NP-MRD: Showing NP-Card for (4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one (NP0292963)

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Record Information

Version

2.0

Created at

2022-09-10 00:44:27 UTC

Updated at

2022-09-10 00:44:27 UTC

NP-MRD ID

NP0292963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one

Description

NSC285223 belongs to the class of organic compounds known as pyrrolo[2,1-c][1,4]benzodiazepines. These are heterocyclic aromatic compounds containing a 1,4-benzodiazepine ring system that is fused to, and shared a nitrogen atom with a pyrrole ring. Based on a literature review very few articles have been published on NSC285223.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202442D          

 38 42  0  0  1  0            999 V2000
    3.0061    0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205    0.9683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1731   -0.9467    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


  Mrv1652309102202442D          

 38 42  0  0  1  0            999 V2000
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 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 31 36  1  6  0  0  0
 36 37  1  0  0  0  0
 24 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0292963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)N=C[C@@H]1CC[C@H](O)N1C2=O.COC1=CC2=C(C=C1O)N=C[C@@H]1CC[C@@H](O)N1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/2C13H14N2O4/c2*1-19-11-4-8-9(5-10(11)16)14-6-7-2-3-12(17)15(7)13(8)18/h2*4-7,12,16-17H,2-3H2,1H3/t7-,12+;7-,12-/m00/s1

> <INCHI_KEY>
DOZXCNCPKXGGBC-VKKUPAEUSA-N

> <FORMULA>
C26H28N4O8

> <MOLECULAR_WEIGHT>
524.53

> <EXACT_MASS>
524.190713878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
26.374802048627636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,7S)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),8,11,13-tetraen-2-one; (4S,7S)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),8,11,13-tetraen-2-one

> <JCHEM_LOGP>
0.34270980900000036

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.48082672695709

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.503795320196256

> <JCHEM_PKA_STRONGEST_BASIC>
4.057044303864336

> <JCHEM_POLAR_SURFACE_AREA>
82.35999999999999

> <JCHEM_REFRACTIVITY>
69.64729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R,7S)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),8,11,13-tetraen-2-one; (4S,7S)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),8,11,13-tetraen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.611   1.337   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.145   1.808   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.004   0.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.538   1.243   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.398   0.208   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.723  -1.297   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.190  -1.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.330  -0.732   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.797  -1.203   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.250  -2.490   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.790  -2.473   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.737  -1.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.272  -1.379   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.861   0.044   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.690   1.044   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.811   2.579   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -2.377   0.239   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -0.982   0.892   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.965   2.432   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.484   1.337   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      19.018   1.808   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      17.877   0.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.411   1.243   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.270   0.208   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.596  -1.297   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.063  -1.767   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.203  -0.732   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      19.670  -1.203   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0      14.623  -2.490   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      13.083  -2.473   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.136  -1.258   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.601  -1.379   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.011   0.044   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.182   1.044   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.062   2.579   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0      12.496   0.239   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      13.890   0.892   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.908   2.432   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   12   18                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   37                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   25   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   31   37                                                  
CONECT   37   36   24   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈N₄O₈

Average Mass

524.5300 Da

Monoisotopic Mass

524.19071 Da

IUPAC Name

(4R,7S)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),8,11,13-tetraen-2-one; (4S,7S)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),8,11,13-tetraen-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)N=C[C@@H]1CC[C@H](O)N1C2=O.COC1=CC2=C(C=C1O)N=C[C@@H]1CC[C@@H](O)N1C2=O

InChI Identifier

InChI=1S/2C13H14N2O4/c2*1-19-11-4-8-9(5-10(11)16)14-6-7-2-3-12(17)15(7)13(8)18/h2*4-7,12,16-17H,2-3H2,1H3/t7-,12+;7-,12-/m00/s1

InChI Key

DOZXCNCPKXGGBC-VKKUPAEUSA-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 pyrrolo[2,1-c][1,4]benzodiazepines. These are heterocyclic aromatic compounds containing a 1,4-benzodiazepine ring system that is fused to, and shared a nitrogen atom with a pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

Pyrrolo[2,1-c][1,4]benzodiazepines

Alternative Parents

Substituents

Pyrrolo[2,1-c][1,4]benzodizepine
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Propargyl-type 1,3-dipolar organic compound
Alkanolamine
Ether
Carboxylic acid derivative
Organic 1,3-dipolar compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Imine
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Not Available

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	0.34	ChemAxon
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	4.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.65 m³·mol⁻¹	ChemAxon
Polarizability	26.37 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

286595

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

323607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one (NP0292963)

MOL for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

3D MOL for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

3D SDF for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

3D-SDF for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

PDB for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

3D PDB for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

SMILES for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

INCHI for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

Structure for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)

3D Structure for NP0292963 ((4r,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one; (4s,7s)-4,12-dihydroxy-13-methoxy-3,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(10),8,11,13-tetraen-2-one)