

3D MOL for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

3D SDF for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

3D-SDF for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

PDB for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

3D PDB for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

SMILES for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

INCHI for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

Structure for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)

3D Structure for NP0208858 (10-(hydroxymethyl)-7,18-dimethoxy-6,17,21-trimethyl-5,8,16,19-tetraoxo-11,21-diazapentacyclo[11.7.1.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4(9),6,15(20),17-tetraene-12-carbonitrile)