NP-MRD: Showing NP-Card for delorazepam (NP0309023)

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Record Information

Version

1.0

Created at

2022-09-11 03:17:08 UTC

Updated at

2022-09-11 03:17:08 UTC

NP-MRD ID

NP0309023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

delorazepam

Description

Delorazepam, also known as dadumir, belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. Delorazepam is a moderately basic compound (based on its pKa). Delorazepam is a potentially toxic compound. Liver disease has a profound effect on the elimination rate of delorazepam, resulting in the half-life almost doubling to 395 hours, whereas healthy patients showed an elimination half-life of 204 hours on average. Delorazepam is available in tablet and liquid drop formulations. delorazepam is found in Artemisia dracunculus and Triticum aestivum. When being used on an as-needed basis the need for delorazepam therapy should be re-evaluated each time a new prescription for delorazepam is issued, and alternative medications should be considered if patients begin to take delorazepam habitually (many days in a row).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    2.8366   -3.3081    0.9266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -2.4041    0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243   -2.7554   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.9673   -0.0465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2194   -0.6396    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -0.1060    0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5895   -0.9886    0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261   -0.6720    0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0509    0.5784    1.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    1.4323    1.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039    1.1060    0.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    2.2668    1.3559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.2505   -0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847    1.3571   -1.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2584    2.3050   -1.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6861    3.7198   -2.3892 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6200    2.1155   -1.3406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    1.0254   -0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    0.1064   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313   -1.0818    0.3380 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -3.8194   -0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489   -2.6168   -1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4176   -1.9815   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6586   -1.3555    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0282    0.8442    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1235    2.4156    1.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6924    1.4164   -1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.8799   -1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1728    0.8257   -0.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7330   -0.9485    0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 19  2  0
 19 20  1  0
 20  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 19 18  1  0
 18 17  2  0
 17 15  1  0
  5 13  1  0
 11  6  1  0
 14 27  1  0
 20 30  1  0
  3 21  1  0
  3 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 18 29  1  0
 17 28  1  0
M  END

1511
  Mrv0541 02231215322D          

 20 22  0  0  0  0            999 V2000
    2.5466   -2.3592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6079   -1.4649    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3402    2.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0374    0.9709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1106   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8539    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4988   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880   -1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6981    1.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075   -1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759   -1.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2668   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9118   -0.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7888   -1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 16  1  0  0  0  0
  3 13  2  0  0  0  0
  4  8  1  0  0  0  0
  4 13  1  0  0  0  0
  5  7  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  2  0  0  0  0
 10 14  2  0  0  0  0
 11 13  1  0  0  0  0
 12 15  2  0  0  0  0
 14 15  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10Cl2N2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)

> <INCHI_KEY>
CHIFCDOIPRCHCF-UHFFFAOYSA-N

> <FORMULA>
C15H10Cl2N2O

> <MOLECULAR_WEIGHT>
305.159

> <EXACT_MASS>
304.017018366

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.440928184810463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.8160651750000003

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.293636772928373

> <JCHEM_PKA_STRONGEST_BASIC>
2.049184533048919

> <JCHEM_POLAR_SURFACE_AREA>
41.46

> <JCHEM_REFRACTIVITY>
81.50080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
delorazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1511                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.754  -4.404   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       6.735  -2.734   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       4.368   4.404   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.076   1.812   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.536   1.812   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.806  -0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.194   0.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.419   0.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.398  -0.649   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.951  -1.955   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.576   3.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -0.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.036   3.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.633  -2.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.187  -2.173   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.168  -2.172   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.831  -0.087   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.372  -3.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.035  -1.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.806  -2.569   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   16                                                            
CONECT    3   13                                                            
CONECT    4    8   13                                                       
CONECT    5    7   11                                                       
CONECT    6    7    8   10                                                  
CONECT    7    5    6    9                                                  
CONECT    8    4    6   12                                                  
CONECT    9    7   16   17                                                  
CONECT   10    6   14                                                       
CONECT   11    5   13                                                       
CONECT   12    8   15                                                       
CONECT   13    3    4   11                                                  
CONECT   14    1   10   15                                                  
CONECT   15   12   14                                                       
CONECT   16    2    9   18                                                  
CONECT   17    9   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Dadumir	Kegg
Chlorodesmethyldiazepam	MeSH
2'-Chloronordiazepam	MeSH
7-chloro-5-(2-Chlorophenyl) 1,3-dihydro-2H-1,4-benzodiazepin-2-one	MeSH
Chlordemethyldiazepam	MeSH
Chlordesmethyldiazepam	MeSH

Chemical Formula

C₁₅H₁₀Cl₂N₂O

Average Mass

305.1590 Da

Monoisotopic Mass

304.01702 Da

IUPAC Name

7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

delorazepam

CAS Registry Number

Not Available

SMILES

ClC1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2Cl)C=C1

InChI Identifier

InChI=1S/C15H10Cl2N2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)

InChI Key

CHIFCDOIPRCHCF-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
Artemisia dracunculus	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Imine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organohalogen compound
Organochloride
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	3.46	ALOGPS
logP	3.82	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	2.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.5 m³·mol⁻¹	ChemAxon
Polarizability	29.44 Å³	ChemAxon
Number of Rings	3	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

DB01511

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

Delorazepam

METLIN ID

Not Available

PubChem Compound

17925

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for delorazepam (NP0309023)

MOL for NP0309023 (delorazepam)

3D MOL for NP0309023 (delorazepam)

3D SDF for NP0309023 (delorazepam)

3D-SDF for NP0309023 (delorazepam)

PDB for NP0309023 (delorazepam)

3D PDB for NP0309023 (delorazepam)

SMILES for NP0309023 (delorazepam)

INCHI for NP0309023 (delorazepam)

Structure for NP0309023 (delorazepam)

3D Structure for NP0309023 (delorazepam)